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Our trip today was just under thirty miles. We left around 9am and got to Nantucket around 1pm. Again we are going to anchor out and we have found we can usually find a spot just outside of mooring fields. We entered the harbor and scoped out the listed anchorages but they were too far away for our liking. There were a couple of larger yachts anchored by the mooring field so we stayed away from them but found a spot for ourselves. We dropped the anchor and did our usual: waiting to make sure it had set. The nice thing we’ve noticed is that dinghy docks seem to be plentiful around here. That makes a big difference in our ability to easily get to shore, especially with the bikes. Once we had waited and made sure we were secured it was time to head to shore. We loaded up the bikes and set out for the dinghy dock. As we cruised to the dinghy dock we passed by some mega yachts. One was named “Friendly Confines” and was flying a Cubs flag. We speculated but couldn’t confirm that it was owned by the Cubs owner. Once on land we decided to visit Cisco Brewing, a highly praised establishment with an on site distillery called Triple 8. It was a beautiful 20 minute ride passed historic homes that all seemed to be competing for the best gardens. Although the brewery had ample out door space, it was packed and there was a pretty long line of not distanced patrons waiting to get in. We weren’t comfortable with the situation so we ordered some beer and a bottle of their blueberry vodka to go and took it to a beach about 20 minutes away. The brew was worth the trouble and the beach definitely worth the ride.

On the way back we stopped at a fancy market and got a couple of prepackaged meals and lemonade for the vodka. It will be nice to not have to eat our own cooking for a change. We made our way back to the boat and relaxed with dinner and cocktails, enjoying a perfect evening on the water.

Day 2- The next day Lauren had her heart set on visiting a town called Siasconset on the other side of the island. The area was settled as a fishing village in the 17th century. The core of one of the older fishing shacks known as “Auld Lang Syne” is believed to date from the 1670s, potentially making it one of the oldest houses on Nantucket. Various other cottages date from the 18th and 19th centuries. Many of the houses were haphazardly expanded, contributing to the unique look of these Nantucket cottages.The bike paths on the island are extensive and nicely paved but it was still 8 miles one way. We headed out and enjoyed the ride for the first few miles. The last couple of miles I wasn’t enjoying it anymore, but we finally made it to town. We found a general store which had ice cream too, so we enjoyed some of cones. We biked around the town a bit and Lauren was aware of a ‘bluff walk’ she wanted to see. Travel + Leisure says this about it: “The ‘Sconset Bluff Walk (also known as the Cliff Walk) is the most scenic path in Nantucket. It goes from the picturesque village of Siasconset—where small fishing cottages covered in roses cluster along the bluff—to Sankaty Head Lighthouse. This public walkway cuts in front of some of the most beautiful properties on the island. To one side, walkers see lavish summer homes, and to the other, the bluff down to the Atlantic Ocean.” We found the beginning and walked it. It very much had breathtaking views. One of the residents left some painted shells on the path with nautical themed jokes. One of my favorites was “How do sailors wash their clothes? They throw it overboard and it’s washed ashore”

We ended up at the lighthouse- It was built in 1850, was automated in 1965, and is still in operation. It is located at the easternmost point of the island. It was one of the first lighthouses in the United States to receive a Fresnel lens. The lens has been called “the invention that saved a million ships.” We explored the grounds and found out this one was moved too due to the deteriorating cliffs. Now we had to bike back. We took a different path back and it was about the same distance. I was feeling pretty beat at this point. We finally made it in to town and back to the boat but not before grabbing some chowder and lobster roll at Sayles Seafood. I also got a pound of Nantucket Bay Scallops to cook later. We also made a quick stop at the grocery store for some supplies to take back with us. Frank was taken to shore and we relaxed the rest of the night.

Day 3- We hung out on the boat in the morning and took Frank to shore a couple of times. By afternoon we were back on shore and back on the bikes. I really didn’t want to ride far today so Lauren found some great spots close to town. We stopped at The Juice Bar Homemade Ice Cream. Lauren sure knows how to pick the spots! After our treat, we walked the cobblestone streets admiring the historical architecture and beautifully kept homes.

We took a short bike ride and ended up at Sandbar at Jetties Beach Bar & Restaurant, which is right on the beach. We had waited for happy hour and was able to get a table in the sand and enjoy the beverages. Later we stopped at Walters Deli for some sandwiches. I was happy we didn’t bike another twenty miles! We loaded the bikes and returned to Klondike. Tomorrow we are going to continue north and head to Fairhaven, Massachusetts…

We departed Cuttyhunk around 9:30am headed for Martha’s Vineyard which is about twenty miles away. The tricky part today is an area called Quicks Hole. By consulting the Eldridge book, we knew when the current would be in our favor. When we got to Quicks Hole we were being pushed almost eleven knots- that’s four knots faster than we normally go! We made our destination of Vineyard Haven is two and a half hours. We were again going to an anchorage as all the marinas past Port Jefferson charge almost three dollars a foot which is too rich for us. As we entered the harbor I called the harbor master on the radio and inquired where I could anchor. He directed me to an area where we could see a few sailboats already anchored. We inched up as close to a small beach as we felt comfortable and dropped the hook. The anchorage was kind of exposed to rolling waves and wakes but it wasn’t too bad. We waited for a while to ensure the anchor was holding then I took Frank to shore for a walk. Once we returned Lauren and I loaded the bikes and went to the town dock and unloaded. We rode along and passed a cemetery which Lauren noticed a headstone that said “Firm but fair.” I looked at the name and it was Mike Wallace. That made me google the tv news anchor and sure enough he was buried here. We continued on to West Chop, which of course has a lighthouse. “The first 25-foot rubblestone lighthouse and dwelling were built on the bluffs of West Chop in 1817. Following constant erosion, the lighthouse was moved back in 1830, and again in 1846.” You’d think they would have learned not to build them so close to the edge! We looped around the awesome bike path and came back to town, then decided to go to Oak Bluffs. Google Maps said it was three miles and there was a brewery there in my future, so I was agreeable. We made it there and saw an old carousel: Flying Horses Carousel- “The Flying Houses Carousel is the nation’s oldest platform carousel. Since 1884, the Flying Horses Carousel has delighted visitors in the town of Oak Bluffs. Constructed by Charles Dare of New York Carousel Manufacturing in 1876, it is one of only two Dare carousels that still exist. Originally operated as an attraction on Coney Island, it was moved to Oak Bluffs in 1884 and includes stationary carved wooden horses with manes and tails of real horse hair and inset glass eyes. Each horse is brightly painted and fixed to the rotating platform by a metal post.” Cool. Now time for the beer. We found the Offshore Ale Co. and sat on their patio and enjoyed a snack and some beer. We kept on truckin’ and found the Gingerbread Cottages also known as the Painted Ladies. From Country Living: “The 318 whimsical Victorian cottages found in Oak Bluffs on Martha’s Vineyard are an exceptionally well-preserved collection of Methodist camp meeting houses. Laced with fanciful gingerbread details in an array of shapes and colors, they also happen to be the most adorable homes we have ever laid eyes on.” They are pretty cool to see and walk around the neighborhoods- they look like doll houses to me. We walked around the main drag and did a little hat shopping and got some ice cream. At this point to was time to head back before it got dark. On the way back we stopped at a seafood market and picked up some clams and chowder and returned to the boat. We left the bikes locked up on shore since we were going to be using them again tomorrow.

Day 2- We had to see Edgartown while we were here so we biked there. It was about a ten mile ride from Vineyard Haven, but we felt up to the task. There were again awesome bike trails to ride on so it was a pleasant ride. We made it to town and walked around a bit then figured we needed some food. We got a couple of pieces of pizza from A Slice of Edgartown. We had picked up some ciders too, so we took our food and drinks and sat on a beach overlooking the water next to the Edgartown Yacht Club. We then were still a bit hungry and noticed a small shop Macphail’s Corner Cafe selling lobster rolls so I got one of those too. After eating we hiked over to another lighthouse: the Edgartown Harbor Light. “It is one of five lighthouses on the island of  Martha’s Vineyard. The first lighthouse, a two-story wooden structure that also served as the keeper’s house, was constructed in 1828. It was demolished, and replaced by the current cast-iron tower, in 1939. Originally located on an artificial island 1/4 miles from shore, the lighthouse is now surrounded by a beach formed, since 1939, by sand accumulating around the stone causeway connecting it to the mainland.” Now it was time to head back to the brewery. We had stopped earlier but they didn’t open until 4pm. It was about that time so we went to Bad Martha Farmers Brewery. We got there around 4:20pm and it was already packed. They sat us at a small table and we ordered two beers. It took over twenty minutes to get them! We were getting ready to leave when the beer showed up. We drank those which they comped and got two more. Now it was time to bike back. Instead of going back the way we came, we followed the beach road all the way up to Oak Bluffs and then back to Vineyard Haven. We probably biked well over twenty miles for sure, but it was a nice day. Our plan for tomorrow is to go to Nantucket- it seems silly not to since we’re here.

We had some good information about this place. Supposedly the anchorage was pretty good and it was a laid back small quaint town. We learned that “Cuttyhunk Island is the outermost of the Elizabeth Islands in Massachusetts. A small outpost for the harvesting of sassafras was occupied for a few weeks in 1602, arguably making it the first English settlement in New England. Cuttyhunk is located between Buzzards Bayto the north and Vineyard Sound to the south. The island has a land area of 580 acres and a population of 52 persons as of the 2000 census. This is a place to do a whole lot of nothing. It has a small beach, a great harbor, good fishing, a few dozen houses, some great ice cream, and some beautiful hiking trails. Cuttyhunk does not have discos, bars, malls, a singles scene, a party life, video games, parking lots, traffic, or much action. What Cuttyhunk does have is a quiet, isolated, beautiful, ocean environment”. It is also a dry island, but we knew that ahead of time and came prepared. The trip was about thirty five miles across Rhode Island Sound and in to Buzzards Bay. We again had to time the current so we left around 8:30am and arrived about 1:30pm. We really needed water so I had called the harbor master and had received permission to come to a dock to fill the tanks, then we were going to a mooring ball. The mooring are $45 per night, but we figured we would get one today, get water and scope out the small anchorage area they have. The harbor is small and moorings take up a lot of the room, leaving room for only about eight good sized boats to anchor. After another chilly ride (it has been in the seventies lately- good for sleeping though) we entered the harbor and I verified about the water. He told me to pull in any open slip and fill up. We did a slow pass and turned around and I chose an empty slip next to a very nice yacht. The wind was blowing pretty good so I didn’t want to go too far down the fairway. I figured the wind was blowing us away from them and I was kind of right. We pulled in next to him and was getting pinned along the pilings, but it wasn’t easy peasy. The captain of the yacht was out and ready to fend off or give a hand if needed, but we got ourselves straightened out and went about filling the water tanks. Once completed we backed out of the slip without much issue (with his assistance-except he tossed our long line in the water which made me yell at Lauren to “get the line up before it gets in the prop!”) and headed to the mooring field. We found an empty ball and got secured. Since we don’t have to wait and make sure the anchor is holding we took Frank to shore pretty quickly so we could walk around and explore. There is a pier with long wood building with small store fronts, each selling clams, lobster, chowder, and various other food items. We walked around and scoped out our options and settled on some chowder and a dozen oysters to start. Yummmmmy. They actually grow their own oysters here in the Cuttyhunk Pond. We walked up the road a bit and then veered off to follow a trail which led past a small schoolhouse which “the single school on the island had one teacher and three students as of August 2009; in June 2019, its final student, eighth grader Gwen Lynch, graduated as the sole member of the class of 2019”.

We continued on up the road and past the end which led to a trail- this led to the highest point on the island, which is Lookout Hill. “Standing at 154 feet above sea level. The Lookout is home to one of the six (one now buried) defensive bunkers built by the United States Coast Guard in 1941 to watch the surrounding ocean for Nazi U-boats. Stripped of their observation equipment and weaponry at the end of World War II, the bunkers are now picnic areas. They offer views of the island and its surrounding waters.“ Indeed the views were amazing. We walked a roundabout way back down to the harbor and returned to the boat. We were hanging loose on the back deck when we noticed the Raw Bar Boat cruising around the mooring field. They have a small boat with some guys that come around and shuck oysters and clams to order. They will also bring you chowder or any items you want from their menu at the pier. We ordered another dozen oysters and some clams- this was my first time having raw clams on the half shell and they were quite delectable. The evening was peaceful and knew we were going to be happy staying here several days.

Days 2: In the morning as we were having our coffee we were watching the anchorage area to see if any of the boats were leaving. One or two did and we talked about moving over there. I was being lazy and ending my coffee when I saw a sailboat come in to the harbor and anchor where someone had just vacated. Uh oh. We’d better get moving or we’ll lose a spot. We fired up the engine, left the mooring and headed to the back of the mooring field. They keep a square area dredged for a ten foot depth, but as soon as you leave that area it starts to get shallow quick. We inched our way back and found a spot that was far enough away yet deep enough. We dropped anchor, made sure it was set and went back to relaxing. This is where the fun started to begin. As the day moved along more and more boats were coming in and either anchoring or taking mooring balls. The small harbor was filling up. We went to shore and had lunch from a stand on the pier, walked around the island a bit and then returned to the boat to get our swim gear. We went and hung out on a beach which we had to ourselves for a while. Frank was enjoying the land time and we had our raft and was alternating from sandy beach to floating in the refreshing water. By the time we returned to Klondike more boats had filled the harbor. I noticed the tide had dropped and we could clearly see the bottom of the pond just behind our stern. Yikes! With the wind direction we were being blown to the edge of the dredged area, but we were still floating so it was all good. The winds were expected to stay a bit steady on the high side but we had pretty good protection in the harbor.

Day 3: We were hanging out on the boat and more and more boats kept showing up. This was our entertainment each day. Lauren and I were amazed at the amount of people coming in. Many of them were coming to the anchorage either before or after searching for an available mooring ball. There are some private balls, so you have to ‘find’ an empty city ball if there is one available. By the end of the day the harbor master was telling people to take any open ball. The harbor master comes around each night to collect payments and he keeps track of every mooring ball. It was early afternoon and we watched a smallish boat come and drop anchor in between us and a sailboat (who we had met the owners of on the beach yesterday as they brought their dogs to the beach and Frank was in heaven). I had stopped paying attention to them when Lauren said “are they dragging?” I looked over and it sure looked like they were moving.. “Is anyone on the boat?” Lauren asked me. I had seen them anchor then hop in their kayak and paddle off. “I’m not sure” I said, as I was now watching the boat clearly drag in what seemed like slow motion toward our neighbors. “I don’t think so” I was saying as I was getting up and quickly heading to our dinghy-it clicked in my head I had watched them leave. Lauren started calling to our neighbors trying to get their attention as I was pulling away in the dinghy. As I was heading to the boat I saw a small sailing skiff pull up and a guy hopped off and on to the boat. I pulled up and he asked if this was my boat? I said “nope, but it’s sure dragging quick!” He and I had a quick discussion and made a quick plan. We tied my dinghy to the side so I could maneuver us both, then he ducked inside. He came back out and said he was able to start the engine. At this point I was trying to drive us forward and stop the boat from hitting anyone. We had a quick conversation about what to do now and obviously we needed to get the anchor up. I then jumped on to the boat and took over the throttle while he went to the bow and pulled up the anchor. We then motored over to an empty mooring ball and we secured the line. Whew! That was close. Been there done that, so I know how it could happen. Just as we were departing the owners of the boat paddled up and thanked us profusely. All is well that ends well. I returned to the boat and promptly went back to kicking back, still getting entertained by the boats showing up. The anchorage that is good for maybe eight boats now had a dozen or more, all crowding around each other.
We had plans for later to meet our other neighbors who had anchored next to us on the other side for cocktails on their boat. We had chatted with Ron and Marcy and they were interested in our trip. They were an awesome couple who we truly enjoyed hanging out and chatting with. Just before we were to head over to their boat I noticed a guy rowing towards us. He pulled up and gave me a bottle of wine as a thank you for saving his boat from hitting anyone! That was unexpected and awesome. We went and had the cocktails with our neighbors and enjoyed the evening with a sunset view back up at Lookout Hill. With the lack of restaurants on the island, people have gotten creative. We ordered a pizza to take up to the lookout from a “restaurant “ which was basically tables set up in a driveway of someone’s house. I believe they made the food in the basement or maybe the garage and it was delicious.

Day 4: We had to have lobster. We had been scoping out the pier options and finally decided to pull the trigger. We had to pre order them and pick them up at 6pm. Lauren should know be than to send me in, but I was sent in to order. I ordered three large lobsters for us. I kind of got shocked by the price as I had misread the price, but it was worth it. We chilled during the day and visited yet another beautiful beach on the island. On the way back we noticed a looper flag on a newly arrived boat. This was unusual seeing as how we were off the loop route and hadn’t seen anyone in a while. It was nice to chat with them for a bit and Frank was very interested in their cat who had come out to say hello. We picked up our lobsters and returned to the boat to enjoy them. Today being the Fourth of July, fireworks were started at dusk. They kept going and it was a pretty good show, then the fog start to roll in and it was thick. The fog put an end to the fireworks as you could no longer see them it was that thick. Frank was not disappointed in this. We retired for the evening and had our plan for our next destination: Martha’s Vineyard.

The weather looked good with light winds which was great because we are crossing the open Atlantic Ocean. Our destination: “New Shoreham, RI, is the smallest town in the smallest state in the U.S. It was incorporated in 1672 and only encompasses Block Island, although people rarely say they are going to (or are from) New Shoreham; they say they are going to Block Island. The Island has approximately 1,000 year-round residents and 15,000 to 20,000 seasonal visitors at a time. On Block Island, there are some 400 miles of stonewalls and 32 miles of trails, and 43 percent of the Island is preserved open space.” It was only about twenty four miles away, but we still are a little intimidated when we talk about ocean cruising. We left around 8am and the trip took about three and a half hours and was somewhat bumpy. It was a nice day for a boat ride, even if it was a little chilly. The island has two areas to anchor and we chose to go to Old Harbor; the other option is Great Salt Pond. The difference between them is location and size- by choosing Old Harbor we came around the island from the south. As we entered the harbor we could see it was packed. The ferries run from here and they have a huge dock, there was a small marina which was packed and every inch of space in the anchorage was filled with boats, most rafting two to six across and they all were backed up to the break wall with their anchor our and stern lines run to the wall. Hmmm. This isn’t a great situation. In order for us to get to the other anchorage of Salt Pond we would have to circle the island which would take about an hour and half to two hours. With the waves we had just left we weren’t too keen on this idea. We floated around looking and discussing what we should do. We noticed there was enough room at the very end of the wall, close to the entrance where the traffic comes and goes. Fu$k it- were going to give this a try. I’m sure everyone was watching and wondering what we were going to do as there wasn’t much room at all. I maneuvered us around and came to where we were attempting to anchor and positioned us as best I could. The anchor was dropped and I backed up as best I could. Our boat does not back up in a straight line, so there was that. Once I felt the anchor had caught, I turned the helm over to Lauren and went to the bow and let out a little more anchor rode, then jumped in the dinghy and ran a small anchor on a long line back to the break wall and wedged it in the rocks. It definitely wasn’t going to get pulled out. I adjusted the lines some more and we seemed to be good, but I wasn’t one hundred percent confident we wouldn’t drift a little so I put out some bumpers just to be safe. Whew! That was challenging. Now we were anchored and could relax a bit. The ferries were passing us by about fifty feet, but they were going slow in the harbor so we weren’t waked too bad. The amazing thing to watch was the amount of people zipping around in their dinghies. At any given time there were at least a half dozen or more and they weren’t just going to shore- they would go out to the ocean, to shore, or just cruising about in the harbor. It was interesting to watch and guess what they were doing. After an hour or so I took Frank to shore and was walking around when I stopped and asked some people partying on the sand if the dinghies were good to be left here. They said yes, but watch the tide as it is almost eight feet difference. One guy must have noticed my World Series hat and asked if I was from Cleveland? I said yes and explained our trip. He said he used to play for the Cleveland Browns! I met Raymond “Bubba” Ventrone who was having a good time with family and friends. I excused myself and brought Frank back to the boat and told Lauren my scouting report and my chat with “Bubba”. We felt secure enough about our position of Klondike so we loaded the bikes on the dinghy and headed to shore. We beached the dinghy and I tied the line around some rocks as best I could to keep it secure. We rode through town and a few miles up to see the Block Island East lighthouse. This light was built in 1874, with the lamp first lit on February 1, 1875. It is a sophisticated expression of the Gothic Revival executed in brick, and was a marked contrast to earlier lighthouses, which were generally more functional in appearance. the lighthouse has a 52-foot brick and granite tower, and has been named a National Historic Landmark. A big boulder close to the Mohegan Bluffs marks its original location; it was moved 300 feet inland in 1993 due to the erosion of its original perch.
The ride was cool as we got to see the countryside and the views were incredible. The ride down was again a bit vexing and Lauren is running out of rubber on her shoes, but we made it. We rode around town some more and there were a couple of places Lauren had wanted to try but they were all closed today, so I talked her into stopping at Poor Peoples Pub for a drink and appetizer. We had had enough biking at this point so we headed back to the boat. I went to get the dinghy and noticed it wasn’t anywhere near where I had left it, but it was there. Huh. The tide had come in and the beach was all but gone. I retrieved the dinghy and pulled up to the dock, we loaded everything and went back to relax a bit and get Frank. After some time we all went back to shore for an evening walk and to pick up a pizza from Aldos Restaurant. We walked around first and I picked up some fudge from Chapel Sweets and had a fun conversation with the owner about how his wife and sister make the different items and his wife ‘invented’ their signature Sandy Feet Turtles as a final project in her baking class years ago. We had to sample those as well and they definitely deserved an A. . We picked up the pizza and returned back to the boat to eat. When we got o the dock we could see Klondike was now being pulled by the falling tide toward the channel/ harbor entrance. Shit. We were still technically out of the channel, but it was close. And the ferries were still coming and going right past us. As we were pulling up to the boat a guy in a dinghy came by and said “did you find your dinghy in a different spot? It was drifting away and I brought it back and tied it up” and away he took off. I had responded with a yes and was thanking him as he zipped away. Once onboard I attended to the lines but there wasn’t much I could do, especially because of the tide heights. The lines were taut and they were holding. We ate the pizza and decided where to head to tomorrow. It looks like we’re going to continue up to Cuttyhunk, Massachusetts and stay there for a few days as it is getting close to the Fourth of July and we want to get a good anchorage and wait out the partying crowds…

From Shelter Island to Montauk was about twenty two miles. We left our anchorage by 8:15am and arrived around 11:45am. Plenty of time to find our anchorage, make sure we’re secure and still explore with the bikes. We entered Montauk Harbor and followed the channel markers. I was alerted on the charts to make sure to follow them as there is a giant shoal/sandbar that extends out in the lake. I almost missed it as it is a sharp turn to starboard to follow the markers and the lake is straight ahead, but I spotted it and we followed them past the low spots. Once in to Lake Montauk it is deep enough to go back as close to shore as possible. There were a few boats on mooring and a couple boats anchored so we found a spot far enough away from everyone to be comfortable and dropped the anchor. Again we sat and waited about an hour or more before heading to shore- I like to make very sure we are not dragging the anchor. First I took Frank for a walk and explored the dinghy landing which was on the beach. There were a few people around and I inquired if we were cool to land the dinghy here and all said yes. I noticed a group of people setting up some stuff on the beach and was curious to what they were doing but I didn’t ask. I did chat with a guy who told me he would be there all day and would keep an eye on the dinghy for us too. Nice. I went back and dropped off the dog and picked up Lauren and the bikes and we returned to the beach. The guy I had spoken to earlier told us how to get to town. He said we could dinghy closer back on the other side of the lake, but since we already had brought the bikes and unloaded them we decided we would just ride there. It was about a three mile ride along a highway, but there was a wide enough berm/bike lane it wasn’t too scary- except for the hills- still with no brakes. We found our way in to town and passed Memory Motel (made famous by The Rolling Stones song) as well as all of the shops and markets in the area. We eventually found ourselves at Montauk Brewing Co. which was nice because we were thirsty after the long bike ride in the sun. Unfortunately they weren’t allowing people to sit, but they were selling take out. We looked around and could see groups of people hanging out in a park across the parking lot all drinking beer They all were looking enviously at the forbidden brewery patio. . We ordered some to-go brews and headed off to find the beach. We relaxed at the beach enjoying the refreshments, then decided to stop in the grocery store we had passed on the way in. We picked up a couple of items and headed back to the boat. Now we could see what they were setting up when we left- they had electric surfboards! There was an instructor and a group of people taking turns ‘surfing’ on the somewhat flat lake. Cool! We settled in for the rest of the evening except to take Frank to shore again. We looked at our next stop and discussed going even further than we had originally thought as we still have a lot of time waiting for the darn Erie Canal to open. Tomorrow we will head to Block Island, Rhode Island. Wow! Hard to believe we are leaving New York and heading to Rhode Island!

Shelter Island is only going to be a five mile trip so again no need to hurry or go fast. I took Frank to shore in the morning and had to stop back to Grindstone. It was quite busy and the line was out the door due to spacing requirements, but Frank was fine with it. When it was finally my turn to go in I tied him up to a tree outside the door. He was cool and patient but gave me a funny look when I was coming out and another guest was entering with his dog. I guess dogs are allowed- good to know. We took the donuts back and had some with coffee before pulling anchor. The trip only took us less than an hour. We had read about the anchorage and it was clear you must stay within the marked area or the local harbormaster will come yell at you and tell you to move. The anchorage was clearly marked and there were several boats already there but there was plenty of room. We anchored as close to a small island of sorts- at low tide it has a piece of land that connects to the mainland, but at high tide it is an island- this is called a tombolo. and is named Taylor’s Island. It is named after S. Gregory Taylor, a successful hotel owner who donated the land and cabin to the town of Shelter Island.. This little tombolo turned out to be a great little retreat for Frank as we were docked near a nature preserve that did not allow dogs. The wind was picking up and rain was expected. We battened down the hatches and waited for the storm to pass. Eventually it let up enough to take Frank to the island and we explored the house and grounds. More research was done about the town and tombolo as we settled in for the evening feeling secure.

Day 2- “Shelter Island was purchased by Nathaniel Sylvester in 1652. He built a house for his 17-year-old bride, Grissel Brinley of London, and they became the first European settlers. The native Manhanssets, long-time residents when the Europeans arrived, called the Island Manhansack-aha-quash-awamock, meaning “island sheltered by islands.” After breakfast and coffee we took the dinghy and bikes about a mile and half to the town dinghy dock. We unloaded and set off to explore. We found a brewery that was open: Shelter Island Craft Brewery. The ride there was interesting, especially with no brakes on the bikes. We are now into an area with lots of hills so it’s sometimes a gamble on the downhill portion. Lauren has gotten pretty good at using her feet to slow her down, where I just go full on forward as a scout and hope for the best. We also passed a house that was selling oysters out of their garage but we weren’t brave enough to stop for those. We discussed it after some beers, but keeping them cold for our ride back probably wasn’t going to work out so well and we weren’t in the mood for a game of intestinal roulette. We were hungry though so we found a pizza joint: Shelter Island Slice where we shared a few slices of pizza pie. Bellies full and feeling good we made our somewhat harrowing ride down the hills back to the dock and loaded up the bikes to retreat back to Klondike. We looked at our options and decided Montauk will be our next stop in this area, but looking forward we are now discussing Rhode Island and maybe Massachusetts as we still have plenty of time before we have to start heading back to New York…

Sag Harbor is only twelve miles away but we have to go around Shelter a Island which is in the middle of Gardiners Bay. Since we weren’t going far we had a leisurely morning and enjoyed our coffee before heading out. Once the anchor was pulled and we were leaving I could hear the Coast Guard calling out a Pan Pan ( PAN–PAN is the international standard urgency signal that someone aboard a boat, ship, aircraft, or other vehicle uses to declare that they have a situation that is urgent, but for the time being, does not pose an immediate danger to anyone’s life or to the vessel itself- one step below a ‘Mayday’) about a call they had received earlier, but couldn’t locate said vessel. The area isn’t that big so maybe someone called it as a sick joke, but they have to respond accordingly and not stop until it is resolved. Since we were traversing the area I kept a sharp lookout for anything unusual but nothing was out of the ordinary. Because we were taking our time the trip took about two hours. No sense burning through fuel when we don’t have far to go. We found the Sag Harbor harbor entrance and the anchorage that was listed. The anchorage was outside the harbor break wall but there are a ton of moorings there so it was a bit difficult to find a spot. We circled around and finally came back to close to the entrance of the harbor. There were a couple of sailboats anchored there already so we squeezed in between them and the shallow area near the wall. Again we were fairly exposed to wakes and wind, but the wind was forecast to be light and variable. We sat and waited making sure the anchor was securely set before heading to shore. “Much of Sag Harbor is a National Historic Site. Its history centers heavily on its days as a whaling port, although it was inhabited well before Europeans settled here. In the mid-1800s, almost half the total population of Sag Harbor served on whaling ships.” We landed the dinghy and walked around the town. One of our first stops was Grindstone Coffee & Dounts which apparently has a Cleveland connection through Michael Symon. The donuts were amazing. We visited the Whaling Museum but it was still closed due to COVID. We saw the oldest Custom House and old houses and churches in the neighborhoods. We worked our way back to town and stopped in a specialty shop Schiavoni’s Market for some more dinner treats and also got Frank a new collar at a shop next door. Finally we made our way back to the boat and picked up Frank for a walk. We took him to shore and we walked a couple of miles to find a beach, it when we found it it was only open to local residents. Damn. That was a long walk for nothing but at least Frank got to stretch his legs and enjoy time on firm land. Dinner was made and we decided we will go to Shelter Island tomorrow since we are here…

Another thirty mile day was ahead of us, but this time we had to leave super early to catch the favorable current. The currents at Plum Gut can reach the four to five knot speed and we don’t want to try to fight that. We departed Mattituck around first light or 5:45am. The wind was calm and we wound our way back out to Long Island Sound and turned northeast. We timed it perfectly again and had no issues going through the cut between the north end of Long Island and Plum Island. Plum Island is government property and closed to the public, but the small gap between the two is what is called Plum Gut. Even the charts say “tides rip”! We are now in Gardiners Bay and winding up to Greenport. We found the area listed as an anchorage and it was pretty exposed to boat wakes and wind from the south/southwest, but this was the only option we could see and Lauren really wanted to visit the town. “Greenport, settled in 1682, remains encircled by bucolic landscapes and is a low-key and peaceful seaside village. Because of its deep and protected harbor, Greenport became a major whaling port between 1795 and 1859. The town was also a very busy shipbuilding center. By the mid-1800s, the menhaden fishing industry employed thousands of people. The Long Island Railroad arrived in 1844 and became the driving force in development for Greenport and the North Fork of Long Island. During the first half of the 20th century, Greenport became a huge oystering center. When the oyster industry began to shrink, Greenport turned to tourism and became a destination for global visitors.” Once we had anchored and made sure all was set well, we loaded the bikes on the dinghy and set off to shore. It was a bit long of a ride but we made it there with no issues and unloaded. We biked around the town and explored quite a bit. We found a brewery that was closed, so that was disappointing, but we found a great lunch spot at Lucharitos where we enjoyed some margaritas, tacos and burrito. We biked around some more and came back to get some ice cream at Greenport Creamery. Before heading back we stopped at a grocery store for some more supplies. Now we were loaded up and headed back to the boat for the evening. There was a beach close to where we anchored that I was able to take Frank to for his shore excursions. We determined our next stop will be around the corner to Sag Harbor.

Again we were going about thirty miles. That seems to be a nice distance as we can cover that in about four to five hours. We departed Port Jefferson around 9:15am after our morning coffee. We were making way and getting close when I noticed a boat on AIS moving in the same direction but a bit closer to land. I noticed the name and mentioned it to Lauren. She reminded me it was the same boat moored next to us in Port Washington and we had seen them in Oyster Bay. I called them on the VHF and inquired about their destination and explained we had seen them in the last few ports. They told me they were even in Port Jefferson with us, but on the other side of the bay, and they were heading to Mattituck as well. I inquired if they were familiar with the anchorage/area and they said yes. They travel through here almost every summer and said it was a good choice to stop. We concluded our chat and they took the lead as they travel a bit faster than us. We were soon turning into the inlet and wound our way back Mattituck Creek. There are several marinas through here so we had to go slow. Once we got to the end we saw the marked anchorage and several boats already there. A couple of them looked like permanent boats and there were a couple of other cruising boats including our friends I spoke to on the radio. We circled around and found a spot along the edge of the anchorage and dropped anchor. We went through our anchor routine and we sat for a while making sure all was good. It was a well protected small area with a city dinghy dock at the end of the harbor. By around 2pm we decided all was good and we departed on the dinghy with Frank to explore the town which was close by. We walked up the quaint main strip of Love Lane and looked at all of the shops and restaurants lining the street. Lauren had found a place she wanted to go to but they were closed today. That sucks. We saw a place called The Village Cheese Shop and Lauren sent me in. She should know better than to let me loose in a cheese shop. I came out with a bag of cheese which just had her shaking her head. I didn’t really get that much, but I did walk out with at least four different types. We then settled on lunch at Ammirati’s of Love Lane where we both got some delicious sandwiches which we enjoyed on a close by patio of a closed restaurant. After lunch we walked up and around to Main Street and found a donut shop: North Fork Doughnut Co. which we had to stop in as they had the walk up window still open. Unfortunately they were sold out of most everything but the couple we did get were awesome. There just happened to be a liquor store next door too so I stopped in to replenish our rum rations. After a little more walking we headed back to the boat for the night. After dinner we planned our next stop at Greenport, New York.

We weren’t in a hurry to leave so we didn’t depart until about 9am. We were going about thirty miles to our next port. “Port Jefferson, known less formally as “Port Jeff,” is the last major harbor on the north shore of Long Island when eastbound from New York City. Known to Connecticut and New York cruisers as “PJ,” it is a beautiful village located right on the harbor.” We had seen an anchorage and planned on dropping the hook at one of the few in the area. Upon approach we could see massive sand dunes and was able to get fairly close to shore around the dunes. We dropped anchor and waited a while before heading to shore. Once we got to shore there was nothing around except a large stretch of dunes and beach, so we explored that for the afternoon with Frank. We came back to the boat and hung out and hung on due to the wind and wakes from other boats. Eventually it calmed down a bit once the pleasure boats stopped coming and going. Our next stop as we continue northeast and up the Long Island Sound is Mattituck. We have good information on an anchorage there so it should be a good stop.