If you are sailing in the Long Island Sound, these three islands are a MUST SEE: Cuttyhunk, Thimble Islands, and Block Island. In this episode, we review each of the islands based on 1) Cruiser Friendliness, 2) Things to Do, 3) Hang Time, and Overall Rating. This is strictly our opinion based on our experience.
After Port Jefferson, we motored over to the Thimble Islands as the seas were flat and the winds nonexistent. We only had one night to spend in the Thimbles so we dropped anchor and jumped in the dinghy, determined to see as much of it as possible. While we didn’t have time to go ashore, we did get around to see the nearby islands and their summer homes. We dreamed of a bit more time to take it all in, but our time was stay was limited. We had places to go and people to see.
The next morning, we took off to Sag Harbor and the South Fork. From Sag, we ventured to Montauk and then from Montauk, we headed out to Block Island. It was the perfect stopover before Newport. Block Island is sailor’s dream location. The harbor has great protection, a strong cruising community, and ample marine services. The island offers amazing hiking, biking, and endless enjoyment, as well as fantastic restaurants. We would have loved to stay longer than two nights, but we were on a schedule. We loved biking the island, hitting all the major highlights in the bike tour. Our favorites were the Animal Farm and the two lighthouses.
Sadly, we took off Block Island long before we desired and headed for Newport, a new destination for us. From friends in Newport, we learned of the island called Cuttyhunk, the only non-private island in the Elizabeth Islands. It’s a tiny island with few cruiser services, however they do have a marina. The island has about 5 miles of roads, most are dirt and the most interesting place to visit is Lookout Hill, the hill where the military built a bunker during WWII, to stand lookout for German submarines. It was a great couple of days at Cuttyhunk, but it was time to no longer delay our trip to Martha’s Vineyard, one of our holy grails and summer destinations.
We have reviewed and rated three amazing islands in the Long Island Sound and you don't want to miss it: Cuttyhunk, Thimble Islands, Block Island. The amazing thing about these three islands is that they are located in three different states and have very distinct cultures. But, the one thing they do share is their incredible beauty and remoteness.
#sailing #sailboat #sailingprojects #CUTTYHUNK #THIMBLEISLANDS #BLOCKISLAND #NEWPORT #RHODEISLAND #MASSACHUSETTS #LOOKOUTHILL #MONTAUK
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Hey guys! Hey there! Welcome to Warderick Wells and the Exumas and this big blow that we're having.
Boy, we're gonna be here for what, four or five days? Yeah, at least. We need to sit it out until
the gusts of 30 to 35 start to slow down a little bit. Tonight's gonna be the worst of it and then
tomorrow it should start to dissipate. It's okay, we're in a very protected cove and that's the
best part about it and it is absolutely stunning. And you know what the other good part about it is?
We've got time to work on videos. Yes, we do and even though we're down to one laptop,
first world problems, we're going to see if we can get through this. This video that we're
going to talk about today is going to be really unique. It's our continued journey through the
Long Island Sound but we're going to focus on three unique islands in three different states
and two of these islands we had never heard of before we started cruising. Yeah and just for
disclosure's sake, we blew through some of these places because we wanted to allow enough time
to see people that we had already pre-scheduled. We wanted to make sure that we saved plenty of
time for the crowning jewels which we'll talk about in the next video and we also had to get
all the way back down to Deltaville to haul out and get some work done so we could come back down
to the Bahamas which is where we're at right now. So we didn't give some of these places
a great chance. We're going to admit that but we did some research to fill in with the details
that we found out from actually being there. So we're going to use our rating system that we
started in our last video for this video. Our scorecard. Our report card. Our report card. We
approve the teaching profession. I mean it's just natural right? We're going to look at Thimble
Islands in Connecticut, Block Island which is Rhode Island, and then Cuttyhunk which is
Massachusetts. So we're going to look at those three and we're going to rate them according to
cruiser friendliness, things to do, hang time, and then an overall rating for you. And ask yourself
right now have you heard of these three islands? I had heard of Block Island but never the Thimble
Islands and Cuttyhunk because they're super small. Block's pretty small but its proximity
to a bunch of different places makes it probably more popular. Had you ever even heard of Thimble
or Cuttyhunk? I had not heard of Thimble Islands and I had not heard of the Elizabeth Islands
which is where Cuttyhunk is but I had been to Block Island before when I lived in New York.
And here's the good thing. You're going to learn about these places. They're definitely worth going
to for different leaps of time and we will reveal that. But this is all about going new places and
learning new things. And we're so thankful as always for our subscribers and our patrons. First
of all a huge thank you to our patrons for your generosity and your encouragement. But also thank
you to our subscribers and viewers for watching our channel. We really appreciate it and we continue
to ask you to like our videos, share them, and subscribe if you're not a subscriber. It really
helps us out. So let's get this one going. That's right. Let's do it. We're going to start with the
Thimble Islands in Connecticut and a bunch of people told us about the Thimbles. They said
these are islands not to be missed. You need to go for a day or two to see them. So we did make
a point to get over there. We went over from Port Jefferson. Some people said they reminded them of
Sweden and some of the islands in Sweden. Yeah that's right. I mean that appealed to me so we
took the chance and we're glad we did. We only spent one night there. We came over and we spent
the afternoon just cruising around on our dinghy checking it out. But if we had to do it over again
and had a little bit more time we would have spent two nights there. Okay you've seen the movie
American Vacation with Chevy Chase and he takes the whole family out to the Grand Canyon.
Puts his arm around his wife and goes oh okay and they hop back in the car. Well this wasn't that
short but it was close and I think that it deserved more and we'll talk about that later.
Sure. For cruiser friendliness we rated this a 6 out of 10 and a lot of that is just based on
research. We actually didn't go to the town dock which has a four hour maximum.
We didn't see the yacht club. We didn't take advantage of any marine services. We didn't need
to provision which in this case is a cab ride away from the dinghy dock so it's not in walking
distance. What we did experience though was a little bit of trepidation coming into Granite
Islands and the continual warning that if you do not carefully plot your course and watch
where you're going you're going to destroy your keel because keels don't do well. Yeah this is
like cruising up in Maine. It was the first time that we had come to a place where there wasn't
mainly sand where we could run aground if we if we had to and there were no consequences. So
the other the other hazard that we had to really be careful about which we were warned was
underwater cables and seabed pipelines which they make it very clear if you drop anchor on one and
damage it it is your financial responsibility. Man and that's not going to be a small bill either.
No. So we anchored in the exact same spot that our friends on NVS thank you Stefan and Dorothy for
those coordinates where they anchored and then we just hoped for the best and it was okay. We had
good holding and we didn't tear up a cable. They're called the thimble islands because many years ago
the islands were completely covered with thimble berries and thimble berries resemble blackberries
or red I think they're called red blackberries red raspberries black red they're called black
black raspberries. Hey no matter what they're called I'm gonna eat them because I like those
Well the thimble berries apparently are a little bit more sour and bigger but they are no longer
found on the islands but that's why they're called the thimble berry islands. In terms of things to
do we rated it a five out of ten and the reason is it's really fascinating to take your dinghy
around all of the rock islands. We really enjoyed that. There is an outer island that has a wildlife
refuge on it. There are some restaurants though some of them are not close but other than that
it's really just a place to relax. Yeah and truthfully we didn't want to find anything that
would keep us there for another night because we didn't have another night. So our overall rating
was a six out of ten. We highly recommend that you put this on your list if you're in the Long
Island Sound because we just think it's super unique and cute and worth a visit. Glass this is
beautiful. Very dewy. You can see the boat is completely covered in dew.
Birds everywhere. So peaceful. We're gonna try and take off. It's about 6 30.
Exciting times. Caught a fish already. I think it's gonna be a throwback
because it looks a little bit small but who knows. Oh pretty.
What is it? No way. Another fish coming in. So we caught a mackerel a little while ago and now
we have caught a another mackerel but he's a tiny one so we're gonna throw him back.
Captain Brown with fish number three of the day. Let's go ahead and move on to Block Island. It was
perfect stopping point between Montauk and Newport because it's about halfway. It's in the middle of
going everywhere. Well it's like a hub really and if you can tuck in there it's great protection and
if you can find a place to anchor. Man it's popular. It's a big anchorage but I'm telling
you it's packed with boats, charter boats, local boats. They've got moorings and marinas and
everything but we managed to carve out a little real estate. We did. We did and I think the key is
is getting there during the week. You wait until the weekends and forget about it. This place is
gonna be all carved up and full. The place where everyone anchors or grabs mooring ball is called
the Great Salt Pond and there really isn't a lot of space for anchoring. There's anchoring on the
outside of the salt pond but then you deal with some sand but the conditions may not be great
holding. There's an area that has rock bottom which obviously has terrible holding. So trying
to find a place to drop anchor is a bit of a challenge but Block Island has a great really
strong cruiser community. It has incredible facilities, a dinghy dock, a grocery store.
It has a marina and all of the facilities that you really need as a cruiser. And one thing it has too
it has protection and it has protection in an area out in the middle of the sound closer to the
Atlantic open ocean where things can get a little dicey. So that's another reason to go there. I
think it was pretty blustery kind of like it is here today. Yeah so because of all those things
they offer to cruisers we gave this a 9 out of 10. For things to do in Block Island we also rated
it a 9 out of 10. There is so much to do there. Well we biked. These things were indispensable
for exploring the island. We went on back dirt roads. We went to beaches. We went to lighthouses.
We did a circle around the entire island. There's actually a published map that gives you stopping
points. It was fantastic and easily done in a day. We stopped at the animal farm where they have
unbelievable exotic animals from llamas to kangaroos. There were just really interesting
animals at the animal farm. We loved it. And just a lot of historic buildings. The inn is one of the
historic hotels on the island with a beautiful view over the sound. And that has wonderful
flower gardens as well. We were able to see those. What I loved about it is once you get away from
the main town it gets very rural. And it kind of reminds me of what we're going to experience in
Nantucket and Martha's Vineyard. Especially Nantucket being a one city town. It did not
disappoint. You can just get out there and explore. There aren't a lot of cars. The roads are really
good. They're great hills so you get a lot of exercise. They're used to having bikes on the
island so the drivers were really slow and very careful which was great. Yeah it has a good bike
culture. I think one of our favorite two of our favorite sites were the lighthouses. We went to
the southeast lighthouse and then the north lighthouse. And they're just beautiful historic
buildings. And the southeast lighthouse actually was going to fall off the Mohegan Cliffs into
the sea at one point and they ended up moving it back in the 90s. They raised enough money
to pick up that lighthouse. That lighthouse is a big lighthouse. It's not just the lighthouse
it's the building as well. They actually picked it up and moved it back off the bluffs a couple
hundred feet I think. And so that lighthouse was preserved. Just think how important those
lighthouses were back before radar. You definitely don't want to run into Block Island. So we did not
get to stay very long in Block Island which again we were on a schedule. I think we were there two
nights. We could have stayed probably four or five. Yeah Block Island's a place that's got some hang
time and you can definitely stay there for quite a while. We didn't because we're in a hurry but we
should have. But we couldn't. So there you go. So we still rated hang time as a nine out of ten and we suggest
building in four or five days to be able to stay there. Absolutely. Let's move on now to our three
island three state review. Our report card. Obscure islands. Yeah very obscure other than Block. Which
makes it so interesting. My gosh this is just yeah. We learned a lot. We did. So we're moving to the Elizabeth
Islands which I'd never heard of off the coast of Massachusetts and the island of Cuddehunk. Yeah.
Well we thought we'd be out of here a little bit earlier but the raw water that's coming into the
engine is coming in a little bit more slowly than normal so we wanted to give that a good check. The
telltales look good and so now we're going to try and pick up the anchor. There is a twist in the
anchor chain because we did a couple 360s so we're not sure how that's going to work. The bridle
came off on its own which is really good. Means the chain must have sorted itself out last night.
We're good to go. Beautiful day. Can't complain can you? No. We were recommended to go to Cuddehunk
by Brown's friend Jim who lives in Newport. Recommended that we stop there on our way to
Martha's Vineyard and it really was the perfect place to stop similar to coming from Montauk
to Newport. And I mean it's in the neighborhood right? I think the Elizabethan Islands a lot of
them are owned by the Forbes family. It's privately owned under a trust. Cuddehunk has this private
aura about it but it's open to the public. In terms of cruiser friendliness it doesn't have
a lot to offer. It's a really small island and I think it only has 10 year-round residents on
the island. I think maybe 25 houses. Yeah. It's a small quantity. In terms of cruiser friendliness it
didn't offer a lot but one thing it did offer was great holding outside in the harbor. The bottom
was great and so we were able to stay there in a protected area. They do have a marina. They do have
moorings. They don't offer marine facilities really. There's a self-serve pump out which is good.
Fuel is iffy. You need to call ahead if you want diesel or gasoline. But the harbor master could
not have been a nicer person and we enjoyed interacting with the cruisers. You know one
thing they have that's really unique is the nudist beach. Remember that? A nudist beach that doesn't
have a beach on a pond. And I think they have like one restaurant. It's a pizza place. Yeah Sopranos
Pizza. Remember how the Sopranos sitting out the figurines sitting outside? It's just really cute
and maybe we could have stayed there an extra night. The weather was kind of rough and stuff
but we had places to go and people to see so we had to leave after one night. So for cruiser
friendliness we gave it a 6 out of 10. For things to do we gave it a 4 out of 10. We did cycle the
island. It was about 5 miles of roads. Very little acreage and roads to ride on. I think one of the
most unique places was lookout hill which housed the bunker that the soldiers used back in world
war ii to spot submarines coming in through the waterway. It's a 360 degree view at the top of
the mountain. So now it has incredible views. It has a viewing platform for anyone to go up and
visit. That was really unique. And maybe I'm being a little judgmental but I'm saying you kind of have
to be an introvert to live there and have a lot of books to read because yeah there's not a lot to
do but if you're into reading books and leading a chill lifestyle Cuttyhunk's the place for you
wouldn't you say? Absolutely. For things to do we rated it a 4 out of 10. For hang time we suggest
one night there. 3 out of 10 for hang time reading and you can move on and overall a 4 out of 10.
Yeah this is one place we spent one night there and we're glad it was only one night so we moved
on. We hope that you enjoyed this review of these three islands and thank you so much if you've
gotten this far you are a true star and we want to say thank you to you. Thanks so much for watching.
We love you guys and we'll see you next week.