Thimble Islands Cruise

Just a Thimbleful
Thimble Islands Cruise, Branford
October 2025

I must apologize up front.

My wife Hoang and I took the Sea Mist Thimble Islands cruise in the middle of my self-imposed (and much enjoyed) hiatus from CTMQ. As such, I didn’t approach this excursion as an “assignment” for this website but instead just sat back and enjoyed myself.

I didn’t take notes.

I didn’t listen to the guide as intently as I might otherwise have.

And I took no care to even try to take decent pictures.

You can therefore correctly assume I had a wonderful time. For the affordable price and the ease, I highly recommend doing a Thimble Island Cruise at some point. We happened to ride The Sea Mist from Thimble Island Cruises, but there are a few different options and I imagine they’re all pretty similar.

A coworker of mine, who lives in Virginia, appeared on my screen for a meeting one day wearing a Connecticut sweatshirt. I asked her about that and she relayed that she had just visited the state for a girlfriend’s wedding and absolutely loved it. I asked what she did here and one of the things the bridal party did was a Thimble Island Cruise.

Huh. I’d never done that. Neither had Hoang. So we did it.

The Thimbles are officially an archipelago of 100 to 365 small islands off the coast of Branford. To get the larger number, you must count every rock that peeks an inch above low tide. In reality, there are a couple dozen actual islands here. Several of them are large enough for homes – and several more are not, yet still have them. Which, in the end, is a large part of the Thimbles’ charm.

Another part of their charm is their simplistic names. Pot, Money, Horse, Bear, Pig, Hen, Cut In Two, Mother In Law, etc. Islands.

The first building went up in the mid-1800’s when some guy built a hotel on Pot Island and tourism in the area saw a boost when the proprietor began the “Captain Kidd buried treasure here” rumors. A highlight of the cruise was passing High Island and learning that all the houses are painted black and fly Jolly Rogers per tradition.

Our guide, Mike, is a lifelong local who actually owns a house on Governor’s Island. I’m not sure if they still do, but Gary Trudeau and Jane Pauley owned a house on Governor’s for quite a while. But almost no one lives on any of these islands year-round. They are generally a quiet summer community and supposedly 23 of the islands are inhabited, but that’s a stretch. Only six islands get electrical power through underwater cables from the shore; the rest use some combination of generator, solar power, batteries or kerosene and propane. About half the islands get fresh water through underwater pipes from shore; the rest use wells or rainwater, or have containers of water delivered. No sewers serve the islands, requiring the use of septic tanks for all sewage treatment.

There are a total of 81 houses on the inhabited islands and they range from small summer cottages that run on generators to huge mansions complete with caretaker’s quarters and basketball courts. Then there are the ridiculous Thimbles like Grey Rock and Belden, each with a single century-old house. Another island, Cedar Rock I think, has a gazebo and a picnic table and the story behind it was pretty funny, but you’ll have to take the tour to hear it. Because I forget it.

A more sublime single-home island is Potato Island. At one time, it was nothing more than five rock bumps that bore a resemblance to baked potatoes. Builders filled in around the largest of them and created a man-made island with a home and gardens. Today, there’s a beautiful reflecting pool and rather nice little house. (I think it’s “nice” because the previous one was wrecked in 21st century storms.)

There’s also Exton’s Reef, a series of rocks that are submerged at high tide which has a bungalow on stilts. Similar to the gazebo story, this is someone thumbing his nose at Branford I believe. Again, take the tour yourself!

One of the first islands we passed, Cut-In-Two, was home to General Tom Thumb, of P. T. Barnum fame, for a spell. (Actually, I don’t think that’s true. I think he just courted some woman named Miss Emily that did live here.) Most famously for two years in the 1900s, President William Taft had a summer home on Davis Island.

More interesting to me are the unpopulated islands. Bear Island has a granite quarry which, in the past, exported stone to build Grant’s Tomb, the base of the Statue of Liberty, and the Lincoln Memorial. Also, two of the islands are nature preserves. Horse Island, the largest island in the chain, is owned by Yale University’s Peabody Museum of Natural History. The museum is allowing the island to return to its natural state and is using it for marine and ecological research. Outer Island is the farthest from shore and is part of the Stewart B. McKinney National Wildlife Refuge. It was gifted to the federal government by Elizabeth Hird in 1954 to be used for research and education.

Outer Island encourages visits and I look forward to doing that someday soon. You can actually kayak or canoe around the islands yourself and true fact: anything below the mean high water line is public property in Connecticut. Yale’s Horse Island discourages visitors by allowing it to become a Lyme Disease and poison ivy haven – so head’s up on that.

Many of the inhabited islands have their own challenges. High Island can only be docked at during high tide and residents must climb steep staircase to reach their homes. Then there’s the weather of course. In September 1938, a hurricane hit without warning and badly damaged the island properties and stranded residents. The storm swept entire houses into sea, and seven people lost their lives. More recently, Hurricane Sandy did a number and frankly, every large storm batters the Islanders.

One thing that bummed me out was that the relatively bustling Money Island is a little less bustling these days. They used to have an official public library on the island, and it was one of the things I was most excited to visit for this website. Granted, it was a phone booth but it was a legit, recognized public library. (I suppose it’s now likely a Little Free Library). Alas, it is no more.

Our cruise was smooth and quiet, despite it being a fairly blustery day with some choppiness. The Sea Mist is for cruising, and you can buy drinks and bring snacks and have a lovely time with friends over the course of the 50 minute trip.

One question that still plagues me though: We saw regular garbage and recycling bins on… one of the islands. As if it was garbage day and the trucks were coming later. Why?

I’ll leave that mystery be.

Thimble Island Cruise and the Sea Mist
CTMQ’s Cruises