The Thimble Islands Cruise Is a Must-See, Here's Why
Join me as I share my Thimble Islands cruise experience, exploring picturesque islands and the stunning Connecticut shoreline.
When you mention to your friends that you're "taking a cruise", most of them probably picture you sailing through the Caribbean islands or heading to Alaska. But what if I told you there's a cruise that only takes an hour, yet still gives you that thrilling feeling, plus the chance to enjoy other activities in Southern Connecticut all in one day? Well, you're in luck! Just off the coast of Southern Connecticut, in the Long Island Sound, lies a group of islands called the Thimble Islands, and you can hop on a cruise to check them out yourself. Maybe you're en route to New York or Rhode Island; it's a fantastic stop to discover a historic part of Connecticut. Plus, you can't help but wonder what it would be like to own a home on one of these islands. It's an incredible birds eye view into not only a wealthy subculture, but one that values sustainability. Let's dive into why a Thimble Islands Cruise is a must-see destination in Southern Connecticut.
What are the Thimble Islands?
The Thimble Islands is a stunning archipelago located off the coast of Connecticut, and is a hidden gem that captivates visitors with their unique charm and natural beauty. This collection of over 30 small islands (though reports have said there are many as 360 islands!), nestled in the Long Island Sound, is known for its picturesque landscapes, rocky shorelines, and vibrant marine life. Each island has its own character, with some featuring quaint cottages and lush greenery, while others remain untouched and wild, offering a serene escape from the hustle and bustle of everyday life. The islands are named for their thimble-like shape, and they provide a perfect backdrop for various recreational activities such as kayaking, sailing, and fishing. The area is also rich in history, with tales of shipwrecks and pirate lore adding to its allure.
Soundings gives a great succinct history of the Thimble Islands:
Dutch explorer Adrian Block discovered the Thimble Islands in 1614. American Indians inhabited and fished the islands and aptly called them Kuttom-quosh, or “beautiful sea rocks.” The islands were used for sheep grazing, boatbuilding, granite quarrying and by the late 1800s were a popular summer destination for city folks. A number of the islands have passed through families for generations and some have been purchased by the rich and famous.
In 1976, party goods magnate John Svenningsen purchased West Crib Island. After his death in 1997, his widow, Christine, purchased Wheeler Island in 1998, followed by Rogers, Phelps, Jepson, and Cut-in-Two East in 2003; Reel in 2004; Cut-In-Two West in 2005; Beldens in 2006; and East Crib in 2007 — at a total cost of more than $36 million. She is currently renovating the properties, rather than turning them into new developments. Celebrities who own island homes include Doonesbury cartoonist Garry Trudeau and his wife, newscaster Jane Pauley.
It should also be noted that residents of the Thimble Islands have embraced innovative and eco-friendly methods to power their homes and ensure a reliable water supply. Many of them have turned to renewable energy sources, such as solar panels and wind turbines, generating electricity to enjoy the benefits of clean energy. Plus, who wants to see power lines go from island to island? Additionally, rainwater harvesting systems are commonly installed, allowing residents to collect and store rainwater for various uses, from irrigation to household needs. This sustainable approach not only helps preserve the delicate island ecosystem but also fosters a strong sense of community as neighbors share resources and knowledge about best practices for living harmoniously with nature.
My Experience on the Thimble Islands Cruise




Three cruise companies offer tours of the Thimble Islands. In this review, I will focus on the Sea Mist Thimble Islands Cruise. This cruise is conducted on a smaller boat that accommodates about 25 passengers, fostering a more intimate experience. There are several departure times throughout the day, and I opted for the 4:15 PM cruise, which aligned with my Essex Steam Train and Riverboat Cruise excursion. The cruise departs on time, so it's recommended to arrive 10 minutes early to find parking and get in line. Parking can be tricky, but luckily, free parking is available on the side streets just a few blocks from the dock. The cruise lasts for 45 minutes.



Captain Mike took the lead and shared stories during the tour, which covers 25 inhabited islands, mostly filled with summer homes. We kicked things off at Wheeler Island, the closest one to the shore, which has just a single house that recently got power and water. Actually, only nine islands have full electric power. About 40% of the islands get their water from the shore, but most rely on rainwater for their supplies. Given the Southern New England climate, these places are mainly summer homes, closing up for the year in late October and reopening in mid-April. Some notable homes include those of Barnum and Bailey, two man-made islands, and an island that used to belong to a pirate named Captain William Kidd - all that’s left is his “harbor.” There’s also “Money Island,” which has around 20 houses, all running on solar power. Plus, you’ll spot an island with just a gazebo on it, affectionately known as “gazebo island.”



You’ll discover a wealth of information about the islands' history, like how they were established and the lifestyles of the islanders. If you tend to get seasick, make sure to pack some Dramamine just in case. The boat can really rock depending on the waves. What fascinates me about these islands is that it must be a paradise for introverts! Just think about having your own island and a home all to yourself. But I bet it’s a challenge to find a plumber or electrician when you need one!
Why You Should Take a Thimble Islands Cruise
This cruise is an excellent and relatively quick option, easily fitting into your travel plans when journeying through Connecticut to Rhode Island, Boston, or even New York, given its proximity to Interstate 95. If you're exploring the Connecticut Shoreline, this makes for a fantastic scenic stop where you can gain valuable insights while still having time for other activities. Budget-conscious and solo travelers will appreciate the relaxed, intimate atmosphere of the cruise, as the ships accommodate around 25 passengers at a time. The knowledge you gain during the cruise, combined with its competitive pricing, is truly unmatched. If you're curious about how you might enjoy a cruise vacation or even a longer cruise, this serves as an excellent trial run. Finally, this is a cruise you can take multiple times and learn something new each time. It's a fascinating look into a wealthy subculture that values independence and sustainability.
Thimble Islands Cruises can be found at the dock located at 4 Indian Point Rd in Branford, CT. There are three cruise lines that offer tours to the Thimble Islands seasonally: the previously mentioned Sea Mist, the Volsunga IV, and the Islander. To book a reservation, click on any of the aforementioned names to take you to their respective websites for available times. Each of these lines operates on different schedules, with most running during the week, and all three alternate every hour on weekends throughout the summer. They all operate from June to August, and at least one of the lines is available during the spring months of April and May, as well as the early fall months of September and October.
It's important to book in advance for all three lines, so be sure to check their website for availability. Private charters are also offered during the summer months for an additional fee for family gatherings, corporate events, or just hanging out with friends. Parking is available at the church across from the beach for a small donation. You can also use the nearby streets and the parking lot next to the docks, but keep in mind it's first come, first served. Please make sure to use the public restrooms in town before you board the boat. Bathrooms are also available in the grassy park next to the beach.










