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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.

Louis | Red Solo Traveler's avatar
Louis | Red Solo Traveler
Jul 31, 2025
∙ Paid

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.

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What are the Thimble Islands?

One of the over 30+ islands that make up 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.

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My Experience on the Thimble Islands Cruise

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