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, starting at $220 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.
Things to Do Near the Thimble Islands Cruise
With it's location in Branford, Connecticut, the Thimble Islands Cruise is right in the heart of the Connecticut Shoreline, and is within day trip and driving distance of various things to do. In fact, most of the activities noted below are free of charge! Here are some of my picks based on personal experience and Google reviews:
Essex Steam Train and Riverboat Cruise: If the Thimble Island Cruises was your appetizer, I highly recommend this as your main course. This is a delightful journey that combines the nostalgia of a vintage steam locomotive with the serene beauty of a riverboat ride. As you board the beautifully restored steam train, you'll be transported back in time, feeling the gentle rumble of the engine and the warm breeze as you chug along picturesque landscapes dotted with lush greenery and quaint towns. The train ride offers a unique perspective of the Connecticut River Valley, where you can soak in the sights and sounds of nature. Once you disembark, the adventure continues on the riverboat, where you can relax on the deck and enjoy stunning views of the waterway, perhaps spotting local wildlife or simply basking in the sun. The train and the nearby cruise operate several times daily, along with dinner trains and sunset cruises that run together from late spring to early fall. The total duration for both the train and cruise is about 2 and a half hours, making it a great addition to the Thimble Islands Cruise. You can find it roughly 45 minutes away at 1 Railroad Ave in Essex, CT. Read my review for more information!
Yale University Art Gallery: Established in 1832, it holds the distinction of being the oldest university art museum in the United States. The galleries are situated over three interconnected buildings designed by four architects, and built between 1866 and 1953. The Yale University Art Gallery features an impressive array of over 200,000 works, including European paintings, American art, and ancient artifacts, making it a treasure trove for art enthusiasts and scholars alike. Visitors can explore masterpieces by renowned artists such as Vincent van Gogh, Pablo Picasso, and Georgia O'Keeffe, all while enjoying the gallery's stunning architecture, which beautifully blends modern design with historic elements. The Yale University Art Gallery is located on 1111 Chapel St in New Haven, CT and is a short drive from Branford. You can utilize metered parking on streets adjacent to the art gallery, or use the Chapel-York Garage on 150 York Street. It is open 10am-5pm Tuesday-Friday and 11am-5pm Saturday-Sunday. It is closed on Mondays and all major holidays. Check website for closures as it is closed on many holidays and occasionally during the summer and winter months. The best part? The Yale University Art Gallery is FREE to visit for everyone.
Yale Peabody Museum: Established in 1866, this museum boasts an impressive collection that spans various fields, including paleontology, anthropology, and geology. Visitors can see extensive dinosaur fossils, including a nearly complete skeleton of a Triceratops. The museum also features fascinating exhibits on ancient cultures, showcasing artifacts that tell the stories of civilizations long past. With its engaging displays and educational programs, the Yale Peabody Museum serves as a vital resource for students, researchers, and families alike, making science accessible and exciting for all ages. The Yale Peabody Museum is located at 170 Whitney Ave in New Haven, CT just a few blocks north and east of the Yale University Art Gallery. There are several nearby parking garages and you can park along adjacent streets through metered parking. Shuttles are also available. The museum is open Tuesday-Saturday from 10am-5pm, and Sunday from 12pm-5pm, closed Mondays and all major holidays. Check the website, as there could be some exceptions. The Yale Peabody Museum is FREE for all to visit.
West Rock Ridge State Park: Spanning over 1,000 acres, this lovely state park features a diverse landscape of rugged ridges, lush forests, and scenic vistas that provide breathtaking views of the surrounding area, including the New Haven skyline and the picturesque Farmington River Valley. Visitors can explore an extensive network of hiking trails, ranging from easy walks to more challenging climbs, making it accessible for all skill levels. The park is also a popular spot for mountain biking, birdwatching, and picnicking, with designated areas that allow families and friends to enjoy a meal amidst the beauty of nature. In the fall, it's a great place to observe and photograph foliage. You can also observe up to 200 square miles of surrounding views from the summit on a clear day. The state park is located at 29 Main Street on the border of Hamden and New Haven, CT. It is open daily from 8am to sunset, and the drive to the summit is seasonal - open from late May to late October. The park is FREE to visit for everyone.
Where to Eat and Drink near the Thimble Islands Cruise
As this is the Connecticut Shoreline, you'll find numerous options to eat and drink near the Thimble Islands Cruise. Here are my picks based on personal experience and Google reviews:
New Haven's Pizza: I'm putting this in its own category because you definitely need to try the pizza that New Haven offers at its three famous pizza spots, and it's just a short drive away. New Haven's pizza is often referred to as "apizza," pronounced "ah-beets," which reflects its Italian roots. What sets New Haven pizza apart is its thin, crispy crust that is typically cooked in a gas-fired oven or coal-fired oven, giving it a distinct char and flavor. The toppings are often simple yet delicious, with classic options like tomato sauce, mozzarella, and fresh basil, but many pizzerias also offer creative variations that include clams, bacon, and even spicy peppers. The local favorite, known as the "white clam pizza," features a blend of fresh clams, garlic, olive oil, and cheese, showcasing the region's seafood and it's within a short driving distance from the cruise. My personal favorite is Frank Pepe Pizza Napoletana on 157 Wooster Street in New Haven, but you can also try out Sally's Apizza just down the street on 237 Wooster Street in New Haven, and finally, Modern Apizza a few blocks away on 874 State St in New Haven. There's also other pizza restaurants in New Haven that might have less traffic, but similar pizza - and quite honestly, you cannot go wrong!
Stony Creek Market: Local family owned and operated deli serving baked goods, breakfast sandwiches, salads, wraps and sandwiches. In fact, this particular deli uses locally sourced eggs and their own exclusive blend of coffee. Open daily from 7am-2:30pm Monday-Friday, and 7am-2pm Saturday-Sunday. During the summer, the deli reopens from 5pm-9pm for pizza and seasonal specials. Located on 178 Thimble Island Rd in Branford, CT, it's a brisk 5 minute walk up the road from the Thimble Islands Cruise port and it's a terrific option for a first stop for breakfast, a stop for lunch, or to sample some of their pizza on the weekends in the summer.
Lenny and Joe's Fish Tale: Open since 1979, this legendary seafood restaurant is known for their fresh catches and flavorful dishes, and pride themselves on sourcing high-quality ingredients, ensuring that every meal is a memorable experience. From classic fish and chips to innovative seafood pasta, there's something to satisfy every palate. Two locations provide different types of service. If you're looking for a more fast casual, and quick service experience, the location at 1301 Boston Post Rd, Madison, CT will best serve you. If you prefer a more casual sit-down restaurant experience, the location at 86 Boston Post Road in Westbrook, CT will work best for you. Either way, both places provide the same quality of service, portion sizes, and overall customer experience. Both locations also offer similar hours, open Sunday-Thursday from 11:30am to 9pm and Friday-Saturday from 11:30am-9:30pm.
Where to Stay near the Thimble Islands Cruise
If you're planning a visit to the Thimble Islands for a cruise, you'll want to find a comfortable place to stay nearby to make the most of your experience. One great option is to look for accommodations in Branford, which is just a short drive away from the island's ferry terminal. Here, you can find charming bed-and-breakfasts that offer a cozy atmosphere and personalized service, perfect for unwinding after a day on the water. Alternatively, consider booking a room at one of the waterfront hotels in the area, where you can enjoy stunning views of the Long Island Sound and easy access to local dining options. For those who prefer a more home-like setting, vacation rentals through Vrbo are also available, providing the convenience of a kitchen and extra space for families or groups. No matter where you choose to stay, being close to the Thimble Islands will enhance your cruise experience, allowing you to explore the beautiful scenery and unique charm of this coastal gem.