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Welcome to the first of KellyBoat’s Destination Series! Learn about some hidden gems in and around New England that need to be added to your itinerary this summer.

Cuttyhunk Island is a must-see destination this season. Cuttyhunk is nestled cozily between the southwest coast of the MA mainland and Martha’s Vineyard, the last island in the string of Elizabeth Islands. For anyone that’s visited, Cuttyhunk is the favorite island of many possessing New England charm, along with the relaxed feel of the islands. We encourage you to leave you cell phone behind and prepare to unwind on this beautiful island.

This tiny island packs a lot of punch allowing visitors to enjoy its natural beauty and solitude. With a fulltime population of about 20, Cuttyhunk Island is only about a mile and half long, ¾ mile wide, and has a large harbor at the eastern end of the island. The coastline is tricky; your KellyBoat captain is trained to navigate these waters, as well as the currents and tides which make entry into the harbor difficult for the inexperienced boater.

Step ashore this idyllic island and head to Lookout Hill, the highest point, at 154 feet above sea level. Lookout Hill (aka Lookout Park) gets its name from serving as a naval lookout during WWII. From this point, soldiers could watch for any German subs in the surrounding waters. Pack a lunch and enjoy a picnic at one of the tables next to the observation platform, offering unbelievable 360-degree views. Lookout Hill is also the perfect spot to catch a gorgeous sunset over the water. Stay a bit longer after sunset and be prepared for some of the best star gazing you’ve experienced.

This quaint island has limited facilities. Guests will find a general store and an Island Market to grab necessities. The island itself is dry, so plan on burying and bringing your own alcohol before you head out. You’ll find a handful of restaurants on Cuttyhunk, featuring great food to eat in, or takeout. Craving oysters or clams? The Harbor Raw Bar will serve fresh Cuttyhunk oysters and clams, crab spread and chowder right to your boat! This is truly a unique experience you won’t soon forget. Don’t forget to stop at the local ice cream shop to end the day on a sweet note.

One way to spend your time on Cuttyhunk Island is enjoying the beaches. The entire island is lined by beaches, with the most central being Barges Beach on the island’s east side. Guests can walk to the beach from the marina, and with the beaches extending quite a distance, you are sure to find a secluded section of beach to relax.

If your guests like to fish, Cuttyhunk boasts some of the best fishing around. The island is often called the “Mecca” of striped bass as it sits in the middle of the striped bass pre-spawn staging area. Be prepared to catch bass that range from small to up to 50-pound monsters!

KellyBoat is ready to take you on an unforgettable trip to Cuttyhunk Island! Depending on your starting destination, a visit to Cuttyhunk Island could be a full day trip, or you may even want to grab a mooring at the Cuttyhunk Marina and spend the night. What are you waiting for? Explore our fleet and book your boat trip to Cuttyhunk!