Eastern Long Island Sound: The Ultimate 10-Day Escape

Eastern Long Island Sound: The Ultimate 10-Day Escape
A Cruise Plan By Team Dockwa

Looking to stretch your cruising legs without venturing too far from Long Island Sound? This 10-day loop begins on the banks of the Connecticut River and winds its way out to Montauk, Block Island, Watch Hill, and Mystic before circling back. It’s the perfect balance of scenic passages, resort comforts, and classic New England charm, and each stop offers its own flavor of fun, relaxation, and coastal character! Enjoy!

Your cruise kicks off at Saybrook Point Marina, nestled at the mouth of the Connecticut River. It’s a convenient and well-equipped starting point for boaters coming from upriver or western Connecticut. If you're cruising in from Long Island’s North Shore, consider swapping Saybrook Point Marina for Brick Cove Marina in Southold or Sag Harbor Moorings as your staging port. Wherever your coming from, night one is all about getting excited for a great cruise ahead. 

Next up: Montauk Yacht Club. This destination blends resort-level amenities with a relaxed coastal vibe, offering just about everything you could want—steps from your slip. We’re talking waterfront dining, beach access, an onsite pool with serious vacation energy, and more. Trust us: this is a two-night stay kind of place.

No summer cruise feels complete without a stop at Block Island, and after a quick 20ish nautical-mile run from Montauk, you’ll be tying up at Champlin’s Marina and Resort, the perfect place to settle in for a few more days of laid-back fun. Soak in the lively dockside scene, explore the island’s winding roads on a bike, kick back with a good beach read at the infamous Mahogany Shoals, or sip a world famous mudslide while you watch the harbor buzz around you. You can't go wrong with this stop. Enjoy every minute of the Block Island vibes!

From there, we are headed back to the mainland. Cruise on over to the Watch Hill Docks, located in a quintessential Rhode Island town known for its understated elegance, beautiful homes, and long, quiet walks to the beach. It’s the kind of place where time slows down in the best way (perfect for a peaceful reset after livelier stops).

Finally, make your way to Mystic Downtown Marina, a longtime favorite among local boaters. With its iconic drawbridge, seaport museum, and a downtown full of charming shops and restaurants, it’s an ideal final stop. Close enough to major launch points, yet rich with history and small-town character, Mystic offers a relaxed, memorable end to a cruise well spent.

This Eastern Long Island Sound loop is all about accessible adventure - easy to reach, easy to enjoy, and the kind of cruise that’ll have you and your crew counting down the days until the next one. With shorter cruising legs, a well-paced mix of lively harbors and quiet hideaways, and plenty of onshore charm, this 10-day itinerary is pure New England magic.

In our opinion, it’s the kind of trip that reminds you exactly why boating is the best way to experience this coastline. Whether you're recharging, discovering new favorites, or revisiting old ones, this route delivers it all (at a pace that feels just right).

Ready to plan your Eastern Long Island Sound Cruise? With Dockwa’s new cruise planning tool, organizing your trip has never been easier. Plan out your stops, link your Dockwa reservations, track mileage, and more. Whether you’re cruising for a long weekend or a month, start your next journey with the tools to make it smooth from start to finish.