There’s something uniquely satisfying about cruising around the entirety of Cape Cod, and this counterclockwise route offers a fresh way to do it. Designed for those who want to slow down and stay a while, this three-week itinerary combines tucked-away harbors, classic island towns, and scenic passages into one memorable summer cruise.
Your journey begins with one night at Parker’s Boat Yard, a quiet, well-equipped launch point tucked just south of the canal's western exit. From there, you'll cruise out to Cuttyhunk Marina, where a two night stay lets you fully settle into cruising mode. No rush, no craziness, just salty air and sunset views.
Next, it’s on to Martha’s Vineyard, with stopovers in both Tisbury (two nights) and Edgartown (three nights). You’ll experience all the island has to offer, and we encourage you to really soak up the best parts of island life. That means beach time, town time, down time, etc. These early legs are relatively short and sweet, giving you and your crew plenty of time ashore to just enjoy.
Next up, swing out to Nantucket for the long weekend. Book a mooring and enjoy for front-row access to the cobblestone streets, shops, and dining that make this island so beloved. After three nights there, head northwest to Hyannis to re-provision and refuel, and then east to Chatham, a classic New England harbor with beautiful beaches and a great downtown. Ice cream for dinner is required (we don’t make the rules).
From Chatham, prepare for your longest day underway. The run to Provincetown spans over 58 nautical miles and can take sailboats most of the day depending on conditions. This leg is best tackled with an early start and a weather window in your favor, but the reward is worth it. Provincetown is the vibrant, artistic heart of the Outer Cape, and you’ll have three full nights to enjoy its eclectic streets, incredible food, and wide harbor views.
Wrap up your circumnavigation with a stop at Sandwich Marina, located just inside the eastern side of the Cape Cod Canal. It’s a convenient and well-equipped final stop, perfect for regrouping before heading back through the canal and making your way home. Or, if you’re not quite ready to pull the plug on your summer cruise, skip Sandwich and continue on to Scituate to begin your journey north to Maine. (Good news: we’ve mapped that cruise out for you, too 👀).
Whether you’re a seasoned cruiser or looking to stretch into longer passages, this route offers the full spectrum of what Cape Cod has to offer: remote islands, resort towns, dramatic coastlines, pristine beaches, and even working waterfront. All at your own pace, all from the comfort of your boat. Chef’s kiss.
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.