The Southern Cape Circuit: A 10-Day Cruise Through Island Icons

The Southern Cape Circuit: A 10-Day Cruise Through Island Icons
A Cruise Plan By Team Dockwa

Set your course for one of the most rewarding coastal loops New England has to offer. This 10-day itinerary is all about range and rhythm, blending the energy of the Cape Cod islands with iconic harbors and balancing shorter cruising legs with relaxed layovers. Whether you're aboard a sailboat or a powerboat, this route offers a well-paced mix of scenic passages, lively towns, and timeless New England charm.

Start your journey at Cuttyhunk Marina, a peaceful western outpost that invites you to slow down and ease into cruising mode from day one. It’s quiet, scenic, and the perfect place to leave the mainland mindset behind. From there, you'll head to Martha's Vineyard for a stay at Oak Bluffs Marina, where the harbor buzzes with energy. Colorful gingerbread cottages, beachside bars, and a festive boardwalk vibe offer a lively contrast to Cuttyhunk’s calm. We have a feeling you’ll absolutely love this stop!

Next stop: Nantucket. Dock at the Nantucket Boat Basin, a premier spot to settle in for a few nights and soak up everything the island has to offer—shops, restaurants, bike paths, beaches, and plenty of history around every corner. Take time to explore beyond the waterfront, whether by bike or on foot, and don’t be afraid to get a little lost in the cobblestone charm.

From there, you'll cross on over to the elbow of the Cape, where you’ll land in Chatham. This salty, walkable town has serious small-town character. Secure your Dockwa reservation with the Chatham Harbormaster ahead of time, then enjoy the working harbor, beaches, and laid-back atmosphere that makes Chatham a local favorite. While you're there, we highly recommend ice cream for dinner, followed by a stop at The Squire. It’s a classic combo, and a fun night is pretty much guaranteed.

Next, cruise west to Hyannis Marina for a night in one of Cape Cod’s most central and convenient towns. Here you’ll find easy provisioning, great restaurants, and plenty to explore ashore. It’s a perfect place to stretch your legs, stock up, and enjoy a bit of the classic Cape experience before heading back out for a long weekend in one of The Cape's busiest harbors... 

Finally, you’ll make your way back to Martha’s Vineyard to round out this 10-day cruise with a long weekend in Edgartown (because really, where else would you want to toast another epic New England getaway?). Spend your days beaching it, enjoying waterfront dining, window shopping, taking in the iconic views the harbor offers. Just be sure to reserve your mooring in advance. Edgartown is wicked popular peak season, and for good reason.

And just like that, ten days of epic Cape Cod cruising is behind you. Sun-kissed skin, quiet mornings, windswept crossings, and probably a few more lobster rolls than you originally planned for. This route was thoughtfully put together to give you the kind of trip that doesn’t just check boxes. It gives you room to breathe, to explore at your own pace, and to really settle into the rhythm of life on the water. You'll come back to reality feeling full. Full of fresh air, good stories, and the kind of memories that stick with you long after you’ve tied up at your homeport.

Ready to plan your Southern Cape Cod 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.