The Vineyard Loop: A Long Weekend on Island Time

The Vineyard Loop: A Long Weekend on Island Time
A Cruise Plan By Team Dockwa

Looking for the picture-perfect long weekend on the water? This classic New England island-hopping itinerary offers the ideal mix of vibrant harbors, historic charm, and peaceful marinas, all within easy reach for most boaters cruising south of the Cape Cod Canal. It’s the kind of cruise that balances adventure with downtime, giving you just enough distance to feel like you’ve gone somewhere, without spending the whole trip behind the wheel.

Whether you’re departing from Mattapoisett, anywhere near the western exit of the Cape Cod Canal, or even Newport, this route is designed for minimal engine hours and, well, maximum fun. Expect shortish legs, iconic stops, and plenty of opportunities to explore ashore, it’s the perfect way to make the most of a long weekend on the water.

You’re kicking off your long weekend on the Vineyard at Oak Bluffs Marina, where colorful gingerbread cottages, beachside bars, and the iconic Flying Horses Carousel set the scene for a lively start. It’s the kind of place where you can grab a drink by the water, catch some live music, and really kick back. Settle in, soak it up, and enjoy that first-night buzz, because the island pace starts now.

The next morning, you’re just a quick 7-nautical-mile hop away from your well deserved reservation with the Edgartown Harbormaster. This is the Vineyard at its most polished. Think cobblestone streets, upscale shops, and postcard-perfect charm at every turn. The leg is short enough to enjoy a lazy morning in Oak Bluffs before heading out, and you’ll still have the afternoon to stroll downtown, grab an ice cream cone, or even dinghy over to Chappaquiddick for a little adventure.

As always, Sunday comes way too quickly, and it’s time to start retracing your wake (not because you want to, but because your PTO ran out and reality’s knocking). That said, the adventure’s still far from over. You’re sun-kissed, salty-haired, and already mentally plotting your next island escape. (Our unsolicited words of wisdom? It's always a good thing to leave wanting more.)

So make your last night aboard count. Cuttyhunk Marina is the perfect final stop: quiet, scenic, and just close enough to western homeports to soften the sting of a Monday morning trek back to reality.

One final note on this cruise plan just in case it's needed: If your Friday departure didn’t go as planned, and the day escaped you quicker than you could say "Out of Office", no worries. Flip the itinerary and kick things off in Cuttyhunk instead of Oak Bluffs. Both make for a strong opener.

This route delivers the perfect mix of New England charm, open water stretches, and laid-back island vibes that make a long weekend feel like a full-on escape. We hope you enjoy every dang minute of it!

Ready to plan your Vineyard 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.