If you’ve ever cruised north from Cape Cod and thought, “We should stop there next time,” well, this one’s for you. This eight-day itinerary from The Eastern Exit of the Canal to Portland, Maine is all about taking the scenic route and actually stopping to enjoy the harbors that often get passed over en route to “somewhere else.”
If there’s one thing we appreciate on a long cruise, it’s a marina that checks all the boxes, and Sandwich Marina fits the bill. Convenient, well-equipped, and perfectly positioned at the entrance to the Cape Cod Canal, it’s an ideal spot to fuel up, rest up, and kick off your journey north. Your first stop? Provincetown, of course. With its colorful streets, lively culture, and sweeping harbor views, it gets you a little closer to Maine, and gives you a quintessential Cape experience to kick things off. From there, cross over to Scituate and tie up at TPG Mill Wharf, a walkable location with excellent dining, easy provisioning, and one of the South Shore’s most charming downtowns.
Next, make your way to Gloucester, one of the oldest working waterfronts in the country. Dock at the Ocean Alliance Docks, located in the heart of the harbor, and spend the evening enjoying fresh seafood, a bit of history, and the gritty charm of this iconic fishing town.
The trip continues with a stop in Newburyport, where brick-lined streets and a lively downtown await just a short walk from the docks. Then head to Wentworth by the Sea in New Castle, New Hampshire, one of the most picturesque marinas in New England, with resort-level amenities and a quiet elegance that invites a slower pace.
On day seven, you officially cross into Maine… but not before a recommended lunchtime detour. If the weather aligns, consider dropping anchor or picking up a mooring at the Isles of Shoals for a memorable lunch stop. Just be sure to check your charts and guidebooks ahead of time, and know that the moorings are managed by a private yacht club, so if you pick one up, be prepared to move along if a member needs their spot.
After your detour, make your way to Chicks Marina in Kennebunkport, where postcard-worthy views meet boutique shopping, waterfront dining, and timeless Maine charm. But hold your horses because you’re not in Casco Bay just yet. Your final leg will take you and your crew right past Portland Headlight en route to DiMillo’s Marina, located in the heart of Portland’s historic Old Port. A favorite cruising destination among food lovers and culture seekers alike, Portland is the perfect place to wrap up your transit. Grab a lobster roll, wander the cobblestone streets, and raise a glass to the journey. You’ve made it to Casco Bay.
This cruise is perfect for boaters who want to slow down, check out a few new harbors, and enjoy the stretch between the Canal and Casco Bay instead of just passing through. It’s a reminder that sometimes the best parts of the trip are the stops you didn’t rush past. One-way or round trip, it’s a solid route with good food, good docks, and plenty of reasons to keep the chart-plotter zoomed in.
Ready to plan your Cruise to Portland? 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.