Sometimes the best cruising isn’t about how far you go, it’s about how good the stops are. This Casco Bay long weekend itinerary is designed for boaters who want to unwind close to port, trading long days underway for short scenic hops, exceptional food, and classic Maine charm. With three memorable stops and easy cruising distances, it’s the ideal escape for a quick Friday-through-Monday adventure.
Your weekend kicks off at Diamond’s Edge Marina, located on Great Diamond Island. Just a short cruise from Portland Harbor or Falmouth, it’s an easy first stop, especially for boaters sneaking out of work early on a Friday. Once docked, you’ll feel worlds away from the mainland. Enjoy a relaxing night on the island with multiple dining options just steps from your slip and plenty of space to stretch your sea legs.
Saturday brings a ~16 nm cruise to Sebasco Harbor Resort, a true gem tucked into a classic Maine cove. Plan to spend a full day and night here as there’s no shortage of things to do. This waterfront resort offers a saltwater pool, full-service spa, on-site dining, an old-school arcade with candlepin bowling, ice cream, and even a nine-hole golf course. Whether you're up for activity or just want to kick back with a view, Sebasco delivers.
One note for the overnight stay: a southeast swell can sometimes wrap into the harbor on a rising tide, making for a less-than-perfect night’s sleep. If the forecast calls for it, consider anchoring in The Basin, a beautifully protected spot just a few miles west. It’s a serene alternative, but be sure to study your charts closely as the entrance is narrow and requires careful navigation.
Round out your weekend at Dolphin Marina & Restaurant, a family-run favorite back the way you came that’s beloved for its sweeping views of western Casco Bay and welcoming vibe. Make sure to be there for golden hour and enjoy dinner on shore with a clear view of the Western Casco Bay. And don’t skimp out at dinner… their world-famous blueberry muffins are legendary. (So much so that Oprah drops in by helicopter every summer just for a bite.)
With three standout stops, easy day trips, and a perfect blend of food, fun, and downtime, this Casco Bay itinerary proves that sometimes the best adventures are just around the corner. You don’t need to cover hundreds of miles to have a memorable cruise, just a few good marinas, a solid crew, and enough time to enjoy where you are. Whether it’s your first time exploring Casco Bay or your fiftieth, this loop offers a refreshing reset that hits all the right notes for a weekend on the water.
Ready to plan your Casco Bay 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.