A Two-Week Downeast Cruise: Casco Bay to Mount Desert Island

A Two-Week Downeast Cruise: Casco Bay to Mount Desert Island
A Cruise Plan By Team Dockwa

There’s no coastline quite like Maine’s, and no better way to explore it than by boat. This two-week cruise from Casco Bay to Mount Desert Island invites you to take your time, hit the highlights, and uncover a few off-the-beaten-path gems along the way. With a dozen thoughtfully spaced stopovers, this route is about soaking in the scenery and not checking off as much mileage as possible each day.

Your journey kicks off in western Casco Bay at Dolphin Marina & Restaurant, a longtime local favorite for its warm hospitality and sweeping views. Fuel up, grab a table (be sure to enjoy one of their world-famous blueberry muffins with your entree), and ease into cruise mode. After all, you’ve got two full weeks of Maine magic ahead. Cruising to your next stop, Sebasco Harbor Resort, will transit almost the entirety of Casco Bay. It’s a beloved destination offering a full-service spa, saltwater pool, old-school arcade and bowling alley, and more. Just keep an eye on the forecast as a southeast swell can creep into the mooring field on a high tide. If needed, flag The Basin on your charts as a calm, protected alternative anchorage just a few miles west.

From there, you’ll cross the Sheepscot River, pass Seguin Island Light, and cruise into Boothbay Harbor, a classic Maine town buzzing with summer energy. For a classic downtown experience check out Boothbay Harbor Marina (they have over 100 five star reviews from boaters, and for good reason) or make a reservation at Carousel Marina if you need to fuel up and hit the ships store. Expect working waterfront charm, fresh seafood, and shops galore. The following day, hop over to Linekin Bay Resort (just a 3 mile jump), where laid-back luxury meets incredible value. When you reserve a mooring at LBR, you'll enjoy full access to their amenities. That means saltwater pool, pickleball courts, and even complimentary breakfast. Yep. You read that right.

Next stop: You’ll cruise further east to Coveside Restaurant & Marina, tucked into the peaceful harbor of Christmas Cove. Study your charts prior to arrival as the approach is a bit detailed, but no problem. With a drink in hand, a lobster dinner on the way, and a quiet sunset ahead, this stop offers a true “hidden gem” feel.

Continue around Pemaquid Point and into Muscongus Bay, charting your course toward Port Clyde. If it’s puffin breeding season (June-Julyish), do yourself a favor and pass Eastern Egg Rock to starboard (you’ll thank us later). Awaiting you at the edge of the bay is a salty working waterfront with character to spare. Tie up at the dock to refuel, stock up at the general store, take a stroll to the local science center, and grab a drink with locals at the Red Barn Café.

The next leg takes you around Mosquito Island and into Penobscot Bay! You can opt to navigate through the scenic (yet slightly technical) Muscle Ridge Channel for a beautiful welcome to this new section of coastline on your way to your slip at the Landings Marina in Rockland. Follow that with a stop at Lyman-Morse in Camden, where you can reset with a proper shower, shore power, dockside cocktails, and some of the best small-town harbor vibes on the coast. You really can’t go wrong. 

Pause. You made it to Penobscot Bay. You’ve stopped at some of the most iconic marians on the east coast along the way. The best part? You’re just getting started. This is where Penobscot Bay really begins to shine. 

Drop the hook at Pulpit Harbor on North Haven, a favorite among cruisers for its quiet beauty and secure anchorage. Take the dinghy out to Pulpit Rock for sunset where schooner silhouettes drift past the Camden Hills in one of Maine’s most iconic views.

Next up is Belfast Marina, a rising favorite for its welcoming community, walkable downtown, and laid-back energy. You'll want to cast off early the next morning for the ~29-mile run to Blue Hill Bay so maybe keep that dockside bar tab in check. Then again, who are we to stop you? Make your next stop at Atlantic Boat Company in Brooklin, a quiet, working harbor with strong service offerings and an authentic, unpolished Maine vibe. It’s a good place to reset and catch your breath before the final stretch.

Cruising into the iconic Frenchman Bay, you’ll feel the landscape shift. The bold, pine-lined shoreline of Mount Desert Island and Acadia National Park will come into view as you round up an iconic two weeks of cruising. First up is a night at Dysart’s Marina in Southwest Harbor, the perfect base for exploring Acadia’s quiet side. Restock, stretch your legs, and relax before heading to your final stop: Bar Harbor Municipal Pier. Wrap up your two week journey Downeast right in the heart of it all. We’re talking lobster, ice cream, and, if you’re feeling bold, a sunrise hike to the top of Cadillac Mountain, for the first glimpse of a new day.

This cruise is everything Maine is meant to be: dramatic coastlines, working waterfronts, unforgettable meals, and the kind of pace that makes you want to stay just one more night. Whether you’re in it for the adventure, the anchorages, or the food, this route delivers it all (and leaves you already planning the next trip). Just keep an eye out for those lobster pots!

Ready to plan your Downeast 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.