5 Great Boating Things to Do in Casco Bay


1. Visit Great Chebeague

Some three nautical miles from the mouth of the Royal River in Yarmouth and some six nautical miles northeast of Portland Harbor, Great Chebeague Island is the ultimate boater’s escape.

The island is mostly private, but visitors can gain access to its lovely white-sand beaches and quiet, bike-friendly roads by staying at the venerable and cozy Chebeague Island Inn, located on the island’s northwest tip. Originally built in the 1880s, the inn was destroyed by fire, but rebuilt to its original form in the 1920s. Today, the yellow, 3-story clapboard building overlooks a rolling lawn and private golf course, with magnificent views of Casco Bay.

You can stay overnight, or simply enjoy brunch, lunch or dinner at the inn. If you plan to arrive by boat, call ahead to check on mooring availability. There is good water depth in the cove, and the approach is marked by private aids. Passengers and gear can be dropped off at the pier in front of the Inn, after which you can grab a mooring or anchor. The inn staff can give you a ride to shore, or you can dinghy to the pier. Once ashore, it’s a short walk to the inn, or you can arrange for a shuttle to pick you up.

Boaters can arrange for a mooring while visiting Great Chebeague. | Photo by Joe Vallier

The inn features a sprawling porch where you can enjoy hors d’oeuvres and a cocktail as the sun sets. There’s indoor and outdoor dining, with a varied menu that includes everything from salads to steak. The inn is well known for its Sunday jazz brunch, with live music provided by local musicians.

If you choose to stay overnight, you can use one of the inn’s bicycles to get around the island’s quiet roads. Several white-sand beaches are within easy reach. Room rates range from $225-$255 for a double-occupancy, European-style room with garden views to $360-$410 for a double-occupancy, ocean-view room with private bath. A gourmet breakfast is included.

Nearby launch ramps include the Yarmouth Town Landing, on Yarmouth Harbor, just minutes from Rte. 295 and Rte. 1. There is a $15 launch fee and $5 overnight fee. Another nearby launch facility is Portland’s Eastern Promenade ramp. There is a $10 fee for non-residents to launch and park.


2. Paddle Peaks Island

If you happen to visit Peaks Island, home to Peaks Island Marina, be sure to arrange a guided sea kayak paddle with Joe DuPont of Maine Island Kayak.

One of DuPont’s best trips is a scenic paddle along the coast to nearby White Head, a spectacular cliff that drops into deep water. Along the way you’ll see lots of local waterfowl and enjoy a unique view of the Portland skyline.


3. Dine Great Diamond

Getting to Great Diamond Island, just 2 miles from Portland Harbor, is half the fun of dining at Diamond’s Edge.

The island, once home to a military fort and training ground built in the late 1800s, now welcomes visiting boaters. The upscale Diamond’s Edge restaurant occupies a former munitions warehouse that was part of Fort McKinley, built during the Spanish-American War. There’s indoor seating and a cool bar, but nothing beats a table on the porch or in the shady grove overlooking lovely Diamond Cove. Menu items include oysters, gourmet burgers, salads, seared scallops and grilled tuna—all of it delicious. Dockage and moorings are available at the Diamond Cove Marina on a first-come, first-served basis. Call ahead on VHF 9 or call (207) 766-5694; or visit the marina website.


4. Peruse Portland

Don’t let mammoth international tankers, towering cruise ships and fishing boats deter you for visiting downtown Portland—the largest, most diverse and interesting metropolitan area north of Cape Ann.

Indeed, it’s Portland’s commercial roots that make arriving and tying up along the waterfront so easy. Take, for instance, the floating restaurant and marina known as DiMillo’s, a dominant presence on the harbor since the 1980s. Only in Portland could a 72-year-old retired car ferry become a focal point of dining and boating along a busy waterfront. Within a few blocks of DiMillo’s are at least half a dozen 5-star restaurants. Wine bars, coffee houses, bakeries, at least 2 breweries, street vendors and even a few diners add to the city’s gustatory diversity.

If you wish to drop off or pick up crew, there’s a public dock at Bell Buoy Park next to the Casco Bay Ferry Lines terminal on the State Pier. Tie-up limit is 10 minutes. Long-term dockage can be arranged through DeMillo’s (207) 773-7632.


5. Fish Back Cove

The Back Cove and the mouth of the Presumscott River, just north of downtown Portland, serves as a terrific spots to pursue striped bass.

Since the cove largely drains of water at low tide, anglers are best off fishing here on the flood and upper half of the dropping. The edges of the flats hold some surprisingly large bass, which eagerly whack topwaters such as Slug-Gos, Hogys, Zara Spooks, Jumpin’ Minnows and a variety of poppers. Jigs and flies will also take fish. At high water, look for the tails and wakes of feeding fish as they cruise the flats. For a guided trip, contact Harry Wright of Casco Bay Casting, (207) 712-3724.

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