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Dockside Dining - Options for Your Next Portland Boat Charter

Updated: Jan 18, 2022

A cruise on the water is just that much better when you know you have a destination, and there is nothing quite like stepping off your boat to grab a drink or a bite while looking out at the water you were just exploring. Whether showcasing the coast of Maine to a business client, seeking a romantic meal, or simply looking for a summertime escape, taking a cruise to a waterside restaurant makes for a quintessential Maine experience. Below you will find a list of restaurants accessible on our charters.


The Dolphin Marina and Restaurant


Casual fine dining and an open aired atmosphere overlooking Casco Bay makes The Dockside Grill a favorite for both visitors and locals alike. There is a great vibe to dining on a dock as local boaters come and go and the fresh sea breeze makes its way through the open bay doors. Local seafood like Bangs Island Muscles and a plethora of oyster options are offered and harvested on the waters you'll be overlooking while you eat. (4 hr charter or longer recommended)

Located on Great Diamond Island situated in one of the most quaint, protected coves in all of Casco Bay, Diamonds Edge feels like a hidden gem you're lucky to discover. With outside dining on their porch and shaded dining on their lawn, Diamonds Edge is the perfect Maine Island escape. Have us wait at the dock for you to finish dining, or time it out to take the ferry back to Portland after your meal, dining at Diamonds Edge is easy to incorporate into your charter. (Accessible with a 4 hr charter or with a Casco Bay cruise if taking the ferry for your return.)

On the back side of Chebeague Island, one of the largest and least inhabited islands of Casco Bay is a boat yard that serves as a one-stop-shop resource for island residence. The Niblic, a gift shop and deli attached to the boat yard is perfect for a stopover to pick up sandwiches for your charter as well as a unique item or two you wouldn't find anywhere else. The Niblic is one of our favorite spots, and the cruise to and from is beautiful. Highly recommend! (Accessible with 4 hr charters or longer.)

On the coastal facing side of Chebeague Island lies one the historic Inn's of the Maine Coast. Dating back to the 1880's, the inn feels like a throw back in time updated with a few modern amenities and fine food. The view and the grounds are beautiful and is a common site for weddings on the weekend.

(Suggest a 5 hr charter to not feel rushed during your meal)

"The Dolphin" is a destination boaters look forward to all winter because a visit often marks the best of their Maine summer. Virtually all of the tables at The Dolphin have a water view which can not be beat. Overlooking Pott's Harbor, at the end of Harpswell neck, you'll be looking over lobster boats and natural beauty alike while you eat in this off-the-beaten path destination. They are famous for their fresh chowders and blueberry muffins baked fresh daily. The cruise to Dolphin Marina extends the length of Casco Bay so you will see all the bay has to offer to and from your meal. (Accessible with 5hr charter)


With a boat charter from Portland Maine, the food options do not end when you leave the shore. Whether creating an experience to wow a client, spending a special day with family and friends or looking for a romantic getaway, pulling up to a restaurant by boat is sure to leave an impact!

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