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Maine Yacht Charter Itinerary

Feast on Lobsters, Linger at Lighthouses, and Behold the Spectacular Scenery that Surrounds You

Want to discover all the wonders of Maine from the best side possible? Hop aboard a luxury Maine sailing charter yacht…and you can!

Here’s what you can expect on a weeklong Maine yacht charter itinerary:


  • Day 1 Portland, Maine

    From humble shipping outpost to hip and happening seaside town, Portland's transformation, over the last few decades, has been nothing short of sensational. If you've heard about the exceptional food, amazing art galleries, fantastic breweries and gorgeous architecture for which Portland is so renowned, then no doubt you've planned to spend a few days here before your Maine sailing charter trip. You really should!

    On the first day of your Maine yacht charter itinerary, you'll hop aboard your luxury yacht charter. Settle in, unpack, meet your crew and start exploring your gorgeous new ‘home’. There will still be time for you to explore and delight in Portland's attractions in the afternoon. Tonight, we’ll dock in Dimillo’s Harbor just Downtown and you can savor your first gourmet dinner, prepared by your private chef under a canopy of sparkling stars.

    It’s the start of a magic week!

  • Day 2 Boothbay Harbor

    On your Maine sailing charter, sail along the dramatic rocky coastline to Boothbay Harbor, cruising ing past innumerable historic lighthouses and charming seaside villages. Once docked at Boothbay, alight to explore this picturesque village, and make sure you pay a visit to the historic shipyard. Boatbuilding has been at the core of this town’s existence for over five centuries, and in old town center, you can admire wonderful exhibits of priceless memorabilia. The harbor itself is a natural wonderland, and you may find yourself kayaking alongside a seal with an eagle soaring overhead. A local fisherman may deliver his catch of the day to your personal onboard chef, who’ll serve it up on a silver platter cooked to mouthwatering perfection.

  • Day 3 Monhegan Island

    Renowned as the ideal contemplative artists’ hideout, Monhegan Island is postcard-perfect. She’s remote, boasts stunning landscapes and is chock-full of wonderful hiking trails that’ll guide you through her wild, rugged heart during your Maine sailing charter trip. Reachable only by boat and home to fewer than 100 people (and no cars), Monhegan is a popular weekender destination. People head here to get away from it all, to relish in the quietness and isolation and, above all else, cast their eyes on the open Atlantic. The coastal walks here are utterly breathtaking. On our Maine yacht charter itinerary, a sunset outing on a kayak is the best way to work up an appetite. A sundowner on deck, the ideal indulgence.

  • Day 4 Camden

    For a bit of contrast on your Maine yacht charter itinerary, today we leave serene Monhegan, headed for Camden Harbor, one of Maine’s most vibrant port towns. Brimming with interesting shops, charming cafés, gorgeous restaurants, and Maine’s largest fleet of windjammers hugging the harbor’s edge. Enjoy a long lazy seafood lunch by the sea, or work up a sweat hiking to the top of Mt Battie. The hike may be hard-going but the views are out of this world! In the afternoon, stroll down Bayview Street, where you’ll find boutiques, souvenir shops, and super inviting wine bars.

  • Day 5 Stonington

    Continue on your Maine sailing charter for the southern tip of Deer Isle today, and visit bustling Stonington, a scrumptious little port town that just oozes charm, history and good ol’ fashioned hospitality at every corner. When the tide streams out, children will delight in the tidepools brimming with scallops and sea critters. This working lobster fishing town is a foodie’s paradise and if you don’t believe us then go ahead and delight your taste buds on a Lobster Benedict for brunch. You’ll see! Spend the afternoon on a walking tour of this quaint village and you’ll swear you’ve just been transported back to the late 19th century!

  • Day 6 Northeast Harbor and Mt. Desert Island

    Mt Desert Island, and Northeast Harbor in particular, are the quiet achievers in Maine. VIPs who wish for a quiet retreat head here in droves, attracted by the slow-paced life and outstanding scenery. It may not seem like a rich and famous hideout, yet the exclusive and opulent Maine sailing charter yachts in this harbor do give its popularity away. Besides…the designer shops, great art galleries and upmarket cafés and restaurants are also indicative of the island’s fame. Enjoy a stroll in town, visit the outstanding Japanese-inspired Azalea and Thuya Gardens or go for a hike to Upper Hadlock Pond.

  • Day 7 Bar Harbor

    The springboard for trips to the Acadia National Park – Maine’s largest protected reserve – Bar Harbor is Mount Desert Island’s largest and prettiest town. Steeped in history and charm, Bar Harbor (pronounced Bah-Hah-Bah by locals) is a true highlight of any Maine yacht charter itinerary. With the colorful shopfronts, this gorgeous bayside location is a delight to explore on foot, most especially in the evenings. Two amazing museums showcasing local Native-American history and an immensely picturesque shore side walking path – not to mention splendid shops and boutiques – will undoubtedly capture your interest. At low tide, take a walk up to Bar Island on the northern end of the pier, just make sure you head back in time before the tide drowns the sandbar away. Too late? No problem! Your luxury Maine yacht charter's tender will be right there to pick you up!

  • Day 8 Disembarkation

    Dare your travel companions on a last morning swim (it shall be a chilly affair!) before delighting in a scrumptious breakfast on the last day of your Maine sailing charter. On Day 8 of your Maine yacht charter itinerary, you’ll bid farewell to the wonderful crew aboard your luxury yacht and head on home. But don’t worry…Maine and all her wonderful treasures will be right here waiting for you to return.

Our Expert Opinion

Maine is drenched in beauty with a rugged coastline and hundreds of islands- more than the Caribbean. Unless you have Neanderthal roots (like our own Brad Lavigne), this is an on-the-water vs. an in-the-water destination as temperatures hover around 60 degrees F (16C) in the summer months. So think kayaking, paddle boarding, wave runner, hiking, biking, sightseeing and magnificent sailing. One of our favourite summer time spots.

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