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Top 10 Maine Boat Cruises & Sailing Trips

These Ten Maine Boat Cruises Top Our List for 2024

Lighthouse Lovers Cruise in Portland Maine

Portland Discovery Land & Sea Tours: Lighthouse Lovers Cruise

Portland, ME

A fully narrated 60-minute scenic cruise through busy Portland Harbor, Casco Bay and its innermost islands to see lighthouses, forts, lobster boats, seals, porpoises, and seabirds. As many as four lighthouses can be seen including a close up view of famous Portland Head Light, Maine’s oldest and most photographed lighthouse.

170 Commercial Street
Portland, ME 04101

Daysail aboard the Schooner Eastwind out of Boothbay Harbor, Maine

Eastwind 2 Hour Day Sail

Boothbay Harbor, ME

Experience the romance of an authentic Maine windjammer on the Schooner Eastwind’s 2-hour Day Sail from Boothbay Harbor. Cruise along the scenic Maine coast in a beautiful historic vessel. Help hoist the sails or just relax and enjoy ocean breezes and views. An unforgettable sailing experience for all ages showcasing Maine’s natural beauty and maritime heritage. Book your adventure today!

20 Commercial Street
Boothbay Harbor, ME 04538

Humpback whale breaching surface near Bar Harbor, Maine

Odyssey Whale Watch

Portland, ME

Experience the wonder of seeing whales off the coast of Maine. Odyssey Whale Watch offers daily tours aboard comfortable, modern boats with experienced guides providing narration and insight. Get incredible up-close views of whales in their natural habitat. An award-winning family business providing exceptional whale watching tours in Portland for over 30 years. Join us for memories to last a lifetime!

170 Commercial Street
Portland, ME 04101

Top 10 Maine Badge


Maine, with its rugged coastline and picturesque harbors, is a sailor’s dream. For those looking to experience the state’s maritime magic, boat cruises and day sailing excursions provide the perfect window into Maine’s coastal landscapes. From beautiful sunset sails to informative lighthouse cruises to amazing whale watching tours, the choices are as varied as they are breathtaking.

Whether you’re an avid mariner or a first-time sailor, the Pine Tree State has something special to offer. Here we delve into the top 10 boat cruises and day sailing trips in Maine, guiding readers on a journey through clear waters and iconic landscapes. Prepare to set sail and uncover the state’s best coastal boat excursions and nautical adventures!


Portland Schooner Co.

56 Commercial Street, Portland, ME 04101

A Day Sail Aboard Schooner in Portland, Maine

The Portland Schooner Co., based in picturesque Portland, Maine, offers a nautical adventure that’s hard to resist. Embarking from the city’s historic waterfront, these majestic schooners sail into Casco Bay, providing tourists a glimpse into Maine’s rich maritime history. Tourists can embark on the company’s classic schooner and experience a fun sailing adventure along the picturesque Maine coast. Guests can help hoist the sails, take a turn at the helm, and enjoy the saltwater breezes.

Knowledgeable crew provide information on sailing and local history. Trips include views of Portland’s harbor, scenic islands, and Maine lighthouses. Guests may even spot seals or whales. Whether you choose a short jaunt or a sunset cruise, the captivating views of lighthouses, islands, and marine life are unparalleled. The skilled crew adds to the authenticity, sharing tales of the sea and the state’s sailing legacy. 

With a variety of public and private sailing options, the Portland Schooner Co. is a top choice for tourists looking for an authentic Maine sailing excursion. The company’s beautiful schooners and experienced crew ensure a delightful day on the water. For those seeking a genuine Maine sailing experience, the Portland Schooner Co. stands out as a top 10 choice in Maine.


Maine Duck Tours

177 Commercial Street, Portland, ME 04101

Maine Duck Tours in Portland, Maine

Maine Duck Tours offers a unique boating experience for tourists visiting Portland, Maine. Guests board an amphibious vehicle called a “duck” for a fully narrated 90-minute tour of Portland by land and by sea. Knowledgeable drivers highlight Portland’s historic Old Port, architecturally significant buildings, and scenic coastal views.

The tour concludes with a splashdown into Casco Bay for a boat ride offering stunning vistas of Portland’s skyline and the surrounding islands in Casco Bay. With the capability to explore by both road and water, Maine Duck Tours showcases the best of Portland. Offering fun, family-friendly tours, Maine Duck Tours is a top choice for tourists looking for an entertaining overview of coastal Maine’s largest city.


Schooner Lazy Jack II

Bay View Landing, Camden, ME 04843

Schooner Lazy Jack II in Camden, Maine

Schooner Lazy Jack II is a top sailing excursion for tourists visiting the coast of Maine. This classic two-masted schooner offers scenic sails from picturesque Camden Harbor. Guests can relax on deck and soak in stunning views of the rocky Maine shoreline and islands dotting Penobscot Bay. Knowledgeable crew provide interesting details on sailing history and local marine wildlife as guests help hoist sails or try their hand at steering the boat.

Trips include the option to disembark on an island for swimming, beachcombing and a lobster bake. With its historic appeal and opportunities to get out on the water, Schooner Lazy Jack II gives tourists an authentic taste of classic Maine windjammer sailing. Whether you’re aboard for a scenic morning sail or a magical sunset cruise, the Schooner Lazy Jack II offers an intimate and timeless experience. For those seeking genuine maritime charm, this vessel is a top pick in Maine’s day sailing offerings.


Odyssey Whale Watch

170 Commercial Street, Portland, ME 04101

Odyssey Whale Watch boat tours offer premier whale watching cruises out of Portland, Maine. Tourists can board one of the company’s comfortable boats for a fully-narrated whale watching adventure along the scenic Maine coast and the Gulf of Maine. Knowledgeable naturalists provide commentary and insight on the marine wildlife encountered, including massive humpback and finback whales feeding in the nutrient-rich Maine coastal waters.

The cruises also provide opportunities to observe seabirds, seals, dolphins, and other wildlife. With guaranteed whale sightings and an onboard marine biologist, Odyssey Whale Watch boat tours give tourists an exceptional opportunity to get out on the water and witness some of the giants of the sea. Offering the best whale watching experience in the Portland Maine area, Odyssey Whale Watch is a top choice for tourists hoping to glimpse these magnificent marine mammals. For tourists seeking a blend of learning and wonder, Odyssey Whale Watch boat tours stand out as a premier Maine maritime experience.


Schooner Eastwind

20 Commercial Street, Boothbay Habor, ME 04538

Schooner Eastwind in Boothbay Harbor, Maine

Schooner Eastwind is a top day sailing excursion for tourists in Boothbay Harbor, Maine. This classic 1921 schooner provides scenic day sails along the rugged Maine coastline. This traditional windjammer, with its tall sails and polished wood, offers a genuine taste of Maine’s maritime heritage. As it glides through the pristine waters around Boothbay Harbor, passengers can relax on deck and enjoy invigorating sea breezes and breathtaking views of of the rugged Maine coastline, nearby islands, iconic lighthouses, busy waterways, and marine wildlife. Knowledgeable crew share historical facts about sailing and provide hands-on lessons in hoisting the sails or taking the helm.

Day sailing trips include options to stop at an island for hiking or swimming in refreshing ocean waters. With its old-time charm and personalized sailing experience, the Schooner Eastwind gives tourists a memorable taste of windjammer cruises along the Maine coast. Offering breathtaking scenery and adventure, it’s a premier choice for tourists seeking an authentic Maine sailing adventure. Indeed, for travelers to Maine, this sailing experience is a must-try coastal adventure.


Rugosa Lobster Tours

95 Ocean Avenue, Kennebunkport, ME 04046

Rugosa Lobster Tours in Kennebunkport, Maine

Rugosa Lobster Boat tours offer tourists a unique way to explore Maine’s scenic coastline out of Kennebunkport. Guests can hop aboard an authentic lobster boat with an experienced lobsterman for a hands-on, educational cruise. The captain provides an insider’s look at hauling lobster traps, the lobstering industry, and local marine wildlife. Tours spotlight the area’s famously rocky coast, lighthouses, Bush family estate, and opulent waterfront mansions.

During the ride, guests learn about lobster boat construction, regulations, and the life of a lobsterman. With its behind-the-scenes look at lobstering and close-up coastal scenery, Rugosa Lobster Boat tours give tourists an immersive taste of this iconic Maine profession aboard a real working lobster boat. It’s a one-of-a-kind cruising experience along southern Maine’s coastal shores. Combining education, adventure, and breathtaking views, Rugosa Lobster Boat Tours stand out as a top Maine coastal boat touring attraction.


Bimini Sailing Charters

5 Bay Avenue, Saco, ME 04074

Bimini Sailing Charters in Saco, Maine

Bimini Sailing Charters offers scenic sailing trips aboard a classic catamaran sailboat out of Saco, Maine. Tourists can set sail on the calm waters of Saco Bay and soak in views of sandy beaches, coastal estates, and the historic Camp Ellis pier. With options for both short sails and full-day adventures, each journey is tailored to provide an intimate view of hidden coves, sandy beaches, and picturesque lighthouses. Knowledgeable crews provide an educational sailing experience, allowing guests to help hoist the sails or try their hand at the helm. 

Charters include complimentary drinks and light fare while shimmering sea breezes fill the sails. With its variety of public and private sailings, Bimini Sailing gives tourists an authentic taste of sailimg along Maine’s southern coast. Offering personalized service and breathtaking scenery, Bimini Sailing Charters is a top choice for tourists seeking a picturesque sailing adventure just minutes from Portland, Maine. For those looking to capture the essence of Maine’s maritime charm, Bimini Sailing Charters presents an unmatched experience.


Camden Harbor Cruises

15 Public Landing, Camden, ME 04843

Camden Harbor Cruises in Camden, Maine

Camden Harbor Cruises offers scenic and educational boat tours showcasing the natural beauty of Maine’s Penobscot Bay. Tourists can embark on one of the company’s comfortable vessels and enjoy fully narrated cruises led by knowledgeable captains. Tours glide past rocky islands, historic lighthouses, quaint harbors, and sprawling waterfront estates. The captains provide commentary on the coastal sights, ecology, and local history. Whale watching, sunset cruises, and private charters are also available.

With its variety of cruise options and stunning coastal scenery, Camden Harbor Cruises gives tourists an insider’s perspective on Maine’s dramatic midcoast region. Offering smooth rides, onboard amenities, and experienced guides, it’s a premier choice for tourists seeking a scenic overview of scenic Penobscot Bay by sea. Merging breathtaking views with educational insights, Camden Harbor Cruises ensures a delightful and immersive experience, making it a top choice for those wishing to exploring Maine’s coast by boat.


Schooner Appledore II

18 Bay View Street, Camden, ME 04843

Schooner Appledore in Camden Harbor, Maine

The Schooner Appledore II offers scenic day sailing trips along the rocky Maine coast out of picturesque Camden Harbor. Tourists can climb aboard this classic 86-foot schooner and experience the romance of windjammer cruising. Knowledgeable crew provide hands-on lessons in raising the sails, steering the boat, and traditional sea shanties. Cruises include views of forested islands, historic lighthouses, seals, and seabirds.

During the summer season, guests can also opt to disembark on an uninhabited island for swimming, hiking, and a lobster bake. With its traditional charm and personalized adventures, the Schooner Appledore II gives tourists a memorable sailing trip along midcoast Maine’s dramatic shores. Whether basking in the midday sun or witnessing a spectacular sunset, the Schooner Appledore II promises a blend of relaxation, nostalgia, and natural beauty, making it a must-do for Maine visitors. Indeed, offering stunning scenery and authentic sailing fun, it’s a top choice for visitors looking for a genuine windjammer experience on the Maine coast.


Songo River Queen

841 Roosevelt Trail, Naples, ME 04055

Songo River Queen in Naples, Maine

Songo River Queen Lake Cruises offer scenic tours of Maine’s spectacular Sebago Lake region from the charming town of Naples, Maine. Tourists can embark on the riverboat-style Songo River Queen, a majestic replica of a vintage Mississippi River paddle wheeler, for a fully narrated cruise led by knowledgeable captains. Tours embark from the dock in downtown Naples and glide through Long Lake, showcasing the lake’s pine-dotted islands, winding nature trails, and opulent waterfront homes.

Cruises highlight Naples’ unique history and offer spectacular views of autumn foliage in season. With its blend of sightseeing and local lore, Songo River Queen gives tourists an insider’s perspective on Maine’s second largest lake. Offering smooth rides, onboard refreshments, and picture-perfect scenery, it’s a premier way for visitors to discover the natural beauty surrounding the Sebago Lake region of Maine. Combining old-world charm with modern comforts, the Songo River Queen stands out as a truly unique top boat touring experience in Maine.


Discover the best of Maine with our travel blog highlighting special travel tips, sightseeing suggestions and regional interest stories to make the most of your Maine vacation trip. We bring you insigthful articles about unique places, kid-friendly activities, and regional entertainment that will help in planning your trip to Maine.

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