Top Maine Cruises & Sailing

Experience the beauty of Casco Bay and set sail from Portland, Maine for an unforgettable sunset cruise. Bring your own snacks and drinks, kick back, and relax as your captain sails towards incredible views. Feel free to ask your captain and crew questions about the scenery, and remember to keep your eyes peeled for seals and seabirds.

Cruise through the scenic waters of Frenchman Bay during a leisurely sailing trip. Admire views of Acadia National Park in Maine during this sightseeing boat tour. Keep an eye out for wildlife including eagles, seals, and porpoises during the sail. Check out views of the Porcupine Islands from the spacious decks on board a Windjammer. Picnics are welcome on board.

Enjoy a one-of-a-kind perspective on Maine’s picture-perfect sunsets on this early-evening sailing tour. Departing from the scenic Camden Harbor, travel aboard a large, elegant windjammer that was built according to traditional methods. Sail past Curtis Island Light, admire Mt. Battie, and take in the ruggedly beautiful coastal scenery. En route, spot wildlife, enjoy drinks on board (available for purchase), and toast to the sunset.

Step back in time and immerse yourself in Maine's maritime heritage on a sailing trip onboard the only historic day sailing schooner out of Camden. Soak up views of Maine's lighthouse-dotted coastline while the crew points out wildlife, tells you the history of the area, and shows you local landmarks. Get hands on by learning to haul sails or just relax with a bottle of wine and a picnic (byob).

Board your boat, the Elizabeth Grace, near the Portland ferry terminal and cruise around Portland Harbor at sunset, when Casco Bay and the coast of southern Maine are the most romantic. See lighthouses, historic forts, and stray groups of swimming seals and enjoy local craft beer from the boat. As the sun sets, turn toward Portland to see the town light up before returning to harbor.

Sail away from it all on your two-hour voyage aboard Boothbay Harbor's schooner to relax and see the Maine coastline. Lighthouses, fishing lobstermen, wildlife, and remote islands accessible only by boat dot the seascape. Our goal is for you to experience the best two-hour classic sailing trip in the world. We have been working on this experience in Boothbay Harbor for almost 50 years, have a strong local following, and have been featured in national, best-selling publications. We have the best sailing vessel for exploring Boothbay Harbor. We use an onboard engine to get us to the sailing grounds quickly. The size of our vessel is perfect for exploring all the areas of our rocky harbor to see life along the Maine coast. There are no obstructions on our deck other than the masts, so you always have a full 360-degree view from every seating position.

Cruise Camden’s scenic coast aboard the Appledore II, a historic wooden schooner that's a thrilling taste of traditional Maine sailing. You can take the helm, raise the sails, or just find a comfortable spot on deck; an environmentally-friendly alternative to motorized Camden cruises, this sailing tour is a great way to explore the coast with just the sounds of the wind, sails, and sea to keep you company.

Sail with us for a two-hour Windjammer Sail on Casco Bay in Portland, Maine — the perfect way to experience the beauty of the rugged coastline, complete with lighthouses, seals, and seabirds (NOTE: This is NOT a narrated tour, but our crew is happy to answer any questions you have about the sites). Pack a meal, bring your favorite wine or beer, and sit back and relax as you slip through the pristine waters of Casco Bay. All ages are welcome! Whether you are nine years old or 99, sailing aboard one of our Maine historic schooners is a unique adventure. All of our wooden windjammers were built in Maine and three are listed on the National Register of Historic Places.

Welcome Aboard Schooner Applejack in Boothbay Harbor; your Maine Vacation starts here! Join the Schooner crew for a sunset sail adventure on Boothbay Harbor’s oldest windjammer. Help hoist sails or take a turn at the wheel as we set a course out past Burnt Island Light, Squirrel Island, Ram Island Light and the outer islands of Boothbay. Keep a sharp eye out for porpoise, Osprey, Bald Eagles, and harbor seals as we slip by local boats setting their pots or hauling in the lobster catch of the day. We have the best, most intimate sailing vessel for exploring Boothbay Harbor. Enjoy the beautiful coastline on our deck with a 360 degree view from every seat.

Small groups of up to six. Two staff members to take care of you. Cushioned seating for all. Fastest boat in the harbor

Embark on an unforgettable 1.5-hour cruise along Maine's breathtaking coastline at sunset. See four of Maine's most iconic lighthouses, spot seals and seabirds, and take in the historic forts that dot the landscape. Bring your favorite wine or beer and a delicious meal, and unwind as we cruise through the serene waters of Casco Bay. Journey aboard Ruth—a charming 39-foot classic picnic-style tour boat crafted in 1935 at Handy Boat in Falmouth, Maine. Don't miss out on this unique sunset experience!

Sail with us for a two-hour morning Windjammer Sail on Casco Bay in Portland, Maine. This is the perfect way to experience the beauty of the rugged coastline, complete with lighthouses, seals, and seabirds. (NOTE: This is NOT a narrated tour, but our crew is happy to answer any questions you have about the sites). All ages are welcome, whether you are nine years old or 99, sailing aboard one of our Maine historic schooners is a unique adventure. See Fort Gorges, Bug Light Park, and the beautiful Portland coastline. Pack a meal, bring your favorite wine or beer, and sit back and relax as you slip through the pristine waters of Casco Bay. All of our wooden windjammers were built in Maine and three are listed on the National Register of Historic Places.

Sail away from it all on your two-hour voyage aboard Boothbay Harbor's schooner to relax and see the Maine coastline. Lighthouses, fishing lobstermen, wildlife, and remote islands accessible only by boat dot the seascape. Our goal is for you to experience the best two-hour classic sailing trip in the world. We have been working on this experience in Boothbay Harbor for almost 50 years, have a strong local following, and have been featured in national best-selling publications. We have the best sailing vessel for exploring Boothbay Harbor. We use an onboard engine to get us to the sailing grounds quickly. The size of our vessel is perfect for exploring all the areas of our rocky harbor and seeing life along the Maine coast. There are no obstructions on our deck other than the masts, so you always have a full 360-degree view from every seating position.

Step aboard for an unforgettable journey along Maine's stunning coastline! Join us for a two-hour sail and create memories to cherish forever. Experience the beauty of Maine as you glide through the waters of the Saco River and Saco Bay on our intimate sailboat. No prior experience necessary! Our knowledgeable crew will share fascinating stories about the eight captivating islands of Saco Bay and the picturesque Old Orchard Beach. Admire the iconic New England charm of Wood Island Lighthouse and Biddeford Pool as you soak in the wonders of the ocean and sun. Take in the breathtaking views of the endless horizon and keep an eye out for wildlife along the way! If you're feeling adventurous, you can even try your hand at sailing the boat yourself. Most importantly, take this opportunity to relax and unwind as you escape the hustle and bustle of everyday life. Come aboard and let us show you the beauty of Maine's coastline as you enjoy a well-deserved break on our two-hour sail.

See a new vantage on Portland and the Maine coast—and enjoy a relaxing excursion out on the water—on this sailing tour. Make your own way to the Maine State Pier, and hop aboard a traditional, Maine-built windjammer. Once you set sail, soak up the sea breezes, look out for seals, and even take a turn at hoisting the sails or behind the ship’s wheel.

What sets this experience apart is its simplicity, timing, and sense of place. This isn’t a busy sightseeing tour—it’s a small-group, early-morning experience designed around the calmest, most beautiful time of day on Penobscot Bay. With a maximum of six guests, the atmosphere stays personal and unhurried. You’re not following a script or rushing between stops—just easing into the day on the water as the coast quietly comes to life around you. Traveling on a classic wooden lobster boat adds to the authenticity, offering a true connection to Maine’s working waterfront. Fresh coffee and breakfast are served on board, turning the experience into something more than a cruise—it’s a moment. It’s the kind of start to the day that feels simple, but stays with you long after.

Set sail on a memorable 2-hour sunset cruise through the stunning landscapes of Kennebunkport, ME. Glide along the Saco River and take in the picturesque views of Biddeford Pool, Camp Ellis, and the iconic Wood Island Lighthouse. Ideal for small groups of up to 6, this intimate sailing adventure welcomes all ages, ensuring a delightful experience for families, friends, or couples. Enjoy the beauty of the Maine coast as the sun sets, creating lasting memories on the water. - 2-hour sunset cruise along the scenic Saco River - Limited to 6 passengers for a cozy experience - All ages welcome—perfect for families and couples - Daily departures based on sunset times, ensuring a unique experience each time

Discover Maine's picturesque coastline on the South Coast Tour, featuring iconic locations like Nubble Lighthouse and the charming villages of York, Ogunquit, and Kennebunkport. Enjoy breathtaking ocean views along Marginal Way, savor the freshest New England clam chowder, and indulge in delicious Maine lobster. This private driving tour, lasting 6.5 hours, is perfect for couples, families, or groups, with flexible pick-up options along the coast. Whether you're an avid photographer or a history enthusiast, the knowledgeable guides will tailor the experience to your interests, ensuring a memorable adventure along Maine's stunning shores. Explore coastal gems including Nubble Lighthouse and Perkins Cove Enjoy lunch featuring Maine lobster along the water Private tour accommodating up to 5 passengers. We have larger vehicles at an additional cost. Guided experience with insights into local history and culture

Visitors to Portland can easily miss some of Maine's most stunning sights, since you really need a car to explore the scenic coastline. Avoid the headache of arranging your own transportation or renting a car on this small-group guided tour of Portland's must-see sights. Stop in downtown Portland and visit three lighthouses, including Portland Head Light—an historic lighthouse perched on the rocky coast.

One hour walking tour - pirates, sardines, and a captured city - the history of Eastport and how life has changed in Downeast Maine. Leaving from the cruise pier, the tour will cover the downtown area of Eastport, stopping along the way for views of historic buildings, sweeping ocean views, and evidence of industries from long ago. Learn about the different fishing industries that shaped the town. Join this tour of downtown Eastport and learn about what makes this coastal village unique and how it's been important throughout history. The tour will meet and end near the cruise ship terminal making it perfect for those coming to port. We will stop for great views of the waterfront and your local guide will teach you about the way of life in Downeast Maine. This one-hour tour is a great opportunity to learn a little bit about the area and get recommendations from your guide about how to spend the rest of your time!

Be among the first in North America to greet the new day from the jagged granite summit of Cadillac Mountain. Skip the stress of the notoriously elusive vehicle reservations that vanish in seconds; we handle all the red tape, entry passes, and logistics for you. Our pre-dawn pickup whisks you up the mountain while the stars are still bright, bypassing the crowded parking scrambles. Instead of perched on cold, uneven rocks, you’ll relax in premium, high-back camp chairs positioned at the optimal vantage point. As the horizon ignites in shades of violet and gold, savor the true taste of Maine with a warm, local wild blueberry muffin and a steaming cup of locally roasted coffee. Settle into your front-row seat with a blanket and experience Acadia’s crown jewel in total, delicious comfort as the guide take pictures with your cameras of the moment.

Charter a vintage lobster boat, dubbed MONHEGAN, and set sail with this two-hour tour into Casco Bay. You'll get great views of the Maine coastline, passing by four lighthouses as you go. This is a great opportunity to take photos of the coastline and waters, while learning about local nautical history from a knowledgeable captain.

Take a deep dive into Bar Harbor, Acadia National Park, and Mt. Desert Island on this half-day bus tour. Since your transportation is provided, you can focus on the scenery and taking in the insightful narrative instead of driving and directions. Make three stops within the town of Bar Harbor and the National Park to witness firsthand the views and wildlife that make this island so special. Stops include Cadillac Mountain, Sieur de Monts Spring, and Thunder Hole.