Top Maine Sailing

Afternoon Windjammer Cruise Along the Coast of Portland Maine

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).

Day Sails and Sunset tours on Schooner Surprise in Camden Maine

Sunset Windjammer Cruise Along the Coast of Portland Maine

1.5 to 2-Hr Windjammer Sailing Trip in Maine w/ Licensed Captain

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.

Windjammer Classic Sunset Sail from Camden, Maine

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.

Schooner Eastwind Sunset Sail to see the Maine Coastline

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.

Windjammer Classic Day Sail from Camden, Maine

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.

Sail Away: Explore Maine's Coastal Beauty on a 2-Hour Excursion

Luxury Camden Sailing Experience

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.

Schooner Eastwind 2 Hour Day Sail in Boothbay Harbor

The Real Portland Tour: City and 3 Lighthouses Historical Tour with a Real Local

1 hour 45 minutesFree Cancellation

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.

Schooner Applejack Sunset Sail Tour in Boothbay Harbor

Portland Tall Ship Cruise on Casco Bay

Welcome Aboard Schooner Lazy Jack in Boothbay Harbor; your Maine Vacation starts here! Join the Schooner crew for a 2hr. day sail 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.

Schooner Applejack 2-Hour Day Sail from Boothbay Harbor

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.

Narrated Bus Tour of Bar Harbor and Acadia National Park

2 hours 30 minutesFree Cancellation

Private Sightseeing Charter on a Vintage Lobster Boat with Drinks

Price varies by group size

Known for its rocky coastlines, wealth of wildlife, and evergreen forests, Acadia National Park promises dramatic scenery—and this fully narrated driving tour makes for an easy way to discover it. Set off from Bar Harbor in a luxury Berkshire minibus, and discover highlights like Cadillac Mountain (the highest point on the East Coast), Thunder Hole (where ocean waves roar), Sieur De Mont's Spring, Jordan Pond, and much more.

Premium Narrated Bus Tour of Bar Harbor and Acadia National Park (3.5 Hours)

4 hoursFree Cancellation

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

Relaxing Saco River Public Sunset Sail

Looking for a romantic way to watch the sunset while in Maine? How about chartering a vintage lobster boat and heading out to Casco Bay, where you'll take in great views of the sea and coastline. Your captain and guide will be on board to point out lighthouses, historic forts, and natural features. A round of drinks is included to toast the sunset with, but more beverages are available to purchase onboard.

Private Sunset Charter on a Vintage Lobster Boat with Drinks

Price varies by group size

Acadia National Park is as big as it is beautiful, making it simple to get lost when going on your own. Instead, choose this self-guided driving audio tour and see the park’s pristine wilderness while hearing about its history from the safety of your own vehicle. Follow a route through the park on an easy-to-download app that gives recommended speed limits and commentary for a unique experience.

Ultimate Acadia National Park Self-Guided Driving Audio Tour

Ultimate Acadia National Park Self-Guided Driving Audio Tour

2 to 3 hoursFree Cancellation

Indulge in a private sailing experience along the serene Saco River and Saco Bay. With a maximum of six guests, this exclusive journey allows you to soak in the stunning scenery while learning about the rich history of the area, including the iconic Wood Island Lighthouse and Biddeford Pool. Perfect for all ages, this charter offers a relaxing atmosphere where you can create lasting memories with family and friends amidst the beautiful Maine coastline. Alternative Biddeford Pickup - From Kennebunkport area this location will save 40 minutes of driving.

Private Sailing Experience along the Southern Maine Coastline

2 to 6 hoursFree Cancellation

This two-hour sunset private sail is the perfect way to experience Maine's sunset on the coast - complete with lighthouses, seals, and seabirds. Sail aboard Heart's Desire, a 101 year old schooner, designed by famed yacht designer, John Alden. Heart's Desire measures 53' feet and features some of John Alden's trademark design elements including a long bowsprit and dramatic, raked transom. Built in 1925 by T.S. Soule in South Freeport, Maine, Heart's Desire has been used mainly for chartering along the Eastern seaboard in New York, New Jersey, Massachusetts, and Maine.

2 Hours Sunset Private Charter on Heart's Desire in Casco Bay

This experience combines three things you rarely get in one outing: a small-group boat tour, yoga on a Casco Bay island, and a celebratory drink on the water. Choose a morning experience with mimosas and bakery favorites or an afternoon flow followed by a guided four-wine tasting and savory bites. With only a handful of guests, the experience feels personal, relaxed, and completely different from a traditional boat tour or yoga class.

Portland ME: Casco Bay Boat Tour w/ Island Yoga + Mimosas or Wine

3 hoursFree Cancellation

Experience the Magic of our Private Sunset Sail. Witness the enchanting transformation as the setting sun bathes the world in mesmerizing hues, crafting memories destined to endure. Set sail along Maine's exquisite coastline aboard our vessel, where every moment unfolds as a cherished tale. Explore the hidden wonders of the Saco River and Saco Bay under the guidance of our seasoned crew. Surrender to the serene embrace of the moment as the ocean murmurs its secrets and the sun paints the horizon with a radiant glow. Seize the opportunity to take the helm and experience the exhilaration of sailing firsthand. Whether craving adventure or seeking inner peace, our private sunset sail promises an unparalleled experience. Allow us to craft an unforgettable journey that lingers in your heart long after the sun has dipped below the horizon. Alternative pickup available in Biddeford for added cost, saves 40 min of driving, contact us for availability.

Golden Hour Escape: Private Sunset Sail in Coastal Maine

Narrated Bus Tour of Bar Harbor and Acadia National Park

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Must-Dos in Maine

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What are people saying about Maine

Ilene_M, Sept 2026

Acadia National Park narrated tour

This was a fabulous tour….and our guide, Rick, in particular. We learned so much history about Acadia National Park and the surrounding area - ‘never would have even thought of some of the things he brought up! The stories he recounted were rich with facts and commentary - go ahead and take this tour, you won’t be sorry!

Day Sails and Sunset tours on Schooner Surprise in Camden Maine

Tim_K, Sept 2026

Sail and Sigh with fresh air and fun!

Captain aTaylot and First Nate Ian are friendly, fun and knowledgeable. It's an out-an-back sailing of Penobscot Bay, and is beautiful if the weather is right. The 108-year-okd schooner is beautiful and comfortable. Wonderful experience. Our sailing was in mid?-September, and the weather was perfect! Allow time to shop and stroll around Camden.

The Real Portland Tour: City and 3 Lighthouses Historical Tour with a Real Local

Julie_H, Sept 2026

Its a do not miss. Derek...

Its a do not miss. Derek was fantastic and very knowledgeable about all things Portland. He was born and raised here and is the local college librarian. Has top notch comedian skills too. Small group. Very succinct tour. PS. Do not miss Holy Donuts. Derek gave us this tip too.

Afternoon Windjammer Cruise Along the Coast of Portland Maine

Donna_F, Sept 2026

A fun afternoon on the sea!

It was a perfect afternoon on the water. The crew was amazing, very friendly, and the weather couldn’t have been better. Some folks brought their own picnic and beverages as we did the 12-2pm cruise. You won’t find a better activity on such a beautiful sunny day!

Private Sightseeing Charter on a Vintage Lobster Boat with Drinks

Jason_P, Sept 2026

Quintessential Portland ME on the Water!

Hands down one of the best highlights of our trip! The vintage lobster boat was super comfortable, and the route captured quintessential Maine beauty. Our guide was top-notch, sharing all the history and local info you could ask for. Highly recommend this private sightseeing charter to everyone—10/10!

Sunset Windjammer Cruise Along the Coast of Portland Maine

Marinna_H, Sept 2026

Peaceful Sailing

Such a fun experience! I was a little worried about getting sea sick, but the ride was so smooth despite it being pretty windy so don’t let that scare you! Definitely bring layers. No “official” tour so it was pretty peaceful and quiet on our boat, but got to see an amazing sunset over the harbor and Portland Head Light.

Premium Narrated Bus Tour of Bar Harbor and Acadia National Park (3.5 Hours)

Sandra_M, Aug 2026

Small Group was perfect

from start to finish it was a wonderful experience and loved a small group and the bus was very comfortable. Heather was extremely knowledgeable and kept in life by telling jokes throughout the experience. You definitely catch all the highlights of Acadia. It would be nice on Cadillac Mountain to have a little more than 25 minutes and I guess after having this drive-through you could go back.

Schooner Eastwind 2 Hour Day Sail in Boothbay Harbor

Pamela_G, Aug 2026

We have a great time! We...

We have a great time! We had 3 teenagers with us and although they were skeptical about it being “boring”, it ended up being their favorite part of vacation. It was about 80 degrees on land and chilly/windy when we got out on the water so if you get good easily definitely bring a light jacket or sweatshirt. My oldest son and husband were fine with just jeans and a tshirt. The captain and crew woman were super nice.

Portland Tall Ship Cruise on Casco Bay

Leonard_B, July 2026

The trip was amazing! We...

The trip was amazing! We were on the smaller of the 2 boats and had a great time! The crew was great! We were mostly interested in seeing lighthouses and this trip did not disappoint. We booked this through Viator, and that was a mistake. Their custom service is terrible. We kept trying to get out tickets online and couldn't. We had to download the app, then received a link in an email, which pretty much took us back to same page that showed that this is not the ticket, that we need to download the app to get the tickets. We went round and round on this for days. Finally on the morning of the cruise, about 2 hours before we were scheduled to sail, we called Viator customer support. We spent a lot of time on the phone and were told that they couldn't contact anyone with the ship company because they wouldn't be open for a couple more hours since they were on the west coast. Our trip is in Portland Maine on the east coast. This woman didn't have it together. Much like trying to get the tickets, this just kept going round and round. We finally just went to the location and asked if we were on the list, and we were, but the boat was sailing from a different dock. The cruise company tried to contact all the passengers, but we were never notified of the change. Luckily we had time to walk to the other dock and made it on the ship in plenty of time. The trip was amazing, Viator, not so much.

Windjammer Classic Day Sail from Camden, Maine

CHARITY_W, June 2026

Smooth Sailing

The crew were very kind and helpful. They shared their knowledge and stories which made it a more enjoyable trip on the water. The Appledore is a beautiful and well kept sail boat from late 1800s. Such a treat to sail the bay on her. We got to participate in hosting up the sails and get to understand history of the light house. It was smooth sailing the whole way.