Top Maine Sailing Tours

Afternoon Windjammer Cruise Along the Coast of Portland Maine

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.

4.7

(245)

from $69

Windjammer Classic Sunset Sail from Camden, Maine

Windjammer Classic Sunset Sail from Camden, Maine

Sunset Windjammer Cruise Along the Coast of Portland Maine

(486)

from $65

Likely to Sell Out

Luxury Camden Sailing Experience

4.7

(184)

from $77

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).

(14)

from $125

Day Sails and Sunset tours on Schooner Surprise in Camden Maine

Day Sails and Sunset tours on Schooner Surprise in 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.

(125)

from $78

Schooner Eastwind Sunset Sail to see the Maine Coastline

Schooner Eastwind Sunset Sail to see the Maine Coastline

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

4.7

(69)

from $60

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.

4.1

(686)

from $70

Windjammer Classic Day Sail from Camden, Maine

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.

4.8

(440)

from $60

Take your turn at sailing the boat if you wish

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

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.

(58)

from $139

Casco Bay Morning Windjammer Sail

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.

(37)

from $61

Schooner Applejack Sunset Sail Tour in Boothbay Harbor

Schooner Applejack Sunset Sail Tour in Boothbay Harbor

Portland Tall Ship Cruise on Casco Bay

(53)

from $60

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.

4.6

(242)

from $102

Schooner Eastwind 2 Hour Day Sail in Boothbay Harbor

Schooner Eastwind 2 Hour Day Sail in Boothbay Harbor

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.

4.6

(158)

from $55

Schooner Applejack 2-Hour Day Sail from Boothbay Harbor

Schooner Applejack 2-Hour Day Sail from Boothbay Harbor

Private Sightseeing Charter on a Vintage Lobster Boat with Drinks

4.4

(38)

from $55

MONHEGAN is equipped with a finely finished wooden table in between cushioned "booth style" benches

Price varies by group size

(67)

from $380

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

1 hour 45 minutesFree 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

(1,623)

from $74

Relaxing Saco River Public Sunset Sail

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.

(1)

from $149

Private Sailing Experience along the Southern Maine Coastline

Private Sailing Experience along the Southern Maine Coastline

2 to 6 hoursFree Cancellation

(2)

from $747

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.

Special Offer

Narrated Bus Tour of Bar Harbor and Acadia National Park

Narrated Bus Tour of Bar Harbor and Acadia National Park

2 hours 30 minutesFree Cancellation

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

(43)

from $407

Special Offer

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

Acadia National Park is as big as it is beautiful, making it simple to get lost when going on your own. Instead, choose this Acadia National Park Self-Guided Driving Audio Tour and see the park’s pristine wilderness while hearing about its history from the safety of your own vehicle. You’ll 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

2 to 3 hoursFree Cancellation

4.2

(551)

from $17

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

Golden Hour Escape: Private Sunset Sail in Coastal Maine

(22)

from $849

Come sailing aboard Heart's Desire, designed by famed yacht designer - John Alden, measures 53' feet and features some of his trademark design elements. Built in 1925 by T.S. Soule in South Freeport, Maine, Heart's Desire is 100 years old this year and has been used mainly for chartering along the Eastern seaboard in New York, New Jersey, Massachusetts, and Maine. This two-hour private, morning sail is the perfect way to experience Maine's coastline. Whether you are interested in getting married in an intimate setting, a special way to celebrate a reunion, birthday or anniversary, or just want to enjoy sailing at its finest, step aboard and plan an event never to be forgotten!

2 Hour Private Morning Charter on Heart's Desire in Casco Bay

2 Hour Private Morning Charter on Heart's Desire in Casco Bay

4.5

from $550

Windjammer Classic Sunset Sail from Camden, Maine

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Top Attractions in Maine

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What are people saying about Maine

Loretta_K, Aug 2026

Sunset cruise will not disappoint

We had a fabulous time on the Appledoorc sunsets cruise. Captain Pablo was very friendly and informative during our sail. The schooner was at full capacity and the mates, Ryan and Andy raised the sails and made sure everyone had fun. The drinks and beautiful weather for our sunset sail also helped made this a memorable trip. Highly recommend!

Afternoon Windjammer Cruise Along the Coast of Portland Maine

Dan_T, Aug 2026

Tour was as described....

Tour was as described. The captain and crew are very knowledgeable but don’t bore you with endless narration. We brought on drinks and snacks but saw others bring a takeout lunch. It’s up to you how involved or relaxed you want to be. Tour was fantastic and a nice break from walking the streets of Portland.

Day Sails and Sunset tours on Schooner Surprise in Camden Maine

margaret_m, Aug 2026

Highly Recommended

Our 2-hour sail on the Schooner Surprise is a memorable way to connect with Maine’s long maritime heritage, as well as seeing what makes coastal Maine so special. The couple that owns the Surprise are very approachable/friendly and have been sailing for decades so the definitely know what they are doing. Highly recommended.

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

Wendy_H, Aug 2026

A must do tour!

Everyone should take this tour before you do anything in Acadia National Park. You get tons of historical and geological information. Plus you get taken to all the top sites and you don't have to mess with the traffic or parking. You can go back the next day if you want to see more of a particular location or venture out to other areas of Acadia National Park. And you may be lucky enough to get Eric Jordan as your driver who has lived in the area for 40 years. He is extremely knowledgeable.

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

Ines_d, Aug 2026

Afternoon sail

Beautiful afternoon sail! Captain Bob and Chloe took such great care of us. We brought our own snacks and they served it beautifully. They do offer food or drinks for purchase. They educated us about the lighthouse and the lobster traps. We had a 5 year old boy and they made sure he was safe and entertained. I would definitely recommend this tour. Thank you

Schooner Eastwind 2 Hour Day Sail in Boothbay Harbor

tracylfearon, Jul 2026

Great way to spend an afternoon!

Matt (Capt) and Brian (mate) were awesome! Personable, professional, and informative. The boarding process was easy, with seats assigned so groups were able to be guaranteed a seats together. Drink menus were offered and service was swift. The weather was perfect and we were treated to seal and porpoise sightings. We didn’t go out as far as I thought we would, and I wish there was narration/information about what we were seeing. I don’t think either of those things detracted from the experience, though. I highly recommend this as great activity while visiting Maine!

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

Mary_A, Jul 2026

Informative and Enjoyable Portland, Maine Tour

We took an excellent tour of Portland and the 3 lighthouses. Our guide was incredibly knowledgeable and funny. He shared fascinating history about the buildings and the city itself. We visited the 3 lighthouses, with plenty of time to take photos and enjoy the views. I highly recommend if you want and informative and enjoyable experience

Portland Tall Ship Cruise on Casco Bay

Leonard_B, Jul 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.

Narrated Bus Tour of Bar Harbor and Acadia National Park

Patricia_W, Jul 2026

Informative and carefree drive!

It was great seeing some of the park with someone else driving the park roads! Our driver was informative about the history of the park and the points of interest along the drive. He was friendly with all of us and even had our 9-year-old “help” count the number of passengers at each stop. It is definitely worth the cost to be escorted and learn about the park at the same time!

Windjammer Classic Day Sail from Camden, Maine

CHARITY_W, Jun 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.

Casco Bay Morning Windjammer Sail

Steven_C, Sep 2025

Try this cruise-you won't be disappointed

We got to sail on a 101 year old schooner. The weather was great but we did not have enough wind to fill the sails. The sails were raised and anyone who was willing was able to join in. It was lovely to see the huge sails ready to push us along . Even if we could not have the wind take across the water-the crew was great. Heill was a great tour guide and so interesting. She answered all our questions and listened to our stories. We felt very safe having her and Jake crew the boat. Our captain was very friendly and made us know we were safe.