Top Maine Sailing Tours

Day Sails and Sunset tours on Schooner Surprise in Camden Maine

Experience the scenic coastline of Casco Bay in Portland, aboard a traditional Maine windjammer. Sail past lighthouses, rocky islands, and wildlife while enjoying the peaceful pace of a classic schooner cruise. Bring your own picnic and drinks to enjoy on board as you take in the views. Suitable for all ages, this relaxing sailing experience offers an authentic way to discover the beauty of the coast.

Afternoon Windjammer Cruise Along the Coast of Portland Maine

Sunset 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.

Windjammer Classic Sunset Sail from Camden, Maine

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

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

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

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

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

Luxury Camden Sailing Experience

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

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

There are a lot of ways to get out on the water in Maine, but at Sailing Sasa, we make every charter feel personal, relaxed, and genuinely memorable. We’re a small, family-run sailing charter, and Sasa is a thoughtfully restored and beautifully outfitted yacht designed to feel warm, welcoming, and comfortable from the moment you step aboard. Every sailing day trip in Maine we offer is fully customizable and built around your group’s vision of a perfect day on the water. Whether we’re exploring the islands, sailing past lighthouses, or anchoring at a secluded cove for a swim, the goal is simple: give you a day that feels easy, personal, and genuinely fun.

Private Half Day Sailing Charter in Penobscot Bay

4 hoursFree Cancellation

5% savings

from

$475$451

Price varies by group size

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

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

3 hoursFree Cancellation

A half-day sailing charter offers a unique and personalized way to explore the stunning Maine coast. Departing from downtown Portland, this private experience aboard Sasa, a family-run small business charter sailboat, with a coast-guard certified captain, allows you to cruise through Casco Bay, enjoying views of iconic landmarks like Portland Head Light. With options to swim in secluded spots or simply relax, every charter is tailored to your group's preferences. Enjoy light refreshments and the chance to take the helm or trim the sails, making for an unforgettable day on the water.

Private Half Day Sailing Charter in Portland Maine

4 hoursFree Cancellation

Price varies by group size

There are a lot of ways to get out on the water in Maine, but we make every charter feel personal, relaxed, and genuinely memorable. We’re a small, family-run sailing charter, and Sasa is a thoughtfully restored and beautifully outfitted yacht designed to feel warm, welcoming, and comfortable from the moment you step aboard. A half-day sail is the easiest way to get out on the water and see the Maine coast from a completely different perspective. This small group Maine sailing charter is perfect if you want a relaxed few hours to cruise, take in the views, brush up and your sail trim, or just relax and maybe sneak in a swim on a warm day.

Casco Bay Sailing Escape: Half Day Custom Boat Charter

Casco Bay Sailing Escape: Half Day Custom Boat Charter

4 hoursFree Cancellation

5% savings

from

$199$189

What better way to see the delights than in the style of a private charter for you and five friends or family members? Experience the beauty and serenity of the rugged coastline as you gaze upon seabirds, sea houses, and islands. Guests are encouraged to help raise the sails with a deckhand and steer the ship for themselves. Your charter is your time to relax, celebrate, entertain, and sail, so you get to set the pace and atmosphere. Beer, wine, and other alcoholic beverages are permitted on board.

Portland Tall Ship Private Charter on Casco Bay

Portland Tall Ship Private Charter on Casco Bay

This two-hour afternoon private cruise is the perfect way to experience Maine's coast, your special event, or a family get-together that will never be forgotten. Ride aboard Heart's Desire: designed by famed yacht designer - John Alden, measures 53' feet and features some of his 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, and most recently Massachusetts.

Casco Bay: Private Afternoon Charter on Heart's Desire

Day Sails and Sunset tours on Schooner Surprise in Camden Maine

Must-Dos in Maine

1 / 2

What are people saying about Maine

Micheal_D, Oct 2026

Lovely Sea Day at the Beginning of Fall

This sailing was an enjoyable experience. The water was smooth and the owners were operating during our tour. They shared much about the town and the vessel. The boat is well maintained and in great condition for its age. You can see that the owners take pride in it.

Sunset Windjammer Cruise Along the Coast of Portland Maine

Tara_R, Oct 2026

Such a lovely and...

Such a lovely and relaxing ride. We went out right before sunset and things couldn’t have been more perfect. Luke and his team provided a smooth sailing with lots of great convo and information about the area. It was the perfect end to our trip to Portland.

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

Simone_S, Sep 2026

We went late sep right as...

We went late sep right as a nor’easter was blowing in and captain wanted to ensure everyone was comfortable so we only saw a couple of islands before headed back to the Saco river and sailed across river , little disappointing but good experience none the less , will def recommend

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

Philip_W, Sep 2026

Brilliant tour well worth booking.

This was a brilliant tour with Derek the owner/guide keeping everyone amused with his knowledge and anecdotes of the surrounding area. You will not be disappointed and because it is a relatively small group there is plenty of interaction. Make sure you look up the photo of his Minibus so you reckonise it when you are waiting about 3 Blocks down from the cruise terminal it’s not far.

Narrated Bus Tour of Bar Harbor and Acadia National Park

Ilene_M, Sep 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!

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

Sara_M, Sep 2026

Excellent tour

I was lucky to be on this tour. As our driver gave wonderful narrative of the sights and park history, we were escorted to very convenient spots to view. We watched other, private cars driving around and trying to find parking. This tour was absolutely wonderful with a well informed host, comfortable van and great tour.

Afternoon Windjammer Cruise Along the Coast of Portland Maine

MaryLou_G, Sep 2026

Sailing the harbor

We had a beautiful and relaxing ride on the water. Everything was great and the crew were knowledgeable and friendly. The only problem was my own fault as I thought this was a lighthouse tour and it was not. I’m not sure how I messed that up. Even without seeing lighthouses up close, it was an amazing experience.

Private Sightseeing Charter on a Vintage Lobster Boat with Drinks

Jason_P, Sep 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!

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.

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.