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Your Guide to the BEST Maine Sailing Tours | Windjammers, Sailboats, & Schooner Tours

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Everyone knows that Maine has a stunning coastline and breathtaking views of the Atlantic Ocean from pristine beaches to rugged cliff walks. But, have you ever considered seeing Maine from the water? Set sail on an exciting adventure on one of the best Maine sailing tours onboard a windjammer, sailboat, or schooner.

We think it’s the best way to view the Maine coast , and what could be more exhilarating than setting sail out of a Maine harbor aboard a tall-masted schooner? Down the coastline from the Downeast & Acadia region to the Southern Maine Coast , there are so many sailing excursions to choose from.

The best part? You can sit back and relax while someone else does the sailing and navigating. Or, you may lend a hand and hoist a sail if you prefer. There’s no better way to experience the beauty of Maine than on a historic sailing trip, so check out these options for your next visit to Maine.

Downeast & Acadia Sailing Tours

Downeast windjammer cruise lines.

If you’re looking for a variety of options for sailing, Downeast Windjammer Cruise Lines in Bar Harbor has you covered. Offering a Sunset Sail, a Morning Sail, and an Afternoon Sail, there’s a wonderful experience no matter the time of day. Each sail has its own vibe.

The Sunset Sail is the most popular cruise that Downeast offers. It includes live folk music, beer, and wine for sale. Or, enjoy sailing in Frenchman Bay during the Morning Sail, which is more relaxed but still offers breathtaking views of Acadia National Park .

The Afternoon Sail is perfect for those looking for a narration during the sail. The captain will point out points of interest, regale you with the local history, and discuss wildlife.

No matter the sail, you can bring a picnic of snacks along, and most sails are pet-friendly.

Downeast Sailing Adventures

Southwest Harbor

Step aboard the Real Maine for an unforgettable experience sailing around the Cranberry Islands, Acadia, and Somes Sound. This tour will take you by lighthouses, past gorgeous homes on the shore, and by working fishing boats.

Book a private charter or a group day sailing adventure for up to six passengers. Downeast Sailing Adventures has daily sails on its 33-foot boat Surprise and its 38-foot boat Swan .

Sail Acadia

Northeast Harbor & Southwest Harbor

Sail Acadia offers trips out of two harbors, Northeast Harbor and Southwest Harbor . Sailing trips can be either shared or privately chartered. Private charters can be catered to your preferences with sailing instructions or a stop at an island for a picnic included.

Book a morning sail for calm waters with gentle sea breezes and good opportunities to view local wildlife. The morning sail is suggested for first-timers and children.

Or, book an afternoon sail for stronger winds that will make the sailboat cruise faster. This sail typically sees seals along the route, and the captain will often give a narration of the wildlife and history of the area.

Another option is a sunset sail for a romantic experience. This sail will have you seeing gorgeous sunset views on calm waters.

Schooner Tours in MidCoast Maine

Schooner stephen taber.

If you’re looking for an all-inclusive overnight experience, book a sail aboard the 150-year-old Stephen Taber . Each sail includes accommodations in one of 12 cabins, meals, wine (on evening sails), a lobster bake and barbecue on the beach, and evening entertainment.

Guests can choose from a themed trip or a private charter from Rockland Maine . Themed trips are a lot of fun and span from three to six nights, depending on your preference.

Enjoy trips such as Culinary Explorations; ‘Wine, Dine, and Chocolate;’ Yacht Racing Regatta; Penobscot Bay’s Hidden Gems; and more. These trips are sure to be memorable experiences, and by the end of the trips, you’ll feel like family with the other guests on board.

Here are more MidCoast Maine boat tours that are part of the Maine Windjammer Association like the Schooner Stephen Taber : Schooner American Eagle | Captain Tyler King | Rockland, ME Windjammer Angelique | Captain Dennis Gallant & Candace Kuchinski | Camden ME Schooner Grace Bailey | Captain Sam Sikkema | Rockland, ME Schooner Heritage | Captains Sean Grims & Ben Welzenbach | Rockland, ME Schooner Ladona | Captain J.R. Braugh  | Rockland, ME Schooner Lewis R. French | Captain Becky Wright and Nathan Sigouin | Camden, ME Schooner Mary Day | Captain Barry King and Jen Martin | Camden, ME

A Morning in Maine

If you’re strapped for time and want a shorter sail, A Morning in Maine’s sailing trips are a wonderful experience. The two-hour sailing adventures take place aboard a 55-foot ketch that passes lighthouses and other schooners.

The morning trip is perfect for those looking for calm sailing. The mid-afternoon sail has windier conditions for a faster sail. Evening and sunset sails feature beautiful sunset views and a relaxing ride. Guests are often given the chance to try to steer the boat as well.

Schooner Surprise

The Schooner Surprise has been sailing for over 105 years, with 30 of those years setting sail out of Camden Maine . Guests can book a two-hour sail with views of the lighthouse, summer houses and views of Penobscot Bay .

These family-friendly sails let guests, including children, take the wheel while out at sea. Special sails include a Full Moon Sail that features live music during sunset and a trip lasting two hours into the night. Or, book a fireworks view sail or a Birding and Marine Life Tour with an ornithologist.

Portland & Casco Bay Sailing Tours

Portland schooner co..

Portland Schooner Co. sets sail from Portland Maine and cruises through Casco Bay for a delightful trip along the coastline and past lighthouses and ocean life, like seals. On the two-hour sail, bring your own picnic and even alcoholic beverages for a relaxing, scenic time on the water.

These sails are perfect for all ages. Sails take place throughout the day on one of the five historic wooden schooners. The sails are relaxing and do not include narration, but the crew is available to answer any questions that guests may have.

Maine Sailing Adventures

Maine Sailing Adventures offers traditional two-hour and themed sails through Casco Bay . What sets it apart from other sailing companies is its unique themed sails. Try an acoustic sail that features live music. Or, try a wine sail that includes a wine tasting for adults.

Have you ever heard of a yoga sail? This ship can accommodate up to 12 guests for a yoga class that you won’t experience anywhere else. Enjoy amazing views of the water while working on your poses.

Sail Portland Maine

If you’re looking for an intimate sailing adventure, Sail Portland Maine has you covered. Guests can choose a private charter or a public trip. The public trips’ capacity is 12 people, so you know that your sail won’t be too crowded.

Day and sunset trips are two hours in length and pass by all of the famous Casco Bay features — like historic forts, lighthouses, and if you’re lucky to spot them, seals. Guests are welcome to bring their own food and drinks, while bottled water is complimentary on board.

Schooner Tours on the Southern Maine Coast

The pineapple ketch.

Kennebunkport

There’s no better way to see the Kennebunk River than sailing on it. The Pineapple Ketch departs from Nonantum Resort for a dazzling trip along the river and the Kennebunkport coastline.

You’ll see gorgeous seasonal cottages, including the famous cottage of President George H.W. Bush. Enjoy views of the Goat Island Lighthouse, local harbors, seabirds, and seals.

Each sail includes complimentary bottled water and sodas, but guests are also welcome to bring their own food and beverages.

Silverlining Sailing

Silverlining Sailing offers one of the most intimate sails in Ogunquit Maine . Each boat has the capacity for up to six passengers, making for a small group sail. Sails typically last two hours, departing from the quaint Perkins Cove village.

There are five trips daily (weather permitting) from early morning through to a sunset sail in the evening. Enjoy stunning ocean views, gorgeous waterfront homes, views of local beaches, and harbors.

Since this is a smaller group sail, guests get the opportunity to try their hand at taking the wheel and steering the schooner.

Broad Reach Adventures

Broad Reach Adventures has two-hour sails, half-day and full-day sails, and chartered sails from Saco Maine , so there’s a sail to accommodate your busy schedule.

Each one allows guests to see beautiful views of the Saco River, Saco Bay, Biddeford Pool, Old Orchard Beach , and lighthouses along the way. Longer sails provide guests with the opportunity to disembark and explore uninhabited islands.

A unique feature that Broad Reach Adventures offers is the opportunity to add a massage or professional photographer. These experiences are available on certain dates and times, so book ahead if you’re interested in these add-ons.

Sailing Lessons & Boat Rentals

If you want to learn to sail, sailing instruction is often available as part of your charter package.  Private charters  of sailboats on the Maine coast allow experienced sailors to explore the coastline on their own.

Private sailors will find  hotel marinas  for lodging in Maine’s best harbors. If you time your sailing cruise right, you might witness seals, porpoises, whales, or other tall ships.

Watching the sunrise from the deck of a schooner is one of life’s simplest, most satisfying pleasures. Of course, the spectacular Maine scenery is always included on your sail.

Set Sail on Sailboat & Schooner Tours From Maine This Season

Now that you know about all of the sailing trip options, it’s time to set sail into the open waters of Maine. From two-hour trips of the bays and harbors to overnight excursions, there’s an experience awaiting you on your next getaway.

Each Maine sailing company offers its own unique trips aboard safe, well-maintained schooners. Relax, unwind, and feel the ocean breeze in your hair as you cruise through the lapping waves of Maine’s Atlantic shoreline.

The VisitMaine.Net team is the small team of authors and editors that research and write our in-depth guides throughout the site and update past articles to make sure they're still super valuable to you. We have one goal: to help you fall more in love with the state of Maine!

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Travel+Discover Maine – The unofficial guide to exploring the great state of Maine. Not affiliated with any official tourism entities.

Copyright Travel+Discover Maine 2024 Images Courtesy Greg and Heather Burke unless otherwise noted.

Dump out your bucket list.

This is the adventure you’ve been looking for..

Windjamming is, quite literally, like nothing else on Earth. By turns exhilarating, relaxing, surprising, and nurturing, it’s like no other vacation you’ve ever experienced.

Wake up to the quiet solitude of Maine’s coast, find renewal in the wind and sun, and surprise yourself as you help steer the ship. Aboard our vessels, with itineraries tossed to the wind, our guests find both a spark of adventure and time to reflect.

Is there a sailor in your soul?

Welcome to the Maine Windjammer Association – the largest fleet of traditional tall ships in the Americas. Our iconic windjammers offer multi-day, all-inclusive, sailing adventure cruises in one of the most acclaimed cruising grounds in the world.

When you sail aboard a Maine Windjammer Association vessel, you can be sure that your hosts hold themselves to the highest standards of safety and quality. As your captain and guide they will treat you to honest, heartfelt Maine hospitality and personalized attention.  Explore our fleet and offerings to find your perfect cruise.

The Windjamming Experience

Simply put, windjamming is about reconnecting with our essential enjoyment of life. It’s about gorgeous scenery, human connection, soul-nourishing meals, and taking time for both adventure and reflection. Our playground is the sparkling sea and the spruce-clad granite islands that rise from it.

Whether you join us for a three-night cruise or a week, we promise you a total escape from the ordinary. Be prepared to get closer than you ever have before to breathtaking wildlife like eagles, seals and porpoises, to visit some of North America’s most spectacular coastal scenery, charming villages and unspoiled islands, and to savor the freshest, fire-cooked Downeast fare. With only 16-31 guests on our ships, you’ll experience the kind of honest, heartfelt hospitality that keeps our guests coming back year after year.

Welcome to the only place in the world where schooners play in abundance. Where steady breezes, glittering bays, and literally thousands of islands make Penobscot Bay one of the most revered cruising grounds on earth.

On our small ship cruises, we have complete liberty to explore secret anchorages, remote fishing villages, and charming gallery towns. Schooners have been an intrinsic part of the Maine Coast for centuries, and there is something very special about rounding the point and arriving at anchorage under sail. Come touch this culturally distinct, pristine and physically breathtaking part of America.

Explore by Schedule

Use our cruise finder below to explore sailing options that fit your schedule. If your dates are flexible, or you just want to learn more, visit our fleet page and each vessel’s website. Reservations can be made directly with the Windjammer of your choice. Have fun exploring! Whichever vessel you choose, you are sure to have the sailing adventure of a lifetime.

Find My Trip

Leave your fancy clothes home for this low key, relaxing cruise. Experience quiet morning sunrises; the wind and sun on your face as you fly sailing across the water; beautiful scenery; and the most amazing (and never ending!) food. Maine lobster cooked right on the beach, ocean swims, and music night. This is a trip for making lifetime memories.

Stay in the Know

With our monthly newsletter, you’ll receive tips and hints from folks who have sailed as well as information about the best dining and attractions the area has to offer, special packages, windjammer history, events, and more!

You can request a mailed or digital packet of brochures, or you can find individual ships’ brochures under each listing on the fleet page.

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Check out our newest sail the Hurricane Island Aquaculture Experience

A Morning in Maine

Sailing tours on beautiful penobscot bay, featured sailing trips.

• Most Popular!
• Users All Ages
• Clock 2 Hours

2-Hour Sailing Trip

The best way to get a taste of the Maine coast! Sail out of Rockland Harbor past the breakwater lighthouse on your way to Penobscot Bay and the rugged coastal islands.

• Users Ages 11+
• Clock 9.5 Hours

Hurricane Island Aquaculture Experience

Join us for an exclusive opportunity to visit the Hurricane Island Center for Science and Leadership (Hurricane Island) aboard Morning in Maine!

• Clock 6 Hours

Monroe Island Adventure

Your island adventure awaits! Maine has over 3,000 miles of coastline, and almost half of that is on islands only accessible by boat.

• Clock 3 Hours

Science under Sail

Join us and a science educator from our partners at Herring Gut Coastal Science Center in Port Clyde as we set sail to learn about the ecology of Penobscot Bay!

Day Sails on Penobscot Bay

Enjoy the Maine Coast’s beauty from the deck of Morning In Maine. Relax and watch the seabirds and harbor seals as the ketch glides through the waters of Penobscot Bay… or lend a hand in sailing the boat!

On most Maine sailing trips we see Rockland Breakwater Lighthouse, Owls Head Lighthouse, and historic schooners. Monday morning is the best time for a day sail in Rockland, Maine, where we watch the schooners sail out of the harbor for their week-long cruises.

We look forward to having you aboard!

The boat accommodates 21 passengers and can fill up quickly, so make your reservations early!

#1 Outdoor Activity in Rockland, Maine! Our Customers Love Us!

Maine is best by sailboat.

“Loved our afternoon on Morning in Maine. The wind was great and the boat is really lovely. Capt Tyler and George were great crew. Saw eagles, a harbor seal and all the sights you’d want to see in Rockland. Sailing really is the best way to get to know Maine.”

Best "boat ride" in Maine

“As Mainers, we have had the opportunity to go on various “boating adventures” along the Maine coast. This was the most pleasant and fun one ! 2 hours was perfect. The captain allowing the kids to help with the sails was very cool and even steer… Totally made their day. The captain was very personable and made the trip interesting. I was concerned about getting seasick, but the ride was actually very smooth.”

“We had a wonderful time on our sailing expedition and learned a lot about the area. Definitely worth the time to spend some time on the water with folks that live in the area sharing lots of good stories.”

Great experience!

"Our sail on a Morning in Maine was one of the highlights of our trip. The views were beautiful and the ride was smooth and relaxing. It was a great experience and one that I highly recommend!"

Our 37th Year in Camden!

Celebrating our 105th anniversary 1918-2023, on the national register of historic places, schooner surprise.

Book Online Now!

Day trips :

Join us for a two hour daysail on the elegant Schooner Surprise out of Camden, Maine. We sail around the magnificent Penobscot Bay. On our Camden day cruises we will see lighthouses, wildlife, private yachts and summer estates. We offer Sunset sails, Tuesday night Sunset sails with live music, Full moon sails and Fireworks sails. We sail 7 days a week from mid May to mid October. Get involved and help raise sails or steer the boat, we are great with kids! Come and join us for a cruise on board the most famous windjammer in Maine. We offer environmentally friendly boat tours. We have limited amount of passengers with cushioned seating for all. Come sail the Maine Coast with us.

See our schedule and rates

Private Charters :

Join us for your Camden Maine Charter on the Schooner Surprise. Special events, weddings, birthdays, family reunions, anniversaries and corporate  events. Two hour, half day and full day cruises on the beautiful coast of Maine. Have us cater your Camden cruise and serve exquisite appetizers on a sunset sail or a lobster lunch. Our Maine windjammer cruises will give you an unparalleled view of Camden Hills. We have been highly rated tour operators in Camden Maine for 35 years. Rated #1 on Trip Advisor!! Book your Camden Charters with us.

Learn more about private charters on the Schooner Surprise

Special Events

Full moon sail with live music.

Watch the sunset over Camden Hills and the full moon rise over Penobscot Bay.

June 21 (7:15pm - 9:15pm) July 20 (7:15pm - 9:15pm) August 18, 19 (7:15pm - 9:15pm) Rate: Adults $65 / Kids $47

September 17 (5:30pm - 7:30pm) Rate: Adults $65 kids $50

Fireworks over Camden Harbor

July 4 7:15pm - 9:15pm Rate: Adults/Kids $76

Sunset Sail with Live Music

Watch the sunset over Camden Hills and listen to live acoustic music.

July 1, 3, 5, 8, 10, 12, 15, 17, 22, 24, 26, 29, 31 (7:15pm - 9:15pm)

August 2, 5, 7, 9 (7:15pm - 9:15pm)

August 12, 14, 16, 19, 21, 23, 26, 28, 30 (5:15pm - 7:15pm)

September 4, 12, 14 (5:15pm - 7:15pm)

Rate: Adults $71 / Kids $62

Birding and Marine life tour with ornithologist Richard Podolsky

July 2, 3, 4, 9, 10, 11, 16, 17, 18, 23, 24, 25, 30, 31 (10am - 12pm)

August 1, 6, 7, 8, 13, 14, 15, 20, 21, 22, 27, 28, 29 (10am - 12pm)

Rate: Adults $65 / Kids $60

Contact Us:

Schooner Surprise Ramiro and Nicole de Acevedo Ramos 207.236.4687 1 Bay View Street Camden, ME 04843

[email protected]

Sloop Anjacaa

Check out our sister ship: Sloop Anjacaa

Camden Rockland Maine  Chamber of Commerce Camden, Lincolnville, Maine Inns, B&B’s and Hotels Rockland, Rockport, Maine Inns, B&B’s and Hotels Vacation Rentals Camden Maine Weather Schooner Surprise Trip Advisor Schooner   Surprise Facebook Page Schooner Surprise Yelp Schooner Surprise Instagram Down East Magazine Maine Magazine Penbscot Bay Pilot Web News Maine Boats, Home and Harbors website