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Book Early For Best Availability!

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- Schooner Applejack
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⛵️ Book your Private Charter on the Historic E

⛵️ Book your Private Charter on the Historic Eastwind & Applejack Schooners in Boothbay Harbor! 🌅🥂 Sail in style aboard Eastwind, the largest schooner in Boothbay Harbor at 65 feet, or enjoy an intimate adventure on Schooner Applejack, perfect for two-hour sails or custom charters. ⚓️⛵️ These stunning schooners accommodate up to 28 passengers on Eastwind and 14 passengers on Applejack, boasting impressive spars and wide beams.

Celebrate your special event in grand style! Imagine a breathtaking Maine destination wedding on the deck of a historic schooner, exchanging vows with the magnificent New England sunset painting the sky in hues of pink. 🌺🌅 Even corporate events shine against the picturesque shoreline of Boothbay Harbor!

With a full liquor license, indulge in a wide selection of cocktails, champagne, wines, and beers. 🍹🍾🍷 Customized food service options are available, ranging from steaming bowls of New England chowder to fancy hors d'oeuvres and buffet-style dinners. Let your imagination run wild and create an unforgettable experience on the water 🌊🥂

Stay connected for the latest specials and events, follow us @boothbaysailing
📍 @VisitMaine

⛵️ Experience the Best 2-Hour Classic Sailing

⛵️ Experience the Best 2-Hour Classic Sailing Trip in Boothbay Harbor! 🌊✨ Unparalleled views, 50 years of excellence, and national recognition. Join us aboard our schooner Eastwind, perfect for exploring Maine's coast. No obstructions, just panoramic beauty from every seat. 🌅 Don't miss out on the ultimate sailing adventure! ⚓️📸

Stay connected for the latest specials and events, follow us @boothbaysailing
📍 @VisitMaine

Your Maine Vacation starts here. 🌅 Join us for

Your Maine Vacation starts here. 🌅 Join us for an unforgettable experience on Boothbay Harbor's oldest windjammer. ⛵️ Set sail on a 2-hour day sail or embark on a private charter adventure. Help raise the sails or take the helm as we navigate past breathtaking sights like Burnt Island Light, Squirrel Island, Ram Island Light, and the enchanting outer islands of Boothbay. 🏝🐬 Keep your eyes peeled for playful porpoises, majestic Ospreys, Bald Eagles, and adorable harbor seals as we glide past local fishing boats tending to their lobster pots. 🦞 Come aboard and create memories that will last a lifetime! 📸

Stay connected for the latest specials and events, follow us @boothbaysailing
📍 @VisitMaine

Come sail on Eastwind! ⛵ Built in 1999 and meas

Come sail on Eastwind! ⛵ Built in 1999 and measuring at 65-feet, is the largest schooner whose home port is Boothbay Harbor. Eastwind was built by Herb and Doris Smith on their farm in Albion and has a 14-foot beam, a frame of local white oak, planking out of Oregon cedar two inches thick. She was named for a Coast Guard cutter Herb Smith once served on.

Stay connected for the latest specials and events, follow us @boothbaysailing
📍 @VisitMaine

Our day sails sell out fast! Book ahead so you don

Our day sails sell out fast! Book ahead so you don't miss out on a true Maine vacation experience on one of the most beautiful stretches of water in the world! ⛵

Stay connected for the latest specials and events, follow us @boothbaysailing

📍 @VisitMaine

⛵ Sail away from it all on your two-hour voyage

⛵ 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!

Stay connected for the latest specials and events, follow us @boothbaysailing

📍 @VisitMaine

Schooner Eastwind is seeking to hire deckhands who

Schooner Eastwind is seeking to hire deckhands who are enthusiastic about learning and have a strong work ethic. This opportunity provides an excellent stepping stone for accumulating sea time, maintenance experience, and sailing expertise.

Schooner Eastwind operates as a day sailing ship, in Boothbay Harbor, ME Daily Sails include three 2-hour day sails and then a sunset sail. Sails typically consist of 50% sailing and 50% customer service, and deckhands should be personable and eager to share their knowledge of the ship and its operations with passengers.

This schooner provides an excellent opportunity to learn the basics and transition into other positions such as first mate, bosun, engineer, or captain. For further inquiries, please do not hesitate to contact me at rod@schoonerappledore.com. Interested applicants should email their questions, resume/CV, and basic information about themselves.

⛵ @boothbaysailing
📍 @VisitMaine

Tours are on the horizon! Experience the beauty of

Tours are on the horizon! Experience the beauty of Maine's coastline like never before with Schooner Eastwind & Applejack! Our 2-hour day sail or private charter adventures aboard Boothbay Harbor's oldest windjammer are the perfect way to explore the stunning scenery and rich maritime history of this iconic New England destination.

Stay connected for the latest specials and events, follow us @boothbaysailing
📍 @VisitMaine

We can't wait to share the magic of Maine with you

We can't wait to share the magic of Maine with you! Whether you choose a day sail or sunset sail, you'll be treated to stunning views of the Maine coastline. During the sunset sail, you'll be able to watch the sun sink below the horizon as the sky is painted with a beautiful array of colors.

Stay connected for the latest specials and events, follow us @boothbaysailing
📍 @VisitMaine

In addition to the Schooner Eastwind, we will also

In addition to the Schooner Eastwind, we will also be adding Apple Jack to our fleet. Built in 1947 by renowned builder and designer Fred Whittier, Apple Jack is a beautiful example of the traditional Gloucester fishing schooners that were so important to the maritime history of New England.

Stay connected for the latest specials and events, follow us @boothbaysailing
📍 @VisitMaine

With so much to see and experience, Schooner Eastw

With so much to see and experience, Schooner Eastwind & Applejack are the perfect choice for a romantic getaway, family adventure, or unique vacation experience. Don't miss out on this unforgettable adventure. Book your Schooner Eastwind & Applejack tour today and get ready to set sail on one of the most beautiful stretches of water in the world. We can't wait to share the magic of Maine with you!

Stay connected for the latest specials and events, follow us @boothbaysailing
📍 @VisitMaine

Starting on May 26th, join our experienced crew fo

Starting on May 26th, join our experienced crew for a true Maine vacation experience. As you step aboard the Schooner Eastwind or Applejack, you'll be transported back in time to a bygone era of sailing. These beautiful vessels offer a unique opportunity to experience the beauty of Boothbay Harbor from a whole new perspective. Private charters are also available for those looking for a more intimate and personalized experience.

Stay connected for the latest specials and events, follow us @boothbaysailing
📍 @VisitMaine

We can't wait to share the magic of Maine with you

We can't wait to share the magic of Maine with you! Book your Schooner Eastwind & Applejack tour today and get ready to set sail on one of the most beautiful stretches of water in the world.

Stay connected for the latest specials and events, follow us @boothbaysailing
📍 @VisitMaine

Starting on May 26th, join our experienced crew fo

Starting on May 26th, join our experienced crew for a true Maine vacation experience. Relax on deck as we navigate the tranquil waters of Boothbay Harbor, taking in the breathtaking views of the rocky coastline, historic lighthouses, and local wildlife. Private charters are also available for those looking for a more intimate and personalized experience.

Stay connected for the latest specials and events, follow us @boothbaysailing
📍 @VisitMaine

Whether you choose a day sail or sunset sail, you'

Whether you choose a day sail or sunset sail, you'll be treated to stunning views of the Maine coastline. During the sunset sail, you'll be able to watch the sun sink below the horizon as the sky is painted with a beautiful array of colors. Stay connected for the latest specials and events, follow us @boothbaysailing
📍 @VisitMaine

During your sailing adventure, you'll have the cha

During your sailing adventure, you'll have the chance to sit back, relax, and take in the stunning views of the Maine coastline. With expert guidance and commentary from your experienced crew, you'll learn about the history, culture, and natural wonders of this beautiful region.During your sailing adventure, you'll have the chance to sit back, relax, and take in the stunning views of the Maine coastline. With expert guidance and commentary from your experienced crew, you'll learn about the history, culture, and natural wonders of this beautiful region. Stay connected for the latest specials and events, follow us @boothbaysailing
📍 @VisitMaine

In addition to the Schooner Eastwind, we will also

In addition to the Schooner Eastwind, we will also be adding Apple Jack to our fleet. Apple Jack was built in 1947 by builder and designer Fred Whittier in the shipyard of Whittier and Lowe in Ipswich, Massachusetts. Apple Jack takes its lines from the traditions of the great Gloucester fishing schooners of the 1800’s. A scaled down topsail schooner, Apple Jack is constructed from long leaf yellow pine planking over white oak frames and measures 48ft. in overall length, with a 12 ft. beam and a full keel that draws 6 ft. Stay connected for the latest specials and events, follow us @boothbaysailing
📍 @VisitMaine

With so much to see and experience, Schooner Eastw

With so much to see and experience, Schooner Eastwind & Applejack are the perfect choice for a romantic getaway, family adventure, or unique vacation experience. So why wait? Book your sailing adventure today and get ready to experience the beauty of Boothbay Harbor like never before.

Stay connected for the latest specials and events, follow us @boothbaysailing
📍 @VisitMaine

Live your dream of being a sailor & help us hoist

Live your dream of being a sailor & help us hoist the sails on one of our majestic wooden schooners ⛵
Stay connected for the latest specials and events, follow us @boothbaysailing
📍 @VisitMaine

Whether you choose a day sail or a private charter

Whether you choose a day sail or a private charter, your sailing adventure will take you past some of the most beautiful sights in Boothbay Harbor. Keep a lookout for local wildlife, including porpoise, osprey, and bald eagles, as we sail past local boats setting their pots or hauling in the lobster catch of the day.
Stay connected for the latest specials and events, follow us @boothbaysailing
📍 @VisitMaine

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207-633-6598
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Pier One, 20 Commercial St., Boothbay Harbor, ME 04538

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