Boothbay Harbor Sailing

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Boothbay Harbor Sailing

Welcome Aboard Schooner Eastwind & Applejack in Boothbay Harbor your Maine Vacation starts here. Join the Schooner crew for a 2hr.

day sail or private charter adventure on Boothbay Harbor’s oldest windjammer.

25/06/2025

Celebrate freedom where the sky meets the sea! Boothbay Sailing is OPEN all 4th of July weekend! ✨ Bonus: Book your sail 7+ days in advance and save 5%!

Secure your spot now, and enjoy the holiday from the best seat in the bay — the deck of a classic schooner.

📅 Long weekend plans? Check.
📸 Breathtaking ocean views? Check.
💸 Early bird savings? Check!

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📍 Boothbay Harbor Maine USA
🗺️ Visit Maine

22/06/2025

Sunday Serenity, Boothbay Style ⛵️ Sometimes the best way to reset for the week ahead is to let the wind take the lead. With the sun on your face and the Maine coast on the horizon, a sail with Boothbay Sailing is the definition of Sunday well spent.

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📍 Boothbay Harbor Maine USA
🗺️ Visit Maine

11/06/2025

Salt air. Tall sails. Pure Maine.
Step aboard for an unforgettable sail along Boothbay Harbor’s iconic coastline.

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📍 Boothbay Harbor Maine USA
🗺️ Visit Maine

06/06/2025

Forget the golf course. This year, give Dad the wind in his sails. 🌬️⛵
Celebrate Father's Day aboard a classic schooner in beautiful Boothbay Harbor, ME.
Whether he's a lifelong sailor or just loves time with his crew — this is a memory-maker.

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📍 Boothbay Harbor Maine USA
🗺️ Visit Maine

30/05/2025

Hoist the sails — it’s Opening Day in Boothbay Harbor! ⛵🌊
The wind’s right, the views are perfect, and the sailing season is officially underway!

Let’s make waves this summer — we’re ready when you are!

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📍 Boothbay Harbor Maine USA
🗺️ Visit Maine

24/05/2025

This Memorial Day Weekend… let the wind do the work. ⛵🇺🇸

Kick back, sip something cold, and set sail aboard a classic windjammer from Boothbay Harbor. Whether it's a sunny day sail or a dreamy sunset cruise, we're casting off all weekend long.

🧭 Day Sails | Sunset Sails | Private Charters
🍹 Adult beverages available on board

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📍 Boothbay Harbor Maine USA
🗺️ Visit Maine

14/05/2025

Opening day in Boothbay, where the sails rise and the sea calls 🌊⛵ Maine magic starts here.

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📍 Boothbay Harbor Maine USA
🗺️ Visit Maine

09/05/2025

Our final tour feature before launch 🌇
Apple Jack Sunset Sail = peaceful vibes + wildlife sightings + epic views. 🖤 Sails again this May.

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📍 Boothbay Harbor Maine USA
🗺️ Visit Maine

30/04/2025

Sailing into the golden hour 🌅
This week’s tour spotlight: Eastwind Sunset Sail. Peaceful skies, calm waters, and classic schooner charm.

Perfect way to end the day in Boothbay. 🎟️ Early bird pricing on now—kids from $39.95

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📍 Boothbay Harbor Maine USA
🗺️ Visit Maine

23/04/2025

Part 2 of our countdown! Meet Apple Jack 🖤—Boothbay’s oldest windjammer.

2 hours. Hands on. Coastal cool. Spot wildlife, take the wheel, and cruise the outer islands. 🎟️ Kids from $39.95 | Adults from $54.95

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📍 Boothbay Harbor Maine USA
🗺️ Visit Maine

17/04/2025

It’s almost go-time! Sailing season in Boothbay kicks off this May—and we’re counting down with a weekly spotlight on each of our unforgettable tours. ⛵️

First up: Eastwind Day Sail – 2 hours of coastal Maine views, lighthouses, lobster boats, and salty sea air.
🎟️ Kids sail from $39.95. Early bird deals available!

Stay connected for the latest specials and events, follow us Boothbay Harbor Sailing
📍 Boothbay Harbor Maine USA
🗺️ Visit Maine

10/04/2025

Ropes are ready. Masts are standing tall. The countdown is ON. ⛵️ Our season launches May 15, and we’re celebrating with weekly tour spotlights to get you excited (and onboard!).

Stay tuned—first up: day sails that deliver classic Maine coastal views. 🌊

Stay connected for the latest specials and events, follow us Boothbay Harbor Sailing
📍 Boothbay Harbor Maine USA
🗺️ Visit Maine

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