Under sail · HISTORICAL TOURS

Sailing Trips with History Worldwide: 5 Worth the Sea Air

5 sailing trips  ·  seats from $16 each

These are the 5 sailing trips with history to put on the shortlist, each with its price, its time on the water and what comes with the seat. Start at the top and work down.

Historical San Juan Bay Sunset Sailing Tour - The J30 boat and what the ride feels like
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Historical San Juan Bay Sunset Sailing Tour

1.Historical San Juan Bay Sunset Sailing Tour

★★★★★★★★★★4.5 · 710 reviews · from $115Top of the fleet

Sail San Juan Bay for about two hours aboard a 30-foot J30 racer-cruiser with no more than six passengers. Your captain, often Ivan, Joe, or Carlos, shares local history while you pass near El Morro and watch the sunset. Beer, sangria, rum and Coke, water, and non-alcoholic drinks are included. Arrive early at the pedestrian gate.

“Very fun and worth it! We had the sunset sail really beautiful and relaxing. Sangria was tasty too. I highly recommend. Thank you for showing us a wonderful time!”

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Lisbon: Sunset Sailing with Portuguese Wine and History - Commerce Square and Lisbon’s riverfront
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Lisbon Sunset Sailing with Portuguese Wine and History

2.Lisbon Sunset Sailing with Portuguese Wine and History

★★★★★★★★★★5.0 · 668 reviews · 2 hours (approx.) · from $54Lowest fare aboard

Spend two hours on a shared sailboat with up to 14 people, guided in English by crew such as Pedro and David. Cruise from Doca de Santo Amaro past Belém Tower, Praça do Comércio, Alfama, and the 25th April Bridge while sipping included Vinho Verde, iced tea, or water. Blankets help when the river breeze turns cool.

“The entire tour was well-paced, organized, and stress-free, which I attribute to the excellent planning and attention to detail of our guides Pedro and David The weather was perfect Tour highly recommended!”

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Private Morning Sail, Dolphin and History Tour on Mystique - Passing the Charleston Battery and waterfront homes
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Private Morning Sail, Dolphin and History Tour on Mystique

3.Private Morning Sail, Dolphin and History Tour on Mystique

★★★★★★★★★★5.0 · 84 reviews · 2 hours (approx.)

Set sail from 17 Lockwood Drive aboard Mystique for a private two-hour Charleston harbor cruise for up to six people. Your skipper and mate share local history while you pass the Battery, Ravenel Bridge, Yorktown, and possibly Fort Sumter. Soft drinks, bottled water, shade, and a restroom keep the morning comfortable, with dolphins a lucky bonus.

“Capt Rob and Maddie were just awesome! The wife and I decided it would be great just take a morning sail around the harbor. Rob and Maddie were the best. It was our first time sailing and they really showed us what sailing was like. We had a great wind that morning and they took full advantage and gave us an amazing experience. Can’t say enough nice things about them. Look forward to our next trip to Charleston and will definitely be sailing with Mystique again!”

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2 hours - Private Sunset Sail along Historic Bay Front - Porpoise Point and Vilano Beach
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2 hours – Private Sunset Sail along Historic Bay Front

4.2 hours – Private Sunset Sail along Historic Bay Front

★★★★★★★★★★5.0 · 29 reviews

You’ll sail privately with your group of up to six from Camachee Cove Yacht Harbor, guided by a captain and crew. Over two hours, look for porpoises near Porpoise Point and view Vilano Beach, Anastasia State Park, the lighthouse, Castillo de San Marcos, and the Bridge of Lions from the water. Bottled water is included.

“Took my wife out for her birthday, it was a wonderful first time on a sail boat. Captain worked hard to capture the wind in the sails. He was very experienced and made us feel very comfortable.”

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2 hours - Private Day Sail along Historic St Augustine Bayfront - Leaving Camachee Cove for Vilano Beach
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2 hours – Private Day Sail along Historic St Augustine Bayfront

5.2 hours – Private Day Sail along Historic St Augustine Bayfront

★★★★★★★★★★5.0 · 16 reviews

Spend two hours aboard a private sailing yacht with a USCG-licensed captain from St. Augustine Sailing Enterprises. You’ll cruise from Camachee Cove along Vilano Beach, Porpoise Point, the Matanzas River, and the old bayfront, with views of the lighthouse, Great Cross, Castillo de San Marcos, and Bridge of Lions. Captains including Chris, Nuri, and Roseanne have helped make the trip personal and hands-on.

“Nuri had all of the boys working and learning to sail. Super fun and engaging. The view of the old city from the water is lovley. Military might ran buy in a training exercise. What a treat.”

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Other ways to get on the water

Sunset Sailing CruisesCatamaran Sailing TripsSailing and Snorkeling TripsPrivate Sailing ChartersIsland Hopping Sailing TripsTall Ship and Schooner Sailing
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