HISTORICAL TOURS

15 Historic Sailing Trips, Coast by Coast

23 sailings  ·  from $16 a head

The 15 best historic sailing trips you can get aboard today, with what each costs, how long it stays out and who it suits. Number one is first for a reason; start there.

Historical San Juan Bay Sunset Sailing Tour - What the small J30 sailboat 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 $115Our pick

Spend about two hours sailing San Juan Bay aboard a 30-foot J30 racer-cruiser with a captain such as Ivan, Joe, or Carlos. Expect views of El Morro, harbor traffic, sunset photos, local stories, and complimentary beer, sangria, rum and Coke, water, and light refreshments. This is an authentic sailing trip, not a yacht party or catamaran cruise.

“It was such a great sailing experience with Captain Ivan. He told us a lot of history about the island and great spots to go to after the tour was over.”

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Lisbon: Sunset Sailing with Portuguese Wine and History - Starting beneath the 25 de Abril Bridge
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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 $54Top rated

Join a small shared sailboat from Doca de Santo Amaro for a two-hour sunset cruise along Lisbon’s Tagus River. Guides such as Pedro and David share stories about the city while you see Belém Tower, the 25th April Bridge, Christ the King, Alfama, and Praça do Comércio. Vinho Verde, iced tea, water, and blankets are included.

“David and Pedro were brilliant hosts. Tjey were friendly, knowledgable, and took the time to get to know everyone on board. The sunset was amazing as was the company, and the wine. We would 100% recommend for anyone who wants to see the sights of Lisbon!”

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Dublin: Jeanie Johnston Tall Ship Irish Famine History Tour - Starting above deck with the masts and Docklands views
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Dublin: Jeanie Johnston Tall Ship Irish Famine History Tour

3.Dublin: Jeanie Johnston Tall Ship Irish Famine History Tour

★★★★★★★★★★4.8 · 431 reviews · from $16Best value

Board the Jeanie Johnston at Dublin’s Custom House Quay for a 50-minute English-language tour. Guides such as Steve, Claire, Eoin, and Katrina explain the famine, the ship’s voyages, and the personal stories of passengers and crew. You’ll see the upper deck, then cramped below-deck quarters. Comfortable shoes are essential.

“Steve was friendly, very informative and entertaining. In all of my visits to Dublin I’ve never managed to make time to see the Jeanie Johnston and I’m so glad I did. I learned a lot about the famine and an important part of Irish history and enjoyed exploring the ship. Thank you, Steve!”

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Lisbon: Sunset Sailing with Portuguese Wine and History - Starting beneath the 25 de Abril Bridge
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Lisbon: Sunset Sailing with Portuguese Wine and History

4.Sunset Sailing with Portuguese Wine and History

★★★★★★★★★★5.0 · 270 reviews · 2 hours · from $49

Set out from Doca de Santo Amaro on a 12-meter sailboat with guides such as Pedro and David. Cruise beneath the 25 de Abril Bridge toward Belém, Cristo Rei, and Praça do Comércio while hearing Lisbon stories, sipping vinho verde, and watching the light fade.

“The Sunset sail was fantastic. It was a beautiful evening with clear blue sky to start. Pedro was a fantastic guide, sharing facts about the sights we were seeing, historical context, as well as his personal stories about growing up and living in Portugal. The Vinho Verde was flowing. When it got colder as the sun set, lovely warm cozy blankets were passed around. I would 100% recommend this activity.”

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Nydri: Sailing Through History. Daily Cruise with Beach BBQ - Papanikolis Cave brings history into the water
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Nydri: Sailing Through History. Daily Cruise with Beach BBQ

5.Nydri: Sailing Through History. Daily Cruise with Beach BBQ

★★★★★★★★★★4.9 · 253 reviews · 8 hours · from $88

Board the wooden Odysseia in Nydri for an eight-hour cruise through Lefkada, Meganisi, and the Prince’s Islands. Swim inside Papanikolis Cave, walk through Spartochori with a guide, visit its 300-year-old Orthodox church, and enjoy a beach BBQ with local pork souvlaki, Greek salad, feta, fruit, wine, and soft drinks. The crew also raises a 45-square-meter sail.

“The Captain and crew consist of a perfect team. We visit very nice places and discover hidden parts of the area's history. The food was delicious. The number of the day's activities is keeping your interest high all the time. I wish them all to have the strength to do what they're doing for a long time. They are doing it perfectly! A very nice activity to try!”

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Camden: Historic Schooner Day Sailing Trip - Learning how Appledore II sails
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Camden: Historic Schooner Day Sailing Trip

6.Historic Schooner Day Sailing Trip

★★★★★★★★★★4.7 · 181 reviews · 2 hours · from $59

Spend two hours aboard the 49-passenger schooner Appledore II, sailing from Camden Harbor into Penobscot Bay. You can help hoist the sails, take a turn at the wheel, and hear about the ship from the English-speaking crew. Blankets, restrooms, and drinks for purchase make this a comfortable coastal outing.

“Our crew was knowledgeable in the history and in their skill of boating. They were friendly, attentive and engaging. We enjoyed our trip immensely! Thank you all for the wonderful hospitality and experience.”

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San Juan Historical Bay Daytime Sailing Tour - Leaving San Juan Bay Marina
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San Juan Historical Bay Daytime Sailing Tour

7.San Juan Historical Bay Daytime Sailing Tour

★★★★★★★★★★4.5 · 173 reviews · from $99

Sail San Juan Bay for about two hours aboard an authentic sailboat with a maximum of six people. Captain Joe, Ivan, or another local captain may guide the trip, pointing out Old San Juan, Castillo San Cristóbal, El Morro, La Fortaleza, and Isla de Cabras. Beer, sangria, rum and Coke, and water are included.

“The experience was amazing with breathtaking views. The captain was very knowledgeable and informative, his love of sailing and the island made the excursion top tier.”

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Sailing on Historic Schooner Yacht in Salem, MA - Setting sail across Salem Sound
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Sailing on Historic Schooner Yacht in Salem, MA

8.Sailing on Historic Schooner Yacht in Salem, MA

★★★★★★★★★★5.0 · 172 reviews · 2 hours (approx.)

Spend about two hours aboard a beautifully maintained classic schooner from Salem’s Blaney Street Wharf. You can help raise the sails, ask crew members such as Kos and Kate about the vessel, and watch the coast, lighthouses, Marblehead, and Salem Sound slide by. Bottled water is included, with beer, wine, cocktails, cider, and drink specials available to buy.

“Great crew, fun ride. Staff was super knowledgeable. I felt safe on the boat. Love the hot apple cider and wish they had medium sized shirts.”

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Key West Historic Schooner When And If Sunset Cruise - Finding the boat at Perry Marina
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Key West Historic Schooner When And If Sunset Cruise

9.Key West Historic Schooner When And If Sunset Cruise

★★★★★★★★★★5.0 · 114 reviews · 2 hours (approx.)

Sail Key West aboard the 1932 schooner When and If, built for General Patton. Captain Matt, Captain Zach, and crew members such as Veronica and Jahn have led recent cruises, inviting you to help raise sail and take the wheel. Select beer, wine, soft drinks, and water are included during this two-hour sunset trip.

“Great crew. They made the trip personal and informative! Beautiful boat and amazing sunset! Highly recommend!”

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Lisbon Small Group Day Cruise with Historic Commentary & a Drink - Starting at Doca de Belém
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Lisbon Small Group Day Cruise with Historic Commentary & a Drink

10.Lisbon Small Group Day Cruise with Historic Commentary & a Drink

★★★★★★★★★★5.0 · 93 reviews · 2 hours (approx.) · from $49

Cruise the Tagus River from Belém with an English-speaking crew, historic commentary, and a welcome drink. The route passes the Discoveries Monument, Belém Tower, 25 de Abril Bridge, Christ the King, Praça do Comércio, and São Jorge Castle. Groups are limited to 12, with morning and afternoon departures.

“This cruise was one of the highlights of our two week visit to Portugal. The tour guide and skipper are really terrific. We learned so much about the history of the area, the architecture and how the earthquake of 1755 changed Lisbon forever. Mark, who is an experienced sailor, was delighted to have the opportunity to steer the boat for much of the cruise. Our guide gave us great suggestions of places to visit on our journey north. Making the arrangements, finding the meeting point, and the friendly attention of the staff to all of us on board made this a truly wonderful tour and we highly recommend it.”

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Salem: Historic Schooner Sailing Cruise - Boarding at Pickering Wharf Marina
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Salem: Historic Schooner Sailing Cruise

11.Salem: Historic Schooner Sailing Cruise

★★★★★★★★★★4.9 · 84 reviews · from $39

Spend 100 minutes aboard the gaff-rigged Schooner Fame, a full-scale replica of a War of 1812 privateer. From Pickering Wharf Marina, you can help raise the sails, take the tiller, and hear stories from the crew, including Captain Mike, while viewing forts, lighthouses, islands, and waterfront homes. Drinks and snacks are available onboard.

“The crew was very polite and helpful. First time I have ever been sailing and it was so much fun.”

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Private Morning Sail, Dolphin and History Tour on Mystique - Setting out from 17 Lockwood Drive
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Private Morning Sail, Dolphin and History Tour on Mystique

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

★★★★★★★★★★5.0 · 84 reviews · 2 hours (approx.) · from $575 whole boat, up to 6

You’ll spend about two hours aboard Mystique with a private crew of up to six, sailing past the Charleston Battery, Ravenel Bridge, Yorktown, and sometimes Fort Sumter. Captains Will, Rob, Scott, and Dustin have led trips, with crew members adding local history, sailing know-how, drinks, shade, and a chance to spot dolphins.

“A highlight of our trip to Charleston was riding with the crew on this magnificent boat. Spotless boat, with beautiful sails and ropes, tables to hang out outside and inside, great sound system and an amazing experience. It was a little too easy in fact to book and go on this tour - but amazing nonetheless!”

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Private Sunset Sail BYOB Dolphin/History Tours on 43ft Mystique - Leaving From Lockwood Drive
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Private Sunset Sail BYOB Dolphin/History Tours on 43ft Mystique

13.Private Sunset Sail BYOB Dolphin/History Tours on 43ft Mystique

★★★★★★★★★★5.0 · 42 reviews · 2 to 4 hours (approx.) · from $599 whole boat, up to 6

Set sail from Lockwood Drive aboard the 43-foot Mystique for a private Charleston sunset cruise. Bring your own wine and food, then watch for dolphins while Captain Scott, Will, Sam, Maddie, or another crew member points out the Battery, Ravenel Bridge, Yorktown, and possibly Fort Sumter. Soft drinks and bottled water are included.

“This was amazing! The boat was beautiful and the captain and crew, Dustin and Sam, were the best. They literally knew everything about the area and narrated the whole trip. We will do this again, highly recommend!”

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Lisbon Sunset Sailing – Small Group (max 10) Wine & History - Meeting Rui, your Lisbon storyteller
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Lisbon Sunset Sailing – Small Group (max 10) Wine & History

14.Lisbon Sunset Sailing – Small Group (max 10) Wine & History

★★★★★★★★★★4.8 · 41 reviews · 2 hours · from $29

Set out from Doca de Santo Amaro aboard MABI IV for a two-hour sunset sail on the Tagus. Skipper Rui Domingos shares Lisbon stories in English, French, Spanish, Portuguese, and some Italian while you enjoy two glasses of white wine, port, or fruit juice. Expect landmark views, a calm pace, and a chilly breeze after sunset.

“The tour was good However, initially booked with this tour and was cancelled last minute, so he moved us to a child with Suzana was nice however wanted to get more about the history and the wine but overall it was beautiful”

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Private Afternoon Sailing/Dolphin & History Tour on 43ft Mystique - Passing under the Arthur Ravenel Jr. Bridge
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Private Afternoon Sailing/Dolphin & History Tour on 43ft Mystique

15.Private Afternoon Sailing/Dolphin & History Tour on 43ft Mystique

★★★★★★★★★★5.0 · 32 reviews · 2 to 4 hours (approx.) · from $575 whole boat, up to 6

Take a private afternoon sail on the 43-foot Mystique with your own group of up to six. Captain Scott, Sam, Rob, Sophia, Adam, Darby, Dustin, and other crew members may guide the trip, pointing out Charleston’s Battery, Ravenel Bridge, Yorktown, and Fort Sumter. Dolphins are possible, but never guaranteed.

“Rob and Sophia were great! Very informative and helpful. Sophia was very attentive and catered to our every whim. Book your trip now”

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Newest in Historical Tours

★ 5.0Yacht Sailing Tour With Portuguese Wine and HistoryFrom $235 whole boat, up to 64 reviews
★ 5.01 Hour Private – Lisbon: Sailing Tour With Wine and HistoryFrom $265 whole boat, up to 123 reviews

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