Sailing trips · HISTORICAL TOURS

Top 3 Historical Tours in the World

3 trips  ·  from $55 a head

The 3 best historical tours you can book today, with what each costs per person, how long it runs and how much of it happens under sail. Number one is top for a reason; start there.

Historical San Juan Bay Sunset Sailing Tour - Captains Who Add More Than Directions
Bay, Harbour & Coastal Sailing, Evening Experiences, Historical Tours, Puerto Rico Sailing Trips, Sailing Trips, Sunset Sailing Cruises, Tour Reviews, Tours

Historical San Juan Bay Sunset Sailing Tour

1.Historical San Juan Bay Sunset Sailing Tour

★★★★★★★★★★4.5 · 710 reviews · from $115Our pick

Spend two hours sailing San Juan Bay aboard a 30-foot J/30 racer-cruiser with a captain such as Ivan, Joe, or Carlos. Expect close views of El Morro, Puerto Rican history, sunset photos, and complimentary beer, sangria, rum and Coke, water, and light refreshments. The boat is small and the departure is strict.

“First it was on small sail boat very hard to get on seating was awful. We got drinks no snacks were provided. I would not recommend this tour to anyone”

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Lisbon: Sunset Sailing with Portuguese Wine and History - Starting under the 25 de Abril Bridge
Evening Experiences, Historical Tours, Lisbon Sailing Trips, Portugal Sailing Trips, Sailing Trips, Sunset Sailing Cruises, Sunset Sailing Cruises in Lisbon, Sunset Sailing Cruises in Portugal, Tour Reviews, Wine Tours

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 $54Best value

Set out from Doca de Santo Amaro for a two-hour shared sail on the Tagus. Guides such as Pedro and David point out Lisbon landmarks, while Vinho Verde, iced tea, water, snacks, and blankets keep the ride relaxed. The boat carries no more than 14 people.

“This was a wonderful experience on the last night of our trip. The sailing was very peaceful, the weather perfect, and wine plentiful. Karolina was very helpful. Any other time I’d be disappointed by not learning enough about the building gs we were sailing by but this time I was happy just enjoying the peaceful beauty.”

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Private Morning Sail, Dolphin and History Tour on Mystique - The Battery and Charleston’s waterfront homes
Charleston Sailing Trips, Historical Tours, Morning, Private, Sailing Trips, Tour Reviews, Tours, USA Sailing Trips, Whale & Dolphin Watching Sails, Whale and Dolphin Watching Sails in the USA

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.)

Book a private two-hour morning sail for up to six people aboard Mystique with Charleston Sailing Charters. Your skipper, such as Will, Rob, Scott, or Dustin, guides you past the Battery, Ravenel Bridge, Yorktown, and sometimes Fort Sumter, with drinks, shade, a restroom, and a chance to spot dolphins.

“Captain Dustin and Captain Adam were amazing! It was so relaxing and they know so much about sailing. We are just beginning our sailing adventures and we’re certified. We really enjoyed our afternoon with them.”

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