Where to Start: the 2 Best Sailing Trips Worldwide

1.Historical San Juan Bay Sunset Sailing Tour

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

You’ll sail San Juan Bay for about two hours aboard a 30-foot J30 racer-cruiser with a captain such as Ivan, Joe, or Carlos. Expect views of El Morro, harbor traffic, local history, sunset photos, and complimentary beer, sangria, rum and Coke, soft drinks, and water.

“What an incredible experience! The sunset sail was intimate, relaxing, and absolutely beautiful. Our captain was interesting, knowledgeable, and genuinely funny—he brought so much personality to the trip and made the whole experiRead more”

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2.Lisbon Sunset Sailing with Portuguese Wine and History

★★★★★★★★★★5.0 · 668 reviews · 2 hours (approx.) · from $54Best value

Join Pedro, David, or another two-person crew for a relaxed two-hour shared sail from Doca de Santo Amaro. With no more than 14 people aboard, you’ll hear Lisbon history, pass Belém Tower and Commerce Square, and sip included Vinho Verde as the sun drops over the Tagus.

“David was the best possible tour guide! Knowledgeable and personable, he provided great commentary and a fun experience. The ship was comfortable and the wine was good! Highly recommend this experience to any and all travelers!!!”

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