PUERTO RICO

Top 12 Puerto Rico Sailing Tours

12 sailing trips  ·  from $99 a head

The good puerto rico sailing tours fill up weeks ahead and the small boats go first. Below: the 12 to book early, what each includes and how they differ.

Icacos Island Catamaran Day Sail from Fajardo - Snorkeling, swimming, and beach time
Catamaran Sailing Trips, Island Hopping Sailing Trips, Puerto Rico Sailing Tours, Sailing Tours, Tour Reviews

Icacos Island Catamaran Day Sail from Fajardo

Historical San Juan Bay Sunset Sailing Tour - Leaving from the San Juan Bay Marina
Bay, Harbour and Coastal Sailing, Historical Tours, Puerto Rico Sailing Tours, Sailing Tours, Sunset Sailing Cruises, Tour Reviews, Tours

Historical San Juan Bay Sunset Sailing Tour

2.Historical San Juan Bay Sunset Sailing Tour

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

Review of San Juan’s two-hour sunset sail, with fortress views, local history, drinks, practical meeting tips, and honest value advice.

“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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San Juan Catamaran Sunset Sail with Drinks Included - San Juan Bay at sunset, stop by stop
Catamaran Sailing Trips, Puerto Rico Sailing Tours, Sailing Tours, Sailing Tours with an Open Bar, Sunset Sailing Cruises, Tour Reviews

San Juan Catamaran Sunset Sail with Drinks Included

3.San Juan Catamaran Sunset Sail with Drinks Included

★★★★★★★★★★5.0 · 622 reviews · from $119

Review of San Juan’s intimate sunset catamaran cruise, with Old San Juan views, drinks, friendly crew, practical tips, and honest drawbacks.

“Was a great afternoon. Expected rain, but held off and we did have a nice sunset. Cat had 6 people as guests. Fun. Captain and Sophia the Mate were great. Hardest thing was finding the entrance to the docks. Security was not a lot of help. Look for the Sizzlers and you will be close.”

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San Juan Bay Day Sail with Drinks Included - What the 90-minute route gives you
Bay, Harbour and Coastal Sailing, Puerto Rico Sailing Tours, Sailing Tours, Sailing Tours with an Open Bar, Tour Reviews

San Juan Bay Day Sail with Drinks Included

San Juan Historical Bay Daytime Sailing Tour - Seeing the forts from the seaward side
Bay, Harbour and Coastal Sailing, Historical Tours, Puerto Rico Sailing Tours, Sailing Tours, Tour Reviews, Tours

San Juan Historical Bay Daytime Sailing Tour

Sailing and Snorkeling Day Charter in Fajardo, Puerto Rico - Piñeros, Palomino, and the first water stop
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Sailing and Snorkeling Day Charter in Fajardo, Puerto Rico

6.Sailing and Snorkeling Day Charter in Fajardo, Puerto Rico

★★★★★★★★★★5.0 · 144 reviews · from $285

Review of Fajardo’s small-group sailing and snorkeling charter, with island stops, reef time, barbecue lunch, drinks, pricing, and practical tips.

“Great experience! Captain Bill and first Mate Scotty were great . Scotty cooked a great lunch and Captain Bill was very informative about our tour. Captain Bill even let my son sail the boat back. It was a trip my family will never forget.”

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Puerto Rico Private Catamaran Sail from Fajardo - Cayo Icacos and the nearby islands
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Puerto Rico Private Catamaran Sail from Fajardo

Janise Sailing Afternoon Charter in Fajardo, Puerto Rico - The short sail along Fajardo’s coast
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Janise Sailing Afternoon Charter in Fajardo, Puerto Rico

Island Hopping and Snorkeling Sailing and Boat Tours Fajardo - Cayo Icacos: clear water and an easy half-day plan
Island Hopping Sailing Trips, Puerto Rico Sailing Tours, Sailing and Snorkeling Trips, Sailing Tours, Tour Reviews, Tours

Island Hopping and Snorkeling Sailing and Boat Tours Fajardo

9.Island Hopping and Snorkeling Sailing and Boat Tours Fajardo

★★★★★★★★★★4.5 · 13 reviews

Review of Fajardo’s private island-hopping boat tour, with snorkeling at Icacos, optional Vieques trips, food, drinks, and practical tips.

“This was the highlight of our trip! Nomar and Laura are excellents. They offered fresh fruits, Sandwiches and drinks, all for free. We did a half day excursion and visited isla Lobos where we snorkelled and cayo Icacos which has the most beautiful beach we’ve seen Thank you for the great experience!!”

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Private Janise Sailing Full Day Charter in Fajardo, Puerto Rico - The Lagoon 380 makes the ride part of the trip
Full-Day, Private Sailing Charters, Puerto Rico Sailing Tours, Sailing Tours, Tour Reviews

Private Janise Sailing Full Day Charter in Fajardo, Puerto Rico

10.Private Janise Sailing Full Day Charter in Fajardo, Puerto Rico

★★★★★★★★★★5.0 · 6 reviews

Review of the private Janise sailing charter in Fajardo, with snorkeling, island beaches, barbecue lunch, drinks, and practical tips.

“An unforgettable sailing experience from start to finish! The crew was professional, welcoming, and made sure our family felt safe and relaxed. The boat was clean and comfortable, and the food… Delicious! Plenty to drink as well! They know all Read more”

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Private Sunset Escape: Sailing an Island Paradise - Reaching Isla Palominos before sunset
Island Hopping Sailing Trips, Puerto Rico Sailing Tours, Sailing Tours, Sunset Sailing Cruises, Tour Reviews

Private Sunset Escape: Sailing an Island Paradise

11.Private Sunset Escape: Sailing an Island Paradise

★★★★★★★★★★5.0 · 6 reviews

Review of Fajardo’s private sunset boat trip to Isla Palominos, with pricing, timing, guides, swimming, romance, value, and booking tips.

“Our family of 6 booked this sunset cruise through Viator (but you can book directly through Encanto boat tours) after our sailboat cruise earlier in the week was canceled due to weather. We had a great experience with Jamille as our boat capRead more”

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Private Half-Day Sailing and Snorkeling Tour - Choosing between Icaco Island and Palomino Island
Half-Day, Puerto Rico Sailing Tours, Sailing and Snorkeling Trips, Sailing Tours, Tour Reviews, Tours

Private Half-Day Sailing and Snorkeling Tour

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