Puerto Rico · SAILING

12 Puerto Rico Sailing Days That Hold Up

12 tours  ·  from $99 a head

Catamarans out of Fajardo, monohulls out of San Juan Bay, and sunset runs that come with the drinks. These 12 compare deck space, group size and price, with a note on which ones actually put the sails up.

Culebra Snorkeling Tour by Catamaran from Fajardo - The 50-Minute Catamaran Crossing
Cruises & Boat Tours, Cruises & Boat Tours in San Juan, Culebra & Icacos Island Trips, Sailing, San Juan Tours, Snorkeling, Snorkeling in San Juan, Tour Reviews, Tours

Culebra Snorkeling Tour by Catamaran from Fajardo

Icacos Deserted Island Catamaran, Snorkel, and Picnic Cruise - Icacos beach time: the heart of the outing
Cruises & Boat Tours, Cruises & Boat Tours in Fajardo, Culebra & Icacos Island Trips, Culebra & Icacos Island Trips in Fajardo, Fajardo Tours, Sailing, Sailing in Fajardo, Snorkeling, Snorkeling in Fajardo, Tour Reviews

Icacos Deserted Island Catamaran, Snorkel, and Picnic Cruise

Icacos Island Catamaran Day Sail from Fajardo - Reaching Cayo Icacos after an hour at sea
Cruises & Boat Tours, Cruises & Boat Tours in Fajardo, Culebra & Icacos Island Trips, Culebra & Icacos Island Trips in Fajardo, Fajardo Tours, Sailing, Sailing in Fajardo, Tour Reviews

Icacos Island Catamaran Day Sail from Fajardo

3.Icacos Island Catamaran Day Sail from Fajardo

★★★★★★★★★★5.0 · 1,483 reviews · from $140

Review of the Icacos Island catamaran from Fajardo, with snorkeling, beach time, lunch, rum drinks, costs, tips, and honest drawbacks.

“Our catamaran excursion was the highlight of our vacation! We had the most gorgeous weather, the best crew and most incredible Captain, Jose! The food and drinks were delicious and it was 6 hours of non stop fun!”

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Historical San Juan Bay Sunset Sailing Tour - What the two-hour route feels like
Cruises & Boat Tours, Cruises & Boat Tours in San Juan, Evening Experiences, Historical Tours, Historical Tours in San Juan, Sailing, San Juan Tours, Tour Reviews, Tours

Historical San Juan Bay Sunset Sailing Tour

4.Historical San Juan Bay Sunset Sailing Tour

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

Review of San Juan Bay’s two-hour sunset sail, with fort views, drinks, captain commentary, meeting tips, value, and honest drawbacks.

“This was our 26th anniversary trip and captain Joe and Carlos did not disappoint! This was such a peaceful experience and would highly recommend to anyone visiting Puerto Rico!”

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San Juan Catamaran Sunset Sail with Drinks Included - Leaving the dock for a gentle bay cruise
Cruises & Boat Tours, Cruises & Boat Tours in San Juan, Evening Experiences, Sailing, San Juan Tours, Tour Reviews

San Juan Catamaran Sunset Sail with Drinks Included

Culebra Full Day Beach and Fun Experience by Catamaran - The ride toward Culebra and Culebrita
Cruises & Boat Tours, Cruises & Boat Tours in Fajardo, Culebra & Icacos Island Trips, Culebra & Icacos Island Trips in Fajardo, Fajardo Tours, Full-Day, Sailing, Sailing in Fajardo, Tour Reviews

Culebra Full Day Beach and Fun Experience by Catamaran

Icacos Double Dip Power Catamaran Snorkel & Beach Tour - Leaving Fajardo for the Cordillera Cays
Cruises & Boat Tours, Cruises & Boat Tours in Fajardo, Culebra & Icacos Island Trips, Culebra & Icacos Island Trips in Fajardo, Fajardo Tours, Sailing, Sailing in Fajardo, Snorkeling, Snorkeling in Fajardo, Tour Reviews, Tours

Icacos Double Dip Power Catamaran Snorkel & Beach Tour

7.Icacos Double Dip Power Catamaran Snorkel & Beach Tour

★★★★★★★★★★5.0 · 236 reviews · from $135

Sail from Fajardo to Icacos for two reef swims, beach time, lunch, drinks, and gear included on this highly rated four-hour catamaran tour.

“We booked this tour a day before we went on it. This was not on our plan initially but we ended up having this tour. It turned out to be one of the best experience we have here in Puerto Rico!”

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San Juan Historical Bay Daytime Sailing Tour - Meeting the crew at San Juan Bay Marina
Cruises & Boat Tours, Cruises & Boat Tours in San Juan, Historical Tours, Historical Tours in San Juan, Sailing, San Juan Tours, Tour Reviews, Tours

San Juan Historical Bay Daytime Sailing Tour

8.San Juan Historical Bay Daytime Sailing Tour

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

Sail San Juan Bay on a small wind-powered boat, see Old San Juan forts, enjoy drinks, and get practical tips before booking.

“Excellent cruise. Not a big boat, it was just myself, wife and daugher along with the captain and mate. Our captain was extremely friendly and knowledgeable on PR history, restaurants, sailing, etc. I highly recommend for a relaxing and fun two-ish hours on the bay.”

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Sailing and Snorkeling Day Charter in Fajardo, Puerto Rico - Piñeros and Palomino: two possible island settings
Cruises & Boat Tours, Cruises & Boat Tours in Fajardo, Fajardo Tours, Sailing, Sailing in Fajardo, Snorkeling, Snorkeling in Fajardo, Tour Reviews

Sailing and Snorkeling Day Charter in Fajardo, Puerto Rico

9.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, barbecue lunch, drinks, pricing, tips, and booking advice.

“We loved being on the water with Ricardo and Ashley. It was relaxing and chill. They were very attentive with food and drink and otherwise just let you relax on the boat and in the water. It was nice to sail part of the time.”

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Icacos: Luxury Sailing Catamaran All Inclusive Beach and Snorkel - Snorkeling For Beginners, With Realistic Expectations
Cruises & Boat Tours, Cruises & Boat Tours in San Juan, Culebra & Icacos Island Trips, Sailing, San Juan Tours, Snorkeling, Snorkeling in San Juan, Tour Reviews, VIP

Icacos: Luxury Sailing Catamaran All Inclusive Beach and Snorkel

10.Icacos: Luxury Sailing Catamaran All Inclusive Beach and Snorkel

★★★★★★★★★★5.0 · 96 reviews · from $195

Review of San Juan’s Icacos catamaran cruise, with snorkeling, Puerto Rican lunch, water toys, drinks, pricing, tips, and practical details.

“This was an amazing experience. Highly recommend it to everyone. Best crew and best group of people on this catamaran. Food was amazing. Arroz con gandules, pernil, pollo asado, ensaladas, pan for lunch. Then fresh fruit and cn the way back helado de coco and passion fruit on a cone. Perfect trip.”

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Vieques: Beach and Snorkeling Tour by Catamaran from Fajardo - Swimming and snorkeling in clear Vieques water
Cruises & Boat Tours, Cruises & Boat Tours in Fajardo, Fajardo Tours, Sailing, Sailing in Fajardo, Snorkeling, Snorkeling in Fajardo, Tour Reviews, Tours

Vieques: Beach and Snorkeling Tour by Catamaran from Fajardo

Puerto Rico Private Catamaran Sail from Fajardo - Sailing toward Cayo Icacos and the nearby islands
Cruises & Boat Tours, Cruises & Boat Tours in Fajardo, Fajardo Tours, Private, Sailing, Sailing in Fajardo, Tour Reviews

Puerto Rico Private Catamaran Sail from Fajardo

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Where to go in Puerto Rico

Pick a coast, a bay or a rum bar.