Category Sailing

Puerto Rico · SAILING

The 12 Best Sailing Trips in Puerto Rico

12 reviewed

Culebra Snorkeling Tour by Catamaran from Fajardo

Culebra Snorkeling Tour by Catamaran from Fajardo - The High-Speed Catamaran Ride: Fun, Fast, and Sometimes Rough

1.Culebra Snorkeling Tour by Catamaran from Fajardo

★★★★★★★★★★4.5 · 2,534 reviews · from $180Our pick

High-speed catamaran to Culebra for reef snorkeling, an island buffet, and a beach chosen by weather, with drinks included and sea-sickness warned.

“Had an amazing time !! the crew was super friendly and such a vibe to chill with for the day, DRINKS were amazing MUSIC was the vibes and the FOOD was also good !!!!!!”

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Icacos Deserted Island Catamaran, Snorkel, and Picnic Cruise

Icacos Deserted Island Catamaran, Snorkel, and Picnic Cruise - Lunch on a Catamaran, Real Food Beats the Usual Boat Plate

Icacos Island Catamaran Day Sail from Fajardo

Icacos Island Catamaran Day Sail from Fajardo - The Crossing: Where the Views Actually Matter

Historical San Juan Bay Sunset Sailing Tour

Historical San Juan Bay Sunset Sailing Tour - How the sailboat layout affects comfort and movement

4.Historical San Juan Bay Sunset Sailing Tour

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

Small-group San Juan Bay sunset sail near Morro, 2 hours with included drinks and commentary, plus calm-water photos of Old San Juan.

“Meeting directions were not good. We were told to go to a green gate. We did. Now they say it was the pedestrian gate. No way to contact them.”

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San Juan Catamaran Sunset Sail with Drinks Included

San Juan Catamaran Sunset Sail with Drinks Included - The 2-hour sunset cruise: what you see and why it feels different

Culebra Full Day Beach and Fun Experience by Catamaran

Culebra Full Day Beach and Fun Experience by Catamaran - The start in Fajardo: Safe Harbor Puerto del Rey

Icacos Double Dip Power Catamaran Snorkel & Beach Tour

Icacos Double Dip Power Catamaran Snorkel & Beach Tour - The Catamaran Ride: How the Group Size Changes the Day

7.Icacos Double Dip Power Catamaran Snorkel & Beach Tour

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

Catamaran snorkeling at Cayo Icacos with La Cordillera reefs, lunch and drinks, plus beach time from Fajardo. Double Dip tour.

“I messed up and got there a little late but the crew were kind enough to hold the last shuttle for us to get there and make it. Overall, amazing experience with the snorkeling and the island beach. It was my first time putting on fin shoes and swimming with live fish. We anchored right near the beautiful reef in between the Caribbean and Atlantic sea and were able to get up close for a better view. I definitely recommend this trip to any couple that want an amazing 4 hour getaway. Will definitely do it again when i come back to Puerto Rico. Make sure you’re appreciative and tip…”

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San Juan Historical Bay Daytime Sailing Tour

San Juan Historical Bay Daytime Sailing Tour - Finding the meeting point at 482 Av. Manuel Fernández Juncos (and avoiding a stressful start)

Sailing and Snorkeling Day Charter in Fajardo, Puerto Rico

Sailing and Snorkeling Day Charter in Fajardo, Puerto Rico - Snorkeling and swimming: gear included, stops designed to feel less crowded

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

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

Small catamaran sailing from Fajardo to Piñeros or Palomino for secluded snorkeling, BBQ lunch, drinks, and a calm group of six.

“Wonderful trip on a clean, friendly, accommodating boat with Ricardo and Ashley. A nice trip on the water, snorkeling, and beach lounging if you choose (we chose to float and snorkel all excursion!) The provided lunch was such a nice added touch. It was delicious, lean, and healthy. Drink selection was great. This was a 10/10 experience.”

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Icacos: Luxury Sailing Catamaran All Inclusive Beach and Snorkel

Icacos: Luxury Sailing Catamaran All Inclusive Beach and Snorkel - The Getaway Too catamaran, luxury that helps you enjoy the day

Vieques: Beach and Snorkeling Tour by Catamaran from Fajardo

Vieques: Beach and Snorkeling Tour by Catamaran from Fajardo - The Vieques beach stop: Sun Bay, Blue Beach, Green Beach, and Isla Yayí

Puerto Rico Private Catamaran Sail from Fajardo

Puerto Rico Private Catamaran Sail from Fajardo - Cayo Icacos and nearby islands: where your “swim and chill” day happens