Puerto Rico · SAILING

Top 12 Sailing Trips in Puerto Rico

12 tours  ·  from $99 a head

The 12 best sailing trips you can book right now, with the price, the shape of the day and who each one suits. The first is first for a reason.

Culebra Snorkeling Tour by Catamaran from Fajardo - Choosing your seat on a 60-person catamaran
Boat Tours in San Juan, Cruises & Boat Tours, Sailing, San Juan Tours, Snorkeling, Snorkelling Trips in San Juan, Tour Reviews, Tours

Culebra Snorkeling Tour by Catamaran from Fajardo

Icacos Deserted Island Catamaran, Snorkel, and Picnic Cruise - Icacos island, sand, and clear water
Boat Tours in Fajardo, Catamaran Trips in Fajardo, Cruises & Boat Tours, Fajardo Tours, Icacos Island Tours, Sailing, Tour Reviews

Icacos Deserted Island Catamaran, Snorkel, and Picnic Cruise

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

Icacos Island Catamaran Day Sail from Fajardo

3.Icacos Island Catamaran Day Sail from Fajardo

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

Sail from Fajardo to Cayo Icacos for snorkeling, swimming, a deli lunch, rum drinks, and El Yunque views on a six-hour catamaran trip.

“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!”

Check availability →Read our full review

Historical San Juan Bay Sunset Sailing Tour - What the two-hour route feels like
Boat Tours in San Juan, Cruises & Boat Tours, Evening Experiences, Historical Tours, 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 intimate sunset sail, with fortress views, local history, drinks, practical meeting tips, and honest value advice.

“Had a great time with our Captain. Talked about the history of the area and sailed out to the fortress at the mouth of the inlet and back. Was an enjoyable experience and would recommend to my friends and familly.”

Check availability →Read our full review

San Juan Catamaran Sunset Sail with Drinks Included - Meeting the boat at San Juan Bay Marina
Boat Tours in San Juan, Cruises & Boat Tours, 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 Early Morning Start in Fajardo
Beach Tours, Boat Tours in Fajardo, Catamaran Trips in Fajardo, Cruises & Boat Tours, Fajardo Tours, Full-Day, Sailing, Tour Reviews

Culebra Full Day Beach and Fun Experience by Catamaran

6.Culebra Full Day Beach and Fun Experience by Catamaran

★★★★★★★★★★4.5 · 563 reviews · from $195

Review of the Culebra catamaran tour from Fajardo, with beach time, lunch, drinks, kayaks, paddleboards, and practical booking advice.

“The ride was a little scary for me! But you will be ok , they are great hosts !! You will be there for about four hours, we are food and drank the whole time! Thank you David and the rest of the crew! And of course to the captain! Extremely friendly people!!! They all speak English also! Please leave a TIP for the crew at the end of the ride.. they really go out their way to bring you drinks in the water and everything. Amazing ! Muchisimas gracias!! WEPAAAAAAAAA 🇵🇷”

Check availability →Read our full review

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

Icacos Double Dip Power Catamaran Snorkel & Beach Tour

San Juan Historical Bay Daytime Sailing Tour - Leaving San Juan Bay Marina
Boat Tours in San Juan, Cruises & Boat Tours, Historical Tours, 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 in a six-person boat, with Old San Juan forts, local history, wind-powered sailing, beer, sangria, and rum drinks.

“Captain Joe and Marie were fabulous! They were very good at paying attention to every detail, safty and shared their knowledge of the area.”

Check availability →Read our full review

Sailing and Snorkeling Day Charter in Fajardo, Puerto Rico - Snorkeling at quieter island reefs
Boat Tours in Fajardo, Catamaran Trips in Fajardo, Cruises & Boat Tours, Fajardo Tours, Sailing, Snorkeling, Snorkelling Trips in Fajardo, Tour Reviews

Sailing and Snorkeling Day Charter in Fajardo, Puerto Rico

Icacos: Luxury Sailing Catamaran All Inclusive Beach and Snorkel - The first water stop: snorkeling for beginners
Beach Tours, Boat Tours in San Juan, Cruises & Boat Tours, Icacos Island Tours, Sailing, San Juan Tours, Tour Reviews, VIP

Icacos: Luxury Sailing Catamaran All Inclusive Beach and Snorkel

Vieques: Beach and Snorkeling Tour by Catamaran from Fajardo - Four hours at a Vieques beach
Beach Tours, Boat Tours in Fajardo, Catamaran Trips in Fajardo, Cruises & Boat Tours, Fajardo Tours, Sailing, Snorkeling, Snorkelling Trips in Fajardo, Tour Reviews, Tours

Vieques: Beach and Snorkeling Tour by Catamaran from Fajardo

11.Vieques: Beach and Snorkeling Tour by Catamaran from Fajardo

★★★★★★★★★★5.0 · 58 reviews · from $180

Spend six hours sailing from Fajardo to Vieques for beach time, snorkeling, lunch, rum, beer, and El Yunque views.

“We had such a great time! I had motion sickness but the boat had snacks and carbonated drinks to help. Definitely bring motion sickness medicine if you have a sensitive stomach! The island we went to was Culebra, about an hour ride. It was BEAUTIFUL. Definitely need to see if you’re in PR.”

Check availability →Read our full review

Puerto Rico Private Catamaran Sail from Fajardo - Starting at Marina Puerto del Rey
Boat Tours in Fajardo, Catamaran Trips in Fajardo, Cruises & Boat Tours, Fajardo Tours, Private, Sailing, Tour Reviews

Puerto Rico Private Catamaran Sail from Fajardo

12.Puerto Rico Private Catamaran Sail from Fajardo

★★★★★★★★★★5.0 · 45 reviews

Charter a private catamaran from Fajardo to Icacos for snorkeling, sand, swimming, and six relaxed hours at sea with your own crew.

“Captain Leo & Hiram go above and beyond to make this trip a once in a lifetime tour. They meet you at the reservation desk you take a golf cart over to the boat they cater to every need every moment of the trip. The food is amazing and caRead more”

Check availability →Read our full review

Scroll to Top

Where to go in Puerto Rico

Start from a coast, a mountain road or a table.