Under sail · PUERTO RICO SAILING TOURS

7 Puerto Rico Sailing Tours Worth Booking

7 sailing trips  ·  seats from $99 each

Short on days in Puerto Rico? Give one of them to the water. Below, 7 sailing trips that earn it.

Icacos Island Catamaran Day Sail from Fajardo - The first hour: El Yunque and the Fajardo coast
Catamaran Sailing Trips, Fajardo Sailing Tours, Puerto Rico Sailing Tours, Sailing Tours, Tour Reviews

Icacos Island Catamaran Day Sail from Fajardo

1.Icacos Island Catamaran Day Sail from Fajardo

★★★★★★★★★★5.0 · 1,483 reviews · from $140Top of the fleet

Spend about six hours aboard an East Island Excursions catamaran from Fajardo, sailing past El Yunque to Cayo Icacos or, if conditions shift, Palominitos. Swim, snorkel with provided gear, eat a deli buffet, and enjoy rum drinks. Captains Jose and Carlos and crew members including Neff and Adrian have earned praise for safety and attentive service, but the boat can feel crowded at full capacity.

“This excursion was absolutely perfect 100/100! The tour guides were incredible and made the whole experience unforgettable. The water was stunning, the food was delicious, and the vibe was amazing. I met so many great people, and the drinks kept flowing all day. Truly an experience I’ll never forget!”

Check sailing dates →Read the whole sail review

Historical San Juan Bay Sunset Sailing Tour - The J30 boat and what the ride feels like
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

Sail San Juan Bay for about two hours aboard a 30-foot J30 racer-cruiser with no more than six passengers. Your captain, often Ivan, Joe, or Carlos, shares local history while you pass near El Morro and watch the sunset. Beer, sangria, rum and Coke, water, and non-alcoholic drinks are included. Arrive early at the pedestrian gate.

“Very fun and worth it! We had the sunset sail really beautiful and relaxing. Sangria was tasty too. I highly recommend. Thank you for showing us a wonderful time!”

Check sailing dates →Read the whole sail review

San Juan Catamaran Sunset Sail with Drinks Included - Boarding at San Juan Bay Marina
Catamaran Sailing Trips, Puerto Rico Sailing Tours, Sailing Tours, Sailing Tours with Drinks, 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

Sail San Juan Bay aboard a 37-foot catamaran with up to six passengers. Captain Hector, Rafael, Victor, Sophia, or another crew member may point out El Morro and San Juan Gate while you enjoy rum punch, sparkling wine, beer, or soft drinks. The two-hour trip returns to the marina after sunset.

“Very chill sunset cruise on the water. Captain and first mate were very friendly and also served as bartenders.”

Check sailing dates →Read the whole sail review

San Juan Bay Day Sail with Drinks Included - What is in your glass
Puerto Rico Sailing Tours, Sailing Tours, Sailing Tours with Drinks, Tour Reviews

San Juan Bay Day Sail with Drinks Included

4.San Juan Bay Day Sail with Drinks Included

★★★★★★★★★★5.0 · 502 reviews · from $99Lowest fare aboard

Spend 90 minutes aboard a small traditional sailboat in San Juan Bay with a captain and mate, complimentary mimosas, beer, rum punch, soft drinks, and views of Old San Juan from the water. The boat carries no more than six people, making this a calm, personal outing rather than a party cruise.

“Great experience and great customer service! Captain and skipper were knowledgeable and fun! Such a great experience!”

Check sailing dates →Read the whole sail review

Sailing and Snorkeling Day Charter in Fajardo, Puerto Rico - Snorkeling near Piñeros or Palomino
Fajardo Sailing Tours, Private Sailing Charters, Puerto Rico Sailing Tours, Sailing and Snorkeling Trips, Sailing Tours, Tour Reviews

Sailing and Snorkeling Day Charter in Fajardo, Puerto Rico

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

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

Set sail from Puerto del Rey Marina with a captain and first mate for a five-hour trip toward Piñeros or Palomino. You can snorkel, swim, visit a beach, lounge on the catamaran trampoline, and help prepare a Puerto Rican-style barbecue lunch. Groups are limited to six, with private charter upgrades available.

“Really nice and the host, as well as captain were very nice. They cooked on the boat, music, food, everything was great !!!”

Check sailing dates →Read the whole sail review

Puerto Rico Private Catamaran Sail from Fajardo - Four hours around Cayo Icacos and nearby islands
Catamaran Sailing Trips, Fajardo Sailing Tours, Private Sailing Charters, Puerto Rico Sailing Tours, Sailing Tours, Tour Reviews

Puerto Rico Private Catamaran Sail from Fajardo

6.Puerto Rico Private Catamaran Sail from Fajardo

★★★★★★★★★★5.0 · 45 reviews

Take a private six-hour catamaran charter from Fajardo’s Puerto del Rey Marina for up to six people. Your captain and crew handle the sailing while you snorkel, relax, and visit Cayo Icacos or nearby islands. Lunch packages are available, and crew members such as Carlos, Ari, Leo, Hiram, and Kalani have helped make past trips especially personal.

“It was a perfect day in every way. Carlos and kalani were perfect hosts. Made us feel so comfortable. Boat beautiful and steady. Great snorkeling and paddle boarding. Saw lots of fish. They gave our 8 yr old special attention so she could enjoy the experience even more. Everyone Loved our day at sea!”

Check sailing dates →Read the whole sail review

Janise Sailing Afternoon Charter in Fajardo, Puerto Rico - A short sail along Fajardo’s coast
Fajardo Sailing Tours, Private Sailing Charters, Puerto Rico Sailing Tours, Sailing Tours, Tour Reviews

Janise Sailing Afternoon Charter in Fajardo, Puerto Rico

7.Janise Sailing Afternoon Charter in Fajardo, Puerto Rico

★★★★★★★★★★5.0 · 14 reviews · from $229

Spend three hours aboard the Janise Lagoon 380 with captains Ivan, Carlos, or Charlie, sailing from Puerto del Rey Marina near Fajardo. You can swim from the anchored catamaran, enjoy appetizers, beer, wine, sangria, and soft drinks, then watch the sunset with Ramos Island behind you. The maximum group size is six.

“Awesome tour. Ivan and Charlie were great hosts. My friends and I had a good time. Would highly recommended!”

Check sailing dates →Read the whole sail review

Other ways to get on the water

Sunset Sailing CruisesCatamaran Sailing TripsSailing and Snorkeling TripsPrivate Sailing ChartersIsland Hopping Sailing TripsTall Ship and Schooner Sailing
Scroll to Top

Explore sailing

Pick a boat, a coast or a time of day.

Kinds of sail

Catamaran tripsTall shipsYacht chartersPrivate chartersLessons

Time of day

Golden-hour sailsDinner sailsParty sailsTwo-hour sailsFull-day sails

On board

Drinks on boardLunch at anchorSwim stopsSnorkel sails

Out at sea

Island hoppingWhales and dolphinsNile feluccasEvery sailing trip