The 15 Best Catamaran & Sailing Trips in Puerto Rico

1.Culebra Snorkeling Tour by Catamaran from Fajardo

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

You’ll ride a fast catamaran from Puerto del Rey Marina to Culebra with East Island Excursions. Expect about 50 minutes at sea, 1.5 hours at a reef, lunch and drinks aboard, then a beach stop at Flamenco or Culebrita. Captain Jose and crew members such as Jose Fernando, Jean Paul, Cindy, and Luis have been praised for attentive service.

“I would 100% recommend this activity to anyone who loves the beach, clear waters, and a good time. The employees were extremely friendly, the music and vibes were amazing. I will definitely be doing this again on my next trip to Puerto Rico!!”

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2.Icacos Deserted Island Catamaran, Snorkel, and Picnic Cruise

★★★★★★★★★★5.0 · 2,202 reviews · from $138Top rated

From Fajardo, sail about 45 minutes aboard the Barefoot IV to Icacos or a nearby island. Swim, snorkel with provided gear, hunt for shells, and enjoy a cold-cut sandwich buffet, fruit, sodas, piña coladas, and rum punch. Captain Robert, Luis, Matthew, Edgar, and the crew keep the day moving, with a maximum of 44 people.

“The whole trip was awesome; we had a great time at Cayo Island, and the crew was very friendly. The sights are beautiful. The food was so delicious The only issue was that a group of girls was too crazy, and everyone else on the cruiRead more”

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3.Icacos Island Catamaran Day Sail from Fajardo

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

Sail from Fajardo to Cayo Icacos or Palominitos on a six-hour catamaran trip with East Island Excursions. You get reef snorkeling, swimming, floating gear, a deli lunch, and rum drinks. Captains Jose and Carlos and crew members such as Neff, Andres, and Adrian have helped make this a well-run choice for beginners and groups.

“This catamaran tour was incredible! The island you go to has pristine soft sand and clear blue water. The staff was so kind and attentive. The lunch was surprisingly delish a build your own sandwich with lots of sides. And of course the rum drinks were great! I would do this again!!!”

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4.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. The small group, limited to six, passes El Morro as the captain shares local history. Expect beer, sangria, rum and Coke, water, sunset views, and possible dolphin sightings. Captains may include Ivan, Joe, or Carlos.

“I had an amazing time on the San Juan Bay sunset sailing tour! Our captain was fantastic! He was knowledgeable, friendly, and had great insights about the area. He also shared some restaurant recommendations. The sail itself was so relaxing and the perfect way to unwind and end the day. Highly recommend this experience to anyone visiting San Juan!”

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5.San Juan Catamaran Sunset Sail with Drinks Included

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

Board Sail PR’s 37-foot catamaran at San Juan Bay Marina for a two-hour sunset cruise limited to six people. Captain Rafa, Hector, Victor, Sophia, Nicola, Diego, or another crew member may point out El Morro Fort, San Juan Gate, and other sights while serving rum punch, sparkling wine, beer, soft drinks, and water. Shoes come off before boarding.

“This was the best ‼️ The staff was amazing helped me get on the book and the trip was amazing this made our trip. I will definitely book this beautiful ride in this beautiful boat again 💃🏽❤️”

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6.Culebra Full Day Beach and Fun Experience by Catamaran

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

Sail from Fajardo to Culebra or a weather-safe beach near Culebrita, Icacos, or Vieques on a six-hour catamaran trip. East Island Excursions includes lunch, snacks, soda, alcoholic drinks, kayaks, paddleboards, and beach games. Captains Jose Perez and the crew keep the day moving, but rough seas and a changing beach destination are part of the deal.

“It’s so fun and relaxing lots to do and all the workers were amazing. The two David and Alex definitely made our trip so much better!”

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7.San Juan Bay Day Sail with Drinks Included

★★★★★★★★★★5.0 · 502 reviews · from $99Best value

You’ll sail San Juan Bay for 90 minutes aboard a small traditional sailboat with a captain and mate, often including Rafa and Francisco. Drinks such as mimosas, local beer, rum punch, rum and Coke, and soft drinks are included in moderation. Expect harbor views, a look at Old San Juan’s last remaining city gate, and a relaxed group of no more than six.

“Everything was amazing. They were both so sweet and attentive! They were so kind to me and my son and made sure we enjoyed our time.”

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8.Icacos Double Dip Power Catamaran Snorkel & Beach Tour

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

From Fajardo, you’ll cruise to Cayo Icacos aboard a power catamaran capped at 30 people. Crew members such as Kenny, Kiwi, Jay, Gabriel, Luis, and Gabe help with snorkeling, drinks, lunch, and safety. Expect a reef stop, beach time, included equipment, and a deli buffet during this four-hour outing.

“Excellent crew - professional, knowledgeable, and friendly. The boat was clean, well run, and smaller than most on the water, which made for a more personal experience. We are very happy we chose this tour over the others that we looked at.”

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9.San Juan Historical Bay Daytime Sailing Tour

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

Sail San Juan Bay for about two hours aboard a small authentic sailboat, not a motorized party boat. Captain Joe, Ivan, or another local captain may point out Old San Juan, San Cristóbal Castle, El Morro, La Fortaleza, and Isla de Cabras. Beer, sangria, rum and Coke, and water are included. Groups are limited to six.

“The experience was amazing with breathtaking views. The captain was very knowledgeable and informative, his love of sailing and the island made the excursion top tier.”

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

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

Sail from Puerto del Rey Marina with a captain and first mate to Piñeros or Palomino. You’ll snorkel secluded reefs, swim from a white-sand beach, float on a lily pad, and eat a barbecue lunch with beer, wine, sangria, and soft drinks. Groups are limited to six, with private charter upgrades available.

“Very relaxing half-day sailing trip, with swimming, snorkeling, snacks, and lunch. Everything was extremely well organized, the food was good, the swimming and beach were great. The snorkel equipment was fine, and we did see a range of relatively small, colorful fish, but it was not the most memorable snorkeling.”

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11.Sail Away: Private Scenic Excursion from San Juan

★★★★★★★★★★5.0 · 138 reviews

Take a private two- to three-hour sail from San Juan with Captain Jimbo or another experienced crew member. Help steer, learn simple sailing skills, or relax with your own drinks from the cooler. The route covers San Juan Bay, Old San Juan, its forts, and possibly open water or a swim stop if weather and time cooperate.

“Wonderful sailing with breathtaking views of San Juan - swimming with a large friendly barracuda was a once in a lifetime. James and Nichole, our skippers, were informative and great fun”

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

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

Sail from Fajardo aboard Getaway Too, a 54-foot catamaran limited to 49 guests. Enjoy snorkeling instruction, water swings, floating mats, slides, shaded seating, private restrooms, a Puerto Rican lunch, tropical rum drinks, and a beach stop in the Cordillera Cays. Captain Gabriel and Stephanie are among the crew names associated with this sailing.

“Such a fun experience with very kind staff! My friend and I loved it! I love the different fun things they have around the boat - swings, water slide and places to float and lay down. Loved the unlimited piña coladas too. Such a great experience!”

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13.Day Sail without transportation

★★★★★★★★★★5.0 · 62 reviews · from $130

Meet the crew at Renaissance Villa Marina in Fajardo for a 5.5-hour sail aboard the 51-foot catamaran SPREAD EAGLE II. After a 40 to 50-minute ride to uninhabited Cayo Icacos, you get several hours for snorkeling and beach time, with lunch, snacks, water, music, and fresh snorkel gear included.

“I have been on quite a few boat snorkeling trips and this is by far the best one!! I cannot recommend it enough. If you are actually interested in snorkeling - this is a great tour. Plenty of snorkeling time, friendly and helpful crew, great food and drinks, music was great. Snacks, fruits and drinks available throughout the day. It could not have been better in any way.”

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14.Beach and Snorkeling Tour by Catamaran from Fajardo

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

Leave Fajardo at 9:30 a.m. for a 45 to 55 minute catamaran ride toward Vieques. Your beach stop may be Sun Bay, Blue Beach, Green Beach, or Isla Yayí. Expect swimming, beachcombing, snorkeling, a deli lunch, rum, local beer, and a friendly crew, with space for up to 60 people.

“This excursion leaves from the main marina. They communicate well via phone and email regarding the process for check in and weather. The crews are working doubles, taking people out twice a day. That means the crews are working Read more”

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15.Puerto Rico Private Catamaran Sail from Fajardo

★★★★★★★★★★5.0 · 45 reviews

Spend about six hours aboard a private catamaran from Fajardo with a captain and crew serving only your group of up to six. Sail toward Cayo Icacos or nearby islands, snorkel with provided gear, relax on deck, and choose a package with or without lunch. Captains and crew may include Carlos, Ari, Leo, Hiram, or Kalani.

“Amazing! Wonderful family day!! Thank you very much. Capitán Carlos González and Ari for Your great Job!! Sailing time, snorkeling, paddle board, food… … everything was perfect 😍😍👍🏻”

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