The 8 Puerto Rico Sailing Trips That Earn Their Price

1.Culebra Snorkeling Tour by Catamaran from Fajardo

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

Spend about six hours aboard an East Island Excursions catamaran from Fajardo, snorkeling at Carlos Rosario or Luis Peña, then swimming at Flamenco Beach or Culebrita. Captains Jose and Danny and crew members such as Luis and Cindy are known for attentive service, but prepare for a rough ride.

“This Culebra boat and snorkeling tour was absolutely amazing from start to finish! The crew kept all of our personal belongings safe on the boat while we snorkeled and swam, so we never had to worry about a thing. We started with about an hour of snorkeling at a gorgeous reef, where the water was crystal clear and full of colorful fish and coral. Then the boat moved closer to shore for the beach portion. You do need to swim to get to the beach, but it’s a short, calm swim—and they provide flotation devices for anyone who’s not a confident swimmer. One of my favorite parts? The crew actually…”

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

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

Sail from Fajardo to Cayo Icacos aboard the Barefoot IV Catamaran, with crew members such as Captain Robert, Luis, Matthew, and Edgar. You get beach time, snorkeling gear, floating devices, a sandwich buffet, tropical drinks, and about five and a half hours on the water.

“Exactly as advertised--the food was great, crew was great--it was a great mix of party on the water and beachsnorkeling experience.”

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3.Icacos Island Catamaran Day Sail from Fajardo

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

Spend about six hours aboard an East Island Excursions catamaran from Fajardo. Swim and snorkel near Cayo Icacos, or Palominitos if weather changes the route, then enjoy a deli lunch and rum drinks. Captains Jose and Carlos and crew members such as Luis, Neff, and Andres are known for attentive service.

“We had a great time!! I would love to thank the captain and his crew, they did an amazing job entertaining us and keeping us safe. We laughed alot with the crew especially Carlos he was helpful and knowledgeable. He had us laughing the entire time.”

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4.Historical San Juan Bay Sunset Sailing Tour

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

Spend two hours sailing San Juan Bay aboard a 30-foot J/30 racer-cruiser with a captain such as Ivan, Joe, or Carlos. Expect close views of El Morro, Puerto Rican history, sunset photos, and complimentary beer, sangria, rum and Coke, water, and light refreshments. The boat is small and the departure is strict.

“First it was on small sail boat very hard to get on seating was awful. We got drinks no snacks were provided. I would not recommend this tour to anyone”

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5.San Juan Catamaran Sunset Sail with Drinks Included

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

Join Sail PR for a two-hour sunset sail from San Juan Bay Marina aboard a 37-foot catamaran limited to six people. Sip rum punch, sparkling wine, beer, or soft drinks while the crew points out El Morro, San Juan Gate, and the city’s historic waterfront.

“Our experience was about as perfect as I could have asked. We lucked out with some weather that passed thru just in time, and had a magnificent sunset to enjoy the cruise to. A relaxed paced tour around the bay of San Juan, amazing view of El Morrow at sunset, Rafa (our captain) was a gracious host and the First Mate was attentive to ensuring everyone had what they needed (great drinks!), and threw in some history about some of the buildings and scenery as we went along. The passengers are limited to six (we were three) and we shared the ride with another couple and enjoyed nice conversation together…”

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6.Culebra Full Day Beach and Fun Experience by Catamaran

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

Join East Island Excursions for a six-hour catamaran day from Fajardo. Captain Jose Perez and crew members such as David, Alex, and Carlitos may take you to Culebra, Culebrita, Icacos, or Vieques, depending on sea conditions. Expect lunch, drinks, beach games, kayaks, and paddleboards, but bring towels, sunscreen, and your own snorkeling gear.

“Incredible time can’t wait to return! Crew was super attentive. Food was delish, music was amazing. I look forward to doing this again.”

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7.San Juan Bay Day Sail with Drinks Included

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

Spend 90 minutes aboard a traditional sailboat in San Juan Bay with Captain Rafa, Francisco, or another Sail PR crew pair. Sip a mimosa, local beer, rum punch, or soft drink while viewing Old San Juan from the water, including the city’s last remaining gate. Groups are limited to six.

“Very nice crew and I meet new friends. Clean boat. I was very happy with the drinks provided. I will return someday”

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8.Icacos Double Dip Power Catamaran Snorkel & Beach Tour

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

Sail from Fajardo to Cayo Icacos on a power catamaran capped at 30 people. You’ll snorkel a reef chosen for the day’s conditions, relax on a sandy beach, and enjoy lunch, soft drinks, juices, and rum cocktails. Crew members such as Kenny, Kiwi, Jay, and Gabriel may vary by departure.

“Well organized fun trip. The crew took extra care to ensure we had a good time. Lunch and drinks provided were good. Met some fun people.”

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