Top Puerto Rico Sailing Tours

Icacos Catamaran deserted Island, snorkeling, sailing and beach

4 hoursFree Cancellation

Sail the calm, azure waters of San Juan Bay at sunset during a cocktail cruise. Enjoy a warm welcome aboard from your friendly captain and crew, then settle in for a scenic ride. Watch the island coastline glide by as the sun sinks toward the horizon. Sip a complimentary rum punch or sparkling wine with your family and friends and listen as your captain points out landmarks like El Morro Fort and San Juan Gate. Arrive back at the dock in time to continue your evening in San Juan.

San Juan Catamaran Sunset Sail with Drinks Included

San Juan Bay Day Sail with Drinks Included

Day Sail with Transportation from San Juan, Condado, Isla Verde

5 hours 30 minutesFree Cancellation

Icacos Deserted Island Catamaran, Snorkel, and Picnic Cruise

5 hoursFree Cancellation

San Juan Historical Bay Daytime Sailing Tour

Sail Away: Private Scenic Excursion from San Juan

2 to 3 hoursFree Cancellation

All Inclusive Beach & Snorkeling Tour at Icacos & Palomino Island

4 hoursFree Cancellation

Live out your island castaway fantasies as you visit the deserted tropical island of Cayo Icacos from San Juan on this catamaran sailing cruise. Escape the crowds on land and sail into the aquamarine waters of the Caribbean, admiring views of the El Yunque mountains in the distance, before arriving at the nature preserve of Icacos for a leisurely day of swimming, snorkeling, lunch, and rum cocktails.

Icacos Island Catamaran Day Sail from Fajardo

6 hoursFree Cancellation

Historical San Juan Bay Sunset Sailing Tour

Get more time, See more do more!, More Space! Welcome aboard your private water tour aboard a choice between a 37 foot sailboat ot a a high performance Powerboat. Enjoy complimentary local drinks. Your personal tour guide and Pro USCG certified Captain will guide you to stunning and interesting historical points of interest full of Caribbean flare in style and with a high quality sound system. Choose between a bay or sunset water tour. For a minimum of 4 guests or pay for 4 and a maximum of 6. Welcome aboard!

San Juan Bay Private Tour with Drinks and Tapas: 4+ people

3 hoursFree Cancellation

Experience the magic of exploring the marine world at a stunning beach in San Juan. Join this beginner-friendly adventure led by a professional guide in small groups of up to 10, ensuring a personalized and high-quality experience for all. The bay boasts a vibrant array of marine life and magnificent Green Sea Turtles. Guests often spot blue tangs, sergeant majors, fairy basslets, yellow snappers, and more! Occasionally, you might encounter rare creatures like squids, seahorses, rays, and manatees. We suggest the morning time slots as the marine life is more active. Receive a complimentary video to commemorate your unforgettable adventure. This Activity is suitable for ages 12 years and above.

San Juan: Snorkeling with Turtles and Complimentary Videos

Enjoy a new perspective on Old San Juan—and soak up Caribbean breezes and sunset views—aboard this evening boat tour. Following pickup at select local hotels, hop aboard the boat and find a comfortable seat on the deck. Then, spy highlights like Paseo De La Princesa, La Fortaleza, the San Juan City Walls, and more, all while the sun goes down. Light refreshments and alcoholic drinks are available on board.

San Juan Sunset Harbor Boat Ride

Explore the Caribbean waters around Puerto Rico on a sailing tour from Fajardo. Join a small group and head to the nature reserve on Piñeros Island to discover the local biodiversity. Your captain makes several stops throughout the day and you can choose to swim in the pristine waters, snorkel in the abundant reefs, or simply sunbathe on the white-sand beaches. A delicious lunch and drinks are included.

Sailing and Snorkeling Day Charter in Fajardo, Puerto Rico

5 hoursFree Cancellation

Janise Sailing Afternoon Charter in Fajardo, Puerto Rico

3 hoursFree Cancellation

First, we sail to the paradise Island of Icacos aboard the modern, 51 ft. sailing catamaran, SPREAD EAGLE II! The brisk 40 to 50-minute sail to the protected anchorage off of this uninhabited Spanish Virgin Island is beautiful. Sparkling beaches and crystal clear snorkeling waters await. We think you deserve the best, don’t you? Over 65% of our guests are repeats or referrals. The reefs are teeming with parrot fish, foureye butterfly fish, sergeant majors, and wrasse. The variety is too long to list, so you should just come see them all for yourself. Ask one of the crew to see the Fish, Coral, and Shell Identifying Charts on board. SPREAD EAGLE II even provides lunch for the fish. With a little patience, you can get the fish to eat bread right out of your hand.

Day Sail without transportation

5 hours 30 minutesFree Cancellation

San Juan: VIP Snorkeling with Turtles Tour

Private Day Sail - South Coast of Puerto Rico

6 hoursFree Cancellation

3 Hours Private Sunset Sail and Swim

3 hoursFree Cancellation

Catch the most amazing sunsets from a secluded spot on the Jobos Bay National Estuarine Research Reserve (JBNERR) with our experienced USCG Captain and crew, in the comfort and privacy of our 36-foot sailboat fit for six (6) passengers. Your departure time is schedule and confirmed according to the sunset hours. Private Day Sail Charters depart from the gorgeous town of Guayama at the docks of the Guayama Fishing Club, famous for its stunning sunset views. The departure dock in the town of Guayama is about an hour drive away from San Juan, through the amazing landscapes of the Cordillera Central, the main mountain range in Puerto Rico.

2 hrs. Private Sunset Sail - South Coast of Puerto Rico

Come aboard the comfortable Janise Lagoon 380 for a memorable 8-hourfull day charter in the beautiful Spanish Virgin Islands. Come experience first class service by our professional and friendly crew. Our great reviews have positioned us as the #5 Tripadvisor company in Fajardo. Our crew including one USCG certified captain and 1 professional first mate will make sure this is the highlight of your vacation in Puerto Rico!

Private Janise Sailing Full Day Charter in Fajardo, Puerto Rico

8 hoursFree Cancellation

Set sail on a private catamaran adventure with Puerto Rico Sailing Trips. Launching from the beautiful Puerto del Rey Marina in Fajardo, enjoy a serene exploration of Palomino or Piñeros Islands. With a maximum of six guests, the experience promises a personalized touch, guided by an expert crew including a USCG-licensed captain. Relax onboard while soaking in the Caribbean sun and sampling exceptional culinary offerings. Ideal for intimate gatherings, this tour combines comfort and adventure in a stunning natural setting. - Exclusive catamaran experience with a maximum of six guests for privacy - Expert crew ensures safety and high-quality service throughout the trip - Explore the pristine islands of Palomino and Piñeros, just one hour away - Depart from Puerto del Rey Marina, conveniently located 45 minutes from San Juan

Private Catamaran Charters to Palomino Island Puerto Rico

5 hoursFree Cancellation

Must-Dos in Puerto Rico

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What are people saying about Puerto Rico

Day Sail with Transportation from San Juan, Condado, Isla Verde

Enedelia_V, Aug 2026

We had such a great time...

We had such a great time on the boat day! The experience was a lot of fun and everything was pretty straightforward and easy from start to finish. They provided transportation for pickup, which was really convenient. The only downside for us was that we were staying at an Airbnb, so we had to figure out which hotel pickup location was closest to us. Once we figured that out, everything went smoothly. We got to go snorkeling at multiple locations, which was one of our favorite parts. They first took us somewhere where we could stand and get comfortable in the water before moving us to another beach where they had floaties and we were able to snorkel around and see even more marine life. They also provided drinks and had a nice sandwich bar set up, which was perfect after being in the water. The entire crew was amazing, friendly, and made the experience even more enjoyable. They got us there and back safely and kept the whole day fun. Overall, we had an amazing time and would definitely recommend this boat experience. It was a great way to spend the day in Puerto Rico!

San Juan Bay Private Tour with Drinks and Tapas: 4+ people

Kristina_S, Aug 2026

The sunset sail was a...

The sunset sail was a wonderful experience. We seen the city walls from the bay which is a completely different perspective everyone should enjoy. Light snacks and sangria was provided and the best sangria I have ever had! Thank you for the wonderful experience, highly recommend!

Icacos Catamaran deserted Island, snorkeling, sailing and beach

Sasha_M, Jul 2026

Absolutely amazing...

Absolutely amazing experience! Captain Andre was super cool, Zoey was amazing, and Angel kept everyone laughing the whole trip. The crew took great care of us from start to finish. The drinks were good, the food was delicious, and the snorkeling was surreal such a beautiful experience! I would definitely book this excursion again and highly recommend it to anyone visiting Puerto Rico.

San Juan Historical Bay Daytime Sailing Tour

Sarah_R, May 2026

Great sail and great conversation

If you are thinking about sailing, book this trip! You go on a J30 - a stable, comfortable, fast sailboat. Captain Joe is experienced and knowledgeable. We had great conversation with him the whole time, and he really maximized our time sailing. It's a classic sailboat that gives a more intimate experience for small charter groups. Highly recommend!

Sailing and Snorkeling Day Charter in Fajardo, Puerto Rico

Douglas_N, Mar 2026

Memory of a lifetime at Isla Palominos!

Memory of a lifetime visiting Isla Palominos. Scott, our guide, chef and DJ was excellent. Set all expectations very clearly, gave great background/ nature info and commentary of the region and where we were going, history etc. He prepared us a fabulous meal. Snorkeling was terrific, but global warming is taking its toll. Saw sea turtles, rays and a decent amount of fish. Was crazy relaxing. The “Janice” was a well kept boat that was sturdy, clean and maintained well. Ricardo is an experienced Captian that made us feel safe, was very communicative and was a master of the sea. We will definitely be returning. A memory of a lifetime.