Top Puerto Rico Sailing Tours

Sail to Isla Icacos on this full-day cruise from Fajardo aboard a modern 51 ft. sailing catamaran. Relax and enjoy the scenery as you travel, then snorkel among reefs teeming with tropical fish and spend time on the beach. Midday, enjoy a sandwich buffet lunch with beverages included. Hotel pickup and drop-off from San Juan, Condado, and Isla Verde areas are provided for convenience.

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.

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.

Set sail across the Caribbean on this 1.5-hour cruise from San Juan and enjoy unforgettable views of the Puerto Rican capital. Hop aboard a traditional sailboat and sip complimentary drinks as you cruise along the coast. Keep your camera to hand as you pass landmarks and spot dolphins and sea turtles swimming and playing around the boat.

This private sailboat charter from San Juan allows you to choose your own adventure. Sail around the bay and harbor of Old San Juan with an experienced captain and crew at the helm; you can choose to help sail or just relax and enjoy the ride. Bring whatever you prefer to sip on, as you watch the scenery. Ask any questions you may have about boating or the area.

Discover the beauty of the Caribbean on a 4-hour tour to the stunning Icacos Island. This trip offers the perfect blend of relaxation and adventure with two exciting stops: one for snorkeling among vibrant marine life and another to soak up the sun on the beach. Savor a delicious buffet-style lunch served aboard the catamaran, along with refreshing drinks and all necessary snorkeling equipment provided. Ideal for families and groups, this unforgettable experience departs from Fajardo at 9:00 AM and returns at 1:00 PM and the afternoon tour from 2:30pm to 6:30pm - 4-hour tour to Icacos Island with snorkeling and beach time - Buffet-style lunch and refreshing drinks included - All snorkeling equipment provided for your convenience - Perfect for families, friends, or anyone looking to unwind in paradise

Navigate the seas aboard an authentic sailboat during this excursion in the Bay of San Juan. While most boats these days have noisy motors, this sailboat experience exclusively uses the power of the wind. Enjoy views of Old San Juan from a different perspective and sip on beer or sangria as you sail; you may even encounter local wildlife like dolphins.

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.

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.

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!

Go sailing and watch the sunset on a cruise from San Juan. Get great photo ops of Puerto Rico’s coastline and enjoy a comfortable sail on the Caribbean Sea. Your captain shares commentary about the region and provides complimentary drinks for your group of no more than six people.

Come aboard the comfortable Janise Lagoon 380 for a memorable voyage in the beautiful waters of the Caribbean Sea ending in an amazing sunset setting. Great for engagements, and any special private event. Come experience the 1st class service by our professional and friendly crew. Our great reviews have positioned us as the #5 Tripadvisor company in Fajardo.

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 8 years and above.

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!

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 8, 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 8 years and above.

Get a taste of island life during this full-day catamaran snorkel and swimming cruise, where you get to explore the tropical isle of Icacos and the area’s fantastic marine life, then stroll the deserted beaches of a protected island for some shell hunting and sunbathing. Along the way enjoy a lunch, with included bottled water, sodas & tropical drinks.

Looking for a travel experience that goes beyond the ordinary? Black Octopus Tours offers more than just sightseeing, we craft unforgettable journeys designed to thrill, inspire, and connect you with the heart of every destination. You'll get personal attention, more flexibility, and the chance to really immerse yourself in the moment.

Enjoy a unique location to experience a sunset sail and swim in the South Coast Of P.R. in a protected anchorage.

Experience the stunning southern coast of Puerto Rico on this full-day, private boat tour. Climb aboard your sailboat with your group and venture out to explore the Jobos Bay Reserve, Cayo Caribe, and other wetland locations. Use the provided snorkel equipment and listen to informative commentary from your captain about local marine life.

On this trip we offer you a sailboat trip experience during 6-hours tour from the coast of Fajardo to two (2) different destinations: Icaco Island and Palomino Island, in combination with snorkeling, swimming experience and much more. The trip include: (1) Food (cold cuts, assorted cheeses, appetizers, assorted dips with chips and snacks), (2) Drinks (water, soft drinks, local beers) and (3) Onboard amenities (Snorkeling equipment, paddle board, floating water mat, open swim platform, music radio, life jacket in all sizes, toilet, ice cooler). We have offered private sailing and snorkeling adventures on Puerto Rico’s east coast (Fajardo) for over 19 years. We’re fully licensed and U.S. Coast Guard-certified, taking you to beautiful spots like Icaco and Palomino Islands. Based in SunBay Marina, we craft unforgettable experiences for up to six guests. This is the perfect way to enjoy an unforgettable day on the water in Fajardo, Puerto Rico! La Isla del Encanto.

On this trip we offer you a sailboat trip experience during 4-hours tour from the coast of Fajardo to one (1) selected Island (Icaco Island or Palomino Island). Customers can swim and enjoy themselves on each island. In some cases, we spend more time in one of the islands, depending on what the customer wants to do.

We are the only excursion that allows you to drive the boat during this private excursion. We are the only boat that sails in the dark, at night, wait till you see that sky and moon.!!

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.