Top Puerto Rico Sailing Tours

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.

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 like San Juan Bay Marina and El Morro Fort, and spot dolphins and sea turtles swimming and playing around the boat.

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.

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.

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.

Explore the colorful buildings and charming streets of Old San Juan in a small group with the help of writer David Rodríguez, author of ‘The Rise and Fall of the Great Barbate.’ During the course of your day, the knowledgeable author helps you discover the area’s key historic sites and gain new insight into Puerto Rican culture. It’s a great opportunity to learn about the many stories of the people who helped to define this unique neighborhood. The length of your walking trip is flexible based on your needs and also includes bottled water.

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.

Explore Old San Juan at the most magical time of day during a sunset walking tour around the historic centre of Old San Juan. Exploring on foot means you’ll notice architectural details that you might otherwise miss if you were traveling in a traditional tour vehicle, while guide commentary brings the town to life with stories you’re unlikely to find in the guidebook.

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.

Boat tours can be crammed with people, creating an uncomfortable experience on the water. Instead, choose this Fajardo Private Island-Hopping Sailing Tour with Open Bar and go from place to place in a private group with no interruptions. Plus, you'll have access to appetizers and an open bar stocked with local beer, rum, vodka, tequila, and white wine.

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.

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.

See more do more! 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!

Paddle board experience on a tour of the Condado lagoon, where you can appreciate the old historic "Los Hermanos" bridge, the maritime life of our reef in a natural reserve, we can see turtles, manatees, and fish of different species. We focus on making the tour to your liking and enjoying the time.

Experience Puerto Rico’s eastern shore aboard your own charter boat during this full-day excursion. Sail from Fajardo and enjoy snorkeling. We can also create an itinerary that fits your group's interests. Enjoy plenty of amenities including paddleboards, floaties, assorted beverages, and beach snacks for a hassle-free experience.

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.

Venture away from the main island and explore the smaller, eastern islands of Puerto Rico aboard your own charter boat. Sail from Fajardo and spend the day swimming, sunbathing, paddleboarding, and snorkeling in and around Palominos Island. Enjoy drinks while you sail and bring your own meal/snacks aboard for the perfect day on the water.

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.

For maximum flexibility, choose a schedule and activity to suit you during this boutique snorkeling, swimming, and sailing excursion. Skip the large tour groups and benefit from the personalized attention of your captain, something few travelers get to enjoy, while making the most of the provided paddle boards, floats, snorkels, as you sail to either Icacos or Palomino Island.

Discover the eastern islands off the coast of Puerto Rico during this private day trip. Board your boat and sail off into the Caribbean and stop at Palominos, Lobos, and/or Icacos islands, depending on the weather conditions. Enjoy plenty of time to paddleboard, snorkel, swim, and soak up the sun over the course of the day, and indulge in a selection of appetizers and an open bar aboard the vessel.

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

See Fajardo at its most magical during a private sunset sailing tour that lets you escape the crowds on land and capture photographs of the Caribbean Sea at golden hour. You’ll have plenty of room on board your private boat, and will enjoy the undivided attention of your captain and crew as you admire the coastline and refresh with cocktails and snacks.

Take in the picturesque views and experience a refreshing breeze as you sail to an island paradise on a spacious, 54-foot (16-meter) catamaran from San Juan. Swim in the turquoise waters, then enjoy a lunch with tropical drinks on the beach. During the cruise back to San Juan, relax in the shaded cabin area or on the open-air deck of the boat.