Top San Juan Cruises & Sailing

Explore the historic area of Old San Juan on a small-group walking tour. Step back in time, over 500 years, and learn about the island of Puerto Rico from your guide. As you walk, pass by important landmarks while your guide regales you with history and tidbits about the local culture.

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.

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.

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.

This private sailboat charter from San Juan allows you (maximum 6 passengers) 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 about owning a boat; your crew is there to educate you on potential future boat sailing and ownership. Our prices already include all taxes and fees.

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.

Live out your island castaway fantasies aboard a luxury catamaran as you visit the deserted tropical island of Cayo Icacos from San Juan on this half-day sailing cruise. 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, and a lunch buffet with drinks.

Spend an adventurous day exploring two of Puerto’s most incredible natural wonders on this full-day excursion to hike in the El Yunque Rainforest and kayak at the island’s famed Bioluminescent Bay. Start your morning with a hike in the only tropical rain forest in the United States National Forest system, enjoying incredible mountain views and an optional waterfall swim to cool off. Then continue with a nighttime kayaking trip to the magical Bioluminescent Bay, which features a unique variety of plankton that glow when the water is touched or moved. Your Puerto Rico outdoor adventure also includes round-trip hotel transport, professional guide, and national park fees.

Join a nighttime adventure into the waters of Laguna Grande as you visit the area’s amazing bioluminescent bay during this half-day excursion. Hop aboard a clear-bottomed kayak as you paddle through the dense mangrove forests, heading to the area where the microscopic plankton puts on its surreal aquatic light show when you glide through the water. Your professional guide also tells you more about this fragile ecosystem and how visitors can help protect it.

Kayak through the waters of Laguna Grande, a stunning bioluminescent lagoon, during this half-day tour from San Juan. Watch the glowing organisms in the water light up as your kayak slides through the water. Paddle through stands of mangrove trees and watch small fish dart through the water underneath your boat like shooting stars. Stop for a break with snacks and refreshments before heading back to your starting point. Use of all kayaking equipment and round-trip hotel transfers are included.

Explore the waters around San Juan on a miniboat, which holds a small group of up to four people. You'll get great, photo-worthy views of the shoreline and listen to guided commentary as you travel. A small group means personalized attention from your guide and an intimate atmosphere.

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.

Get a comprehensive tour of the island of Puerto Rico during a single outing from San Juan. Spend the day in the company of a guide who will follow a carefully curated itinerary that includes many points of interest that typical tours don't cover. You'll see many of the island's natural features, including caves, beaches, and rivers, and listen to in-depth historical commentary. Your small group is limited to just 14 people for an intimate atmosphere.

Hike through Puerto Rico’s lush El Yunque Rainforest, observe local wildlife, and take a dip in one of the park’s pristine waterfalls. Journey through the varied micro-climates and vegetation zones of this unique natural area. Hike through the jungle, learning about the plants and animals that inhabit the area and passing by a series of waterfalls, stopping to cool off with a swim.

Feel like a true Puerto Rican explorer during this day of "off-the-beaten path" discovery in El Yunque rainforest. Avoid the big crowds from the cruise ships and hotels as you blaze a trail to the lesser-known attractions of this lush tropical eden. Admire gorgeous orchids, exotic birds and wildlife like the Coquí (tree frog) as you hike to secret waterfalls and hidden swimming spots, enjoying your secluded adventure amidst the fresh air and beautiful scenery of this Puerto Rican paradise. National park fees, plus round-trip hotel transport, are included.

Combine two of Puerto Rico’s top attractions, Luquillo Beach and the Rainforest, into one great trip on this full-day excursion from San Juan. Enjoy the lush beauty of this tropical forest as you complete a short hike to nearby natural water slide for wildlife viewing, sightseeing, and swimming. Finish the day with time to sunbathe and swim along one of the island’s more scenic stretches of sand. •Discover two of Puerto Rico's top attractions—Luquillo Beach and the Rainforest—on a single trip •Walk through a scenic natural river and look for rare plants and animals in Rainforest •Cool off with a refreshing swim in a natural river (time permitting) •Enjoy the sand, sun, and surf at Luquillo, one of Puerto Rico's most popular beach areas •Includes roundtrip transport and entrance fees •Great way to get out of San Juan for a day in the outdoors

Explore the historic area of Old San Juan on a small-group walking tour. Step back in time, over 500 years, and learn about the island of Puerto Rico from your guide. As you walk, pass by important landmarks while your guide regales you with history and tidbits about the local culture.

Get back to nature in Puerto Rico thanks to this guided exploration of the El Yunque National Forest. Immerse yourself in the beautiful surroundings of this rainforest paradise as you 'stop to smell the flowers’ (the park has over 240 native species), visit the picturesque ‘La Coca’ Falls, and enjoy the views from Yokahú Tower. Park entrance fees are also included.

Lose yourself in the wild landscapes of the El Yunque National Forest on this full-day tour from San Juan. Follow your guide on a thrilling hike, trekking off the beaten path to cascading waterfalls, natural pools, and waterslides in the rain forest. The moderately strenuous trail is ideally suited to physically fit travelers who can scramble across rocks and rivers. Along the way, you’ll learn about Puerto Rico’s diverse ecosystem.

Feel like a real-life explorer as you get off the beaten path to spend hours of hiking, swimming and exploring in Puerto Rico’s El Yunque rainforest. Journey into the beautiful tropical scenery of this lush national park as you hike, visit the amazing mountain views and enjoy a natural waterslide where you can zoom 20 feet (6 meters) into a pool of sparkling water below. The more adventurous can even jump from a 40-foot (12-meter) cliff! Finish your day with an authentic Puerto Rican lunch. Your El Yunque trip also includes round-trip hotel transport, a certified tour guide, national park fees and bottled water.

Experience the lush rain forest of the east side of Puerto Rico on a small-group half-day tour to El Yunque National Forest from San Juan. Get great views over the landscape from Yocahu Tower, then visit scenic spots including La Coca Waterfall and Mameyes River. Have time to swim and purchase lunch at a local restaurant before making the return drive to San Juan.

Combine visits to Flamenco and Culebra beaches, two of the San Juan area's best, on this guided tour via speedboat. Learn about the area's marine life and environment from your guide between relaxing on the beach or exploring the underwater world with a provided mask and snorkel. Midday, refuel with a provided lunch. San Juan hotel pickup and drop-off included, as well as snorkel instruction for beginners.

Get a deeper look at Puerto Rican culture and experience San Juan like a local, with a local, on this immersive, in-depth private tour. Discover sights from street art and murals, and bars and restaurants, to 16th-century forts. Hit the tourist areas, including Ocean Park, explore the 500-year-old city of Old San Juan, and see the La Perla shanty town where the Despacito music video was filmed.

See many of Puerto Rico's top natural attractions in a single day on this half-day experience from the San Juan area. Walkthrough the rainforest and relax on the beach with a guide who will teach you about local wildlife as you go. Highlights: •Learn about local wildlife on tour to the Rainforest •Kid-friendly choice ideal for families •Hotel pickup and drop-off included Pick up at 10:00 am, and we will return at 5:30 to 6:30 pm approximately (May vary depending on the number of participants) Our guide can change the order and logistics of the tour to avoid big groups or weather conditions. We will stop for authentic Puertorrican lunch, but it’s not included. Round trip transportation

Enjoy Puerto Rico at its best! Visit the Rainforest and enjoy beautiful views of this tropical paradise. The first stop will allow you to purchase last-minute snacks (not included) before you are taken to discover a river and a nature-created water slide. Pictures are a must! After enjoying this hidden gem, you will spend time in one of our most popular beaches where you may sunbathe, catch some waves, or indulge in a large selection of authentic food for purchase. The tour includes round-trip transportation from San Juan and Rio Grande area.