Top San Juan Cruises & Sailing

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 Puerto Rico's waters from a luxurious 54-foot catamaran. How you spend your time is up to you: Recline on daybeds, shoot down water slides, or head to the open bar. Visit hidden parts of the Cordillera Cays where you can dive into the water with less crowds of tourists. Dine on an authentic Puerto Rican meal featuring pork, roasted chicken, and more.

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.

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.

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.

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.

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.

Turn a visit to Culebra into a smooth, all-in-one island escape on this high-speed catamaran day trip from Fajardo. Instead of arranging boats, meals, and beach time separately, cruise out for a full day of snorkeling over coral reefs and relaxing on pristine beaches. Optional round-trip transportation from Old San Juan, Condado, or Isla Verde makes getting there just as easy as the day itself.

Explore the underwater world of Puerto Rico on a guided snorkeling adventure. Receive a lesson from a professional diver and enjoy a hassle-free outing with all the equipment you need. Then swim through the tropical waters off Guaynabo and see brilliantly-colored tropical fish, sea turtles, and other marine creatures. Afterward, revisit your experience with a GoPro video of your snorkeling excursion included in the tour price.

Explore Puerto Rico’s lush rainforest on this small-group half-day tour to El Yunque. Relax in an air-conditioned vehicle with hotel pickup as you drive to the hike's starting point. Following your guide, learn about the nature you walk past as you make your way to your destination. Slide down natural waterslides, jump off cliffs, and soak in the tropical environment. Perfect for travellers, especially cruisers, who want a taste of the jungle but are tight on time.

Experience the thrill of a VIP adventure with a water jet car. Drive a luxurious jet car that feels just like a sports car—on the water! Cruise through the crystal-clear Caribbean waters of San Juan Bay while taking in breathtaking views of iconic landmarks such as Old San Juan, La Fortaleza, and Castillo San Felipe del Morro. Whether you’re looking for an exciting ride for two or a fun-filled outing for the entire family, there’s a car that suits your needs. Feel the rush of speed as you explore the coast uniquely and exhilaratingly. This experience requires that drivers be 21 years of age or older, while passengers must be at least 12 years old, making it a perfect adventure for a wide variety of participants.

We provide excellent private transportation services for tourists and corporations Our chauffeurs are very professional, friendly, reliability, knowledgeable, and and detail-oriented so that you can meet all of your travel demands and exceed your expectations. This is an One Way service.

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.

“3 Tours in 1 Day” This tour bundle visits 3 must see locations in the Island. 1st Discover the rich history of Old San Juan on a hop-on, hop-off tour, 2nd explore tru the lush trails & visit two natural waterslides in El Yunque Rainforest, and 3rd visit Los Kioskos Beach a beautiful and fun spot for relaxation and Puerto Rican cuisine. All with convenient Round-trip transportation. This is the ultimate island day experience. Join us! Reserve your spot, We do the rest!

Go snorkeling in an area that's known for turtle sightings with this small-group tour, led by a local guide. You'll head down into waters of a marine sanctuary area where turtles are known to congregate and having a guide on hand will help you increase your chances of spotting the aquatic creatures.

Condado Lagoon is one of the best places to kayak in Puerto Rico, which means it often gets crowded. This guided tour lets you sidestep the crowds by taking you out onto the water in the early morning. Best of all, you'll paddle through the lagoon in a glass-bottom kayak for full, 360-degree views.

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.

Gain access to a private Puerto Rican ranch, where you will explore on horseback during this half-day tour. Get matched up with a well-trained Paso Fino horse, according to your skills and experience, then set out to see the vegetation and wildlife. You'll get views of the surrounding mountains and coastal plains and listen to commentary on the history of the Paso Fino horses. Cool down with drinks after the ride at the hilltop bar (own expense).

Combine a trip to El Yunque with some beach time at Luquillo with this full-day group tour. You'll start in El Yunque, where you'll take a walk out through the forest and get the chance to swim in crystalline rivers and slide down natural waterslides at Las Paylas. You'll then continue to Luquillo, where you can spend time at the local beach, shop, and grab food (own expense) at Los Kioskos at before returning to San Juan.

Discover the fascinating history behind Old San Juan’s iconic landmarks on this two-and-a-half-hour walking tour. A local guide will walk you through Puerto Rico’s rich history, culture, and nature as we visit landmarks including El Castillo San Felipe del Morro Fort, San Juan Cathedral, the Governor’s Mansion, and the San Juan Gate. Local guides are fluent in both English and Spanish.

Discover the Jewish heritage of Casablanca on a private, expertly guided tour with Typically Morocco Tours. Led by an official licensed guide with advanced academic training in Jewish heritage, this experience offers an authentic insight into Jewish life . Visit Temple Beth El, Casablanca’s most prominent synagogue, the Museum of Moroccan Judaism, the historic Mellah (Jewish Quarter), the Jewish Cemetery, and Eim Habanim Synagogue, a vibrant center of community life still active today. Designed especially for Jewish American, Canadian, and Israeli travelers, this tour highlights shared history, traditions, and centuries of coexistence between Jewish and Moroccan cultures. The experience is private and fully customizable, ideal for families, heritage travelers, and multigenerational groups. Cruise-friendly: Flexible timing makes it perfect for shore excursions from Casablanca Port. Travel-trade ready: Ideal for DMCs and U.S., Canadian, and Israeli travel agencies.

Enjoy the beauty of El Yunque Rainforest and Playa Luquillo on this half-day tour from San Juan. Hike through the rainforest, swim and slide in the Luquillo River, then visit Luquillo Beach to swim, shop for souvenirs, or grab lunch (own expense). Hotel pickup is included for your convenience.

See the spectacular bioluminescent bay at La Parguera during this afternoon and evening tour from San Juan. Learn about this natural phenomenon from your guide's commentary during a boat trip through the mangrove forests and cays. At the bay, see the tiny, harmless dinoflagellates that light up when the water’s surface is disturbed. Includes convenient round-trip transportation from selected areas of San Juan.