Top Puerto Rico Night Cruises

Bioluminescence in La Parguera, Puerto Rico. During your visit to Puerto Rico, this is a must-do experience—enjoy this natural phenomenon on a unique Chiliboats Waterbike adventure. Tiny microorganisms make the water glow at night, creating sparkling light with every movement of your hands or feet. We will pedal for approximately 25 minutes on our Chiliboats Waterbikes to reach the bioluminescent bay. Unlike traditional kayak tours, this experience offers greater stability, comfort, and smooth pedaling. This bay is part of a protected natural reserve, where you can enjoy the ecosystem and, on clear nights, a sky full of stars. All tours are conducted on double Chiliboats. Participants must meet height (54" – 6'5") and weight limits (240 lbs per person / 450 lbs combined). Join our professional local guides and enjoy one of the most unforgettable nighttime experiences in Puerto Rico.

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.

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.

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.

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.

Escape the crowds on land and see a part of Puerto Rico that most travelers miss on a sailing tour by catamaran to Culebra Island —home to white-sand beaches and coral reefs, and hailed as one of the most beautiful islands in the world. Lunch, alcoholic drinks, and snacks are included on board, to keep you hydrated and refreshed. A visit to Culebra is weather-dependent, so other possible beach stops include the beautiful Icacos island or one of Vieques' beaches.