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Enjoy sparkling views of San Juan and cooling ocean breezes on this small-group, 2-hour evening sailing tour, limited to just six passengers. Grab a glass of sparkling wine and some strawberries as you admire the view of the city’s glittering lights and UNESCO World Heritage sites, like the fortress of San Felipe del Morro and La Fortaleza, from the boat. This nocturnal sailing cruise also includes the services of a guide, who will provide an overview of the area’s history during your trip.


  • 2-hour nighttime sail in San Juan
  • Admire views of San Juan and its harbor lit up at night
  • Enjoy fresh strawberries and two glasses of wine, beer, sparkling wine or soda
  • See World Heritage sites like San Felipe del Morro Fortress and La Fortaleza
  • Watch for marine life like dolphins and sting rays
  • Small-group cruise with maximum six passengers ensures a more intimate experience

What You Can Expect

San Juan Small-Group Night Sail

Enjoy the views from the water!

Experience an unforgettable and romantic evening sailing cruise on this small-group adventure. Enjoy complimentary drinks and strawberries while you take in the view, help the crew sail, or simply relax on deck in the crisp nighttime air.

Start your evening sailing odyssey at San Juan Bay Marina, where you’ll board the 38-foot (11.5m) Jeanneau Sloop sailboat. Listen to a short safety overview, and then pick from a selection of refreshments including wine, beer, sparkling wine, rum or soda. Your sailing trip begins as your sloop pulls into San Antonio Canal. As the ship gets underway, feel free to learn a few sailing basics from the crew while you take in the twinkling coastline of San Juan and the nearby port.

Out on the open water, you’ll pass by some the city’s most important historical landmarks, including 500-year-old San Felipe del Morro, and La Fortaleza, now the home of Puerto Rico’s governor. Listen as your guide shares a historical overview of nearby landmarks including the Puerto de Tierra area, San Juan harbor and the city walls, plus a few stories about Caribbean pirates.

Take some time to soak in the beautiful views, chill out on deck and watch for marine life including dolphins, stingrays and seabirds, and feel free to indulge in some additional hors d’oeuvres and drinks, which are available for purchase. Finish your 2-hour cruise with a return to San Juan marina, where you can continue the fun.

Customer Reviews

Eric R

5 star rating: Highly Recommended April 2015

If you go to San Juan you have to make it out with Capt Judy. Great time cruising around the harbor and very knowledgeable. Will be back for another cruise next year at our wedding.


5 star rating: Highly Recommended January 2015

Captain Judith kept us with drinks in hand and up to date with info as we passed through different areas in the harbor. I recommend the rum and mango juice. The night sail is nice because the hot sun isn't bearing down on you. We were under power for most of the trip but it was still a nice time.

Kent S

5 star rating: Highly Recommended December 2014

Excellent experience. We greatly enjoyed the perspective of the city from the water. Excellent boat captain and crew. Very attentive;. I would recommend this for everyone.

Jamie C T

5 star rating: Highly Recommended March 2014

Absolutely loved this! Captain Judith treated us like the royal family and made this one of the most memorable experiences during our visit to this great city. We would recommend this tour to everyone and will go again every time we visit San Juan. DO NOT LEAVE THE ISLAND UNTIL YOU HAVE SAILED WITH HER!

John F

5 star rating: Highly Recommended February 2014

We enjoyed this tour thoroughly. It ended up being just the 2 of us and the crew - captain and first mate. It was fun to see the sights from the bay at night. The fort was interesting to see at night from the water. The drinks were tasty too.

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