5 star rating: Highly Recommended 5 Reviews

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  • Location:San Juan, Puerto Rico
  • Duration:2 hours (approx.)
Enjoy the perfect evening out in San Juan on this intimate nighttime cruise, limited to just six passengers. Enjoy sparkling wine and strawberries as you admire the views of the San Juan waterfront after dark. Help sail if you wish, or just lounge on a deck chair, basking in the refreshing nighttime breeze. You’ll pass UNESCO World Heritage sites like San Felipe del Morro Fortress and La Fortaleza, and hear about the history of these attractions from the crew. Plus, you may spot dolphins, sting rays or other sea life!


  • 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!

After making your own way to San Juan Bay Marina, hop aboard your 38-foot (11.5-meter) Jeanneau Sloop sailboat and begin your nighttime cruise from San Juan. You’ll be welcomed with a quick safety briefing, and then, as you sip your two complimentary beverages (choose your poison – wine, beer, sparkling wine, rum, soda), sit back on a reclining deck chair and enjoy the twinkling views of the San Juan coastline and the cruise liners in port.

Cruise along the San Antonio Canal, learning the basics of sailing as you watch the jib sail going up. You can take the helm for a bit if you want, or stay on the side lines, snapping photos and enjoying the sea breeze.

Pass by Juan’s World Heritage-listed attractions – the 500-year-old San Felipe del Morro Fortress and La Fortaleza, the residence of the Governor of Puerto Rico. Hear commentary about city attractions like the Puerto de Tierra neighbourhood, the city walls and San Juan Harbor, and listen to stories about the pirates of the Caribbean.

As you enjoy the views and listen to relaxing music, keep your eyes open for local marine life like dolphins, sting rays and seabirds, and snack on a tray of fresh strawberries (additional hors d’oeuvres and drinks are available to purchase). After a couple of hours on the water, return to the marina to continue your night out in San Juan.

Customer Reviews

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.

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.

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!

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.

From USD $ 119.71

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Tour code: 5888NIGHT


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