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Sail away from the hustle and bustle of the city on this relaxing, intimate 2-hour cruise of San Juan Bay, limited to just 6 passengers. Refresh yourself with two complimentary cocktails and fresh strawberries as your sailboat plies the waters near San Juan, the second-oldest city in the Americas. Catch great views of the city’s San Felipe del Morro fortress, a UNESCO World Heritage Site, and maybe even spot some wildlife along the way.


  • 2-hour sailing cruise on San Juan Bay from San Juan
  • Sail past the UNESCO World Heritage Site of San Felipe del Morro Fortress and La Fortaleza
  • Hear live commentary from the captain about Old San Juan and its history
  • Take the helm with a brief sailing lesson or relax on a reclining deck chair
  • Enjoy two complimentary drinks (alcoholic or non-alcoholic) and a platter of fresh strawberries
  • Small-group tour limited to 6 people ensures personal attention from your guide

Recent Photos of This Tour

What You Can Expect

San Juan Small-Group Sailing Cruise

Enjoy views of Old San Juan from the water

Kick back on a lounge chair, cocktail and fresh strawberry in hand, as you enjoy a scenic and historical 2-hour sailing cruise along the coastline of San Juan. Best of all, this small-group excursion is limited to just 6 passengers, ensuring you’ll have a memorable experience with personalized attention.

Start your tour by making your way to the departure point at San Juan Bay Marina, where you’ll board the Jeanneau Sloop, a 38-foot (12m) sailboat. First receive a historic and practical overview on the basics of sailing, and hear a safety briefing. 

Then set sail for adventure as your crew pulls into the San Antonio Canal, heading for San Juan Bay. Relax and make yourself at home as you sip on your choice of complimentary drink, (including wine, beer, sparkling wine, rum, Cava or a soft drink) fire up your choice of music and even take the helm of the ship for a great photo opportunity.

As you cruise the coast, make your way past the enormous San Felipe del Morro fortress and impressive La Fortaleza, residence of the Governor of Puerto Rico. Listen as the crew shares interesting historical insights into these two UNESCO World Heritage Site landmarks, and learn more about the nearby attractions, including the Punta de Tierra neighborhood, the Capitol House and San Juan harbor.

Continue your voyage with a second cocktail as you take in views of the distant El Yunque Rainforest and northern mountains, visible on the horizon. Make sure to keep watch for some of the area's amazing sea life like dolphins, turtles, sea birds and stingrays that inhabit the Puerto Rican coastline, or just chill out and enjoy the fresh ocean breeze. You’ll return to the marina around two hours after your departure.

Customer Reviews


5 star rating: Highly Recommended October 2014

Wonderful, smooth trip, beautiful views, spoiled by the 'crew' - expensive but really terrific. I would do it again. Oh, the marina is a little hard to find!


5 star rating: Highly Recommended July 2014

What a wonderful day we had spending time on a sail boat and hearing the history about Old San Juan, Puerto Rico. Our Captain was fun and very knowledgeable. Judith gave us a chance to see some beautiful sights. Yes, the sights were incredible! What a way to take in the sights and history...
D and J

Jeff I

5 star rating: Highly Recommended August 2013

Very intimate, relaxing and enjoyable. The Captain gave us a great tour of the harbor. We loved every minute on the boat. Plenty of room, with good food and drink. I'd definitely do the tour again.

Ashlyn C

5 star rating: Highly Recommended August 2013

This tour was absolutely awesome ! I will go back and do it a thousand times again. Our tour guide was very friendly and informative and provided views of the island that were priceless. If you go to PR you must do this tour.

Mary lou M

5 star rating: Highly Recommended July 2013

Fabulous. Relaxing Would do this again in a minute. Judith was very informative

pallavi b

4 star rating: Recommended January 2015

I loved the tour, it was such a relaxing and romantic feeling to sail in the sea away from the crowd. Our captain was very nice lady , she explained in such detail the history and even the present of Old San Juan. I know it sounds pricey but it was worth it.

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