5 star rating: Highly Recommended 6 Reviews

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  • Location:San Juan, Puerto Rico
  • Duration:2 hours (approx.)

San Juan Small-Group Sailing Cruise

Sail on San Juan Bay and enjoy views of the colorful Caribbean as you recline on deck during a two-hour cruise! Sip complimentary drinks and taste fresh strawberries aboard the sailboat as you listen to interesting anecdotes and catch magnificent views of San Juan, the second oldest city in the western hemisphere. See the UNESCO World Heritage-listed walled fortress from the water as well as an abundance of nature. Enjoy personal attention with this small-group tour, limited to 6 people.


  • 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

Your sailing cruise departs from San Juan Bay Marina, where you will be welcomed aboard and given basic safety instructions as well as a geographical introduction complete with maps and historical images. Then, recline in your lounge chair on the deck, located on the bow of the 38-foot (12-meter) Jeanneau Sloop sailboat, and prepare for a magnificent journey.

As the crew puts up the sail and you cruise effortlessly from San Antonio Canal to San Juan Bay, your captain will demonstrate the basics of sailing. Relax with a complimentary drink in hand (including wine, beer, sparkling wine, rum, cava or soft drink) while you listen to recorded music of your choice, or take the helm if you'd like – a great photo opportunity!

You’ll hear commentary about the history of San Juan as you skirt the colorful city or pass cruise ships in transit. Sail past the massive stone fortification of the 500-year-old San Felipe del Morro Fortress and La Fortaleza – UNESCO World Heritage-listed sites of historical Old San Juan. Listen to cultural and historical tidbits about the Puerta de Tierra neighborhood, the Capitol House and San Juan Harbor, as well as legends about invaders and pirates of the Caribbean.

As you sip a second complimentary drink of your choice and enjoy a tray of fresh strawberries (appetizers are also available for purchase), enjoy views of the island from the pristine water, including the northern mountain range and El Yunque rainforest far in the distance. Your crew will point out natural attractions such as dolphins, sea turtles, stingrays and a variety of sea birds that inhabit the Caribbean.

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

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.

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.

5 star rating: Highly Recommended July 2013

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

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.

From USD $ 135.99

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Tour code: 5888DREAMED


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