Sail Old San Juan, San Juan

#46 of 100 in Outdoors in San Juan
Boat Tour · Tour
Sail Old San Juan is located in San Juan. A visit to Sail Old San Juan represents just the start of the adventure when you use our San Juan road trip website to plot your vacation.
Create an itinerary including Sail Old San Juan
© OpenMapTiles © OpenStreetMap contributors

Sail Old San Juan reviews

Rate this attraction
TripAdvisor traveler rating
TripAdvisor traveler rating 5.0
102 reviews
  • This is a REAL ride on a sailboat, so buckle up and get ready to watch the captain shorten the sail, move the mast, and head right into the waves. Hold onto your drinks because his sailing J Boat...  more »
  • We sadly had to cancel our sailing this March (2020) but they were great communicating before we reserved and quick and understanding when we had to cancel. Look forward to rescheduling when cruises.....  more »
  • We had a great experience with our private 2 hour sailing trip. Captain Sebastian was very knowledgeable and answered all our sailing questions.
  • Our trip on the Chili Pepper with Capt Sebastion was fantastic. I'd read reviews for other San Juan companies where the sunset cruise ended as soon as the sun went down, which was far from the case here. The trip lasted from 5 until about 7:30, pulling into the dock as it got dark. There were 3 couples and very comfortable seating for all. Sebastion was the perfect captain and host. For instance, he took us into the ocean, but only after checking carefully with everybody to make sure that sounded enjoyable (it was!). Also, near the beginning there were a few light sprinkles, with possibly more on the way, so he offered everyone the opportunity to get off at the end of the dock and get a 100% refund. One couple, concerned it might rain, took him up on that offer - unfortunately they missed an excellent sail. Another nice thing about the trip was the boat itself which was far more stable than I expected (but also quite speedy as a former racing boat). Plus Sebastion was highly experienced and explained what he was doing at all stages and what we could expect the boat to do. As the sun went down we all toasted the sunset. And then the total surprise - once we got back the Capt told us we'd all get a 50% refund. I couldn't believe it, and protested, but sure enough a 50% refund appeared on the credit card. Apparently the discount was because the drinks weren't cold enough and also we'd paused to drop off the one couple. Which was true, the drinks were only cool (not cold) because the ice truck had failed to show that day. But what an honorable move that really wasn't necessary. My suggestion - this is the cruise/company to take.

Plan your trip to San Juan

  • Get a personalized trip
    A complete day by day itinerary
    based on your preferences
  • Customize it
    Refine your trip. We'll find the
    best routes and schedules
  • Manage it
    Everything in one place.
    Everyone on the same page.