Take a Relaxing Sail in San Juan Bay
Old San Juan is one of my favorite places in Puerto Rico. The history, the architecture, and the photo opportunities all make it a must-visit place.
Of course, you can walk around in the city and see what there is to see. But for a whole different perspective, how about sitting back and relaxing while taking in the views of the old city from the sea?
We took a trip in the San Juan Bay, and it was one of the most relaxing hours I have ever spent in Old San Juan. Oh, and we got some great photos, too!
About the Sail Boats
The sailboats are docked at the San Juan Bay Marina.
There are usually a few different options for sails, some are private tours and some are public tours. Usually ranging from 1-hour tours to all-day excursions. The sailboats have a maximum of 6 passengers and all boats there is plenty of room to spread out on deck, as well as a nice table area to sit together and hang out.
During the trip, they usually offer beverages and snacks (depending on the tour), and provide a narrative about sights around the San Juan Bay, and other interesting tidbits about the history of Old San Juan.
We went out on a Sunday morning for a 1-hour tour with Sailing Dreams (they no longer do the trip, but other captains are sailing). Finding the place was easy, and there was free parking at the marina. Captain Judith was so nice, and she is prompt — she won’t keep you waiting to start your trip.
Our captain welcomed us, gave us the safety and trip briefing, asked about our music preferences, and off we went. We had beautiful weather that day. Make sure you apply a lot of sunscreen as the water reflects the sun rays and you can get a pretty bad sunburn in only an hour on the water — we found out the hard way!
Because it was only a 1-hour trip, it was too short a trip to put up the sails, so we motored in the San Juan Bay, past the huge cruise ships and other boats docked in port. Our Captain knew a lot about some of these other boats and yachts, which was made the trip more interesting. They do hoist the sails for longer trips, like their Sunset Sail.
The boat has some nice comfy seats around the front area, so Ray and I sat at the very front, at the bow. They served us drinks (both alcoholic and non-alcoholic available) and snacks.
We had the sun, the sea, the breeze … it was really nice. We slowly rounded the corner into the channel, past La Fortaleza, the San Juan City Gate, and El Morro. And because the ocean was calm that day, we were able to go out a little way into the ocean to get more great photos.
On the way back, our captain told us all about what we were passing, with lots of history and other information about Old San Juan. It was interesting, educational, and relaxing — but over all too soon.
One other thing to note is that the ocean is full of all sorts of wonderful sealife, and you never know what you may see. We saw a number of different types of sea birds, and even watched some pelicans diving for fish. The day before, they had a long visit with a pod of dolphins, and at other times, manatees and even stingrays have been seen at the surface.
Contact Sailing Dreams to book tours and more info. 1/21 They are currently closed due to covid.
The cost for 2 hr day tour $109 pp. The sunset tour is 2.5 hr and includes drinks and Hors D’Oeuvres (about $149) Call or check their web site for current rates. There may be a Minimum age to go on the boat .
If you're happy, let them know it — Don't forget to tip your your bartender, tour guide or trip operator if you enjoyed yourself. Gratuities are appreciated and typically aren't included in the price they charge you.
They offer 2-hour bay sails during the day. Sunset Sails are available and also private charters and special events. Reservations are required, and you must book/pay online through their web site. Tours require a minimum of 2 people, and a maximum of 6.
Wear sunscreen, sun glasses and a hat for daytime sails. With the breeze, you don’t feel the sun, but it is there!
Tours can be given in English, Spanish, or both.
You will be required to leave your shoes on the dock and go barefoot on the boat. This helps keep the boat clean, and it’s safer for you. You’ll get your shoes back at the end of the trip.
Other Sailboats offering similar tours
Sail San Juan Bay Has day sails and sunset tours open to public (book on a per person basis) or private charters. Captain Ivan offers tours of the bay every day. Call (787) 667-7778.
Sail Old San Juan They offer private day sails but their sunset tours can be private or open to public. Call for info and reservations: 787-340-7567.
Located in the San Juan Bay Marina/Club Nautico. The marina itself is located behind Sizzler, and accessed from the south side of the bay (the side with the Puerto Rico Convention Center).
We are in the process of updating the maps we use on our web site. While we're working on that, you can click on the GPS coordinates below to view the location on Google Maps ...
- Sailing Dreams Yacht Charters: (18.458799, -66.089035)
- San Juan Bay Marina, parking: (18.457548, -66.088050)
- Sizzler, Old San Juan: (18.458504, -66.087211)
PuertoRicoDayTrips.com assumes no responsibility regarding your safety when participating in the activities described in this article. Please use common sense! If your mother or that little voice in your head tells you that you are about to do something stupid … then don't do it!