Take a Relaxing Sail in San Juan Bay

Sailing Dreams Old San Juan

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 recently took a trip in the San Juan Bay with Sailing Dreams, 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

Sailing Dreams Old San Juan

The sailboats are docked at the San Juan Bay Marina. The larger catamaran Velauno which docks right by the cruise ships at Pier 6.

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 the catamaran is much larger for bigger groups, but on 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.

Our Tour

We went out on a Sunday morning for a 1-hour tour with Sailing Dreams. 12/13 update-They now only do 2 hr and longer tours, but I think it will just be more of the good things we had in 1 hr! 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.

Sailing Dreams Old San Juan

She 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. Captain Judith 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.

Sailing Dreams Old San Juan

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.

Sailing Dreams Old San Juan (La Perla)

On the way back, Captain Judith 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.


Sailing Dreams Old San Juan

The cost of 2 hr sails with sailing Dreams are about $109/person. Call or check their web site for current rates. Minimum age to go on the boat is 5 years old.

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. The Sunset Sail is a little more as it is about 2½ hours. They also offer sunset sails and moonlight sails. The sailboat is also available for 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!

You can call 787-519-5000 for more information. Reservations must be made online, not over the phone.

Sailing Dreams Old San Juan

You can visit the Sailing Dreams web site for more information or to make your reservation.

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.

There are also other sail companies that do sailing trips in Old San Juan. Sail Old San Juan has Capt Sebastian doing tours during the “winter” – from about mid November to mid May. Room for 6 guests on his boat. English or Spanish narrative of the sights of Old San Juan. He does 2 hr trips in daytime for about $65 per person and sunset sails for $75 pp (with drinks) Call for info and reservations: 787-340-7567.

There is another company Sail San Juan Bay . Also docks at Club Nautico/San Juan Bay Marina. Captain Ivan offers tours of the bay every day. 1.5 hr day sails at $55 pp or 2 hr sunset tour $70 (includes drinks/snacks). Call (787) 667-7778. Private trips available.

Velauno Sailing has a large catamaran sailboat. They are easy to get to- right in Old San Juan! They offer 2.5 hours sails of the bay everyday from 1pm for only $49 pp! They also have a daily 2 hours sunset tour at 5pm also for $49 pp. Both tours include drinks! Call for more info: 787-470-9099.

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).

Use this map to locate places mentioned in this article. You can click on a placemark to view the GPS coordinates for that place.

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! Read more about Safety →

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