San Juan Historical Bay Daytime Sailing Tour
Overview
Available languages
2 hours
Mobile ticket
Authentic sailing is culture, having a conversation with a local, with the power of the wind, no engine noise, no crowds, no fake pirates, no stray cats, no crowds, no need to scream . . . we sail sideways, aboard a real racer-cruiser (J30), with a toilet and a cabin, just real life sailing. You'll get to see a different perspective of old San Juan, with complimentary drinks, feeling safe but free, in small groups (no crowds.) Good for any special moment, or turning this moment into an special one. While in contact with nature elements, sometimes you may get surprised by dolphins. There are 6 people maximum per sailboat. Sailboat model: Jboat J30 (racer-cruiser.) It's not luxury yacht or a catamaran. Let's sail with Sail San Juan Bay!
Additional Info
Infants are required to sit on an adult’s lap
Not recommended for travelers with spinal injuries
Not recommended for travelers with poor cardiovascular health
Not recommended for pregnant travelers
Public transportation options are available nearby
Travelers should have at least a moderate level of physical fitness
Look for SAN JUAN BAY MARINA in Google Maps
Dress code is smart casual
we can not take for phone calls, we may answer relevant texts
We depart sharp, we don't make others to wait
Maximum passenger weight 275
We reserve the right of admission. No bad moods.
Getting to departure location is your responsibility.
Show up at least 15 mins BEFORE departure time
BAd reviews come from individuals who never sailed with us, because didn't showed up BEFORE departure time or didn't read our recommendations here, that for manny of us are obvious
Cancellation Policy
For a full refund, cancel at least 24 hours before the scheduled departure time.
What To Expect
San Juan Bay
From this commercial and historical Bay, the travellers will get the best perspective of old San Juan, and will get the opportunity to get the best photos of this unforgettable memory.
Old San Juan
Seaward side of historical Old San Juan area
What‘s Included
Bottled water
All taxes, fees and handling charges
Beer, Sangria, Rum n Coke
Local operator not available to take phone calls, please read all information thoroughly
Transportation to Meeting Point
Options
Morning Sail Trip
Sunny and Windy, perfect to enjoy our warm weather
Pre-Sunset Sail
Pre Sunset Sail: We sail authentically with the power of wind, hilling the sailboat like it does naturally, sipping your alcoholic drinks, listening to the breeze and the noise of the ocean.
Reviews
189 reviews
Total reviews and rating from Viator & Tripadvisor
Captain Joe and Abraham were the best!
Cheryl M,Mar 13, 2026
- Review from Viator
5.00Captain Joe and Abraham were great tour guides. We all had a lot of fun, saw the sites, drank the sangria and enjoyed the sail. We'll be back again!
Wonderful Sailing Experience
Maribeth F,Mar 11, 2026
- Review from Viator
5.00We had the pleasure to Sail with Captain Joe and Carlos. The other couple was a no show so we had the boat to ourselves which made the experience even more special. The weather was beautiful and Joe was very knowledgeable about San Juan’s History. We would recommend this sailing adventure!!
Sea tour around old san juan
drsherife,Feb 23, 2026
- Review from Tripadvisor
4.00Good view, spent nice time, the boat was small to be comfortable
Nice time out in the bay...
Albert U,Feb 22, 2026
- Review from Viator
5.00Nice time out in the bay on a small sailboat. If you enjoy getting out on the water, and seeing some places you have only seen from land, this could be for you.
Never get to experience sailing in Puerto Rico.
Indra Q,Feb 18, 2026
- Review from Viator
1.00It stated, to be at meeting point at 3pm. I arrived at meeting point at 3pm with Uber and they left early. Would not refund money for tour I didn’t received, even I had a proof of arrival time from Uber App indicating drop off time 3pm. I finally needed to involve AMEX to help me get refund for tour I didn’t receive. I have used boat tours across Europe and never experienced anything like this.
Fun afternoon
Mobile03445283443,Feb 15, 2026
- Review from Tripadvisor
5.00Great captain and crew. I learned a few things too.
A land lover no more!
shawnpZ927AS,Feb 8, 2026
- Review from Tripadvisor
5.00Ivan was a great host and excellent captain! He was very knowledgeable about the history of San Juan and Puerto Rico. He also gave us a good lesson on sailboat racing. Great time!
The tour was great. Our...
Terence M,Feb 1, 2026
- Review from Viator
5.00The tour was great. Our Captain was great and knowledgeable about the culture and geography. I would definitely recommend.
ARRIVE EARLY
Lily D,Jan 27, 2026
- Review from Tripadvisor
5.00We were 4 minutes late and they had already left so arrive 15-20 min BEFORE the departure time! Fortunately they offered us spots on a later tour and it was beautiful!
Sailing and a history lesson with booze!
10caras,Jan 27, 2026
- Review from Tripadvisor
5.00This was an amazing experience. We thoroughly enjoyed the sailing and can honestly say was one of the highlights of our trip! Recommend 💯
From US$99.00
Want a private experience? Upgrade to a private tour
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Operated by Sail San Juan Bay