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
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.
Morning Sail Trip
Sunny and Windy, perfect to enjoy our warm weather
Reviews
177 reviews
Total reviews and rating from Viator & Tripadvisor
Very experienced,...
Jeff G,,Jan 11, 2026
- Review from Viator
5.00Very experienced, knowledgeable,and friendly captain and crew. Meet them at the fence below the Sizzler parking lot near the gated parking area.
Joe was amazing and knew...
Serenate F,,Jan 9, 2026
- Review from Viator
5.00Joe was amazing and knew a lot of great facts while sailed even showed us a few things on the ship. Also gave us amazing places to go after to eat or visit which was super helpful. Would definitely recommend
Sailing with the engine on the whole time
Sarah g,,Dec 31, 2025
- Review from Viator
2.00It's not so much a sailing trip, it's a slow journey around a harbor on a power boat with the main sail partially raised while jib was never unfurled. The hosts were nice, but never intended to actually sail the boat. There was enough wind. The views were partially scenic- we sailed by cruise ship port, a cement yard, saw the Bacardi factory from a distance and learned about a narrow yellow building.
Lovely and Relaxing Sailing Experience
Yolanda G,,Dec 29, 2025
- Review from Viator
5.00This was an awesome experience. The captain and his crew were knowledgeable, very helpful and made this sailing trip a relaxing and memorable experience for my family. This is one of the best experiences and much enjoyed getting away from the crowds.
Worth every penny!
MillieRios,,Dec 20, 2025
- Review from Tripadvisor
5.00It was an amazing experience, the staff was so down to earth! The trip left on time and the staff was truly engaging. Location was easy to find
Informative, relaxing,...
MARTHA W,,Dec 13, 2025
- Review from Viator
5.00Informative, relaxing, great communication. We had a nice time. It was just two couples and the captain and first mate
Our captain was very...
Sierra M,,Dec 9, 2025
- Review from Viator
5.00Our captain was very engaging, pointing out landmarks and interesting sights within the bay. His crewmanwas also knowledgeable. It was a laid back trip with just our group of 4. A new experience for all of us, which we enjoyed very much
Excellent cruise
William G,,Nov 27, 2025
- Review from Viator
5.00Excellent cruise. Not a big boat, it was just myself, wife and daugher along with the captain and mate. Our captain was extremely friendly and knowledgeable on PR history, restaurants, sailing, etc. I highly recommend for a relaxing and fun two-ish hours on the bay.
Beautiful morning sail
D6225KKshannonp,,Nov 24, 2025
- Review from Tripadvisor
5.00It was so beautiful. We really enjoyed our time on the boat and it was so cool to see Old San Juan from the water. Easy to get to the harbor and an amazing way to spend the morning.
Disappointing 😞
Peggi S,,Nov 18, 2025
- Review from Viator
2.00Disappointing 😒😒!! Small boat, no space to walk around for pictures 📷, the guide didn't explain anything about the surroundings, the tour was supposed to be in Spanish but he only spoke English. Very disappointing 😪 and very expensive 💰💰. I don't recommend it. No lo recomiendo!! Bote muy chico, no se puede caminar y nose puede tomar fotos 📷, el precio muy caro 💰💰
From US$99.00
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Operated by Sail San Juan Bay