Tours/San Juan/San Juan Historical Bay Daytime Sailing Tour
Viator · group up to 6 pax

San Juan Historical Bay Daytime Sailing Tour

4.6(199)San Juan1 hour
VIATOR4.5(124)TRIPADVISOR4.7(75)

Description

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!

Tour 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.

Itinerary

Pass by

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.

Pass by

Seaward side of historical Old San Juan area

Pass by

One of the 2 large old Spanish fortresses preserved for the history

Pass by

Little Fort located at Goats Island

Pass by

Oldest fortress in Old San Juan Puerto Rico, Governor's Mansion

Highlights

Bottled water
All taxes, fees and handling charges
Beer, Sangria, Rum n Coke

What's included

Included
Bottled water
All taxes, fees and handling charges
Beer, Sangria, Rum n Coke
Not included
Local operator not available to take phone calls, please read all information thoroughly
Transportation to Meeting Point

Traveller Ratings

4.6
199 reviews
5
168
4
10
3
5
2
4
1
12

Important Information

  • 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

Reviews(199)

C
Candace_H
August 18, 2026
Amazing Day Of Sailing

Great experience seeing San Juan with Captains Joe and Maria. It was educational and beautiful seeing the dolphins while learning of the historic beauty of San Juan.

A
Albalira_R
August 9, 2026
The best, an unforgettable experience.

It is an unforgettable, very beautiful experience, I loved it 10/10, Captain Joe and his assistant are the. Best, I went alone but there were other people and they made me feel like family and I enjoyed it to the fullest, I recommend it.

J
Jenny_T
August 7, 2026
Sailing fun!!!

This was such a last minute booking for us but I wanted to start off my birthday with a bang as we've never been sailing before!!! Omg absolutely wonderful experience!! Captain Joe was so informative and wise!! He shared all his experiences sailing and Dr. Abraham (hehe) was so knowledgeable with all the history of San Juan!! We learned so much and the sailing was so much fun! Highly recommend, 10/10!!! ⛵

M
melaniefT8658XD
August 3, 2026
Great Sailing Tour

It was a relaxing tour. Our guide had great recommendations for food and fun activities in town afterwards. He was knowledgeable about Puerto Rico and super friendly. They made us drinks for the sail. We sailed through the bay and by the fortress. It was just our family on the sail. Would recommend 👍🏼

1 people found this helpful
G
G3328KFgeorgef
July 29, 2026
Great experience

Diego is a great person made the experience good👍

A
Alona_R
May 30, 2026
Puerto Rico Boat

The captains were very friendly , definitely a great experience! Drinks were good as well. I would recommend for anyone!

D
DhruvR78
May 24, 2026
Extremely disappointing

They cancelled 15 minutes before the sail in a perfectly sunny day, where it rained for less than 10 minutes. They gave little clarity about pick up points and no one was available to reach on call.

S
Sarah_R
May 24, 2026
Great sail and great conversation

If you are thinking about sailing, book this trip! You go on a J30 - a stable, comfortable, fast sailboat. Captain Joe is experienced and knowledgeable. We had great conversation with him the whole time, and he really maximized our time sailing. It's a classic sailboat that gives a more intimate experience for small charter groups. Highly recommend!

S
Susan_T
April 20, 2026
Captain Joe and Carlos...

Captain Joe and Carlos did an awesome job explaining the history of Old San Juan and provided us with some great local food places to try. I would highly recommend this to anyone looking for a sail.

T
tynisa_c
April 14, 2026
Boat Tour

Never got to do tour because it was so hard to find needs to give clearer directions, we got lost getting there and got left.So we never got a chance to do this tour

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