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(194)San Juan1 hour
VIATOR4.5(121)TRIPADVISOR4.7(73)

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

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

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
194 reviews
5
163
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(194)

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

C
Cheryl_M
March 13, 2026
Captain Joe and Abraham were the best!

Captain 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!

M
Maribeth_F
March 11, 2026
Wonderful Sailing Experience

We 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!!

D
drsherife
February 23, 2026
Sea tour around old san juan

Good view, spent nice time, the boat was small to be comfortable

Operator response

The sailboat is the right size for what we offer, its an authentic J30 racer-cruiser, and is just the way we described . . . . this is not a disney ride with bucket seats, is a true sailing trip aboard comfy enough real sailboat

A
Albert_U
February 22, 2026
Nice time out in the bay...

Nice 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.

Operator response

The sailboat is a J30, its a 30 feet racer cruiser with a cabin and perfect size for sailing trip we offer . . . . it is not considered small, but if it would be small it would be even more fun, bit you won't get a toilet for the emergencies

I
Indra_Q
February 18, 2026
Never get to experience sailing in Puerto Rico.

It 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.

Operator response

. . for the rest of you it won't be a problem, because everyone knows that when a movies starts at 3pm, or even taking a plane . . . you'll show up before for not missing it. It is just logic. The text we have in the description is very clear. It says "show up at least 15mins BEFORE departure time" so apparently the reviewer didn't read anything. This customer, is not correct. The massive tours in other places, have a fleet of boats departing all the time, so pay in one place and take the next 300 people boat . . . . . . like in disn3y. We are nothing like that. This is n AUTHENTIC sailing trip, very enjoyable and personal, and our business rules are made to keep undesirable ones out. Sharing a little Sailor's wisdom. "don't live back to back, all stressed up in your vacations, is not about efficiency all the time. On vacations, take a real break an commit to one or few things a day and sleep and breath more"

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