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Private San Juan Sailing | El Morro, Sunset, Charcuterie & Signature Cocktails37.5 footer at your service!Private San Juan Sailing | El Morro, Sunset, Charcuterie & Signature CocktailsOverview

Private San Juan Sailing | El Morro, Sunset, Charcuterie & Signature Cocktails

With Captain

100% refund within 14 days of your trip
5.0(72 reviews) ·
195 bookings
·
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    This date is available.

Guests describe a relaxed, scenic sail around Old San Juan with music, sangria, swimming, and unforgettable sunsets that become the highlight of their trip.
Comfortable sailboat with space to spread out, unwind, enjoy the breeze, and easily move from shaded seating to spots ideal for photos and sunset views.
Highly praised captain and crew create a warm, stress-free outing, sharing local history, keeping drinks and snacks flowing, and tailoring the trip to each group.
Renters say this listing is great for:
Sunset CruisingFamily TimeCelebrationsSightseeing
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AI Overview

Owner's Description

Sail San Juan in Style — Your Private Caribbean Escape! Sail aboard Sail La Vie, the yacht featured in a PlayStation × Rauw Alejandro production, and experience Old San Juan like never before! Discover the magic of Puerto Rico aboard San Juan Bay’s largest monohull sailboat, offering exceptional experience and breathtaking views. Cruise past majestic El Morro Fortress, historic La Fortaleza, the colorful walled city, and iconic landmarks while enjoying refreshing Caribbean breezes and spectacular coastal scenery. Indulge in a complimentary charcuterie board, delicious tapas and our famous homemade signature cocktail as our friendly captain and crew share the fascinating history and charm of San Juan. Choose your perfect escape, morning, afternoon, or a romantic sunset sail, with opportunities for a refreshing swim when conditions permit. Perfect for couples, proposals, bachelor parties, families, friends, and special celebrations. Have a special request? We’ll help make it unforgettable! As featured in PlayStation × Rauw Alejandro! Watch Sail La Vie in action: https://youtu.be/LSWvUqBoids Your Private Yacht. Iconic Views. Unforgettable Memories. Book your exclusive sailing experience today! Video Disclosure: Sail La Vie is the sailing yacht featured in the exterior scenes of the PlayStation × Rauw Alejandro production. Interior scenes were filmed aboard a different vessel.

Captain Luis

Captain Luis

325 total bookings
Superowner
Best of 2026
Capacity
6 guests
Sailing
Cruising Monohull

Reviews

5.0 (72 reviews)
  • Listing Accuracy

    Awesome
  • Departure & Return

    Awesome
  • Vessel & Equipment

    Awesome
  • Communication

    Awesome
  • Value

    Awesome
  • Itinerary & Experience

    Awesome
  1. Private San Juan Sailing | El Morro, Sunset, Charcuterie & Signature Cocktails
  2. Private San Juan Sailing | El Morro, Sunset, Charcuterie & Signature Cocktails
  3. Private San Juan Sailing | El Morro, Sunset, Charcuterie & Signature Cocktails
  4. Private San Juan Sailing | El Morro, Sunset, Charcuterie & Signature Cocktails
  5. Private San Juan Sailing | El Morro, Sunset, Charcuterie & Signature Cocktails
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  12. Private San Juan Sailing | El Morro, Sunset, Charcuterie & Signature Cocktails
61 photos have been added by reviewers who booked this listing.
  1. EJ

    Ed

    A beautiful sunset cruise with my family. Wind was amazing on the bay and there was a bright moon and amazing breeze when we sailed back. Captain Luis and his deckhand Gabby were filled with information about Puerto Rico and the history. Highly recommended!

  2. JL

    James

    We took a private boat tour with Captain Luis and Gaby, and it was hands-down one of the best parts of our vacation. From the moment we arrived, we were greeted warmly and walked right over to the boat, which was the perfect size for our group of friends to relax and spread out. Captain Luis is an incredible captain—he navigated the waters with total ease, took us to gorgeous spots all over, and shared fascinating tidbits about Puerto Rico along the way. Both he and Gaby kept the vibes immaculate, sharing delicious sangria and making sure we had everything we needed. We spent the day listening to our favorite music, swimming, enjoying some snacks, and soaking up the sun. If you are looking for a top-tier, stress-free day on the water, I cannot recommend Captain Luis and Gaby enough! We’d book them again in a heartbeat.

  3. JC

    Jose

    Captain Luis & Andrea were incredible. My group enjoyed their energy and appreciation and even though we dealt with some rain and gray sky’s, our experience was phenomenal. I would not only recommend Luis, but I would take another trip out with him when I return to PR. We had an exceptional time at sea. Gracias por todo y hasta la próxima.

  4. GS

    Genevieve

    I booked with Captain Luis for my sister’s 30th birthday trip, and we all had the best experience! There were 4 of us in San Juan for a long weekend and this was the highlight of our trip. We felt safe, welcome, and taken care of the whole ride - the captain brought refreshments including Sangria that his wife had made which we all loved. He sailed us around and anchored at a beautiful spot to jump in and swim which was so fun. I highly recommend!

  5. KP

    Kieta

    It was so much fun ! Captain Luis is very informative and made sure we were all safe ! Andrea is absolutely the best !! She made sure we had everything we needed and we took a lot of great photos! Book I promise you will not be disappointed

Captain Luis

Captain Luis

325 total bookings
Superowner
Best of 2026

Welcome aboard amigos! Our pro Captain is US Coast Guard certified with years of experience on the water. The friendly vibe and accommodating vessel will make the difference aboard. Go to places and see things up close and personal. His extra mile focus will make a difference and contribute to your new great memories that will last a lifetime…

Features & Details

  • Hunter
  • Legend 37.5
  • Capacity: 6 people max

Safety Equipment

Life Jackets (1)

Operating Equipment

GPS ChartPlotter

Guest Amenities

Berths (1)
Cabins (1)
Cooler
Oven
Sun Protection
Toilets (1)

Leisure & Entertainment Equipment

Bar
Bluetooth
Floats
Hammock
Sound System

Accessories

Water Mat
Paddleboards

Departure Location

The boat's approximate location on a map

You’ll get helpful information for your departure after your booking is confirmed.

Street Address For Arrival

Street Address For Arrival

Calle Hoare
San Juan, San Juan, 00907
Puerto Rico
Departure Location

Departure Location

Same as Street Address

Cancellation Policy

Free cancellation up to 14 days before your trip.

Additional Terms & Information

Trips are 3 hours minimum. Photos of your trip might be used for promotional purposes and/or for our community outreach efforts. By booking a trip with us you are acknowledging that there are hazards that are present during your trip(s) and accept that neither our own Captains or mates are liable for any injuries or even death related to the handling of the equipment needed for this activities or any animals that may cause harm in the water. Health, Pandemics, Natural Disasters and/or Outbreaks Policy: All trips cancelled by us or by you due to any situation(s) in regards to health, pandemics, natural disasters and/or outbreaks, the payments won't be lost and will be credited for a future trip. Gratuities are not included and will be greatly appreciated by our professional crew. Looking forward in serving and sailing with you. We reserve the right of admission. All bookings are subject to confirmation since we promote our services on other platforms. RECOMMENDATIONS AND DISCLOUSRE: You should bring, sun screen, sun glasses and the best positive energy possible :) Photos of your trip might be used for promotional purposes. By booking a trip with us you are acknowledging that there are hazards that are present during your trip(s) and accept that neither our Captains or mates are liable for any injuries or even death related or caused by the animals or the handling of the equipment needed for this activities. This is a DRUG FREE operation for your safety and in compliance with local law and order. All trips will be confirmed after booking is received. Life vest or floating device will be required and provided for swimming. We will reserve the right of admission. A now show will be considered after 30 minutes of departure time and full rate will be charged and it will be at the discretion of the Captain to credit the full or partial amount to another day and if the schedule and weather allows it. Payments are final if done 14 days or less before the departure date initially reserved. We will refund 100% of the payment if cancellations are received 15 days before the departure date initially reserved. The trips will be private for you and yours only if the minimum of 2 guests is met. If we receive less than the minimum, we will have the right to cancel. Once boat departs from the dock, the payment will be due in full. If the Captain decides to cancel the trip due to any safety issues, the payment will be due in full. 100% of the payment will be refundable if the captain determines that the weather is not safe or if the boat breaks down.

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