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San Juan

Sailing Dreams Yacht Charters

San Juan, Puerto Rico
About Sailing Dreams Yacht Charters
In Sailing Dreams we speak about LIFETIME EXPERIENCES! We commit to having the most personalized, idyllic, memorable, romantic and relaxing sightseeing experience and ecotour of your whole vacation in Puerto Rico. We offer First Class VIP Private and pampering tours, focused on having a great quality time, while enjoying the best views of unparalleled World Heritage Sites of Historic Old San Juan, including San Juan City Walls, La Fortaleza Castle and El Morro Fortress. Join us in an outdoor activity and be the Captain of your life, while discovering our colorful Old City, enjoying nature and wildlife, like sting rays, sea birds, fish, sea turtles, dolphins, or manatees. Sit relax on a comfortable reclining deck seat or learn the basics of sailing, with you at the helm. On Private VIP Tours you have the option of swimming, or kayaking Old San Juan's shoreline. Travel in time with great music and history, while enjoying strawberries, a glass of Wine or Champagne, a delicious homemade Pina Colada, or a delicious Tropical Rum Mix. You may order Delicious Hors D 'Oeuvres to complete the experience in our welcoming and cozy French Jeanneau 39 ft. Sailboat Sloop Poema de Amor Libertad (A Poem of Love and Freedom). Our tours are limited to a maximum of six people at once, giving you the space and time to feel intimate with your guests. For more details, as well as to make your secure online bookings, please visit our website. We look forward to sharing and living a lifetime experience with you!
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Hours Today: 9:00 AM - 11:00 PM
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Reviewed March 20, 2019 via mobile

We celebrated our 45th anniversary on Sea Dream II March 11-18. We started our cruise in Havana and ended in Cienfuegos, Cuba. SeaDream began offering Cuban cruises in 2019. We participated in Cuba’s “people to people” program for Americans. Our time on SeaDream was 5+...More

Date of experience: March 2019
Thank halolpal
Reviewed July 7, 2018 via mobile

Capitán Judith and the crew were wonderful, warm and accommodating. We enjoyed amazing drinks and food while enjoying the wonders of San Juan bay. The food was more than mere appetizers and exceeded our expectations. We had delicious shrimp, crab and other delights. The music...More

Date of experience: July 2018
1  Thank David W
Reviewed July 2, 2018

My girlfriend and I booked a sunset sail with SAILING DREAMS in February and had a fabulous time. The trip was so fun, so relaxing and soooo beautiful. Captain Judy and first mate took care of everything. The food and drinks were first class. The...More

Date of experience: February 2018
2  Thank 381stever
Reviewed July 2, 2018

We travelled on the sunset sailing trip last Summer and it was the highlight of our holiday. I am so happy to hear that Captain Judith and her team are sailing again after the devastating hurricanes last year. I would really recommend you to book...More

Date of experience: August 2017
2  Thank Twig1986
Reviewed September 27, 2017

We booked our family 2 hour day sail with Sailing Dreams on 8/26/2017. The tour was informative, casual, fun, and was a one of a kind experience. Captain Judy and her first mate had a perfect balance of fun, relaxation, and education. It was only...More

Date of experience: August 2017
1  Thank thecasualtrek
SailingDreamsPR, Manager at Sailing Dreams Yacht Charters, responded to this reviewResponded June 30, 2018

Dear friends; First we want to apologize for this late answer. We had to take a break our operation after Hurricane Maria. in order to help our families and friends to recover. We are finally back! Thank you for reminding us how good our services...More

Reviewed September 26, 2017

Had a "Captain Judith" tour a few yrs ago-- wonderful.. Wondering if she is ok after the storm? Mainland US really needs to step up the help for PR.More

Date of experience: October 2016
1  Thank SmartTravlerLV
SailingDreamsPR, Manager at Sailing Dreams Yacht Charters, responded to this reviewResponded June 30, 2018

Hola SmartTraverLV; We are so sorry we are answering so late. After Hurricanes Irma and Maria, we have been helping our families, friends and country to recover. It has been so tough!. There are still millions of situations to solve and we hope we can...More

Reviewed September 22, 2017

We booked the sunset sailing, there were only two couples on board and it was very relaxing. The only way to see the best views of San Juan. Captain Judith took so many great photos for us and really made the trip perfect for us....More

Date of experience: June 2017
1  Thank ajk109
SailingDreamsPR, Manager at Sailing Dreams Yacht Charters, responded to this reviewResponded June 30, 2018

Dear ajk109; We are sorry we are answering this review so late. You wrote this review only two days after the worst hurricane in the history of the Island. It's been so long and there are still families with no power. We were lacking of...More

Reviewed August 24, 2017

My wife and I agreed that this was our best anniversary celebration ever! As so many others have pointed out, Captain Judith makes sure that your trip is memorable. She is a wonderful person. That night, Marie was her first mate, and she took great...More

Date of experience: August 2017
3  Thank LinniePman
SailingDreamsPR, Manager at Sailing Dreams Yacht Charters, responded to this reviewResponded June 30, 2018

Dear LinniePman; We are so sorry we are writing this answer so late. Maybe you know that Puerto Rico was destroyed with two of the worst hurricanes in the history of the Island, one in early September and the other close to the end. You...More

Reviewed August 15, 2017

We ended up booking the sunset sailing. We was the only couple on board, but that I think made the experience even better. The view of the sunset was breath taking. We had a sightseeing on a sailboat not everyone can say that. We have...More

Date of experience: May 2017
Thank nysteffi
Reviewed August 11, 2017

Having visited San Juan many times as a cruise port destination, we wanted to try something different. We sailed into San Juan via Royal Caribbean and had an early arrival. The timing of our time at port worked perfectly. We arrived off our cruise ship...More

Date of experience: July 2017
3  Thank Davisd01
SailingDreamsPR, Front Office Manager at Sailing Dreams Yacht Charters, responded to this reviewResponded August 14, 2017

Dear Davisd01; Thank you so much for such lovely words and for being part of our Sailing Dream. It is a pleasure for us to know that you had an amazing time sailing with us, that we were beyond your expectations and you had the...More

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Erykah B
September 1, 2018|
Response from David W | Reviewed this property |
I believe the boat will hold up to 4 persons comfortable
June 15, 2018|
Response from SailingDreamsPR | Property representative |
Thank you for your interest in us! Yes, we are back in business starting July. The hurricane was tough with our Island and we have been busy helping our families and friends to recover. We are ready to start sharing with... More