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About Sailing Dreams
Sailing Dreams has been Old San Juan premier's sailing tours company, offering excursions for almost a decade. We cater to Lifetime Experiences that will make you dream again! We commit to having the most personalized, idyllic, memorable, romantic, fun and/or relaxing sailing day of your life, while enjoying great sights of Magical World Heritage and Landmark Sites of Old San Juan in Puerto Rico.
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Hours Today: 12:00 AM - 11:30 PM
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Sailing Dreams
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HSuperSharp wrote a review Aug 2022
Santa Monica, California4 contributions
My niece and I were in San Juan, Puerto Rico for my birthday and decided we wanted to go sailing at the last minute. Not only was Captain Judith able to accommodate us, she went above and beyond with exceptionally personalized service. After asking just a few questions she then over-delivered on perfect execution. We have sailed in various states in the US and countries around the world and the food and drink were hands down the most delicious and varied. The first mate not only kept our drinks full but made us both feel comfortable taking a dip in the ocean! Additionally Captain Judith is super knowledgable about the history of San Juan and is happy to share as much or as little as you wish to ensure you get your perfect combination of relaxation, culture and sailing tips. It was the best day of our trip and the best sailing adventure we've had hands down. Very highly recommended.
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Date of experience: December 2021
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews.
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Ralf W wrote a review Feb 2020
Minneapolis271 contributions99 helpful votes
We had an adventure and more. We booked an afternoon sail, and after a friendly greeting and orientation, headed out under skies with building clouds. Maybe 20 minutes after setting sail, it started to rain. It quickly began to pour. Our captain suited up and sent us below with the friendly first mate, who kept our drinks refreshed, though we had to head for port. Of course the downpour ended about the time we tied up! It's the tropics. We had flexibility so we returned the next day for a full 90 minute+ very sunny and lovely sail out to the fort at the end of Old San Juan. Judith shares history of the area along with helpful tips if one is steering the boat, which she encourages! We had an amazing time - both times! :) (I did find the booking and payment process confusing, but phone support was quick and responsive.)
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Date of experience: February 2020
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews.
4 Helpful votes
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Daniel S wrote a review Feb 2020
4 contributions1 helpful vote
Booked a boat tour with the lovely Captain Judith for Valentine's Day and loved every minute! Captain Judith was very welcoming, accommodating, and knowledgable! This was an incredible way to learn about the history and culture of San Juan while relaxing with amazing views and drinks. Highly recommend!
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Date of experience: February 2020
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews.
1 Helpful vote
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Valerie wrote a review Dec 2019
1 contribution5 helpful votes
Our daughter and son in law treated us to this sunset cruise. Outstanding personalized service-excellent food and drink-was able to dip my feet in the warm water on our way back to the dock. Do not miss this once in a lifetime experience.
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Date of experience: November 2019
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews.
2 Helpful votes
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Response from SailingDreamsPR, General Manager at Sailing Dreams
Responded Jan 30, 2020
Dear Grammithegreat; Thank you very much for your kind words. It was truly a great experience sharing with you and your family. We are delighted to know this was a "once in a lifetime experience". To us those are major words coming from you. We wish you all the blessings and a healthy, happy and prosperous life! Cheers!!
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This response is the subjective opinion of the management representative and not of Tripadvisor LLC.
halolpal wrote a review Mar 2019
Solana Beach, California38 contributions4 helpful votes
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+ stars on a 5 star system. Our time ashore in Cuba was 2.5 stars. The country is naturally beautiful and the Cuban people were friendly and fun. However, because of Cuba’s economy they cannot produce 5 star quality. We enjoyed our time in Cuba and we’re glad we made the trip. This was our second cruise on SeaDream and we booked another before we disembarked. We are in awe of the SeaDream experience. Everything aboard is perfect, i.e. staterooms, food, programs, etc but the staff is the most impressive. SeaDream’s staff is the best that we’ve ever experienced at any hotel, restaurant or company anywhere. It’s expensive but in this case you truly get what you pay for.
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Date of experience: March 2019
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews.
1 Helpful vote
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Response from SailingDreamsPR, General Manager at Sailing Dreams
Responded Jan 30, 2020
We thank you for your review, but you did a trip with the Sea Dream II, not with Sailing Dreams. Anyways, we wish you all the blessings and a healthy, happy and prosperous life! Cheers!!
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This response is the subjective opinion of the management representative and not of Tripadvisor LLC.
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