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Address: 482 Ave Fernandez Juncos | San Juan Bay Marina, Slip 64, San Juan 00907-3187, Puerto Rico
Phone Number:
+1 787-519-5000
Website
Today
09:00 - 23:00
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Hours:
Sun - Sat 09:00 - 23:00
Description:

In Sailing Dreams we speak about LIFETIME EXPERIENCES!

We commit to having...

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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TripAdvisor Reviewer Highlights

Read all 424 reviews
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Amazing experience!

We booked an afternoon sail for a friends birthday. It was one of the best I've ever been on. Captain Judith is fantastic. Her charm and knowledge of the area made the experience... read more

Reviewed 4 days ago
Jill B
,
Milwaukee, Wisconsin

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424 Reviews from our TripAdvisor Community

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Showing 403: English reviews
Milwaukee, Wisconsin
Level Contributor
7 reviews
3 attraction reviews
common_n_attraction_reviews_1bd8 3 helpful votes
Reviewed 4 days ago NEW

We booked an afternoon sail for a friends birthday. It was one of the best I've ever been on. Captain Judith is fantastic. Her charm and knowledge of the area made the experience unforgettable. The food was delicious...best pina coloda I've ever had and she even brought a birthday cake for dessert.

Helpful?
1 Thank Jill B
Level Contributor
4 reviews
3 attraction reviews
common_n_attraction_reviews_1bd8 1 helpful vote
Reviewed 1 week ago via mobile

We booked the cruise to celebrate my birthday, and we had an amazing time. From the food and drinks to the beautiful views, we were all around impressed! Captain Judith and Maria were both funny, friendly, and very attentive! We couldn't have asked for a better trip on the water! Thank you again to our Captain and her first mate!... More 

Helpful?
1 Thank Jennifer B
Elk Grove Village, Illinois
1 review
common_n_attraction_reviews_1bd8 1 helpful vote
Reviewed 2 weeks ago

The owner and her daughter could not have been more delightful to be with. They knew everything about PR. The food and drink were exceptional. We have been on thousands of excursions in 40 years of vacationing and this is in the top 3! You have to hook up with them when you are in PR! The Gorden's

Helpful?
1 Thank jmgorden
1 review
common_n_attraction_reviews_1bd8 1 helpful vote
Reviewed 3 weeks ago

This was easily the BEST thing my friends and I did while on our trip in Puerto Rico. On a rich lovely afternoon myself and 5 friends boarded the boat....I got off with 8 friends. The crew from Captain Judith to 1st assistant Paola were excellent. We talked, took pictures, had great drinks, and ate a lovely lunch. My friends... More 

Helpful?
1 Thank Love A
SailingDreamsPR, Front Office Manager at Sailing Dreams Yacht Charters, responded to this review

Dear Love A; 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 and your friends had an amazing time sailing with us and that this was easily the best thing you and your friends did while in Puerto Rico. We are very happy... More 

Philadelphia, Pennsylvania, United States
2 reviews
common_n_attraction_reviews_1bd8 17 helpful votes
Reviewed 3 weeks ago

My fiance organized this fantastic surprise for us and proposed on the sailboat!! Everything was perfect, from the food and wine, to the sailing itself. Judith is a very sweet, funny, and experienced captain that made the whole experience enjoyable. Her 2 helpers were also fantastic! They did such a good job with setting a romantic mood and taking so... More 

Helpful?
2 Thank Claire B
SailingDreamsPR, Front Office Manager at Sailing Dreams Yacht Charters, responded to this review

Dear Claire B; 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 and your soon to be husband had an amazing time sailing with us and that you said YES to his proposal. Congratulations! We are very happy to know that both of... More 

Waterford, Michigan
Level Contributor
2 reviews
Reviewed 3 weeks ago

From the moment we stepped on the boat, Captain Judith and her awesome crew made us feel welcome, and very well taken care of! Before we even left the dock, we had a drink in hand and had a very cool history lesson of Old San Juan, and the sights we were going to see along the way. During the... More 

Helpful?
Thank Robyn K
SailingDreamsPR, Front Office Manager at Sailing Dreams Yacht Charters, responded to this review

Dear Robyn K; 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 and had an amazing time sailing with us and this tour was the best part of your trip to Puerto Rico. We are very happy to know that both of you... More 

Auburn, New York
Level Contributor
3 reviews
common_n_attraction_reviews_1bd8 7 helpful votes
Reviewed 3 weeks ago

Judith and her first mate were wonderful! They were both very personable and we enjoyed talking with them. They offered several times to take pictures for us. Judith is very knowledgable about San Juan and all the sights. Her first mate surprised us with these awesome little desserts and very good strawberry daiquiris. We would definitely sail with them again.

Helpful?
Thank cmmoore59
SailingDreamsPR, Front Office Manager at Sailing Dreams Yacht Charters, responded to this review

Dear cmmoore59; 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 and your beloved had a wonderful time sailing with us and that it was a relaxing afternoon for you. We are very happy to know that both of you enjoyed the drinks,... More 

Level Contributor
67 reviews
19 attraction reviews
common_n_attraction_reviews_1bd8 34 helpful votes
Reviewed 3 weeks ago

We took the sunset sail in February 2017. The views were breathtaking! We felt like our captain made the cruise feel very personal and memorable. She took pictures of us and then sent them to us back home. The food was delicious and there was plenty of wine. It really stood out in our Puerto Rico trip!

Helpful?
Thank jberhorst
SailingDreamsPR, Front Office Manager at Sailing Dreams Yacht Charters, responded to this review

Dear jberhorst; 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 and your beloved had an amazing time sailing with us and that your tour really stood out in your Puerto Rico trip. We are very happy to know that both of you... More 

Dublin, Ireland
Level Contributor
4 reviews
common_n_attraction_reviews_1bd8 2 helpful votes
Reviewed 3 weeks ago

We went with high hopes and they delivered all that and more. The captain was very personable, attentive, the drinks were great and the boat was amazing. The evening was great for sailing and we had a wonderful sunset. All in all it was romantical, fun and we got to know 4 new people on the trip. Very very recommendable.

Helpful?
Thank Morten_B_84
SailingDreamsPR, Front Office Manager at Sailing Dreams Yacht Charters, responded to this review

Dear Morten_B_84; 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 and your beloved had an amazing time sailing with us and that it was the most romantical and fun night of your entire trip. We are very happy to know that both... More 

Fairview, Canada
Level Contributor
5 reviews
common_n_attraction_reviews_1bd8 3 helpful votes
Reviewed 3 weeks ago via mobile

Judith and her staff were very friendly and knowledgeable hosts. The scenery was beautiful and the rum punch was great. Judith, thanks for recommending Casita Miramar restaurant, it too was excellent.

Helpful?
Thank Ken T
SailingDreamsPR, Front Office Manager at Sailing Dreams Yacht Charters, responded to this review

Dear Ken T; Thank you so much for being part of our Sailing Dream. It is a pleasure for us to know that you had an amazing time sailing with us and that our recommendations were excellent. We are very happy to know that you enjoyed the drinks, the history, the views and the company while relaxing on the boat.... More 

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Typical questions asked:
  • Will you pick up and drop off at my hotel?
  • I have a family of 7. Can your tour accommodate all of us together?
  • How should I dress for this tour?