We noticed that you're using an unsupported browser. The Tripadvisor website may not display properly.We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.
Open today: 12:00 AM - 11:30 PM
Review Highlights
Best sailing trip to date!

My niece and I were in San Juan, Puerto Rico for my birthday and decided we wanted to go sailing at... read more

Reviewed August 4, 2022
HSuperSharp
,
Santa Monica, California
Capt. Judith is a delight!

We had an adventure and more. We booked an afternoon sail, and after a friendly greeting and... read more

Reviewed February 19, 2020
612ralfw
,
Minneapolis
Read all 460 reviews
  
Reviews (460)
Filter reviews
460 results
Traveler rating
451
7
1
0
1
Traveler type
Time of year
LanguageAll languages
Traveler rating
451
7
1
0
1
See what travelers are saying:
Selected filters
Filter
Updating list...
201 - 206 of 460 reviews
Reviewed July 17, 2015

We were blessed with the sailing experience of a lifetime! We have sailed in a lot of locations that we have visited but this experience was the best! Captain Judith is a very experienced sailor as well as woman with a big heart and love of the sea. Her expertise on the history of San Juan was first rate and the boat was impeccable. We cannot rave enough about this experience. If you are looking for a way to top off your vacation in Puerto Rico, I would highly recommend this experience. You will walk away with a song in your heart, a calm in your soul and a peacefulness that is hard to find today. Also, food and beverage were a special topping to this wonderful experience.

Date of experience: May 2015
4  Thank Leona B
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
SailingDreamsPR, Front Office Manager at Sailing Dreams, responded to this reviewResponded July 29, 2015

Dear Leona B;

Thank you for such lovely words and for being part of our Sailing Dream. We are so delighted to know that you were blessed with the sailing experience of a lifetime. We always want our people to leave with the best impression of Sailing Dreams and Puerto Rico.

You are more than welcome to come back and walk away with a song in your heart and a calm and peaceful soul.

Thank you for coming, thank you for taking the time to write us and thank you for your support.

Please remember you have local friends you can count with on your next visit to Puerto Rico.

Blessings and Love!

Report response as inappropriate
This response is the subjective opinion of the management representative and not of TripAdvisor LLC.
Reviewed July 17, 2015

Easily the coolest, most relaxing thing we did for the week. The history of San Juan and the beverages were thoroughly enjoyable!

Date of experience: June 2015
3  Thank Taylor S
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
SailingDreamsPR, Front Office Manager at Sailing Dreams, responded to this reviewResponded July 29, 2015

Dear Taylor S;

Thank you so much for being part of our Sailing Dream. We are so happy to know the coolest and most relaxing thing you did for the week was spending the day with us.

You are more than welcome to come back anytime!

Thank you for coming, thank you for taking the time to write us and thank you for your support.

Please remember you have local friends you can count with on your next visit to Puerto Rico.

Blessings and Love!

Report response as inappropriate
This response is the subjective opinion of the management representative and not of TripAdvisor LLC.
Reviewed July 9, 2015

Over 4th of July weekend, my family (6 ppl) were able to sail with Judith and her staff. Since 6 people is the max - it was perfect as we were able to have a private sail! the staff was very friendly, knowledgeable and accommodating. The food was also AMAZING! It was a very memorable sail and was great that Judith also captured pictures on a phone and boxes them to Box for us to download. Overall - great experience, would recommend to anyone looking for a fun sail, great staff, and yummy food/drinks!!! Having a party of 6 is a plus!

Date of experience: July 2015
4  Thank Megan M
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
SailingDreamsPR, Front Office Manager at Sailing Dreams, responded to this reviewResponded July 29, 2015

Dear Megan M;

Thank you so much for being part of our Sailing Dream. We are delighted to know that we were the highlight of your family’s trip to Puerto Rico. We always want our people to leave with the best impression of Sailing Dreams and Puerto Rico; this is why you come in as friends and leave as family.

You are more than welcome to come back anytime!

Thank you for coming, thank you for taking the time to write us and thank you for your support.

Please remember you have local friends you can count with on your next visit to Puerto Rico.

Blessings and Love!

Report response as inappropriate
This response is the subjective opinion of the management representative and not of TripAdvisor LLC.
Reviewed July 6, 2015

We truly enjoyed our sailing adventure with Judith and her first mate. There was 6 in our party so we had the boat to ourselves with them and we pretty much felt like they were part of our family!!! Judith provided us with lots of information about Old San Juan and El Morro. While she provided the history lesson, her first mate made us some of the best pina coladas around. The food was also quite tasty. It was such a beautiful way to start the day and highly recommend that you take a tour and hopefully get to meet Judith. You will not be disappointed.

Date of experience: March 2015
3  Thank HETS313
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
SailingDreamsPR, Front Office Manager at Sailing Dreams, responded to this reviewResponded July 29, 2015

Dear Hets313;

Thank you for such lovely words and for being part of our Sailing Dream. We are so happy to know that you and your family had a wonderful time with us. Remember, once you join our boat, you become part of the family.

You are more than welcome to come back anytime and have a Piña Colada, while you delight yourselves with our Gourmet Hors D'Oeuvres and we sail away!

Thank you for coming, thank you for taking the time to write us, thank you for your support and thank you for sharing the pictures.

Please remember you have local friends you can count with on your next visit to Puerto Rico.

Blessings and Love!

Report response as inappropriate
This response is the subjective opinion of the management representative and not of TripAdvisor LLC.
Reviewed July 5, 2015 via mobile

Booked a 2 hour sail with Sailing Dreams the day before and had an amazing experience! Judy and her team were very friendly and extremely knowledgable about the island. We lucked out and had the whole boat to ourselves. The boat was very comfortable and the sights were unforgettable!

Date of experience: July 2015
4  Thank Krista C
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
SailingDreamsPR, Front Office Manager at Sailing Dreams, responded to this reviewResponded July 29, 2015

Dear Nycgirl006;

Thank you so much for being part of our Sailing Dream. We are so happy to know that you had an amazing experience with us.

You are more than welcome to come back and sail away anytime!

Thank you for coming, thank you for taking the time to write us and thank you for your support.

Please remember you have local friends you can count with on your next visit to Puerto Rico.

Blessings and Love!

Report response as inappropriate
This response is the subjective opinion of the management representative and not of TripAdvisor LLC.
View more reviews