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“Highlight of the vacation”

Day Sail High Pockets
Ranked #7 of 30 Tours in East End
Certificate of Excellence
More attraction details
Attraction details
Owner description: Day sail and sightseeing charters in the Caribbean. Join Captain Kathleen Nelson and High Pockets offer an incomparable day of fun with sailing, sightseeing, and snorkeling. About your day: You begin with an exciting sail across protected waters toward St John and the surrounding islands. All inclusive for your day: A wide variety of beverages are available. Full snorkel gear (or bring your own), expert snorkel instruction and flotation are available. Fresh water rinse following swimming. If desired, a dinghy ride to a beach. A fresh lunch is prepared for you onboard by your captain. Flowers, cloth napkins and wine goblets set the pace for your meal. Your day concludes with graceful down wind sail with Kathleen's famous homemade rum cake. About the owner/captain: Kathleen, is a gourmet cook and former Registered Nurse. Her merchant marine credential is licensed for up to 100 ton vessels. She has been crewing and captaining charter boats (sail and power) in the US and British Islands going back to 1987. Kathleen and her husband, Jim have extensively sailed the Caribbean as far as Grenada and the New England Atlantic coast, logging in over 50,000 ocean miles in the past 28 years. High Pockets is a classic and stable yacht, purchased new by the Jim Nelson in 1970 and is fully customized for day sails, as well as long distance offshore sailing and live aboard cruising.
Useful Information: Bathroom facilities, Activities for young children, Activities for older children
Boston, Massachusetts
1 review
common_n_attraction_reviews_1bd8 2 helpful votes
“Highlight of the vacation”
Reviewed 7 August 2014

My wife and I spent a day sailing with Captain Kathleen and Admiral (husband) Jim in early June. It was easily the highlight of our trip to St. Thomas and well worth the price. The best part of the trip is they truly work to meet their guests interests for the day.
My wife and I were most interested in sailing and getting some sun so we set up shop on the bow. With our feet hanging off just above the bright blue water, Kathleen got us drinks and told us about the locations we were passing along with the history of the surrounding islands. Meanwhile, the other couple on the day sail preferred to sit back and relax in the captain's cockpit where it was more stable and...dry. The boat is so big that in some ways it felt like we were on our own private trip.
We sailed around the coves of St. John and settled into a beautiful bay with only a boat or two within view. We then went snorkeling while Kathleen cooked us an amazing lunch. Jim set us up with great snorkeling equipment and reviewed the basics with my wife. After seeing a ton of fish on the snorkel, we enjoyed a great meal with the other couple who had chosen to stay on board. We were all fixed up with drinks (wine, beer, cocktails) from the open bar with Kathleen as the bartender and then enjoyed a leisurely sail home.
I would do this again if we return to the Virgin Islands and have already recommended it to all family and friends.

Visited June 2014
2 Thank jbm12345
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC
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396 reviews from our community

Visitor rating
Date | Rating
  • English first
  • Any
English first
Bronx, New York
Level 3 Contributor
7 reviews
4 attraction reviews
common_n_attraction_reviews_1bd8 10 helpful votes
“Best Part of our 8-day Vacation!!!”
Reviewed 22 June 2014

I found High Pockets on Trip Advisor. I was searching for things to do while our cruise ship stopped in St. Thomas. Having been to St. Thomas before, I wanted something a bit more relaxing and was willing to spend a bit more money to do a private sail vs. going on a crowded party boat from the cruise ships. From my exchange with Kathleen over email, she was very polite and when we finally spoke on the phone, she had such great energy that I kinda just "went with my gut". I had spoke with other companies that offer private sails, but it seemed dry and rushed, yet Kathleen always made me feel like I was not a bother.

We took a taxi from the cruise ship to meet up with her (about $12 per person each way) and from the moment we met, she took wonderful care of us. My husband and I do not sail, nor do we understand the craft of sailing, so her and her husband made us feel comfortable and gave us a information so we were safe on the boat, but also having a good time. She took us to Honeymoon beach, which I loved. It was secluded with a few people (maybe about 12-15) so I was able to float in the calm water in peace, Then we sailed some more while we ate her DELICIOUS lunch. It was so good, I begged for the recipe! She then kept the drinks coming, until we made it back. Lets just say, I did not want to leave.

Overall, if you are looking for a relaxing and peaceful time, while getting in some beautiful sights and having some great food and drinks, go with Kathleen. Hands down, trust this woman! We were looking for relaxation, and we definitely got it.

Visited June 2014
2 Thank Sachiel_F01
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC
Level 3 Contributor
10 reviews
7 attraction reviews
common_n_attraction_reviews_1bd8 7 helpful votes
“Relaxing sail… Had a great time!”
Reviewed 10 June 2014

Been meaning to write a review for a long while now and finally had time to do it. Sailed on High Pockets April 10, 2013. This is one of the highlights of our seven day caribbean cruise. Captain Kathleen and first mate Melissa were very accommodating and well attentive to our needs and safety which made our day very special. We enjoyed snorkeling during this sail, reefs and fishes are amazing. Chatting and exchanging life stories with Kathleen and Melissa was fun. We enjoyed the delicious well presented lunch and of course, the bottomless "Rum Swizzle". That chocolate rum cake during our sail back was yummmmyyyyy!!!
Booking this excursion off the ship was well worth of all the doubts and risk of being not able to making it back in time to the cruise ship and be left behind. Capt. Kathleen will work with your port time and will make sure you are back in time. For all the cruisers, this is a must do excursion when docked in St. Thomas.

Thanks Capt. Kathleen and first mate Melissa!!!

Greg & Liza from California

Visited July 2013
3 Thank greza
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC
New Orleans, Louisiana
Level 4 Contributor
30 reviews
9 attraction reviews
common_n_attraction_reviews_1bd8 12 helpful votes
“Beautiful sale, gourmet food on High Pockets ...”
Reviewed 8 June 2014

We visited St Thomas in December/January 2014 and I have been meaning to submit a review ever since. My wife and I sailed for a day on High Pockets and would recommend it without reservation. We were the only passengers that day. The sailboat would probably accommodate six or eight passengers. The sail was also a tour with commentary on the various things we passed at sea such as beautiful coastal mansions and communities, favorite bays and coves. We stopped for a swim at one point which was delightful while lunch was prepared. The lunch turned out to be spectacular; far more than we had expected with white wine and all. Kathleen was a wonderful hostess and made us feel quite at home right away. I know there was a comment some time ago about the safety of the boat after one of the tourists took a fall. I can assure you that Kathleen was ultra-concerned about passenger safety, especially boarding and disembarking the boat and you should have no worries here at all. Do yourself a solid and take a day to spend on High Pockets ... You'll be glad you did.

Visited January 2014
1 Thank Jazzfiend979
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC
CaptKathleenNelson, Owner at Day Sail High Pockets, responded to this review, 3 July 2014
Greetings from St Thomas! We had such a delightful sail with the two of you. It really was spectacular sightseeing on the water that day. You both took such an interest in everything, which is wonderful for me. It's like seeing it all for the first time. Thank you again for joining us aboard High Pockets. And, thank you for taking the time to write a review. Hope to see you some time soon! All the best, Kathleen.
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Cincinnati, Ohio
Level 1 Contributor
4 reviews
common_n_attraction_reviews_1bd8 7 helpful votes
“Smooth Sailing”
Reviewed 3 June 2014

Kathleen and Melissa made this a day to remember with their sailing expertise, impeccable service, refreshing rum swizzles and delicious lunch. High Pockets is a beautiful boat that glides with ease through the crystal blue waters of the Caribbean. I highly recommend a day aboard High Pockets to complete your trip to the islands.

Visited May 2014
1 Thank skibunny48
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC
CaptKathleenNelson, Owner at Day Sail High Pockets, responded to this review, 11 June 2014
Greetings from High Pockets It was a pleasure to have you aboard. Thank you so much for sharing one of your valuable vacation days with us. And, a big thank you for taking the time to share your experience on TripAdvisor. We'd love to take you sailing for another great day when you're on island again. Kindest regards, Kathleen.
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