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“Wonderful excursion!”

Day Sail High Pockets
Ranked #7 of 28 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 older children, Activities for young children
Norfolk, Virginia
Level Contributor
11 reviews
5 attraction reviews
common_n_attraction_reviews_1bd8 2 helpful votes
“Wonderful excursion!”
Reviewed August 24, 2012

We are a family of three, husband, daughter (age 13) and myself. While planning our cruising vacation on the Carnival Victory leaving from San Juan on July 1, we wanted to do something different in the way of excursions. We’d already been to St. Thomas the first port stop on the itinerary a few years ago, so shopping and seeing the land portion of the island was not something we were interested in repeating. I had read positive reviews about Capt. Kathleen and the sailboat High Pockets and thought that we could give it a try. So I booked us. Everything that I had read regarding the quality of the experience was absolutely accurate and beyond our expectations. From the recommended and reliable taxi driver driving us across the island, to the actual sailing/snorkeling experience, we loved every minute. Though we live in a coastal city on the east coast, we are not necessarily “water babies.” Capt. Kathleen and her first-rate, first-mate Melissa masterfully guided us throughout the day as we sailed from St. Thomas towards St. John. It was truly exhilarating. Kathleen then suggested that we find a tranquil cove to snorkel and have lunch. We headed towards Great St. James Island with its intimate Christmas Cove. Melissa got us all geared up and ready to snorkel and view the sea life. The variety was amazing. From octopus and stingray to a sea pickle and a giant hermit crab, it was a great experience. Then it was time for lunch and Kathleen served us an elegant and delicious meal of mixed greens with a wonderful vinaigrette, pasta, grilled chicken, fresh bread and to top it off a delicious rum cake. The refreshing rum swizzles and chardonnay that accompanied our meal were delightful. When we arrived back on St. Thomas, our taxi driver was waiting to take back to the ship in plenty of time. While we won’t repeat the Victory cruise(that’s another entry), I would recommend High Pockets and Captain Kathleen.

Visited July 2012
1 Thank Karen S
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.
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384 reviews from our community

Visitor rating
Date | Rating
  • English first
  • Any
English first
Denver, Colorado
1 review
“Highlight of the Vacation!”
Reviewed August 19, 2012

Our family had an excellent time on the High Pockets with Kathleen. Her attention to the little details (e.g. bouganvilla on the table at lunch, excellent cooking, and motoring around the sailboat in the dinghy to take a picture of our family on the boat) really made this excursion stand out from other similar trips we had seen advertised and heard about from other travelers. Her first mate was wonderful too, and took lots of time to tell us about the history of the islands. We had a truly wonderful time!

Visited May 2012
Thank Laura B
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.
Chicago, Illinois
Level Contributor
13 reviews
4 attraction reviews
common_n_attraction_reviews_1bd8 7 helpful votes
“What a way to celebrate our engagement!”
Reviewed July 3, 2012

We were in St. Thomas for a week in May 2012, and had gotten engaged at the beginning of our trip. We wanted to do something special on our last day in the islands, so we called around the day before to a few day sail companies that were advertised in the magazines and brochures at the condo. To our disappointment, everyone we called was booked up. But then something really cool happened. One company called us back with a reference. They gave us Capt. Kathleen's name and number, and the name of her boat - High Pockets. We couldn't have gotten luckier! High Pockets was not scheduled to sail the next day, but Capt. Kathleen and her mate Melissa decided to take us out anyway. I believe she said "I'd rather be sailing than running errands." And since they hadn't been scheduled to sail that day, we showed up the next morning and were the only guests on board. (HP can take up to 6 guests per trip.) Capt. Kathleen and Melissa took care of everything - even reminding us to put on our sunscreen since we had such beautiful clear skies that morning. We sailed across the sound, and Melissa brought us delicious Rum Swizzles while we relaxed and enjoyed the ride. (I still need that recipe!) Melissa was incredibly knowledgeable about the surrounding islands and answered all our questions. After a delightful sail, we hit 2 different snorkeling spots off of St. John. Between snorkeling, we were treated to an absolutely delicious lunch on board, and great conversation with our Captain. We were never rushed at all. We could stay in the water as long as we liked, or laze on board and soak in the sun. It was an unbeleivable trip, and the most amazing way to end our vacation and celebrate our engagement - with a private sail on High Pockets! Thank you again, Kathleen and Melissa, for taking us out on your day off!

Stacey and Todd

Visited May 2012
Thank StaceyEM83
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.
San Jose, California
1 review
“High Pockets Rocks!”
Reviewed June 25, 2012

Kathleen was great! This was our family's favorite excursion of our trip. We saw turtles, stingrays, and all kinds of fish. The sailing experience, snorkeling and lunch were all fantastic. She takes care of everything, all you have to do is show up and enjoy your day. She arranged for a driver to pick us up and continued to take care us all day from home made fantastic food to awesome drinks. This a great way to spend your day whether your staying on St. Thomas or visiting as part of cruise. Its great for family's, couples, or a group up to six.

Visited June 2012
Thank John W
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.
White House, TN
Level Contributor
4 reviews
4 attraction reviews
common_n_attraction_reviews_1bd8 4 helpful votes
Reviewed June 18, 2012

What a WONDERFUL day!!!! We were cruising with Carnival Victory and our first stop was St. Thomas. We were met by a driver that Kathleen had arranged and he was there 20mins early. We are usually early to our destinations and I was surprised he was too. We felt very safe on our drive there and back to the ship.

Kathleen met us at the marina and took us to the sailboat by dingy. that was pretty neat. After brief safety instructions, we were off. As soon as we were out of the harbor the first mate Melissa put up the sails. I had read in other reviews of the dissappointment people had, that they ran the motor the whole trip and never put up the sails. That was not the case with us. It was just our family of four that day so we made only one stop at our request. We anchored right off the coast of St. John, where we snorkled, swam, ate a wonderful lunch that Kathleen had prepared and then swam some more. Our family has snorkled in many different places. This was, by far the best location we have been to. The snorkle equipement was top notch. It was the perfect day! No crowds from the cruse ship and as much water time as we wanted. Both Kathleen and Melissa were very friendly. To me, they have the perfect job. If we ever visit St. Thomas again this will be on our list for sure.

Thank you for a once in a lifetime experience!!!

Visited June 2012
1 Thank waternut_9
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.

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