United States Virgin Islands St Thomas St John USVI
Virgin Islands National Park

Caribbean yacht charter adventures featuring sailing and snorkeling.
A picnic afloat. A vacation in one day!

daysail High Pockets

A cut above

Caribbean sailing at it's finest

Questions and Answers

For our friends old and new...answers to some of your questions.

phone 340-690-0587

What is included with our daysail?

Personalized and friendly service. Fantastic sailing. Lively conversation. Exciting stories of adventurous high seas sailing. Learn all about long term live aboard cruising and real offshore sailing. Thirst quenching open bar. Water toys. Quality snorkel gear with experienced instruction. Comfortable swim flotation vests. Large, stable dinghy for beach trips. Sun kissed warm fresh water rinse off. Delicious gourmet lunch prepared fresh onboard. Island music if desired.

What do you do on a day sail charter?

In the morning we sail for a few hours in protected waters taking in the breathtaking sights of our Virgin Islands. Following our morning of fun sailing, we anchor in a peaceful cove for snorkeling, beach combing and relaxing. We then dine in style in our shaded cushioned cockpit. Colorful dish ware, wine goblets, cloth napkins and fresh cut flowers complete the perfect picnic! Perhaps another dip in our warm Caribbean Sea for a snorkel, or lounging about on our comfortable yacht. Then, a nice leisurely sail home.

Where does High Pockets go on a day sail?

We sail out towards St John, the Virgin Islands' National Park and the surrounding cays. Each day offers us different conditions, so we go someplace different everyday! We're so lucky to have so many choices. Some of the cays we go to: Lovango Cay, Congo Cay, Henley Cay, Whistling Cay, and the St James Islands. Some of the bays and beaches on St John we go to: Mary's Point, Francis Bay, Maho Bay, Peter Bay, Hawksnest Bay, Scott Beach, Caneel Bay, and Honeymoon bay.

What do you serve for lunch?

Scrumptious medallions of grilled chicken breast and sweet grape tomatoes in a fresh lemon herb sauce. Salad greens with a light vinaigrette. French Bread and European style butter. A splash of Chardonnay, perhaps? Home baked, mouth watering rum cake.: It is easy to alter our menu for special dietary needs. Please just tell us.

Do you take cruise ship passengers on your daysail charters?

Absolutely! Many of our guests are on a cruise ship and in St Thomas for the day. We are so accessible to those that wish to escape the crowds for a great day on the water seeing the sights.

There is only two in our party. Do you need more people to go out?

We are happy to sail with only two guests. We take only up to six guests out.

Would our children enjoy the trip?

We sail with many children of all ages and delight having their bright, smiley faces onboard. We even offer a children's menu! Children love being out on the water and going to the beach in our big dinghy. We also find they love checking out our sailboat that served as our home for many years.

Is there anywhere to get out of the sun on the boat?

High Pockets offers both the sun and the shade. You choose.

I don't swim. What's for me to do all day?

You don't have to go in the water to have a fantastic day! Certainly, if you wish to put on extra flotation and see the wonderful world underwater, we'll gladly teach you to snorkel! If possible, we'll snorkel with you for your added comfort. Or, you can catch a ride in our stable dinghy to the beach to wade and play in the surf.....or just plain beach comb for treasures. You are also welcome to lounge aboard High Pockets in comfort, soaking up the beautiful sights while sipping one of our special drinks.

What should we bring?

Photo ID, swimsuits, towels, and sunscreen. Oh, and bring your cameras, so we can get some great photos of you while on board.

What days is High Pockets available?

We are available to sail each and every day!

What times do you sail?

We meet you at 9:00 AM. We have you back on the dock around 3- 3:30 PM. To our cruise ship guests: We can adjust sailing times for your party to accommodate a bit of shopping on your way back to your ship.

Where does High Pockets depart from?

We sail from Red Hook Harbor in St Thomas, USVI, which is the closest part of St Thomas to St John and the Virgin Islands' National Park. We greet you at American Yacht Harbor Marina at the waterside entrance of Fishtails resturant.

How do we get to you?

Getting to us is easy! By Taxi: Just ask your driver to bring you to American Yacht Harbor Marina to meet us at the waterside of Fishtails Resturant . For our cruise ship visitors: We are just an easy 15-20 minute ride from where your cruise ship docks. For our St John visitors: A fun 15 minute ferry ride from Cruz Bay, to Red Hook, with a 2 minute walk right to the marina. We can drop you off in Cruz Bay on our sail home. For our island visitors who are renting a car: Parking in Red Hook is at a premium. You may park across from the ferry dock, a 2 minute walk to meet us, for $10 per day.

Can I reserve the sail in advance?

Certainly! Please just contact us by phone or email to do so. We'll be happy to answer any of your questions.

What are your rates for a day sail and do you accept credit cards?

Please contact us by phone or email so we may quote you rates. High Pockets accepts Master Card, Visa and cash.

Will I be charged if the weather is unsafe to sail or my cruise ship diverts from St Thomas?

You will not be charged if your ship diverts from the island. In addition, you will not be charged, if conditions are unsafe to sail. We don't want to be out there anymore than you do! You may call us on the phone the morning of the sail and we will tell you what is going on in regard to the weather.

I'm on a cruise ship out of Florida. Is St Thomas on the same time zone?

Good question! Florida is on Eastern Standard Time. St Thomas and all the eastern Caribbean islands are on Atlantic Standard Time. This means that St Thomas is an hour later than the time on the ship. Please ask your ship which time zone is observed, so you will get to all your shore excursions at the right time.

Please contact High Pockets at

Phone 340-690-0587


Email: RSVP@sailhighpockets.com

High Pockets 6292 Est. Nazareth #100 St Thomas, US VI 00802