USVI Sample Itinerary

Depart from our base in historic Frenchtown surrounded by the natural beauty and culture of the U.S. Virgin Islands and experience an unforgettable charter vacation. Your previously scheduled private cab will be ready to pick you up from the airport.

Waypoints USVI is located near excellent gourmet restaurants, pub-style eateries, and downtown Charlotte Amalie world class duty-free shopping. Spend a night on the dock or anchored nearby to enjoy the sights and lights of our busy Caribbean port.

If you are doing a sleep aboard, you can spend your first night in the marina in Frenchtown, with multiple dining options and provisioning nearby. If your charter begins at noon, we will get you on board, do a boat review, and then get you underway.

Sample Itinerary


Day 1

Your first night will be spent at Honeymoon Beach, Water Island, Christmas Cove, or even at one of the North Shore beaches of St. John, depending on your departure time. St. John brings a variety of dining, nightlife, and shopping options. Are you looking for a night on the town? Mooring at Caneel Bay puts you just a dinghy ride away from all the Cruz Bay attractions.

Day 2

For your second day aboard, take a sail around Pillsbury Sound. There are multiple North Shore beaches in the National Park to explore, such as Hawksnest Beach, Trunk Bay, Maho Bay, and Francis Bay Beach which are all suitable for a day stop or an overnight stay.

Day 3

Next stop – snorkeling! Around the corner from Francis Bay in the narrows between Tortola and St. John lies Leinster Bay, a National Park gem. With Waterlemon Cay, as well as the reef along the shore, the snorkeling here is sure to please anyone. This is also suitable for day stops or an overnight stay.

Day 4

Next, head around to the southeast side of St. John. Coral Bay is a unique harbor that is often forgotten, with great snorkeling opportunities in the mangroves. The National Park has provided day moorings here. Then, head over into Coral Bay where you can anchor out and either venture into town or stop by the Lime Out, a floating Taco Bar. Stargazing and turtles are both in abundance on the south side. End your day exploring the sailors’ choice of either Salt Pond Bay, Lameshur Bay, or Little Lameshur Bay, all in the National Park.

Day 5

Begin your day sailing downwind and head to Magen’s Bay on the North Side of St. Thomas. The huge beach and protected anchorage is one of the most photographed beaches in the world and is a great stop for your second-to-last night. Sail downwind around the West End and enjoy another nice sail. Then, head back toward the base for your last night. You have a choice of exploring Brewer’s Bay, Lindbergh Bay, or Honeymoon Beach for the last night of your trip.

Day 6

The last day you will have a quick stop at a marina for fuel and return to our base in Frenchtown. Make sure to send us pictures of your charter trip and #WaypointsWanderer on social media!