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 – St. Thomas and St. John


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

Spoil your whole crew with a day or night at Lovango Beach Club. Off the northside of St John lies Lovango and Congo Cays. On Lovango Cay you can reserve a private Mooring, then decide if you want a day pass so you can lounge around the pool, have some drinks, or a bite to eat. You can also make dinner reservations as well and dine under the stars.

Day 4

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 even the most discerning adventurers. This is also suitable for day stops or an overnight stay.

Day 5

Next, head around to the southeast side of St John. Coral Bay is a unique harbor that is often overlooked with great snorkeling opportunities in the mangroves. The National Park has provided day moorings here. Then, head into Coral Bay where you can anchor out and either venture into town or stop by the Lime Out, a floating Taco Bar.

Day 6

Take a nice sail out to the south and St John and tack back into one of the south side anchorages. You will be greeted by turtles and fish at any of The National Park mooring fields. Salt Pone, Lameshur Bay, or Little Lameshur never disappoint. Wind down your day with a nice meal onboard and gaze at the stars. The seclusion of these bays and the lack of light noise from shore make for spectacular star gazing.

Day 7

Begin your day sailing downwind and head to Magen’s Bay on the North Sound 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.  Enjoy a nice sail downwind around the West End, then head back toward the base for your last night. You have a choice of exploring Brewer’s Bay, Lindbergh Bay, or Honeymoon Beach.

Day 8

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 don’t forget #WaypointsWanderer on social media!

Sample Itinerary – St. Thomas and Spanish Virgin Islands


Caribbean Charm with a little Latin flair. The Spanish Virgin Islands consisting of Culebra and Vieques as well as several smaller cays beckon back to a simpler time in the Caribbean. 

If you are doing a sleep-aboard, you can spend your first night at our 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.

Day 1

Depending on your arrival time, you will either spend the first night on the dock or at one of the western anchorages around St Thomas. Honeymoon Beach, Lindbergh Bay, or Brewers Bay all make good jumping off points for your sail to the SVI’s.

Day 2

Rise and shine because it is time to make a downwind run. Typically, the next stop is Ensenda Honda on Culebra. It is roughly twenty miles from the west end of St Thomas to Culebra. You will carefully follow the ships’ channel into the harbor.  Once you are anchored in the harbor you can use the ROAM APP to clear your vessel and crew into customs. Then, it is time to explore the town of Dewey. Dewey is home to multiple dining and shopping options. The Dinghy Dock, Zaco’s Tacos, or Mamacita’s are just a few of the great options available. 

Day 3

How about a little land-based excursion? You can rent street-legal golf carts from Jerry’s Jeeps in Dewey. Pack your beach gear and head out for the day. First stop – Zoni Beach! This is a turtle sanctuary located on the North Shore. A long stretch of white sand with views for miles. Then, you can drive to Flamenco Beach on the northwest side of Culebra and explore the large natural beach. With food vendors, pristine white sand, and even a photo op or two on old tanks used for target practice, it is an experience not to be missed. Leave yourself enough daylight to move the boat around to the anchorage Ensenda Dakity. This is a great snorkel spot tucked in behind a barrier reef.

Day 4

Culebrita, the name sounds as pretty as the Cay. Culebrita is home to a spectacular beach, a historic lighthouse, and a natural “hot tub”. There is a lot to see and do here. Or you can choose to do nothing at all. Either way, it is not to be missed. You have your choice of several anchorages depending on the weather.

Day 5

Set sail for Vieques. In most instances you will run around the east end of Vieques, then work your way to any number of south side anchorages. Ensenada Honda, Sun Bay, or Esperanza just to name a few. If the moon is right, book a kayak tour of the  Bioluminescent in Mosquito Bay. This is a protected harbor and you must book with an authorized vendor.

Day 6

Decisions, decisions. Hang out in town for a pub crawl. Rent a jeep and explore. Spend the day in Sun Bay enjoying the beautiful beach, the water, and the sun. There is no wrong answer.

Day 7

Set a waypoint for the west end of Water Island just south of St Thomas. Drag a fishing line if you have one. Or just drop by Dinghy’s Beach Bar at  Druif Bay on Water Island to provide you with the last dinner of the trip.

Day 8

On 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 don’t forget #WaypointsWanderer on social media!

Sample Itinerary – 10-Day Charter from USVI to BVI


Traveling between the USVI and BVI allows you to see world-renowned sights and make unforgettable memories on a multi-day charter adventure.

Start the vacation of a lifetime by flying directly into Saint Thomas and catching a short ten-minute cab ride from Cyril E. King airport to the Waypoints USVI base. If you are doing a sleep-aboard, you can spend your first night in the marina in Frenchtown on your boat, with multiple dining options and provisioning nearby. If your charter begins at noon, we will get you on board, conduct a boat review, and then get you underway.

Day 1

Depart from the marina and head east for your first stop in St. John. Take a mooring at Lind Point/Caneel Bay and go into town, or head up Maho Bay and hang out with the turtles. There are multiple snorkeling opportunities along the way to see some local sea life.

Day 2

The next day, you are on to the BVI! Head over to the West End of Tortola and clear customs at Soper’s Hole. Grab some lunch at any of West End’s delightful restaurants. Then, head over to the Bight at Norman Island, home of the legendary Willy T’s and Pirates Bite, to anchor for the night.

Day 3

The following morning brings an array of wonderful snorkeling spots. You can snorkel the Indians, the Caves, or both. Then, sail up the Sir Francis Drake Channel to overnight at Cooper Island. Make sure to book a reservation at the Cooper Island Beach Club.

Day 4

Sail to Trellis Bay and enjoy a luxurious day at Scrub Island Resort and Marina, or head up to Virgin Gorda and visit the Bath’s. You can’t go wrong with either choice.

Day 5-6

Time for the North Sound of Virgin Gorda. From Leverick Bay, Bitter End, and Saba Rock to Prickly Pear, Biras Creek, and the Sand Box. The possibilities are endless. Plan for two days in the area because one just isn’t enough.

Day 6-7

Anegada is known for sailing, lobsters, and white sand beaches. Tuck in behind the reef at the Settlement and let the fun begin. Spend two days in paradise soaking up every bit of sun and relaxation.

Day 8

Leave Anageda early the following morning and take a smooth downwind sail to Jost. The hardest part of the whole trip will be deciding which anchorage to head to, including Diamond Cay, Little Jost, Sandy Cay and Spit, Little Harbor, or Great Harbor.

Day 9

Set a course back to the USVI on the south side of St. John and then pick from several anchorages. You can settle in at Coral Bay with its funky vibe. Enjoy absolute bliss while star gazing at either Salt Pond or Lameshur, or head on down to Rendezvous Bay.

Day 10

Time for another downwind run with several options for your last night on charter. Head to Christmas Cove and grab a slice at Pizza Pi, or anchor out at Honeymoon Beach at Water Island, the home of Dinghy’s Beach Bar. You can also come on back to the marina in Frenchtown to ease back into reality.

On the day you return your boat, 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 don’t forget to add #WaypointsWanderer on social media!

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