Sample Itinerary: U.S. Virgin Islands

Thinking of chartering the U.S. Virgin Islands? Look no further than Waypoints. Our charter concierge can work with you to develop a custom itinerary based on your goals and desires. Below is a sample to get you inspired for your next charter vacation!

Day One

After your morning chart briefing and provisioning, you will be ready to begin your trip. There are a couple of options if your plans are to head straight to the British Virgin Islands, a relaxing 3-4 hour sail from Charlotte Amalie. You can take the BVI loop either clockwise or counterclockwise, mostly depending on where you want to spend your first or last night. For this sample itinerary, we are going clockwise and starting on Jost Van Dyke. Once you have cleared customs in Great Harbour, dinghy around to White Bay for a Painkiller at Soggy Dollar Bar to officially kick off your vacation.

Day Two

After enjoying breakfast either onboard or ashore, sail or motor to Sandy Spit, a tiny little island that has become a must-see in the Caribbean, made famous by a Corona commercial. From there, you will be right at the mouth of Little Jost where you will pick up a mooring ball for some snorkeling, lunch, and maybe even a hike to the Bubbly Pool. Snorkeling along the shoreline, you are bound to see an array of beautiful marine life, and you may even find yourself engulfed in a school of shiny baitfish as they move along the water’s edge. Lunch at Foxy’s Taboo is sure to please everyone in your group and offers stunning open-air views of the luminescent waters. Take a short hike to the Bubbly Pool, which can be quite spectacular if there is a good North swell.

Day Three

Leaving Jost, sailing east between the beauty of Jost Van Dyke and Tortola head for Monkey Point, Guana Island for a snorkeling stop. Monkey Point, a national park, is home to many friendly yellowtail snappers, grunts, and jacks, along with turtles and some large tarpon. From there make your way to Trellis Bay where moorings are plentiful. This spot is home to The Last Resort which has great food and live music every night. For a quiet evening grab a mooring at nearby Marina Cay and dinner at Pusser’s. You will also have an opportunity to pick up any extra supplies you need at the Trellis Bay Market open 365 days a year. Trellis Bay is also very popular for its famous Fireball Full Moon Party with some of the best BBQ in town! Once per month, the bay transforms into a party atmosphere under the moon with local Mocko Jumbies, BBQ, fireballs, live music, local arts, and bars. Always featuring nightly specials such as BBQ Chicken, BBQ Ribs, Grilled Fish, Jerk Chicken, and Jerk Pork. These dishes are grilled to perfection using our barrel smokers and grills to give you that flavor you’ve been craving! Trellis Bay Market also offers live music to go with the delicious food. Life is a celebration, come on down and “FullJoy” yourself with Trellis Bay Market on Full Moon Party Nights!

Day Four

Get an early start and make your way over to the Baths. Grab a National Parks Mooring and dinghy into the beach. Note you can no longer take your dinghy onto the beach as it’s been roped off. You will have to swim in. Make sure to pack a dry bag to keep your camera and other items dry.

Plan to spend the whole day making your way through the tunnels, caves, and crystal-clear water pools through the maze of massive borders. Make your way over to Devil’s Bay beach for a swim then hike up to the top of the Baths to grab lunch and see the most amazing 360 views of the BVIs. Hike back down to the beach and head back to your boat. Make your way over to Leverick Bay for the night. Grab a mooring ball or make reservations for a space on the dock. This marina has it all. Freshwater, ice, fuel, showers, laundry facilities, spa, shopping, Wi-Fi, and food aplenty here.

Day Five

After breakfast, follow the same path you took into the North Sound to make your way back into the Sir Francis Drake Channel towards Cooper Island, but be sure to stop along the way at the Dogs, a cluster of three small islets, all national parks, with excellent snorkeling and diving. The best anchorage is in the bay to the west of Kitchen Point on George Dog. Pick up a Parks Trust mooring ball just off the beach and stay for a swim and lunch. From there tack over to Cooper Island in the early afternoon and grab your overnight mooring in Manchioneel Bay. Check out Cistern Point for more snorkeling or simply relax on the beach or by the bar at the Cooper Island Beach Club. There is a strict “no anchor” policy in effect at Cooper Island, due to the plentiful turtle grass on the bottom. Make sure you have called ahead for dinner reservations at the Beach Club to be able to enjoy a wonderful meal in a magnificent setting.

Day Six

Upon leaving Cooper Island on your way to Norman Island, take a little detour to Salt Island to snorkel the Wreck of the Rhone. The rudder post comes within 15 feet of the surface and below that is the 17-foot bronze propeller. Also visible, even when snorkeling, is the cargo deck, propeller shaft, midshaft bearing, and gearbox. Surrounding all this is a spectacular reef system full of wreck loving fish. This will be a highlight of your trip. From there, work your way towards Norman Island. While you’re in “snorkel mode” grab a ball at The Indians for some of the most amazing snorkeling in the Virgin Islands. Once you have picked up a mooring ball in The Bight, you can dinghy over to the Caves for an afternoon of unbeatable snorkeling. There are two restaurants to choose from for dinner depending on your group. The world-famous Willy-T is a fun place to hang out and take the famous leap from the upper deck. (Late night at Willy T with young children is not advisable) However, Pirate’s Bight is a beautiful, family-oriented beach bar and restaurant tucked away in the southeast corner. It’s a great place to lounge on the beach and to enjoy dinner in a nice tranquil setting.

Day Seven

From Norman Island, sail downwind along the coast of St John and back towards Cruz Bay. Pick up a mooring ball along Honeymoon Beach and take the dinghy in to clear back into the US. Take some time for last-minute souvenir shopping and grab some lunch at one of the many beachfront restaurants in Cruz Bay or in the trendy Mongoose Junction. Give yourself enough time to pick up a mooring ball for the night in the calm, protected waters of Christmas Cove, on Great St James. There, you can spend some time snorkeling before ordering dinner from Pizza Pi, a world-famous floating pizza kitchen. You can dinghy over to pick up your pizza, or, for a small fee, they will deliver it right to your boat. Take some time to enjoy each other and reflect on your week together. Times like this are precious!

Day Eight

Returning to base . . . Please plan on returning to base no later than NOON, unless other arrangements have been made and agreed upon with the Base Manager.

Think you and your loved ones would enjoy this trip? Contact a charter concierge to get started planning the USVI charter experience you’ve been longing for!