US Virgin Islands Sample Sailing Itinerary

US Virgin Islands Sample Sailing Itinerary

Seize the Day Charters US Virgin Islands Sample Sailing Itinerary

Take Your Dream Vacation to The US Virgin Islands 

The USVI consists of 3 main islands, St. Croix, St. Thomas, St. John, and around 50 smaller islets and cays. The best thing about the USVI is that each island offers something new and unique. St. Croix is the largest island, and yet the least popular tourist destination. It is known as a scuba diver’s paradise and is home to one of the only underwater national monuments in the US-Buck Island Reef National Park. St. Thomas is known for its history and adventure. It offers some of the most sought-after activities in the USVI. So, whether you are looking for relaxation and tranquility or some adventurous fun then St Thomas is the perfect spot for you. Last but certainly not least is St. John, which is the smallest of the main islands but is the best preserved.

One of the best ways to explore the USVI is by chartering a yacht. The islands have facilities that can accommodate various sizes of vessels for short and long-term visits. The islands are also considered one of the best places to set sail in the world. They offer gorgeous sunny weather, beautiful landscapes, protected anchorages, short passages between islands, and dependable trade winds. Imagine this, a romantic honeymoon where you wake up to breathtaking sunrises, explore untouched beaches that are tucked away in hidden bays, jump headfirst into turquoise blue waters, and wind down with a delicious chef-prepared meal paired with a refreshing glass of champagne all the while watching the sunset in the distance. Is there anything more perfect? 

Are you ready to begin your yacht experience in the US virgin islands? Let’s go. 


Day 1: Your crew will be happy to coordinate a taxi pick-up once you arrive at the airport. A driver will meet you at baggage claim and take you to meet the crew at the Yacht Haven Grande Marina, which is located just a short 15 minutes away from the airport. Once aboard the boat, you will be briefed before allowing to settle in and enjoy your welcome cocktail on board as we set sail for Water Island. 

Fun fact, Water Island gets its name from the numerous freshwater ponds that were once found there. Pirates and other seafarers would replenish their water supplies from these ponds.

Once you arrive at Water Island you will enjoy an afternoon on the beach before heading over to have a drink at Heidi’s Honeymoon Grill or Dinghy’s Beach Bar. You will end the day enjoying a tasty and beautiful presented chef-prepared dinner aboard the yacht while watching the sun dip below the horizon. 

Day 2: Wake up at your own pace and get ready for another beautiful day in the USVI. Once you are ready, you will head over to Porpoise Rocks to do some snorkeling, before circumventing the west side of St. Thomas through Savannah passage to Magens Bay. 

Fun Fact, Magens Bay Beach was named one of the most beautiful beaches by Conde Nast and National Geographic. 

Spend the rest of the afternoon sprawled out on the beach’s beautiful white sands or take the adventurous roots and dive head-first into its crystal blue waters. Magens Bay Beach is known for its watersports, so this is the ideal time to go snorkeling, kayaking, or stand-up paddling. If you want to go explore a little more, we’d recommend that you head on over to the Old Stone Farmhouse, which is a 200-year old restored plantation field house. Today it operates as a restaurant and offers a unique ambiance and delicious food 

Day 3: It’s time to leave Magen’ Bay at your leisure, and set sail to enjoy some of the USVI’s most stunning landscapes. You will sail through the cut between Hans Lollick and Little Hans Lollick, before stopping for lunch onboard at Sunsi Bay or Coki Beach. If you fancy a different type of lunch experience, you can head over to Lovango waterfront restaurant to enjoy a delicious lunch and a gorgeous view. After lunch why not take a stroll through Lovango Village’s exclusive boutiques featuring local brands, chic finds, and even your latest beach read. 

Then it’s back into the water. You can either choose to go scuba diving at Carvel Rock or snorkel/dive at Spring Bay. If you are feeling a little more adventurous then you can also go cliff diving at Carvel rock. 

After a full day of adventure, wind down onboard as we dock at Henley Cay or between Lovango/Congo Cay. 

Day 4: Off you go again to St. John and Maho Bay for lunch and a snorkeling adventure. Why St Johns? Because you are guaranteed a turtle sighting. 

Fun fact: Maho Bay Beach: the home of three species of turtle, including the Loggerhead, Leatherback, and the endangered Green turtle. 

Once you’ve finished playing with the turtles, you’ll go for a walk on the beach and grab a drink (or maybe two) at Maho Crossroads. Maho Crossroads is a minimum footprint, energy-efficient, self-powered pop-up village across the street from Maho Beach. Then you will head on over to Leinster Bay/Waterlemon Cay where you can take in local history with a short walk to the Annenberg ruins. A shorter walk to Murphy’s Mansion is another option where you can enjoy the gorgeous views over the bay. This is also a beautiful bay to enjoy paddleboarding and some kayaking. 

Dinner is finally served, and this time around it is freshly caught lobster. Is there anything more delicious? You end off the day with a choice of sunset cocktails at Murphys’ Mansion or opt to stay on board to watch the sunset. 

Day 5: After breakfast on board, it’s time to go back into the water (again) to explore Waterlemon Cay and get up close and personal with its underwater wildlife. As you snorkel, you’ll probably end up seeing spotted rays, spotted flounder, and or squid. For lunch, you head on over to Lime-out, a swim-up bar in Coral Bay that serves mouth-watering tacos and hand-crafted cocktails. 

Then it’s back onboard where you will sail to your destination for the night, either Salt Pond or Lameshur Bay. Those still wishing to get some exercise in for the day may hike to Rams Head and on a clear day see St. Croix in the distance. 

Day 6: Another day, another snorkeling session. This time we are going to explore Yawzi Point and its deepwater structures and canyons, which are home to schools of fish, octopus, barracuda, tangs, parrotfish, brain coral, and a myriad of fan corals. Lameshur Bay is the perfect bay for a peaceful lunch, followed by a paddle or kayak before leaving for Caneel Bay and a beautiful sunset enjoying cocktails and hors d’ oeuvres onboard. 

If you are craving to get off the boat, then the main town on St. John is just short right away. Here you can go shopping and enjoy some late evening cocktails. 

Day 7: After breakfast, you will head on over to see the Jeffrey Epstein compound, before diving back into the water at Ledges or Cow and Calf. After your dive, satisfy your grumbling tummy with a pizza from Pizza Pi, known for having the best pizza in the Caribbean. Pizza Pi, which is only accessible by boat, serves up fresh NY-style pizza while you snorkel. 

In the afternoon we will head on over to Buck Island to hike to the historic lighthouse and then snorkel the old freighter (the Cantanza) in Buck Island Cove. To end the evening we will head back on board to enjoy cocktails and dinner. Sunset will be epic. Make sure to keep an eye out for the green flash. You end the night by playing games and just enjoying the last night on the boat. 

Day 8: Sip a coffee on the deck and soak in all the magic of the USVI. The crew will take you snorkeling for the last time at Turtle Cove before you return to Charlotte Amalie where you will disembark.

*Remember that the crew are there to help you plan your dream vacation, so the itinerary outlined above can be changed to meet your needs. All you need to do is discuss your needs with your crew and they will do their best to make it happen. Do you want to stay one day longer for a particular bay or move on to a new experience? No problem, they are here to make your visit to the USVI unforgettable. 

As always, reminder an itinerary is wind and weather dependent.