Creating Your Dream US Virgin Islands Itinerary

Sail to The Virgin Islands National Park, Buck Island Marine Reserve, Megens Bay, Cruz Bay and more with our Virgin Islands sailing school!

Sailing: The #1 Way To Experience The US Virgin Islands

See more of the US Virgin Islands on your vacation by exploring by sailboat! Sailing gives you the opportunity to visit the top spots and hidden gems of St. John, St. Thomas, and St. Croix seamlessly. In fact, many of the best USVI vacation destinations can only be reached by boat! The USVI offers perfect sailing conditions with crystal clear turquoise waters near 82°F (27°C) and reliable 15 to 20 knots easterly winds.

Learn to Sail vacation in the US Virgin Islands.

Sailing with a knowledgeable Go Sail Virgin Islands ASA instructor provides the safest US Virgin Islands experience for new sailors, families, and adventure lovers alike! Go Sail’s Virgin Island sailing school offers the bareboat certification courses through the American Sailing Association (ASA) year-round in the US Virgin Islands. These active learn to sail courses will provide you with all the instruction, know-how, and internationally recognized certifications needed to sail a catamaran on your own just about anywhere in the world. Go Sail’s weeklong live-aboard vacation offers adaptable itineraries with the opportunity to visit a variety of the most loved USVI vacation destinations and hidden gem sailing locations. You’ll not only become a competent and confident sailor at our Virgin Islands sailing school but also have plenty of time to snorkel, island hop, experience Virgin Islands culture and cuisine, and explore the islands on and off shore!

Frequently Asked Questions About Sailing the USVI

A Sample 7 Day USVI Sailing Itinerary

Go Sail Virgin Islands offers individualized USVI sailing itineraries with the opportunity for sailors to visit a variety of different sailing destinations based on their interests, weather conditions, previous sailing experience, and more! These Virgin Island sailing school itineraries not only offer plenty of sailing time but also provide daily opportunities to explore the islands, snorkel in crystal clear bays, sample the delicious Caribbean cuisine, and relax on board. You can see just how unique each sailing itinerary is by reading our Captain’s Logs that detail the 7 day sailing itineraries of our many students. This sample 7 day USVI sailing itinerary will also give you an idea of what you can expect:

Day 1: Arrival

Fly into St Thomas, USVI (STT) and take a taxi to the marina. We spend the first night on the dock and the Captain will greet you at 5 pm to show you to your cabin. Check out all the details for navigating your arrival to St Thomas in our “Arriving in the Virgin Islands” video!

Day 2: Leinster Bay, St. John

Leinster Bay has so much to offer USVI visitors! Water lemon cay is a perfect snorkel right from the boat. Tropical fish and coral are a must see here. A student favorite is always taking the dinghy to shore and hiking to the Annaberg Estate with a tour of the historic sugar mill!

Day 3: Coral Bay, St. John

Coral Bay is also home to the famous Lime Out Floating Taco Restaurant— a fan favorite among Virgin Islands tourists! Our video, “A Typical Sailing Day with Go Sail VI” gives you an idea of how your days sailing in the Virgin Island will look and also a sneak peak of the delicious Lime Out cuisine!

Day 4: Lameshur Bay, St. John

With some of the best beaches in the Virgin Islands, you won’t regret staying another night (or 5!) along the shores of St. John. Lameshur Bay is also within the Virgin Islands National Park boundaries, making it one of the most peaceful and serene sailing spots you’ll encounter. Visit the old rum distillery near the beach or take a dip in the water for some beautiful snorkeling!

Day 5: Cruz Bay, St John

Cruz Bay is the perfect spot to stop after a day of Virgin Islands sailing if you’d like to get some shopping in, go to shore for dinner, or snorkel with turtles and rays. Maho Bay near Cruz Bay is considered the best location to admire the sea turtles and rays who feed on nearby sea grass.

Day 6: Christmas Cove, Great St. James

Enjoy your last night of sailing in the Virgin Islands by celebrating with a pizza party! Pizza Pi offers dinghy delivered pizza that our students always rave about! They offer unique flavors as well as unique delivery service. It’s a wonderful way to spend your final night aboard your Virgin Islands charter boat.

Day 7: Departure Day

We wake up in a bay near the marina. We will begin early with short sail and return to the marina dock at 9 am to get fuel and say your “see you soons” to your captain! We will will be off the boat by 10 am. The taxi ride is about 20 minute ride to the airtport. Plan to take an afternoon flight so you have plenty of time check in 2 hours early for your flight.

Other Locations to Visit on a US Virgin Islands 7 Day Itinerary

ST. THOMAS, USVI

St. Thomas isn’t just the location you’ll arrive and depart out of on your flights— there are great sailing stops to make on the island as well.

ST THOMAS BAYS TO VISIT:

✔️ Brewers Bay

✔️ Magens Bay

✔️ Christmas Cove, Great St. James Island

ST. JOHN. US VIRGIN ISLANDS

St. John is 80% National Park with a endless supply of pristine beaches with accessible hiking trails all over the island.

ST JOHN BAYS TO VISIT

✔️ Virgin Island National Park office at Cruz Bay
✔️ Honeymoon Beach
✔️ Hawksnest Bay
✔️ Trunk Bay
✔️ Cinnamon Bay
✔️ Maho Bay
✔️ Leinster Bay
✔️ Lamesur Bay
✔️ Coral Bay

ST CROIX, US VIRGIN ISLANDS

St. Croix is the largest of the US Virgin Islands and boasts quiet beaches, locally grown produce, and is a much quieter island.

ST CROIX BAYS TO VISIT

✔️ Christiansted

✔️ Buck Island Reef National Park

✔️ Cane Bay

✔️ St Croix Yacht Club at Teague Bay

Turning Your USVI Itinerary Dreams Into Reality

We offer an International Bareboat Cruising Certification with American Sailing Certifications ASA 101/103/104/114 with (IPC) or 106/114 with (IPC) in a learn to sail week-long course. All courses are customized and designed for you.

We are a crew of expert captains and instructors who have sailed all over the world. We know sailing but better yet we are mastering the art of teaching you everyday with patience and practice. Kindness and respect are at the heart of everything we do. These are 7 key principles we follow and live by.

Encourage active learning
Give and ask for prompt feedback
Emphasize hands-on sailing skills
Communicate with honesty and clarity
Respect diverse talents and ways of learning
Encourage questions and growth mindset
Develop reciprocity and cooperation

We are also providing this service for the betterment of the sailing community. When you are passing down your knowledge, you will have been inspired by the great mentor and Captain.

Meet the Go Sail Virgin Islands Captains and Crew

Check out our Captain’s logs of recent trips.

The Right Trip For Any Traveler

USVI: Private Premium Catamaran Course

Sunday (5 PM) to Saturday (10 AM) November to July
Private Yacht - 1- 6 students and/or ride along guests, No age restrictions.

Setting sail on a luxury sailboat is one of the best sailing trips you can take in the USVI! The premium USVI catamaran courses feature 40-50 foot Lagoon or Fountaine Pajot sailboats less than 5 years old.

Go Sail Virgin Islands provides exceptional hands-on sailing instruction crafted specifically for each individual students’ sailing goals. An ASA bareboat chartering course in the USVI provides ASA 101, ASA 103, ASA 104, and ASA 114 certifications as well as the opportunity to earn your International Proficiency Certificate (IPC).

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USVI: Cruising Couples Premium Catamaran Course

Sunday (5 PM) to Saturday (10 AM) November to July
Group Course - 2-6 guests 18+

Enjoy the beauty of the USVI while learning to sail on a luxury sailboat. The premium USVI cruising couples catamaran courses feature 5 years or newer and 40-50 foot Lagoon or Fountaine Pajot sailboats.

A cruising couples ASA bareboat chartering course in the USVI provides ASA 101, ASA 103, ASA 104, and ASA 114 certifications as well as the opportunity to earn your International Proficiency Certificate (IPC).

Go Sail Virgin Islands provides exceptional hands-on sailing instruction crafted specifically for the sailing goals of you and your spouse.

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Availability

USVI: Solo Traveler Premium Catamaran Course

Sunday (5 PM) to Saturday (10 AM) November to July
Group Course - 2-6 guests 18+

Setting sail on a luxury sailboat is one of the best sailing trips you can take in the US Virgin Islands! The premium USVI catamaran courses feature 5 years or newer and 40-50 foot Lagoon or Fountaine Pajot sailboats.

Go Sail Virgin Islands provides exceptional hands-on sailing instruction crafted specifically for your individual sailing goals. An ASA bareboat chartering course in the USVI provides ASA 101, ASA 103, ASA 104, and ASA 114 certifications as well as the opportunity to earn your International Proficiency Certificate (IPC).

Learn More

Availability