U.S. Virgin Islands – USVI
Yacht Charter & Sailing Vacations

USVI • Where to go • When to go • What you should know • How to Book

A USVI Yacht Charter is exploring the “American Paradise.”  The US territory islands of the USVI make for a popular sailing destination for good reason …  Easy to get to, tropical climate, superb sailing, stunning white beaches, rainforests, Caribbean culture, and delicious food.

St. Thomas is known as the ‘Gateway to the Caribbean’ and is also called ‘Rock City’ by the locals.  Together with St. John (‘Love City’) and St. Croix (‘Twin City’), these islands and their various cays and anchorages provide opportunity for everyone—whether you want to snorkel or dive on the amazing reefs, relax on the beach, hike, explore the natural parks, visit historical sites, or try the delicious local foods.  While most charterers opt to explore St. John and St Thomas exclusively those who want a larger sail can make the passage to St. Croix (often with charter company approval needed).

What is a sailing vacation, yacht charter, etc..? Learn more here ›

NauticEd USVI Yacht Charter explore beautiful beaches


We’ve been there!

We’ve always tended toward the BVI, just mostly because it is always the most talked about, and who can resist another trip to the BVI? But during Covid, we did a USVI yacht charter because of the ease of travel.  We were amazed that the USVI is such a forgotten child of the Virgins. There is plenty to do, lots of beaches, great sailing winds, short sails, tucked away bays with stunning beaches and hikes, and fantastic snorkeling and scuba places. The USVI is simply a must-visit, and you can’t beat the quick 1 flight jump from any USA hub. Got a quick week spare? Jump to the USVI!

Sailing Requirements

USVI Bareboat charter requirements:

Sailing Resume



Learn more at Yacht Charter Resources ›

Sailing Skill Level

Knowledge – Skills – Experience:

✔ Intermediate

Sailing in the USVI is all line-of-sight navigation. You are never more than a few miles from land. There are a few shallow spots and reefs to be aware of thus, as always, navigation knowledge and prudence is paramount.

Sailing Skill Levels ›

When to go?

Due to the consistent warm tropical weather and steady winds, the USVI is a year-round destination.  Many Americans travel to the USVI during the winter months to escape the cold; hence, high season is from December through April.  Other peak high seasons fall in line with the holidays—Christmas and New Years’ time often book up a year in advance and prices can nearly double.  Fall and spring are also ideal times to charter.  Summers are considered the low season as the heat increases and we often recommend air conditioning on board.  Some charter companies close in August through October for hurricane season.


Consistent year-round warm temperatures with highs in the 80’s and low’s in the mid to high 70’s.  Gentle breezes keep the humidity relatively low.  Water temperature is perfect for year-round swimming ranging from 77-85 F.  September through December is considered the ‘rainy’ season.

How to get there?

It’s easy to get to the USVI from the main of the US.  Fly into Cyril E. King Airport (STT), also known as CEKA; most larger American cities offer direct flights to one of the USVI airports.  Or you can reach the USVI through a common hub (ex:  Miami, New York, Chicago, etc).  There are daily flights as well from Puerto Rico.   From Cyril King, a few of the charter bases are about 10-20 min away in nearby Charlotte Amalie; the others are on the eastern side of the island about  30 min away… grab a taxi or we can arrange a transfer for you.

Cuisine / Interest

Although not far from the continental US, the USVI boats a delicious Caribbean cuisine with lots of seafood influenced by the Spanish, Danish, African, and Indian cultures.

The national dish is called “Fish & Fungi” and is a fish meal with Fungi (no—not mushrooms but rather a cornmeal okra blend side dish).  Similar to a gumbo, Kallaloo is a leafy green comfort food stew made with vegetables, herbs, and a protein.  Conch is a popular dish often served as conch fritters with a side of spicy creole remoulade or sliced thin and served with butter.  Or you can opt for Roti, an Indian-type burrito filled with curry flavored meats and veggies.

Traditional USVI desserts include red grout (a tapioca and guava creation), dum bread (sweet round loaf bread made with coconut), sweet potato pie, and rum cake.

And don’t forget the Johhny Cake (a fried cornmeal type cake/biscuit) are a popular USVI treat that can be enjoyed anytime of the day or as desert.

Cocktails:  Nothing says Caribbean like a tropical cocktail.  There’s no shortage of choices in the USVI.  Popular concoctions include the Bushwacker (a chocolatey rum frozen cocktail), Cruzan Confusion (Cruzan banana, coconut and mango rum with topical juice), Rum Punch or Pirate Punch (rum and tropical juices), Limin’ de Coconut (rum, lime and coconut), Bay Breeze (rum, pineapple and cranberry juice).

Must See & Do

  • Visit the capital of the USVI, Charlotte Amalie on St Thomas. Here you can shop, visit Blackbeard’s castle, or take the cable car to view the surrounding islands.  Don’t miss Meagan’s bay on St Thomas; its famous beach and park with blue water and white sands and stunning views makes it one of the most photogenic spots in the US.
  • On St. John, over half the land is considered part of the Virgin Islands National Park. Here you can stop at the beautiful protected bay of Cruz Bay or head to Watermelon Cay.  Watermelon Cay in Leinster Bay offers some of the best snorkeling in St. John offers fabulous snorkeling as well as hiking trails and the Annaberg Sugar Plantation ruins.
  • Coral Bay is the perfect spot to watch the sunrise. Head ashore and check out the charming time.  Here you can restock on groceries, enjoy the inland restaurants, hike, or enjoy a full moon party.  A fun place to visit is Lime Out, a floating taco restaurant near Coral Bay.
  • Christmas Cove. ( St. James Bay).  A quiet and beautiful place to stay.  Stunning snorkeling, perfect sunsets, and Pizza Pi—a yacht based pizza restaurant offering takeaway.
  • Sail to St. Croix and nearby Buck Island. Both are amazing for snorkeling, scuba, and fishing.  Visit the beautiful Cane Bay beach on St Croix or shop the street market in Fredriksted.  Buck Island has an underwater snorkeling trail …a must-do!

Read about the Best USVI Beaches ›

USVI Bareboat Charter Sample Itineraries

Where to go on a U.S. Virgin Islands (USVI) sailing vacation?

Scroll below for sample itineraries or use the map to explore.

Sample Itineraries:

Here above we show a good one-week itinerary.

A 10-day itinerary might include St. Croix. You will need special permission from the charter company to go to St. Croix due to the distance. Zoom out on the map to see St. Croix directly to the south.

USVI Podcast

NauticEd Customer Experience in USVI

Really enjoyed St. Thomas and St. John. Great food and great scenery. Weather was great and everyone had a great time visiting the various coves/taco bars/restaurants. etc.

Yall are great! Def using you guys in the future when we do another charter. Thanks again!

Chris H. and Family

  • Caneel Bay

  • Caneel Bay

  • Lovango Cay

  • Francis Bay

  • Maho Bay

  • Mooring Buoys - maintained

  • Double Tying to a Mooring Buoy

  • Turtle Bay

  • Leinster Bay hike


NauticEd are expert USVI yacht charter agents. We don’t charge you a fee and can more than likely save you money on all your sailing vacations. We search the world’s databases for over 8,000 yachts in 55 destinations. We give expert advice on where and when to go – likely, we’ve been there. Make an inquiry and book your sailing vacations through NauticEd Sailing Vacations.

U.S. Virgin Islands USVI Yacht Charter and Sailing Vacations

Additional Notes

Sailing Skill Levels

Local Knowledge + Education: as Sailing Vacation Experts, NauticEd’s team has chartered and sailed in almost all these locations – providing you with the “local knowledge” you need when planning a sailing vacation. And, as the leader in sailing education, NauticEd assigns different skill levels based on the knowledge-theory and practical/experience needed for chartering in different sailing locations.

Recommended Knowledge-Theory Courses for chartering: Bareboat Charter Master Bundle (six bareboat and near coastal courses), Catamaran Sailing Confidence (if chartering a Cat), Yacht Charter Crew Course (for your crew).

Skill Levels notably emphasize the overall practical experience and competency that is required to sail in certain areas. Of course, the “devil’s in the details” on specifics, and we recommend you contact us when planning a sailing vacation. We’ll save you money on your vacation – which is great – but being prepared to have safe fun experiences that will last a lifetime is priceless!

• Intermediate = Near Coastal <5nm within sight of land, some navigation hazards (always be aware), and generally mild weather conditions. Good seapersonship (i.e., “seamanship”) skills, knowledge, and experience apply.

• Intermediate +Plus = Near Coastal <15nm, within sight of land in clear atmospheric conditions, moderate navigation hazards, and/or challenging weather. Good seapersonship skills, knowledge, and experience apply.

• Advanced = Near Coastal <20nm, within sight of land in clear atmospheric conditions, many navigation hazards, and/or potentially difficult weather. Expert seapersonship skills, knowledge, and experience apply.

*Atmospheric conditions: from the deck of a sailboat, your “visible horizon” is about 12nm on a clear day (considering typical freeboard + your height). Visibility is decreased by haze, fog, rain, smoke, and similar atmospheric considerations. Navigating by line of sight is obviously greater if your destination has features such as mountains, lighthouses, tall buildings, etc…

*Navigational hazards may include features such as rocks, shoals, rough inlets or anchorages, challenging tides and currents, lee shores, commercial traffic, etc…

*Weather: examples of challenging or difficult weather include thunder/lightning storms, areas prone to high winds, or even seasonal risks such as excessive heat.


My vision for NauticEd is to provide the highest quality sailing and boating education available - and deliver competence wherever sailors live and go.
Grant Headifen
Last updated on October 9th, 2023