Skip to primary navigation Skip to content Skip to footer

US Virgin Islands Itinerary

Highlights: Virgin Island National Park, Buck Island Marine Reserve, Megens Bay, St Thomas, St Croix, and Cruz Bay, St John.

Go Sail Virgin Islands, Cruising Guide to ASA Sailing Courses in the U.S. Virgin Islands.

USVI SailingSailing conditions are Champagne every day! Sail, Sail, Sail in this is a year-round sailing destination with fresh breezes and calm seas. The active learn-to-sail experience keeps people coming back to the tropical conditions with daytime temperatures of 80 – 85°F (27°C) and 15 to 20 knots easterly winds year-round.  Serene inviting bays have inviting crystal-clear turquoise waters near 82°F. (27°C)

Sailors find it to be a perfect cruising area! It’s safe for families and groups of friends, the conditions are predictable, and the beaches are beautiful. There are three main islands called St. Thomas, St. John, and St. Croix. The bays are known for great snorkeling, fun beach bars, and very accessible, calm anchorages. These islands will blow you away for their diversity as well as pristine underwater world with turtles, sting rays, tropical fish, and coral.

This area has been intertwined with Sailing since the arrival of Columbus in 1493, on his second voyage to the New World. He first landed on St. Croix, an island with a freshwater source. The area islands were born with piracy with European and Spanish settlements become a treacherous place to be. By 1917, the Danes were happy to sell their Virgin Islands to the United States who were eager to have a military outpost for $25 million.


The three main islands St. Thomas, St. John, and St. Croix.


St. Thomas is the main hub of the virgin islands. Home of the St Thomas Cyril E. King International Airport (STT) is where you fly in and out of.


✔️ Charlotte Amalie
✔️ Water Island
✔️ Red Hook
✔️ Christmas Cove, Little St. James Island
✔️ Magens Bay
✔️ Buck Island Marine Preserve


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


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


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


✔️ Christiansted

✔️ Buck Island Reef National Park

✔️ Cane Bay

✔️ St Croix yacht club at Teague bay

Getting to the Virgin Islands is easy.

Go Sail Travel tips


Cyril E. King International Airport (STT) is an easy airport to fly into. This airport is serviced by American, Jetblue, United, Spirit, and Delta. You won’t need your passport to travel to the U.S. Virgin Islands as a U.S. citizen.

  1. No passport required USVI is a Territory of the US
  2. You can get to the boat in less than 1 hour from the airport.
  3. It is much less crowded than nearby islands.

Learn more here. Top Travel tips for traveling to the Virgin Islands

American Sailing International Bareboat Certifications on Learn to Sail Vacations

Excellent Reviews of our Virgin Island American Sailing Courses and Vacations! ⭐⭐⭐⭐⭐



I had an amazing week of sailing and exploring the US Virgin Islands with Go Sail Virgin Islands and Captain Genevieve Evans. First and foremost, Captain G is a wonderful and knowledgeable teacher. She thoroughly explained concepts and maneuvers, demonstrating them as well, and then gave us the opportunity to practice throughout the week. She was extremely patient and helped to build my confidence behind the helm tremendously. Additionally, she knows the best spots on each island and made the trip not just about learning and growing as a sailor, but also enjoying time away. I will never forget this trip- if you have the opportunity to learn with Go Sail and Captain G, you won’t regret it. Thanks again Captain G for an absolutely perfect adventure!

– Sara V | Google
logo, icon, company name

The whole experience did not disappoint

The whole experience did not disappoint—truly a wonderful life memory. The boat was in nice condition and served us well. Captain J T Quinn was absolutely fantastic at teaching us and was so easy to have around. And doubled as a tour guide. We would recommend it to anyone.

– Matt B | Google

Sail VI premium ASA course!

We took the week live aboard sailing lessons for ASA 101,103,104,114 and it was awesome. Sailed around USVI. Our instructor JT was thorough and a pleasure to be with. Thank you for an awesome experience. Already booked our next sailing excursion as a skipper!

– Stephanie B | Trip Advisor


Just spent a week with Capt. Genevieve navigating around the USVI, a thoroughly enjoyable learning experience. Her teaching style a perfect mix of coaching and hands-on, building my ability and confidence with each passing day. Completed ASA Sailing Certifications 101 103 104 114, such that I’ll look forward to returning next season to charter a boat with my family. We also visited their favorite moorages, snorkeling sites, and places to go ashore for food and fun. Even better, they both provide great hospitality with tasty food, a comfortable boat, and good company.

– Larry C | Google
logo, icon


My family and I sailed with Captain JT Quinn, who provided excellent instruction and is just an all-around good guy. While I went through the hands-on ASA instructions for 101, 103, 104, and 114, my family was able to enjoy cruising around the USVI and BVI. Every afternoon, we would anchor or moor in a bay where we would swim, snorkel, paddle board, and relax for the evening. I was nervous after reading the 4 books and preparing but JT made it really comfortable and easy to learn. He's very knowledgeable and answered every question I had. We shared stories and a lot of laughs. He and Go Sail VI aren't just teaching people to sail, they are cultivating a community of sailors. That's what it's all about in the end — knowing how to

– Tom G. | Google
logo, icon, company name


I can’t believe how much we learned while sailing with Captain G and Trevon! They explained everything so well and really helped us understand the art of sailing. We now feel confident to bareboat our own charter soon! This was definitely the way to earn our sailing experience.

– Ashley S | Trip Advisor
logo, icon

Phenomenal Experience!

Our week-long catamaran sailing instruction for ASA 106, 114 and 118 certifications was phenomenal! We chartered a week-long monohull instruction for our ASA 101, 103 and 104 certifications in Florida a year prior. There was no comparison with our Go Sail Virgin Islands live aboard experience far exceeding our expectations. Sweet & Salty, the 44' cat, was spacious, clean and well provisioned. Trevon is an exceptional instructor. He has a depth of knowledge and experience, was patient and tailored his coaching to our individual needs. Thanks for the learnings, experience and memories! Shirley, Eric and Jeff

– Shirley E. | Trip Advisor