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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!

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. 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! 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 in Cruz Bay is considered the best location to admire the sea turtles and rays who feed on nearby sea grass.

Day 6: Christmas Cove, Little 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. 

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, Little 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 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

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We offer an International Bareboat Cruising Certification with American Sailing Certifications ASA 101/103/104/114 or 106/114 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.

  1. Encourage active learning
  2. Give and ask for prompt feedback
  3. Emphasize hands-on sailing skills
  4. Communicate with honesty and clarity
  5. Respect diverse talents and ways of learning
  6. Encourage questions and growth mindset
  7. 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

Solo sailors open to joining a group of like-minded adventurers learning to sail

Cruising couples interested in meeting other sailors and strengthening their own connection at sea while learning to sail

Families, friends, and couples looking to charter an entire vessel for private sailing lessons

Go Sail Virgin Islands’ 5-star reviews on USVI and BVI Yacht Charters say it all ⭐⭐⭐⭐⭐

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"An eyeopener into life on a sailboat"

Go Sail Virgin Islands provided, my daughter and me, the best possible sailing, learning, and entertaining island and water experience. We achieved our goal of learning and getting certified to charter a bare boat in the most realistic and satisfying way. Captain Genevieve chartered for the ASA classes the appropriate boat for our experiences and desires. Captain Trevon, as our instructor and Captain, quietly assumed responsibility for the wellbeing of his crew and ship. At all times he checked on our actions, and made sure we were proceeding according to the rules and spirit of seamanship. First Mate Stephanie provided us with healthy, tasteful meals, great pictures and videos, and a reassuring graceful presence. The trip was organized as a sail around the US Virgin Islands, as a captain and crew would do in a sailing, exploration, and vacation setting. The one week trip could be replicated as a two weeks’ vacation in USVI, just by expanding the times spent in various places and adding more entertainment and recreation activities. For the aspiring Captains this is, in my opinion, the best first step to take in order to learn, experience, and practice chartering and coastal sailing a blue water vessel. Go Sail Virgin Islands has provided a professional, reasonable priced, and meaningful experience, enabling us to achieve our goals. I would highly and sincerely recommend Go sail Virgin Islands to all aspiring sailors of any level of experience for its classes and trips. Captain Genevieve is one of the best persons to guide and help anyone in the sailing world. It is an honor and a privilege to work with her anytime, anywhere.

– Edi S | Google
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"Learned throughout the day"

It felt like a lot of growth happening in just a few days and each day felt pleasantly long but not overdone and there was something to be learned throughout the day.

– Marc G | Google
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"Allowed us to learn how to sail and develop confidence as sailors."

We had a great experience with Captain Genevieve at Go Sail Virgin Islands. Captain Genevieve kept us up to date and provided alot of good advise preparing and planning for the charter and the ASA training. She took all of the guess work and uncertainties away which made for a great sailing experience. We will definitely use Captain Genevieve for our future ASA classes and future bareboat charters. My wife and I cannot say enough good things about the ASA Sailing Instructor Captain Jalil Jacallen. His instruction was top notch. He was organized and he explained everything clearly so we felt very comfortable during the hands on sailing of the 44 Leopard. His knowledge of sailing is quite impressive. He answered all of our questions and provided plenty of time to practice. He is very patient and calm allowing us to learn how to sail and develop confidence as sailors.

– Mark M | Google
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"A unique experience"

It is a unique experience going from reading your manual, practicing the skills and then wrapping up the afternoon swimming with sea turtles. We took our student level in 2015 and then in 2021 we came back for our instructor course.

– Matt F | Google
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"I recommend Go Sail Virgin Islands without hesitation!"

I completed ASA 103 -114 with Captain Jalil and the only thing that surpassed his patience and passion for sailing was his expertise! A great week building and refining skills in a safe but challenging environment. I recommend Go Sail Virgin Islands without hesitation!

– Michael S | Google
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"A thoroughly enjoyable time learning to sail"

My wife and I had a thoroughly enjoyable time learning to sail with Go Sail Virgin Islands. Captain Jalil was awesome! He has a relaxed and comfortable manner, that allowed us to learn the ropes without making us feel pressured or nervous. He’s also a great cook and makes a delicious painkiller! On top of that, he’s also a wealth of information on the area—knows all the best places for snorkeling and dining. We made this trip with another couple, who are friends of ours, and the instigators of this trip as a steppingstone for future bareboat chartering and possibly owning their own catamaran. Three of us completed the ASA 103, 104, and 114 classes, and the fourth, who already had some previous classes/experience, completed ASA 106 and 118. I feel confident that, after these classes and hands on learning with captain Jalil, we will be able to do it mostly on our own next time. All in all, this was a wonderful vacation and experience, and will open up a whole new set of possibilities for future exploration. Thank you Go Sail VI and Captain Jalil!

– Mike G | Google
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"Great Experience!"

Great experience, boat and instructor/ captain... would thoroughly recommend!

– Rob U | Google
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"Learning from each other"

It was nice to meet new people from other backgrounds in sailing, as well as parts of the country, and learn from them as well since it’s an interactive sport. It was great to have that ability to bounce things off of people and learn from each other.

– Todd F | Google
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"Our instructor JT Quinn was top notch!"

Attended a great 6 day catamaran sailing course in the USVI. Our instructor JT Quinn was top notch! Highly recommend!

– Trish M | Google
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"A super experience."

We took the Cruising couples ASA course through Go Sail Virgin Islands. Our captain/instructor was J.T. He is a wonderful teacher. Great sense of humour. Very patient with everyone. A super experience. Thank you J.T.

– Wendy T | Google
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"Absolutely perfect adventure!"

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
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"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
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"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
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"I highly recommend!"

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
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"Excellent Instruction!'

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
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"So Rewarding!"

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
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"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
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"Exceeded Expectations"

The folks at Go Sail Virgin Islands are wonderful to deal with! From my first inquiry they were very responsive and attentive with clear and timely proactive communications. They provided all the information I needed, including pricing with no hidden fees, in order for me to make an informed decision, and with no pressure. They delivered on every promise and exceeded my expectations. I highly recommend them whether you want to charter or learn, or both. Captain Jalil has years and years of sailing experiences (in addition to a multitude of other interesting life experiences) that have provided him with a wealth knowledge that he humbly shares. He is gentle, kind, clear, wise, practical and is a very good communicator and chef! Without yelling or shaming, he explains and encourages with patience and enthusiasm to help his students understand the “in and outs” and “how’s and why’s of sailing at any level. You will not be disappointed!

– Paul H | TripAdvisor
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"JT is an amazing Captain"

My husband and I had been looking for a company to learn to sail with. He is experienced and I am not. From the start the owner made everything seem so easy and seamless. We initially picked this company because we could study ahead and spend the time on the boat with practical things. Out captain JT was AMAZING and we will be using his again when we charter out next cruise. He allowed up ample hands on time and was very knowledgeable. If you did not comprehend something one way he explained it he was so patient and tried another approach. We adored him. Don't hesitate to use this company.

– Dee W | TripAdvisor
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"Outstanding"

We just completed an amazing sailing course with Go Sail Virgin Islands completing ASA 103, 104 &114. Captain Trevon and his first mate Stephanie were outstanding. Trevon’s knowledge and experience was exceptional as was his teaching ability. Stephanie provide first class food and assistance with procedures during our 7 day course. Also their company and off shore visits was very much appreciated and made for an enjoyable life time experience 👏👏

– Chris F | TripAdvisor