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US Virgin Islands Itinerary

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

Learn to Sail Vacation Cruising Guide and Itinerary in the US Virgin Islands (USVI)

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.

U.S. Virgin Islands Itinerary for a week-long Sailing Vacation

We sail around the three main islands of the US Virgin Islands called St. Thomas, St. John, and St. Croix while learning how to operate the catamaran on a crew-centered adaptable itinerary. We want to schedule time for sailing skills, island hopping, snorkeling and beach time. We will always discuss and consider wind and weather factors.

Day 1: Arrive to the Marina on St Thomas after 5 PM, Sleep aboard on the dock.

Day 2: Maho Bay, St John (Virgin Island National Park) or Leinster Bay, St John (Virgin Island National Park)

Day 3: Coral Bay, St John 

Day 4: Lameshur Bay, St John (Virgin Island National Park)

Day 5: Cruz Bay, St John

Day 6: Christmas Cove, Little St. James 

Day 7: Return to the dock Marina on St Thomas. Plan to take your taxi or flight after 10:00 AM 

Please Note. This itinerary is meant to serve as an example of what a week-long sailing journey aboard a Learn to Sail Vacation on a USVI Yacht Charter, exploring the breathtaking US Virgin Islands, may entail. However, it is important to note that the captain may adjust the schedule to ensure optimal sailing conditions and the best possible experience for guests.

ST THOMAS, US VIRGIN ISLANDS

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.

BAYS WE VISIT:

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

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.

BAYS WE 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, much quieter island.

BAYS WE VISIT:

✔️ Christiansted

✔️ Buck Island Reef National Park

✔️ Cane Bay

✔️ St Croix yacht club at Teague bay

U.S. Virgin Island Yacht Charters

Lagoon 46: 2023-2024Lagoon 46 2024

We love teaching on this yacht. It is easy to bareboat charter and makes for a great group vacation yacht. Lagoon catamaran is a brand of twin-hulled boats that are designed and produced in Bordeaux, France. It sails well upwind and is a smooth sailing ride. It is 46 ft long and 26ft wide which makes it very stable and easy to single hand. The bridge deck provides a wide space to sail from with a comfortable high platform 360 degree view with a large screen Navionics plotter. There are 4 cabins, and each offers a comfortable queen size bed with linens, pillows, towels and blankets and private head with a toilet and shower. The air conditioning keeps you cool at night and the sea breeze keeps you cool in the day.

Aft outdoor saloon is spacious with plenty of seating with an open window area to the indoor salon. The galley has a propane stove with oven, sink, and all the cooking utensils you need to cook. There are two refrigerators and a freezer. The outdoor salon includes a BBQ and an additional beverage refrigerator.

The generator is located on the bow in a noise canceling compartment which keeps the sound to a minimum. We drink freshly made Reverse osmosis water throughout the trip to keep ourselves hydrated.

a small boat in a large body of water

Elba 45

Fountaine Pajot Elba 45: 2022-2024

This yacht is brilliant. The high fly bridge has a lounging couch with spectacular views and ocean breezes. It is attractive and well performing. This is one of our favorites because it is so spacious. Fountaine Pajot Yachts are made in La Rochelle, France.

It sails well upwind and is a smooth sailing ride. It is 46 ft long and 24.7ft wide which makes it very stable and easy to single hand. The bridge deck provides a wide space to sail from with a comfortable high platform 360-degree view with a large screen Navionics plotter. There are 4 cabins, and each offers a comfortable queen size bed with linens, pillows, towels and blankets and private head with a toilet and shower. The air conditioning keeps you cool at night and the sea breeze keeps you cool in the day.

Aft outdoor saloon is spacious with plenty of seating with an open window area to the indoor salon. The galley has a propane stove with oven, sink, and all the cooking utensils you need to cook. There are two refrigerators and a freezer. The outdoor salon includes a BBQ and an additional beverage refrigerator.

The generator is located on the bow in a noise canceling compartment which keeps the sound to a minimum. We drink freshly made Reverse osmosis water throughout the trip to keep ourselves hydrated.

Boat under the seaLeopard 44 2012 Solar Classic Course 

Excellent boat for cruising and live aboard lifestyle

The Leopard 44 catamaran combines luxury and performance, perfect for adventurous sailors. Its innovative design maximizes space and comfort, featuring continuous hull side windows, a sleek hardtop, and an inviting upper lounge area. Inside, natural light floods the interior through well-placed windows and a saloon skylight. The L-shaped galley encourages social cooking, while options for three or four cabins, each with private ensuites and designated shower areas, ensure comfort on any voyage. The Leopard 44 is designed to exceed modern sailing expectations. The owner has installed over 250k of replacements and upgrades to this 44 Leopard (refit in 2021). Including new mainsail, solar panels, RO water filter, electric dinghy, and a huge inverter that can run AC at night without the generator! The 44 leopard is a clean well maintained vessel with comfortable seating.  You will not be disappointed! 

a sign for a photoInternational Bareboat Cruising Certification with American Sailing Certifications in a learn to sail week-long

  • Series 1 ~ ASA courses (take them all together on a weeklong liveaboard course!):
    • ASA 101: Keelboat Sailing
    • ASA 103: Coastal Cruising
    • ASA 104: Bareboat Cruising
    • ASA 114: Cruising Catamaran
  • Series 2 ~ Advanced ASA courses (take them all together on a weeklong liveaboard course!):
    • *Prerequisite 104
    • ASA 106: Advanced Coastal Cruising
    • ASA 114: Cruising Catamaran
    • ASA 118: Docking Endorsement

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

 

You! Solo Sailors, Couples, Friends and Families make our job rewarding and fun.

Solo Sailors who want to join a group course with like-minded sailors and learn to sail.

Cruising Couples who want to learn to work together while learning to sail with a group course.

Couples, Friends and Families who want the entire vessel on a private learn to sail vacation.

Getting to the Virgin Islands is easy.

Go Sail Travel tips

Find out about VI Travel Tips to Make Your Life Easier when traveling to the Virgin Islands

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.

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

I completed ASA 101-114 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 101, 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 five 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 was 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 take the tests ahead of time 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. My only critic would be to have a boat with better beds and linens. That aspect was very bare bones.

– Dee W | TripAdvisor
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"Outstanding"

We just completed an amazing sailing course with Go Sail Virgin Islands completing ASA 101, 103, 104 &114. Captain Trevor 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