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Embark on an unforgettable maritime journey in the stunning Virgin Islands with our premier sailing school, private charter, and bareboat charter services. Whether you're a beginner eager to learn the art of sailing or an experienced sailor seeking to explore these azure waters, our expert instructors offer comprehensive lessons tailored to your skill level. Set sail aboard our well-equipped charters, guided by experienced captains who'll navigate you to hidden coves, vibrant coral reefs, and pristine beaches. For those with a knack for adventure, our top-notch bareboat sailboat charters provide the freedom to create your own nautical odyssey. Discover the magic of the Virgin Islands from a sailor's perspective – where every gust of wind becomes a new horizon, and every wave carries the promise of an extraordinary journey.

Virgin Islands Winter Sailing

Captained Charters

 Let our experienced captains take care of the sailing and navigation! Whether you're seeking a romantic getaway, a family adventure, or a friends retreat, our captained sailboat charter promises an unforgettable and carefree escape into the tranquil beauty of the Caribbean.

Starting at $9,599.00

ASA Certification Courses

Attain your American Sailing certifications while sailing the unbelievable waters of the Virgin Islands. We offer single course weeks and combination course weeks where you can achieve two ASA certifications in the same week! Feel free to bring along a significant other or friend to share your cabin for a deeply discounted rate!

Starting at $3,599.00 per person

Bareboat Charters

Exclusive to SailTime Boston Members and qualified First Reef Sailing graduates, sailors can bareboat charter our 2022 Beneteau Oceanis 40.1, "SV Serenity" and take command of their own vacation! The potential sailing area includes US, Spanish and British Virgin Islands and the incredible anchorages therein.

Starting at $6,999.00

The Boat

2022 Beneteau Oceanis 40.1 

Beneteau's latest cruising model that combines a stiff rig and high performance with maximum interior volume and luxury

Beneteau 40.1 Exterior.jpg

Upcoming Courses and Charters

Our Marina

The trip will begin and end at our dock at American Yacht Harbor, in Red Hook on St. Thomas. 


American Yacht Harbor is a full service marina with on-shore showers and bathrooms, Wi-Fi, and 24/7 Security staff. It is located in the center of Red Hook, the easternmost town on St. Thomas, making it the logical departure point for charters in the USVI and the British Virgin Islands.


Red Hook itself boasts plenty of dining and shopping opportunities within a 5 minute walk of the marina. There is a gourmet supermarket across the street from the marina as well as a full service laundromat.



American Yacht Harbor

6100 Red Hook Quarters #2

St. Thomas, USVI 00802

  • What is First Reef Sailing School?
    First Reef Sailing School is an award-winning and reputable sailing school/ charter company based in St. Thomas, US Virgin Islands, offering comprehensive sailing lessons and captained charters and over 15 years of combined experience leading trips, courses, and vacations in the Virgin Islands.
  • What is a 7-Day Course like with First Reef Sailing School?
    Our 7-day courses and trips provide an immersive experience where you'll learn the fundamentals of sailing, navigation, and boat handling over the course of a week combined with time for other fun activities like hiking, swimming, snorkeling, and even scuba diving.
  • What Does a Course Include or Involve?
    The sailing lesson includes hands-on instruction, theory lessons, practical sailing experience, navigation skills, safety procedures, and more.
  • Who Can Sign Up?
    Our sailing courses are suitable for beginners and those with some sailing experience who want to enhance their skills. Participants must be aware of course prerequisites which typically involve being certified to the previous ASA level.
  • What is a Captained Charter?
    A captained charter offers the opportunity to enjoy a sailing vacation with an experienced captain at the helm, taking care of navigation, safety, and providing local insights. Our charters can be educational where we work on targeted sailing skills, but still allow you time to relax without worrying about taking a course exam. We handle all aspects of sailing and manage the itinerary and activities for you!
  • What Types of Boats Are Available for Charter?
    First Reef Sailing School offers a variety of sailboats and catamarans for charter, depending on availability and group size.
  • Is Wi-Fi Available on the Boat?
    Wi-Fi availability can vary but most places in the VI has good cell connectivity. Inquire with your cell provider for more information.
  • Do I Need Prior Sailing Experience?
    No prior sailing experience is required for a captained charter, but some sailing experience may be needed for our ASA certification courses.
  • Will the week be hands-on?
    Yes, all trips are designed to be hands-on, allowing you to practice sailing skills under the guidance of our experienced instructors.
  • What Should I Bring for the Sailing Lesson or Charter?
    We will provide you an extensive packing list upon signing up for a trip with us.
  • What Is Included in the Charter Package?
    All trips, sailing courses, and captained charters are all-inclusive. This includes breakfast, lunch, and dinners aboard, snacks, non-alcoholic beverages, as well as mooring fees, fuel, garbage removal, and ice. Guests must cover flights, land transportation to our location, meals ashore, and alcoholic beverages. Those interested in the BVI will cover the cost of entry into the country from the USVI.
  • Can I Bring Children on the Charter?
    Of course! Family-friendly charters are available.
  • Is Safety Equipment Provided?
    Yes, safety equipment such as life jackets and other necessary gear are already aboard.
  • Can I Get Certified After the Sailing Lesson?
    Yes! All ASA courses include the cost of the ASA exam and subsequent certification.
  • What is the Booking Process?
    To reserve a spot on a Caribbean course, a 50% deposit is due upon booking. The remaining balance is due 6 weeks before the course start date at which point the course fee is NON-REFUNDABLE. We highly recommend that you purchase trip insurance through a third party so that you are covered!
  • What is the Cancellation Policy?
    In order to receive a full refund (minus a $95.00 processing fee), you must cancel your ASA course registration at least TWENTY ONE DAYS prior to the start of the course.
  • Is Travel Insurance Recommended?
    Travel insurance is HIGHLY recommended to cover unforeseen circumstances that might affect your trip.
  • Can I Extend the Charter Beyond 7 Days?
    Depending on availability, you may be able to extend your captained charter. Let us know if you are interested in a longer trip.
  • What Are Some Local Attractions We Can Visit During the Charter?
    During your charter with First Reef Sailing School, you're in for a treat when it comes to exploring the stunning local attractions and destinations in the US Virgin Islands (USVI) and the British Virgin Islands (BVI). The captain and crew are well-versed in the area's offerings and will be more than happy to guide you to some memorable experiences. Here's a short list of just SOME of the must-visit places and activities: 1. Trunk Bay Beach (St. John, USVI): Kick off your adventure with a visit to the iconic Trunk Bay Beach, renowned for its crystal-clear waters and underwater snorkeling trail. Immerse yourself in the vibrant marine life and capture breathtaking views of the surrounding hills. 2. Hiking to Ram Head Trail (St. John, USVI): Lace up your hiking boots for a rewarding trek along the Ram Head Trail. As you ascend, you'll be treated to panoramic vistas of the Caribbean Sea and the rugged coastline, making it an excellent spot for memorable photos. 3. Dining at Asolare (St. John, USVI): Indulge in a delectable dining experience at Asolare, where culinary artistry meets breathtaking views. This hillside restaurant offers a fusion of Caribbean and Asian flavors, creating a memorable feast for your taste buds. 4. The Baths National Park (Virgin Gorda, BVI): A geological wonder, The Baths beckons with its colossal granite boulders forming scenic pools and grottoes. Embark on an enchanting exploration of this national park and its unique natural formations. 5. White Bay (Jost Van Dyke, BVI): Dive into relaxation at the serene White Bay, known for its powdery white sands and tranquil turquoise waters. Sip on a refreshing cocktail at the famous Soggy Dollar Bar and unwind in paradise. 6. Wreck of the RMS Rhone (Salt Island, BVI): Delve into history with a dive or snorkel at the RMS Rhone shipwreck site. This renowned underwater attraction is a hauntingly beautiful reminder of the past, offering an unparalleled glimpse into maritime heritage. 7. Cane Garden Bay (Tortola, BVI): Feel the rhythm of the Caribbean at Cane Garden Bay, a lively beach lined with swaying palm trees and vibrant local establishments. Enjoy live music, water sports, and a vibrant beach scene. 8. Virgin Islands National Park (St. John, USVI): Immerse yourself in nature at the Virgin Islands National Park, which encompasses pristine beaches, hiking trails, and historical ruins. Explore the Annaberg Sugar Plantation and bask in the beauty of untouched landscapes. Remember, your charter with First Reef Sailing School offers not only the thrill of sailing but also a chance to uncover the hidden gems and treasures of the USVI and BVI. The captain and crew are dedicated to making your journey unforgettable by introducing you to these local attractions and helping you create lasting memories!
  • What is the climate like in the Virgin Islands?
    The Virgin Islands boast a warm tropical climate with consistent temperatures and gentle trade winds. Temperatures reach the mid-80's most days and winds vary between 10 and 20 knots.
  • When is the best time to visit in terms of weather?
    November to April is considered prime visiting months with pleasant temperatures and minimal rain.
  • Is there a rainy season?
    The rainy season occurs from September to November, marked by occasional tropical showers.
  • How warm is the water?
    Water temperatures range from mid-70s to low 80s Fahrenheit (24-29°C), providing a comfortable environment for various activities.
  • How Do I Contact First Reef Sailing School?
    You can reach out to First Reef Sailing School via our website, email, or phone to inquire about booking, details, and any additional questions you may have.

Get in touch to book!

(617) 466 3317

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