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US Virgin Islands, Caribbean

A Learn-To-Sail-Vacation

hosted by Anchors Aweigh Sailing School
  • 2025: Jan 26 - Feb 2
  • 2025: Feb 2 - Feb 9
  • 8 Days | 7 Nights
  • 104 / 114 / 116 / 111

The Destination

Learning to sail in the US Virgin Islands offers ideal weather, stunning scenery, and diverse sailing opportunities. There are opportunities for exploration, from discovering hidden coves and secluded beaches to anchoring in remote areas and experiencing the cultural and historical sites.

Five reasons to take your sailing skills to the next level in the US Virgin Islands with Anchors Aweigh Sailing School.

  • Stunning Location: Starting in Benner Bay, St. Thomas, you will hone your sailing skills as we navigate in and around St. Thomas and St. John.
  • Expert Instruction: Captain Chris Cooper has >40 years of sailing experience and >15 years teaching ASA courses in everything from little sloops to giant catamarans.
  • Comprehensive Courses: Upon successful completion, you will be certified to Bareboat your own monohull or catamaran for you, your family, and your friends.
  • Hands-On Experience: Be the Captain; learn from your mistakes (and you will make mistakes!).
  • 5-star Google rating: Join the growing list of Captain Cooper-trained sailors!

CERTIFICATIONS

This learn to sail vacation with Anchors Away Sailing School offers :

¤ ASA 104 | BAREBOAT CRUISING included
¤ ASA 114 | CRUISING CATAMARAN included
¤ ASA 116 | DINGHY & OUTBOARD ENDORSEMENT + $200
¤ ASA 111 | VHF OPERATION + $200

You must have completed ASA 101 , Keelboat Sailing 1 and ASA 103, Coastal Cruising. Plus you need to have at least 80 hours of sailing experience.

SAMPLE ITINERARY

A typical day on our learn-to-sail vacation looks like this.

  • Morning classroom session with knots, engine systems, sailing theory, navigation, weather, etc.
  • Underway by 10 am.
  • Sailing during the day includes tacking, jibing, reefing, heaving-to, crew overboard, etc.
  • When available, we will anchor/moor during the day at one of the incredibly beautiful snorkeling sites.
  • Pick up a mooring or anchor around 5 pm.
  • Cocktails ashore or on the boat.
  • Dinner either on the boat or ashore around sunset.
Day 1
Benner Bay, St. Thomas, USVI
Day 2
Francis Bay, St. John, USVI
Day 3
Coral Bay, St. John, USVI
Day 4
Christmas Cove, St. Thomas, USVI
Day 5
Megan’s Bay, St. Thomas, USVI
Day 6
Benner Bay, St. Thomas, USVI
Day 7
DISEMBARK

Please Note. The actual itinerary is subject to change due to weather conditions or circumstances beyond our control.

AVAILABLE BOATS
  • Fontaine Pajot Astréa 42 - Catamaran with 4 double cabins + 4 bathroomsThe Fontaine Pajot Astréa 42 is a popular charter boat due to its spacious and comfortable design, featuring ample living space, multiple cabins, and large outdoor areas for relaxation. Its stable and smooth sailing capabilities make it ideal for both novice and experienced sailors. The boat is equipped with modern amenities, including a well-appointed kitchen and advanced navigation systems.
TESTIMONIALS
I can’t say enough positive things about Chris Cooper, and anchors away sailing school… From the professionalism and experience to the friendliness and camaraderie this school gets high marks on all points. I went from knowing very little about sailomg to owning my own boat, and feeling quite confident on it in the last two years in large part thanks to this school.
Tom G.
Chris Cooper at Anchors Aweigh Sailing School is a consummate professional mariner and brings tremendous skill, knowledge and history to every teaching event. I’m a life long sailor and I learn more each time I attend his school
John B.

Wonderful teacher, top class instruction. Chris has an outstanding program and a dedication to training his sailors. You will find the information is easily taken on in the fashion of immersive learning. He uses the language of sail as he brings you along, questions always addressed clearly and patiently. This is your best opportunity to learn the joy of sail. Take yourself to sailing school and find your bliss. I know I will be continuing with further training. Thanks Chris.

Jay P.

Look no further! I just completed the ASA 101 class with Captain Chris. He was very knowledgeable and patient. He made every part of learning enjoyable. Beyond learning about sailing we had a lot of laughs and a great time. I drove an hour everyday to attend this class and it was worth it. I’ll be singing up for all future classes with Anchors Aweigh Sailing School.

Theresa B.

I couldn’t have had a better experience sailing for the first time. Captain Chris provided a safe, respectful, welcoming, and inclusive environment. I attended ASA 101. For those of you wanting to get started, consider this school. Captain Chris is amazing and provides you with feedback on how to get more comfortable with sailing. I’m looking forward to signing up for more sailing hours through this school.

Maralis M.
PHOTOS

HOW TO BOOK

  • Learn-To-Sail Week 1Jan 26 - Feb 2, 2025
  • Learn-To-Sail Week 2Feb 2 - Feb 9, 2025
  • $3,200 USD per personBased on double occupancy

INCLUDES

  • Accommodations For 8 Days / 7 NightsOnboard a Fontaine Pajot Astréa 42 Catamaran
  • Private Stateroom with Full Size Bed & Ensuite HeadPricing is based on double occupancy
  • 104 /114 ASA CertificationsOther certifications available for additional cost.
  • All tips & National Park FeesNo need to tip the “optional” 15-20% found at most other sailing schools; that is a $500 per person savings!!

DOES NOT INCLUDE

  • Airfare or taxis
  • Provisioning (~$250 per person)
  • Alcohol
  • Dining ashore
  • Books / Study material

    Please complete the form below if you have questions or would like to make a reservation.

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