The British Virgin Islands are one of the best sailing destinations in the world. With dozens of islands all within visual range, restaurants and marinas all over the place, and near constant trade winds–the BVI is a great place to charter a yacht.

In three weeks I’ll be setting sail in a three-boat flotilla in the BVI. This is the first time I’ve been a part of a yacht charter and the excitement has me nearly jumping out of my pants.

Our group is completely comprised of people I’ve met through this website. Our paths have crossed through Chesney tailgates, Castaway Beach Bashes, Key West pub crawls, and friends of friends. All island lovin’ salty-souls setting out on a sailing adventure, Castaways through and through.

Two out of the three boats used a company called Virgin Island Sailing to setup the charter and make the process as simple as possible. Through them we were able to find the right charter company (Horizon Charters), the right boat for our needs and they helped us with all the paper work and provisioning.

Here’s a look at our catamaran. Her name is Maples Cookie, not the name I would’ve chosen for a her, but she’s sexy nonetheless.

Virgin Islands Sailing

Here’s a little information about Virgin Islands Sailing.

If you’re looking for the perfect yacht to charter for your next Caribbean vacation look no further than Virgin Island Sailing. For almost 30 years we have been arranging quality charters with the finest privately owned crewed yachts and the best bareboat companies for vacations throughout the Virgin Islands, Caribbean and around the world.

Virgin Island Sailing Vacations – Virgin Island Sailing, Ltd. from VI Sailing on Vimeo.

No matter your level of boating experience, the size of your party or your destination, we’ll find the best yacht for your specific needs.  But our service doesn’t stop there, we proactively help you plan every detail of your getaway, from supplying a complimentary cruising guide, planning chart, dive and snorkel chart, fish guide & all required paperwork to creating a personalized planning webpage with all the information you could possibly need in preparation for your trip. And should anything go wrong we’ll immediately step in to find a quick resolution.

When you work with Virgin Island Sailing you’re getting the best value the most comprehensive selection of yachts and the most knowledgeable brokers in the industry. We offer unsurpassed customer service and expert advice at no additional cost. We make the process seamless worry free and easy, which is why so many of our clients have chosen Virgin Island Sailing as their reliable yacht charter broker time and time again.

Two of our boats are bareboats, meaning we provide the captain (thank you Captain Mike and Captain Shawn!), meals, provisions (rum), and everything else. Our third boat will have a provided captain and will be the dive boat of the group. She’s a big lady at 60 feet and will have a compressor and all the dive equipment we need.

Virgin Islands Sailing

Chartering a yacht and sailing through the Virgin Islands might is easier than you think. If you split the cost between 8 people or 4 couples (for a boat our size), the cost of a sailing adventure goes way down.

If you don’t know how to sail, don’t worry. They have motor yachts selections as well. If you’re uneasy about sailing a yacht through unfamiliar waters, there’s no need to be. They will send you a Sailing Guide book that will act as your sailing bible. It’s full of channel information, water depth, reef locations, mooring locations, fees and anything else you can think of. I’ve had a blast reading through our Sailing Guide that Virgin Islands Sailing sent me. I almost feel like a captain after reading it!

There’s much more to come as the charter nears and I’ll be posting live updates during the sail.

Until then!


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By |2016-12-31T11:57:58-05:00October 8th, 2014|British Virgin Islands, Sailing / Boating|3 Comments

About the Author:

Just a salty pirate looking to explore and document the wonders of the Caribbean. Professional blogger, rum judge, consultant, marketer, and consumer of blue water beauty.


  1. NancieM October 9, 2014 at 8:56 am

    This sounds so exciting! Can’t wait to see and “hear” all about your adventures! Will you stay strictly in the BVIs or stop in at some of the USVIs?
    Either way, have fun Ryan! 🙂

  2. mm
    RumShopRyan October 9, 2014 at 9:31 pm

    Thanks NancieM! I’m spending one night on St. John before heading over to Tortola to get the boat. Sticking just to the BVI on the sail. Can’t wait to share the adventure with you and everyone else!

  3. NancieM October 10, 2014 at 9:55 am

    Lucky you to find a place for one night! 🙂
    Maybe because it’s low, low season places like Tamarind Inn , St.John Inn, etc. are happy to rent for one night.
    And if you can, please stop in at “X” in Wharfside and let us all know what you think. It’s probably the only bar I haven’t been to yet! 😉
    Thanks Ryan! Enjoy!

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