JWorld Annapolis 2026 BVI Flotilla

Curious about sailing vacations? Wonder what it takes to do it yourself? Come to the western hemisphere’s greatest cruising grounds, the British Virgin Islands! Over the course of the week, you, your guest, and other sailing enthusiasts will be guided by our experienced Captains around the BVIs. Interested in a more hands-on experience? Gain valuable sea miles under the keel, charter cruising experience, and practical skills under the watchful guidance of our seasoned Captains. 

Week 1: 28 Feb – 7 Mar, 2026

Week 2: 7 Mar – 14 Mar, 2026

Each day we will sail to a new location and spend 3-4 hours under sail or maneuvering under power. We will get plenty of practice docking, mooring, anchoring, maneuvering in tight marinas, navigating narrow channels, and much more. What’s the fun of flying to the BVIs of you don’t spend some time exploring the area, both on land and below the water. We are very experienced and knowledgeable about the offerings of each island and will be sure to guide you to the best of the best:  hikes, snorkeling, free diving, SCUBA, beach bars, and restaurants.

All levels of sailors are welcome to join! Instructional Charters are perfect for people (a) just starting out and taking a first step towards bareboat, (b) bareboat students uncomfortable with their “first charter”, (c) experienced sailors wanting to have fun while brushing up on skills, and (d) really anyone wanting to learn and actively participate while on a sailing vacation. Also, your guests are welcome!

• This is ‘experiential’ training that blends private instruction with a real-world charter and sailing vacation. Simply, this is vacation + instruction + having fun.
• This is not an intensive certification or licensing course! We’re going to work instruction into much of what we do, but our goal is to have fun doing it!
• Your guest (partner, friend, etc…) can participate or just enjoy the ride. We prefer that your guest is an active participant; that’s part of the fun!
• Certification, SLC Licensing, and endorsements may be available. It really depends on your prior experience, coursework, and training – contact Josh to discuss further.

• Week 1 guests will arrive Saturday, 28 February, 2026 and depart Saturday 7 March, 2026.
• Week 2 guests will arrive Saturday, 7 Mach, 2026 and depart Saturday, 14 March, 2026.
• Starting/ending location will be Fort Burt Marina, Road Town, Tortola, British Virgin Islands

Pricing is by the cabin, whether single or dual occupancy (each cabin is big enough for 2 people).

Monohull: “JADA” Beneteau Oceanis 48

• $4,900 per cabin.
• $500 for provisions (based on dual occupancy). Provisions include all the food and water on board (except alcohol).
• Each cabin includes its own head, shower, and A/C.
• Maximum 7 people on board: 6 guests, one captain. Two people per cabin.

Catamarans: “PARROT ICE” and “CHAMPS ELYSEES” both Fountaine Pajot Saona 47s

• $5,500 per cabin.
• $500 for provisions (based on dual occupancy). Provisions include all the food and water on board (except alcohol).
• Each cabin includes its own head, shower, and A/C.
• Maximum 10 people on board: 8 guests, one captain, one first mate. Two people per cabin.

Provisions and Shared Expenses:

• Meals include continental breakfast and light lunches.
• Dinners ashore are the responsibility of the individual, not included in berth or provisions cost.
• All transportation to-from the BVI’s and ashore is the responsibility of the individual.
• Any group water toy rentals, onboard WiFi, or other extras will be agreed upon by crew vote and costs divided evenly per-person.
• Individual extracurricular activities (ex. diving) may incur additional costs. Note – that’s something that we can discuss and plan ahead for!