BVI's Family Sailing Fleet
What began as a young couple's dream in the mid-1980s is now a 45-yacht, family-run charter and yacht management company that remains personal and locally rooted. Conch Charters' flexibility, owner-friendly management and reputation for warm service have made it a long-standing contributor to the BVI tourism economy.
Conch Charters began as the dream of Brian Gandey and Cindy Chestnut in the mid-1980s and has grown into a 45-yacht fleet while retaining a close, family-run feel. The company’s story — from selling everything to buy two starter boats to greeting repeat guests by name today — reflects both the entrepreneurial spirit and community connections that define much of the BVI’s tourism sector.
Brian first fell for the BVI as an 18-year-old backpacker. Years later, while escaping the Canadian winter with Cindy, a chance conversation at the Castle Maria Hotel helped set the business in motion. Local encouragement, including a casual meeting with the then-governor and support from the Chief Minister, sped the couple’s application for a trade licence.
They bought an Allmand 31 and an O’Day 37 and launched their first charter, a trip that became folklore when six New York firemen, with VHF radio problems, used a beach-bar landline to tease Brian about the boat’s name after setting off on Pearl Harbour Day. That personal touch — humour, warmth and responsiveness — remains central to Conch Charters.
Cindy left a senior banking role to join the operation full-time while Brian applied his hotel management background to run day-to-day operations. The company weathered industry shifts by acquiring boats when competitors folded and by growing a diverse fleet of monohulls and catamarans sourced from both pre-owned charters and new European models.
Conch Charters’ competitive edge is flexibility: guests can start charters any day of the week where available, avoiding the rigidity of Saturday-to-Saturday schedules. Specials include nine nights for the price of seven in high season, ten nights for the price of seven in low season, multi-week and multi-boat discounts, returning-client offers and flash promotions.
They also provide skippered or chef options and act as brokers for fully crewed yachts outside their fleet. Owners benefit from a yacht management programme with no blackout restrictions, allowing personal use at short notice — a rare feature among larger operators. To support quick turnarounds and high maintenance standards, Conch has expanded its team of mechanics and technicians.
Still family-run, the company now involves a second generation through partners and relatives, while many clients have become multi-generational charterers themselves. For BVI residents, Conch Charters represents a homegrown tourism success that supports local employment, sustains visitor loyalty and showcases the islands’ enduring appeal.
The original profile appeared in VIRGIN ISLANDS Magazine.
Primary source: VI Property&Yacht