Eight Friends in the BVI
Four couples in their mid-fifties, wanted a BVI celebration charter that balanced serious sailing with serious relaxation.
Updated September 15, 2025
Meet Jennifer
The Client
Four couples in their mid-fifties, successful professionals with ASA certifications but limited recent sailing time, wanted a celebration charter in March that balanced serious sailing with serious relaxation. All experienced sailors individually, but they'd never chartered together as a group.
They wanted a vacation to let their hair down while doing some sailing. The gold standard of bareboat sailing. Steady trade winds, line-of-sight navigation, and more perfect anchorages than you can visit in a week. They had a budget of $6,000 per couple.
The British Virgin Islands beckoned as the obvious choice, but coordinating eight busy schedules, managing group dynamics, and ensuring everyone's sailing expectations aligned required expert orchestration.
Anchor broker Kasia leveraged her BVI connections to secure the Lagoon 46 catamaran Rope the Wind from Horizon Yacht Charters. Spacious enough for eight adults, stable enough for rusty sailing skills, and equipped for both sailing and sundowners.
At $21,700 for ten days, it represented excellent value for luxury catamaran chartering in the world's premier bareboat destination.
The lead organiser of the trip, Jennifer, takes up the story below.
Tortola to Norman Island
"The first challenge wasn't navigation or sail trim, it was democracy. Eight Type-A personalities, all accustomed to making decisions, suddenly needing to agree on everything from anchorages to breakfast times. Kasia suggested we assign roles early to make things smoother.
We elected Tom as sailing captain, Susan as chief provisioner, and established the sacred rule: whoever cooks doesn't clean up. Democracy in action!
Rope the Wind impressed immediately. The Lagoon 46's spacious layout meant eight people never felt crowded, while the twin engines and shallow draft promised confident anchoring. The afternoon sail to The Bight on Norman Island reminded us why we'd all fallen in love with sailing decades ago.
Norman Island, allegedly Stevenson's inspiration for Treasure Island, provided the perfect first-night adventure. Snorkeling through underwater grottos while tropical fish ignored our intrusions, then sundowners on the aft deck as the Caribbean sun painted the sky Aperol Spritz orange. This was why we'd come here!
The less said about the evening's fun at Willy T's, the better!
Peter island & Virgin Gorda
The passage to Virgin Gorda's Spanish Town tested skills we hadn't used since college sailing programs. Fifteen knots from the southeast, building seas, and eight people rediscovering their sailing legs.
The Lagoon's forgiving handling came in handy, and our sailing muscle memory returned faster than we expected. Within hours, we'd mastered the catamaran's quirks, and remembered what drew us all to sailing in the first place.
Virgin Gorda's Baths delivered the Instagram moments we were after.
Giant granite boulders creating natural pools, underwater passages perfect for snorkeling, and enough scenic beauty to justify the inevitable social media bombardment.
But the real magic happened that evening at Cooper Island Beach Club. Eight old friends sharing sailing stories, comparing notes on kids' colleges, and planning adventures that felt possible again.
Jost Van Dyke and the Soggy Dollar
Jost Van Dyke is BVI sailing culture in a nutshell.
It was, as expected, a bit of a scramble to find a mooring buoy, but we decided to anchor on sand in a quieter part of the bay.
The famous Soggy Dollar Bar (you swim ashore and pay with ‘soggy’ dollars) invented the Painkiller cocktail. Rum, pineapple, orange, and coconut cream in proportions that explain why so many sailing blogs sound slightly drunk.
The evening at Foxy's Tamarind Bar perfectly captured our group dynamic. Four couples rediscovering friendship, sharing spontaneous adventures (via careful planning!).
The impromptu steel drum fun (fueled by several Painkillers) will forever remain classified information...
Anegada
Anegada was a 15-mile crossing from Virgin Gorda. The island is very low-lying, just 28 feet above sea level, so it disappears completely below the horizon, requiring proper navigation to find!
But Kasia's detailed notes proved invaluable: 'Follow the marked channel, ignore your depth sounder's panic, and trust yourselves.'
The reward was worth every anxious moment - an island so flat it felt like sailing into a Caribbean mirage, surrounded by coral reefs that created natural swimming pools for the flocks of local flamingoes.
Our final dinner was sensational - fresh lobster grilled over a driftwood fire, served with local vegetables and enough rum punch to forget our woes.
Tortola
The final morning's sail back to Road Town provided perfect conditions for reflection.
Light trade winds, calm seas, and the satisfaction of having executed a complex group charter without major drama or navigation errors.
We were proud of ourselves - four couples who'd navigated not just BVI waters but group dynamics, weather challenges, and the delicate balance between adventure and relaxation.
Rope the Wind had proved the ideal platform for our celebration jaunt along memory lane - stable, comfortable and plenty of lounging space for soaking up the rays.
What a fabulous vacation - there's already talk of a repeat in 5 years, or maybe sooner?
Total per couple: roughly $3,750—less than many land-based luxury vacations (like a golfing holiday), with considerably more adventure and bonding opportunities
Full breakdown
The Costs
Yacht Charter Fee - $21,700
Damage Waiver - $700
Cruising Permit - $320
VISAR (Search & Rescue) - $40
Fuel - $250
Mooring Fees (3 nights) - $165
Total: $23,175
Need some help?
If you are unsure about charter or boat selection, contact us at Anchor to help you decide.
We only choose boats that are in excellent condition, and we are here to help you every step of the way and to make sure the whole process is as easy as possible.