After a relaxed first evening in West End, our adventure began in true island style. We set course for the iconic White Bay and the famous Soggy Dollar Bar — and it couldn’t have been a more perfect day. Crystal-clear turquoise water, soft white sand, and a cocktail in hand… the kind of scene that makes the BVI feel like paradise made real. After lunch we continued on to Diamond Cay, where we had the entire anchorage to ourselves. A quick hop over to Sandy Spit made the moment even more surreal — just us, the tiny island, and a nurse shark cruising through the shallows in search of a snack.

Day 2 — A Windy, Wild, Laugh-Filled Sail North The day started with a breathtaking sunrise, followed by an early breakfast before we pointed the bow north. The wind was pumping, the northerly swell added some extra excitement, and the sail up to Marina Cay was nothing short of exhilarating. Laughter, squeals, and splashes echoed from the bow — until eventually only Katie remained up front as the rest retreated to slightly drier seats.

After a lunch stop at Marina Cay, everyone enjoyed a refreshing snorkel at Diamond Reef before cruising into North Sound. We made our way to Saba Rock for tarpon feeding and a “quick” cocktail that turned into a mini dance party thanks to a live DJ. Back aboard, we wrapped the evening with a beautiful dinner under the stars. Anegada Bound — Brandon’s 40th & an Island Adventure This was the day everyone had been looking forward to: the big sail to Anegada. With 20–24 knots of wind, we were absolutely flying — averaging 9 knots and hitting 10.5 at times. Naturally, this evolved into a friendly race as Captain Pieter pushed to see how many yachts we could pass on the way. Arriving ahead of schedule, the island exploration began.

The Mini Mokes were a huge hit, and what better way to celebrate Brandon’s 40th than a lively bar-hop across Anegada’s quirky beach bars? The evening ended perfectly with the island’s famous lobster dinner at Lobster Trap. Watersports, Seabobs & Exploring the Baths The next morning we set course back to Virgin Gorda and anchored in front of Cocomaya. With plenty of time after lunch, the water toys came out — seabobs, e-foils, snorkeling… Brandon once again stole the show, launching himself out of the water like a very enthusiastic dolphin.

Later we took a scenic dinghy ride to The Baths — mirror-calm conditions and hardly another soul in sight. Captain Pieter guided everyone through the boulders, sharing stories of how these magical formations came to be. Dinner at Cocomaya followed, and of course Pam couldn’t leave without dancing… which soon became lots of dancing. Pam and Katie ended up closing down the night before heading back to the boat. Dive Day, Rum Bar & a Sunset Sail Excitement was high the next morning — it was diving day! We started at Wreck Alley, where within the first five minutes we spotted a graceful reef shark cruising past, followed by large stingrays resting in the sand. While the divers explored below, the rest enjoyed spectacular snorkeling. Next stop: Cooper Island Rum Bar.

A few cocktails, a bit of shopping (Brandon had to buy Cooper merch — how could he not?), and then we enjoyed a stunning sunset sail to Little Harbour on Peter Island. One of the most peaceful anchorages in the BVI, it was the perfect setting to unwind. More Watersports & The Indians The following day was pure fun — seabobs, e-foils, snorkeling with turtles, or relaxing under the bow shade. Nobody really wanted to leave Little Harbour, but adventure called. We headed to The Indians for another dive and world-class snorkeling. After dinner, a quiet night of stargazing was the perfect end to a full, beautiful day. Final Day — Diving, Caves & The Famous Willie T Anchored in Privateer Bay, we kicked off the last full day with a dive at Angel Fish Reef — an incredible site of massive boulders, winding canyons, and a dramatic landscape.

We swam through caves (sadly no hidden treasure this time!) before heading to the legendary Willie T. The big jump from the top deck was on everyone’s bucket list.

The countdown: 3, 2, 1… GO! Three jumped — and one stayed behind. Pam bailed at the last second, ensuring plenty of laughter and memories. And That’s a Wrap! The Guiffre family trip comes to an end — a week filled with adventure, sailing, laughter, dancing, diving, and unforgettable experiences. What an incredible family and what an absolute joy it was to share this journey with them.