Itinerary (Updated for 2024!)

This is a typical itinerary. We play it a little loose down there, but you can pretty much count on this being our schedule. I’ve updated it with a few changes we’ve made based on previous trips, as well as a couple of changes I want to make this time (2024).

Wednesday

Depart from home. Arrive on Tortola by plane or ferry. Taxi to The Moorings. We’ll have a nice dinner together at the Marina, followed by a trip to the provisioning store to get most our goodies. We’ll spend the night on board our boat.

Thursday

Breakfast at the Marina. We’ll depart sometime in the morning. We’ll sail across the Drake channel to The Caves on Norman Island where we’ll snorkel and have lunch on board. Afterward we’ll sail over to Cooper Island where we’ll moor for the night on the beach at the Cooper Island Beach Club. We rest on board and in the water, sunning and snorkeling until dinner (this will be the usual afternoon/evening activity), which we’ll eat at the club.

Friday

Breakfast on board. Those who wish to stay on the beach at CIBC disembark. The rest take a short trip over to the Wreck of the Rhone, our first dive of the trip. Afterward we return to CIBC to pick up our beach bums and then set sail for the Dogs. We arrive around lunch and moor in a popular snorkeling spot. Lunch on board. We continue our sail across the north side of Virgin Gorda, entering The North Sound where we will moor for the night (Bitter End Yacht Club). We’ll eat an amazing all you can eat seafood buffet dinner at Bitter End Yacht Club with a steel drum band playing in the background.

Saturday

The boat stays in place. We spend the day on Virgin Gorda. We’ll rent a “safari” truck and get some breakfast at Little Dix Bay Resort. Optional Spa activity at LDB spa. Then on to the Baths, famous for its rock formations and snorkeling. Lunch at the Top of the Baths pool and restaurant. We’ll stop in Spanish Town to do some light re-provisioning and souvenir shopping. Then back over the mountain to our boat. We stop along the way for some great photo ops. Dinner at The Fat Virgin for a slightly more local island dining experience.

Sunday

Breakfast on board. Set sail for Anegada. We arrive around lunch. Lunch on board while moored at the Anegada Reef Hotel. Then we rent a “safari” truck and head across the island to Loblolly Bay – Flash of Beauty Beach and then on to Cow Wreck Beach. These two beaches are perhaps the finest beaches you’ll ever be on, and you’ll just about have them to yourselves. Optionally, you can hire a fishing guide and bonefish the Anegada shallows. For dinner we’ll dine on the famous Anegada lobster at the Anegada Reef Hotel.

Monday

Breakfast on board. Set sail for Monkey Point, Guana Island for some snorkeling. Lunch on board underway or once we arrive at Monkey Point. We motor over to Cane Garden Bay and our overnight mooring. For dinner we’re going to try Bananakeet for the first time on this trip.

Tuesday

Breakfast on board. We set out for Sandy Cay for snorkeling and exploring the small island. Then it’s on to White Bay. Here we’ll set the anchor and swim ashore for some relaxing beach time and drinks at the Soggy Dollar while we play the ring toss. Lunch on board. Then set sail for Soper’s Hole, Tortola. We’ll moor here overnight. Dinner at the new Fish n’ Lime (used to be the Jolly Roger).

Wednesday

Breakfast on board. We motor over to the Indians for some snorkeling and our second dive of the trip. Fantastic coral and tropical fish. I’ve seen a turtle here each time I’ve dived it. A couple of years ago we even saw a small shark. Lunch on board as we get underway, sailing across the Sir Francis Drake Channel and into Road Town to turn in the boat. We’ll clear the boat and get settled in our rooms at the marina. Lunch at the Moorings poolside. Dinner at the Marina and maybe dessert at Pussers in Road Town.

Thursday

Breakfast at the Marina. We’ll depart for the ferry terminal, ferry to Charlotte Amalie on St. Thomas. Lunch and shopping in Charlotte until it’s time to check in for our flight.