Thanksgiving Week 2022 Itinerary & Trip Notes (and highlights from past trips)

Overview: This was a seven-day bareboat sailing adventure on a 45′ Nautitech Fly catamaran we chartered out of Nanny Cay, Tortola, with Horizon Yacht Charters. I skippered the boat and our crew of eight shared responsibilities for cooking and entertaining each other.

Itinerary: Nanny Cay, Tortola (arrival night & departure) > Norman Island (1 day) > Virgin Gorda (2 days) > Jost Van Dyke (3 days) > Cane Garden Bay, Tortola (1 day) > Nanny Cay (return to base) > St Thomas, USVI (last night)

Bottom Line: This was Michelle and my fifth bareboat sailing vacation in the Virgin Islands dating back to 1987, with subsequent trips in 1988 (our honeymoon), 2013 and 2016. Even though the islands were devastated by Hurricanes Maria and Irma in 2017, virtually everything has been rebuilt, the waters and beaches as beautiful as ever, and it was wonderful to be back. By now, we know the islands well enough that we have our favorite spots we return to every time, as well as other favorites we missed this trip given the relatively short duration. Seven days is enough time to really unwind and enjoy a few islands, but every additional day you can manage opens up your options significantly; 10 days is the perfect duration, in my experience.

For this trip, we were joined by daughter Katie and son-in law Josh, Michelle’s sister Lisa and husband Mike, and our great friends and life-long sailors Jim and Deb. As Jim has said many times, having sailed most of the world over many years, the BVI is arguably the best cruising grounds in the world, with fair winds, warm seas, and easy, line-of-sight sailing to numerous islands and beaches!

With our first day sailing set for Sunday and knowing it takes a while to get checked out, it was imperative we arrive the day before and stay as close to the marina as possible. Getting to Tortola from California is a verrrrry looong day, with several connections that, if missed, could spell disaster. Despite this and leaving home on a red-eye on Friday night, we barely made it! Weather delayed our connection in Houston, and upon landing in St. Thomas USVI (the closest major airport), we barely made our connecting ferry from St. Thomas to Road Town.

Fortunately, Nanny Cay is a self-contained marina and resort community with our boat charter company, hotel, grocery store, dive shop, coffee shop, bar and restaurant, so once we arrived Saturday evening, we were set, starting with dinner in Road Town at Pusser’s (famous for their rum, and across the street from the ferry terminal) and ending with cold beers at Peg Legs Beach Bar attached to the marina.

See the end of this post for essential planning and logistics tips to ensure you get off to the best possible start.

Sunday morning was all about making all final arrangements to board our yacht and set sail on time. This meant grocery shopping and stocking the bar (planned in advance), renting snorkeling gear, paying the final bill, picking up our cruising license, and getting checked out on the boat. Getting started by 9am allowed us to get this all done by 1pm, and then we set sail heading south past the Indians — a great diving and snorkeling spot if you have time — for our first overnight stop at Normal Island!

Norman Island, the westernmost of five major islands south of the Sir Francis Drake Channel, is famous for three things:

• It’s widely regarded as the inspiration for Robert Louis Stevenson’s Treasure Island, with true tales of buried treasure still in circulation.
• The Bight is a terrific, very well protected anchorage with easy access to excellent snorkeling at the nearby Caves.
• The “Willy T” — a floating restaurant and bar meant to resemble an old pirate ship named after William Thornton, a BVI native and architect of the U.S. Capitol building, that can get quite wild when the bar fills up.

We grabbed a mooring ball in the Bight, made our obligatory dinghy ride to the Willy T for late afternoon cocktails, and returned to our boat for our first on-board dinner and rum-assisted banter about the next day’s sailing opportunities.

Monday. First morning waking on board, and resumption of a longtime morning ritual for me: get up, hurl self into the sea, swim around the boat, get out, shower off, get coffee, and prepare to set sail. World’s best wake up call!

While Katie and Josh cooked breakfast, our foredeck crew of Deb, Lisa and Mike cast off our mooring lines and we headed back out into the Sir Francis Drake Channel. After checking wind, tides and current, we opted to sail north between St. John (USVI) and Tortola’s West End (BVI), split Little Thatch Cay and Frenchman’s Cay, leaving Soper’s Hole to starboard, and then head east along Tortola towards Virgin Gorda, our destination at the eastern end of the BVI. We figured it would be smoother sailing than heading due east from Norman through the Drake channel.* But with winds gusting to 25 knots, the ride was still a bit choppier than I’ve usually seen once we cleared Tortola and were exposed to the open sea. Four hours after departing Norman Island, we entered Virgin Gorda’s North Sound, passing between Prickly Pear and Eustacia Islands, and heading up to Saba Rock where we picked up a mooring at close to the island. Of course, that meant our next round of “welcome cocktails”!

As North Sound is one of our favorite spots in the BVI, we spent two nights here. Highlights:

• Saba Rock has always had a great bar with great views of the Sound, but since it’s post-hurricane rebuild, it has a few very nice looking lodge rooms as well. Not to mention one of the fancier restaurants in the islands, friendly staff, fun shops for the shopaholics, and the all-important ice for sale.
• Checking out the rebuilt Bitter End Yacht Club just across the water. Michelle and I spent a few days of our honeymoon here in 1988, and while it is much smaller now than before it was completely flattened by the hurricanes, they’ve done a very nice job. Nice beach, bars, a few high end bungalows, and spectacular views past the bigger yachts visiting the BVI.
• Dinghy ride out to Sandbox Beach on Prickly Pear Island for sunset cocktails. Watching Jim kitesurf into the beach for his painkiller was particularly fun.
• In fact, this anchorage is Jim’s favorite kitesurfing spot and he’s very good – so cheap entertainment for the rest of us!

One disappointment, to be honest, was the quality of snorkeling. Years ago, this area was rich in corals, tropical fish and interesting marine life. Now, between overuse, climate change, and the hurricanes, most of that is gone. The snorkeling we did was middling at best here.

Wednesday. After the morning sea-swim-coffee ritual and our double rainbow greeting, we made an early departure from Virgin Gorda, heading back out to sea and westward, sailing above the Dogs and Great Camino Island before turning south and crossing below Monkey Point between Guana Island and Tortola.

Monkey Point is another beautiful, small beach tucked behind a large rocky point that Michelle and I had stopped at for lunch on our honeymoon many years ago. We thought it might be a nice lunch and snorkel stop on our way to Jost Van Dyke. Unfortunately, there were a fair number of boats already there occupying a pretty small anchorage, so we pulled anchor after a short stop and continued on to Jost. We had originally thought about two days at JVD, as it has the largest concentration of white sand and beach bars in the BVI, but we ended up staying three nights at three different anchorages — two spots we knew well from past trips — and one new location. No regrets at all.

On arriving, we tucked into the small Long Bay between Little Jost Van Dyke and JVD, grabbing a mooring ball just between the two. This was a well-protected spot and equidistant between two spots we wanted to explore: the B-Line beach bar on Little JVD (see below), which we had never seen, and Foxy’s Taboo for dinner, where we had eaten once before and enjoyed very much. And that’s exactly what we did. (There is also a much advertised “bubbly pool”, but we skipped this as we heard it’s an overrated tourist attraction and a general waste of time.)

Thursday, Thanksgiving Day. After a quiet night at Long Bay, we set sail early the next morning around the point to Great Harbour for a lazy day of paddleboarding, swimming and, eventually, Thanksgiving dinner of famous island turkey (aka grilled Anegada spiny lobster), more Painkillers, and live entertainment at Foxy’s Tamarind Bar. My only disappointment here was that one of my all-time favorite BVI bars, Corsairs, was closed!

After five separate cruising holidays in the BVI, Foxy’s has always been a highlight and never disappoints. When we first started coming down here in 1987-88, Foxy used to sit outside his little beach bar — long before he became a huge operation with two restaurants and a big retail gift shop — and sing songs while playing guitar for bar patrons and passers-by strolling the beach.

This is me and Foxy in 2016.

Okay, Day 6 arrives — it’s Friday, and we are heading just around the corner from Great Harbour to White Bay, the most notorious and long-awaited of our destinations. White Bay has long been well known for its gorgeous turquoise water and long, beautiful, palm-tree lined, white sand beach practically lined with funky beach bars from one end to the other. It has wide, shallow anchorage just inside large reef with two channels admitting entrance and egress. Mooring balls tend to go fast and it gets crowded, especially on the weekend, when day trippers from St Thomas often come ashore. So, getting there early is key.

We managed to do just that and snagged a mooring comfortably off the main beach. That left plenty of time for a nice lunch, some more stand up paddleboarding, and then, with energy reserves replenished, we hopped into our dinghy to ferry our crew ashore to start our obligatory bar crawl down the beach.

The shore break is pretty tricky and bringing the dinghy all the way in is not advised; fortunately, we got our crappy little dinghy anchor to hold in about 10 feet of water off the beach and then swam in. From there, we hit a our three favorite bars, starting with Seddy’s One Love, then on to Gertrude’s, and finally the famous Soggy Dollar, comparing Painkillers, Bushwhackers, Dark ‘n Stormys, and other island specialties along the way. Not for the faint of heart, but it sure is fun!

In past years, we always seem to stagger back to our boat after finishing up at the Soggy Dollar — to the extent our veteran sailor, Jim, swears they must “put something” in their Painkillers (I think it’s just called rum) — but this year we managed to keep our wits about us.

Saturday. Our morning routine of “wake up, hurl self into the sea, grab coffee” completed, we cast off for our penultimate day of sailing and island hopping. Our destination is Cane Garden Bay on Tortola’s north shore, another anchorage we have visited every prior trip to the BVI. But it’s a beautiful day and we are in no rush, so our first stop is Sandy Cay, a pretty, small and uninhabited island just off JVD. Sandy Cay has been a VI National Park since 2008 thanks to a large donation by Laurence Rockefeller. It’s a great spot to swim to the beach, walk some of the lush trails on the island’s interior, and enjoy a relaxing lunch back on board.

After lunch, we made our one-hour sail to Cane Garden Bay where we caught our mooring and dinghied ashore for arrival cocktails at Myett’s Bar & Grill. Cane Garden Bay is considerably more developed than it was years ago, and we got our first glimpse of roads, cars, and multi-story hotels since we left Road Town. We skipped our old favorite bars, Quito’s and Rhymer’s, as they are lively at night but not as inviting mid-day. But Cane Garden Bay does boast one of the best sunsets in the BVI when caught from the stern lounge of your boat, and since we planned to have our last dinner aboard, we made sure to get back in plenty of time.

Sunday. All good things must come to an end, but one of the other nice things about Cane Garden Bay is it makes for a nice, two-hour sail back to Nanny Cay Marina — plenty of time to enjoy the morning ritual and breakfast and still get back well before noon. Interestingly, despite Horizon’s instructions, they did not respond to our radio hails on our return, but we had no trouble getting onto the fuel dock for refueling and our final boat check out.

With a few hours to kill before our scheduled ferry back to St. Thomas, we stopped at Pusser’s in Road Town for lunch. Many hours later — after our ferry was delayed by a breakdown and having to clear customs in St. John — we arrived at our final night lodging in Charlotte Amalie’s Frenchtown district. Olga’s proved to be a perfect spot to overnight, given its close proximity to the airport (early morning flight home the next day) and a short walk to the French Quarter Bistro, a good restaurant with even better service. Highly recommended.

Essential Tips for Bareboating the BVI:

• Book your flights to and from St. Thomas (there are no direct flights to the BVI) well in advance and make sure you have plenty of room for possibly missing connections; the airport is small and there are only a handful of daily flights. I’d rather arrive two days early than half a day late! You want every possible minute on the boat you’ve paid for.
• Shop carefully for bareboat charter companies and their locations. Road Town, Nanny Cay, and the West End, all on Tortola, have many options and are ideal departure/return points for your sailing adventure. West End is a little more convenient for the ferry to and from St. Thomas. I’ve always liked Sunsail, but our experience with Horizon was just as good and a little less expensive.
• Shop carefully, too, for the boat you want and can afford. You can save money by getting a slightly older (>3 years) boat, but new boats are less likely to encounter problems and have all the latest tech, which. For a group of eight, we have found going with a 45′ catamaran with four staterooms and four heads is the only way to go.
• If you seek convenience over price and, possibly, selection, consider paying for provisioning with your yacht charter. All done online and your groceries on waiting for you when you board. We now prefer to do our own grocery shopping when we arrive. If you do your own shopping, decide in advance how many meals you will cook and eat on board vs. dining out, then make your shopping list in advance. With several people, an online spreadsheet makes this easy. And it saves lots of time in the store. For seven days, we chose to splurge for dinner out three nights and split the other meals on board, one for each couple.
• Buy your inter-island ferry tickets in advance, too. One last thing to hassle with after you arrive and time is of the essence. This can be done easily online via Native Son, Smith’s, or Road Town Fast Ferry, all departing St. Thomas about 10 minutes from the airport.
• Make sure you have your passport — while St. Thomas (USVI) is part of the United States, the BVI is not, and you will have to clear customs coming and going.
• Despite that fact, everywhere you go in the BVI will happily take your U.S. dollars (and several places will take plastic), so no need to change currency.

If You Have More Time:

As I said at the beginning of this post, seven days is really a minimum sailing trip and enough to enjoy yourself immensely. That said, more is better… and here are some of our favorite places from past trips we would absolutely have returned to, had we had more time, in priority order:

• Anegada — This large, coral archipelago, a solid two-hour sail north of Virgin Gorda and the only BVI destination outside the main “loop” around Tortola, has spectacular beaches, one of our favorite beach bar/resorts — Big Bamboo at Loblolly Bay — a large population of pink flamingos, and very, very few people. It is more “off the beaten track” than any other BVI destination. Most charter companies did not allow bareboaters to approach Anegada 20 years ago because the massive coral reefs surrounding the island have sunk a great many boats — there is only one, narrow channel to the only safe anchorage, but it is well marked. We went there in 2013 and 2016. Only suboptimal weather and sailing conditions and a game-day decision prevented us from going there this trip, and with optimal conditions we would gladly have traded that third day at JVD for one night at Anegada.

• Cooper Island — Halfway between Norman Island and Virgin Gorda in the Sir Francis Drake Channel, Cooper Island is home of the Cooper Island Beach Club on Manchioneel Bay. This is a great place to make a last night before returning to Road Town, as it has a very nice, palm-tree lined beach, fantastic restaurant and rum bar. (It also has a hotel, but who needs that when you have your own floating hotel.) It also has excellent snorkeling — at least it did in the past — where I saw more barracuda than anywhere else. We stopped here in 1988 and 2016.

• The Baths — Another VI national park located on the southwest end of Virgin Gorda, this huge collection of massive boulders at the water’s edge is very popular attraction for day-trippers. Overnight anchoring is not permitted, but day-trippers anchor out and either swim in to the beach or get dropped off by dinghy outside the roped off swimming area. A maze of tunnels snake through the boulders with some spots requiring swimming through. Lots of fun, especially for first timers.

Here’s a great 10-day BVI sailing itinerary from another blogger with whom I have no affiliation. Go do it, the islands are calling, mon!