Justin and I had the unique opportunity to travel to the British Virgin Islands with some dear friends of ours for a week this January 2022.
One of our friends, Keith, is an accomplished sailor, and has been sailing and racing sailboats his entire life. When some of our dear friends, Zach and Karen, asked us to come with them on a sailing trip through the BVIs with Keith leading the charge as our Captain, our answer was a resounding, “YES!”
Little did we know what an epic adventure we were in for!
After saying farewell to our kids, who were lucky enough to spend the week with their Grandparents (THANK YOU!), we headed to the airport to begin what would be over 24 hours of travel before arriving in the British Virgin Islands.
After flying through Newark (on the red eye) and San Juan, Puerto Rico, we arrived on the island of Tortola, where we met up with Keith and headed to our chartered catamaran, “Moonshadow.” After a 45 minutes taxi ride from the airport to Manuel Reef Marina, we greeted our 44′ catamaran and dropped our duffels and gear (shout out to the Osprey Duffels that were a godsend to us on this voyage!). The five of us grabbed a late dinner that night, and our first “Painkiller” cocktail of the trip (a fabulous mixture of rum, pineapple juice, and cream of coconut, and topped with a little shaved nutmeg). This drink would become a mainstay for us on our island-hopping that week. Dinner at Gene’s Bar and Grill did not disappoint, and we loved sampling the curries, tiki masala, fresh seafood, and conch fritters that the islands are known for. These would all become mainstays for us on our adventure.
Sleeping on the boat proved to be heavenly for Justin and me, and our time on the boat felt remarkably familiar to to our time in the RV! After a good night’s sleep we headed out on our water journey, departing the marina and heading first to Cooper Island. On our way, we enjoyed our first snorkel of the trip. The fish were incredible, and we loved seeing them up close! Bringing our own snorkel gear was essential, as snorkeling was nearly a twice-a-day activity on the trip. Having the freedom to hop in the water and explore whenever we felt like it was freeing and amazing.
That evening, we enjoyed dinner at Cooper Island Beach Club. The food was incredible, and Zach and Justin shared an obscenely massive rack of ribs, and our first few Bushwackers of the trip. The Bushwacker cocktail is awfully close a mudslide, and I liked to call them “milkshakes”! The views from the restaurant of the Beach Club were spectacular, and the sunset magical.
On our dinghy ride back to the catamaran that night following dinner, we followed a school of flying fish the entire way. As we followed them, I felt something slimy and wiggly hit my foot, realizing that one of these fish had flown straight into our dinghy! As you can imagine, we all had some fun when that ensued.
The next morning, our group enjoyed some amazing coffee on Cooper Island, and then departed for our next destination, the island of Virgin Gorda. Our stops there included swimming in to a private beach on Fallen Jerusalem National Park, and exploring he Baths National Park and Devil’s Bay National Park. Despite having visiting 52 US National Parks, Justin and I both joked remarked that this was our first time “swimming to a National Park”!
At the Baths, visitors hike in and out of crevices and over and under massive boulders and water, on a series of trails and stairways and planks. We loved exploring, and it reminded us of a smaller and less intense seaside version of our family favorite exploration, the Fiery Furnace in Arches National Park.
After our time hiking at the Baths, we enjoyed a 2-3 hour afternoon cruise to the North Sound. We found a mooring ball right between Saba Rock Resort and The Bitter End Yacht Club, one of our group’s favorite destinations of our journey. I couldn’t contain my excitement, and took some boat jumps to celebrate my joy. These would be the first of many on this trip!
We took the dinghy over to the Bitter End Yacht Club for some afternoon refreshments. Our favorites were some awesome Painkillers and a crazy lemonade where they blended a half of a lemon (rind and all!), in it. Bitter End had literally just reopened after rebuilding for over two years after Hurricane Irma decimated the resort.
After heading back to the boat for a quick shower off the back (we became pros at this and, despite having shower nozzles in each of our bathrooms, learned to prefer this “boat shower”), we headed to Saba Rock for dinner. Saba Rock was a hip, swanky resort with awesome sunset views and an amazing view of Eustatia Island, a private island rumored to be owned by Google founder, Larry Page. We had a blast at dinner, people watching and hanging out, and the food was wonderful. I know we would all recommend a stop there for anyone in the area!
After dinner, our group headed upstairs at Saba Rock to their amazing bar, where we played pool, enjoyed the swings at the bar, and watched the AFC Divisional playoff game with small crowd of Chiefs and Bills fans. I could have stayed there all night.
After our time at Saba, we departed in our dinghy, only to discover that we couldn’t locate our boat in the dark (despite our headlamps), and spent a good half hour zigzagging across the mooring field looking for our boat. We had forgotten to turn on the LED string lights, which we used to identify our boat among many, when we departed for dinner. It turns out that finding a dark boat in the pitch black darkness isn’t easy! Luckily, after about 20 minutes of weaving in and out of sailboats in the dark, we eventually located “Moonshadow.”
The next morning, we slept in a bit and had coffee at Saba Rock before departing the North Sound mid-morning and heading to the Dog Islands. The snorkeling at Great Dog looked treacherous at first with 3’ swells, but it was still beautiful. We snorkeled off the boat for about a half hour before cruising around Scrub Island to Diamond Reef for some more snorkeling.
That afternoon, we spent some time on the boat, and then made our way to Trellis Bay on Tortola, where we hit up the Trellis Bay Market to stock up on provisions. We arrived 10 minutes after the market was already closed, but they opened it back up for us to briefly breeze through and stock up. We enjoyed dinner at The Loose Mongoose nearby, a less than 5-minute walk to the airport on Beef Island. Keith’s wife, Mary, flew in that night after much difficulty leaving Chicago for the BVI. She had stayed behind intentionally when their first weekend childcare fell through with COVID, and then had to deal the fiasco of an invalid proctored at-home COVID test kit, which delayed her even further. We were happy to have her finally join us, and we all finished dinner and took the dingy back to the boat where we hung out for a bit (and I took a night swim – my favorite!) before turning in that night.
The next morning, we woke up early to begin our 3 hour sail to the island, Anegada. Anegada is the most remote of the British Virgin Islands, and is known for many of its secluded, white sand beaches.
Because Anegada is a larger island, we rented an SUV to explore for the day. Our first stop was Flash of Beauty, a bar and restaurant on an almost-deserted beach, were we all enjoyed a Carib and the expansive view of the North Atlantic.
We then headed on our way to Big Bamboo for lunch, where I was a big fan of the hammock time after our meal, and checking out Loblolly Bay, another gorgeous beach.
That afternoon, we traveled the rugged roads of Anegada, sprinkled with goats, to the Anegada Beach Club, which looked like a great place to stay for anyone in the area. We enjoyed the gorgeous beach there, and loved our time in the water and on the white, fine sand.
Finally, before heading back to “Moonshadow,” we stopped at Cow’s Wreck Beach, a gorgeous beach, where the sand almost felt like kinetic sand. Beautiful!
That evening, we watched an amazing sunset from our boat, and then made our way to shore on our dinghy to the Anegada Reef Resort for a dinner featuring local Anegada lobster. The fresh lobster was amazing (we had put in our orders earlier in the day, and even saw the fishermen bringing the lobster in from the dock), and it was a beautiful outdoor dining spot.
The next morning, we sailed a few hours from Anegada back across the ocean. It’s amazing how long it takes to travel 15 miles on a sailboat, but it’s so peaceful and relaxing, and we enjoyed sitting in the nets in the front of the catamaran and getting some sun on our way. Some of my favorite memories of our trip were the quiet, peaceful moments on the front of the boat while sailing.
During our journey, we stopped at Monkey Point off Guana Island to do some snorkeling. The fish were AMAZING, but the visibility was a bit difficult, so our trip didn’t last long.
We spent a few morning hours on the water making our way to the next island on our route, Jost Van Dyke, and Justin and I even took a snooze in the sun during our journey.
That afternoon, we arrived at Diamond Cay and Jost Van Dyke, and headed to shore for a short, 30-minute hike to the Bubbly Pool. This was a fun spot, and several groups of people were there to enjoy the water coming through the rock crevices and making some good waves. We enjoyed swimming in the Bubbly Pool and it felt really good to stretch our legs.
We enjoyed some cocktails at Foxy’s Taboo, a fun spot right on the water in the bay before heading back to our boat to enjoy the sunset. On our way back to the boat, however, I jumped off the dingy to swim in to a small restaurant hut on the water called the “Bee Line,” where the kind owner allowed me to borrow his kayak to paddle out to our friends on the dinghy to take their orders for dinner that night. Now that’s island life!
Dinner was great, and the BBQ chicken and Jamaican Curry Chicken were awesome. Not to mention some corn hole to finish off the night, and the fact that we were able to “leave our mark” on the restaurant!
Our next day on Jost Van Dyke started off with a quick sail around the corner of the island from Diamond Cay to Sandy Spit and then to Sandy Cay.
Sandy Spit is a tiny island with a couple palm trees that you can literally walk around in a few minutes. With one side opening to the Atlantic, and the other side to the channel, it was an incredibly unique and heavenly place to enjoy our morning coffee!
After a couple of boat jumps (these had quickly become my favorite), we boated to Sandy Cay (Sandy Key). While not quite as small as Sandy Spit, Sandy Cay National Park was just as deserted, and Justin and I both remarked that this was our second time “swimming to a National Park,” our first time being when we swam to The Baths and Devil’s Bay earlier in the trip. We took the dinghy over and beached it, and were the only ones the island for a while. Each of us enjoyed a small “Painkiller” that Justin had poured into our Yeti from earlier that morning when he stopped at Foxy’s Taboo for ice. Our group even saw a small shark swimming off the shore, and Justin dove in, attempting to get closer with our GoPro, before pretending the shark had attacked him to get a rise out of everyone…Ha!
After our time on Sandy Key, we rinsed off and headed back to Jost Van Dyke.
That afternoon, after being forewarned by Keith that we’d be “going big,” we kicked off an afternoon and evening relaxing in hammocks at the Soggy Dollar, an island bar known for inventing the “Painkiller” in the 1970’s and for having patrons “swim in” from the their boats. We played the “swing ring” game, and laughed at some 20-somethings who were remarkably bad at it.
The sunset from the Soggy Dollar was one to remember, with our feet in the sand and a cocktail in hand. Heaven!
After Sunset, we walked next door from the Soggy Dollar to Gertrude’s, and enjoyed another great island dinner
Admittedly, there was a good amount of shenanigans at Gertrude’s, including couple photos in the giant Adirondack. Justin also surprised Zach with a hat that read “Dinghy Captain”, which he bought at Sidney’s, a restaurant right on the beach where we moored the boat.
That night, our cab driver from from the Soggy Dollar (and for the rest of the night) was Eugene, the same cabbie that our friends Keith and Mary had also had used on a previous trip. He was driving a new SUV with lights and indicators going off like crazy, but he nonchalantly told us to “pay no mind” to the incessant beeping. He was kind enough to drive us to Foxy’s, where we finished off the night in one of the most famous bars in the BVIs.
We had a blast at Foxy’s, despite much consternation and debate about the DJ’s song choices. The DJ was clearly leaning into popular mainland “wedding music” in lieu of the island music Foxy’s is known for. I “paid no mind” to what we may have been missing out on, and we all had a great time dancing, laughing, and even hopping in to play oversized Jenga. Mary even danced on a table!
On our last full day in the islands, we traveled from Jost Van Dyke to Norman Island, sailing past St. John on our way (man, did that bring back some wonderful memories of our spontaneous trip there last year) and hitting a couple amazing snorkeling spots. It was a blast spending most of that journey checking out the spectacular houses on the cliffs, and the sail was beautiful.
First up for snorkel that day was the Indians, a collection of several rocks jutting out of the bay with reef below. The visibility was slightly muddled with the water churned up a bit, but the spot was teeming with vibrant tropical fish and amazing underwater life.
We had a lazy afternoon following our first snorkeling adventure, with almost everyone getting either a nap or some sunbathing on the boat in, or even both. After we’d moored at our 2nd stop, I dove in and swam a couple hundred yards into shore, and Justin eventually followed. The beach was incredibly jagged with rocks and washed up coral, but interesting nonetheless.
The Caves was a short dinghy ride away from our mooring location in The Bight, so Justin, Keith, and I went snorkeling in the late afternoon. It was really incredible, and arguably the best of the trip. We followed an eel for several minutes, and just swam along shore wall of Norman Island, exploring small nooks of tropical fish and more reef.
We enjoyed our last sunset on the boat, followed by a tasty dinner at Pirates Bight and a trip to Willy T’s, the famous “pirate bar” on a tanker in the middle of The Bight. Willy T’s is infamous for people jumping off the 2nd deck of the tanker naked. While we didn’t go “all-in” on the naked jumping, Justin and I wouldn’t be denied an opportunity to jump off the top of a boat at night into the illuminated water below. It was so fun we did it twice, and were surrounded by several massive tarpon in the water below each time!
On our departure day, Keith and Justin enjoyed one last snorkel at the Indians at sunrise, as the rest of us enjoyed our coffee on the boat. About 10 feet below the surface, one of the rocks had a small underwater opening about 10 feet long. Justin had to take the opportunity to swim through it. It was a little scary, but exhilarating, and he came out on the other side into a school of what had to be 50+ bright blue tropical fish.
We then began our hour-long sail back to Tortola, where we pulled in to the harbor, executed our proctored virtual COVID testing on the dock, and checked out of “Moonshadow” with Captain Brent.
Our group took a taxi over to the Beef Island airport, where we hung out for 90 minutes and had lunch before going our separate ways with Keith and Mary on a separate flight.
WHAT AN AMAZING WEEK WE HAD ALL HAD TOGETHER in the British Virgin Islands! This trip, the perfect concoction of adventure, beauty, rest, and friends, was just what we all needed. Pure magic!
It was a quick hop to Puerto Rico on a VERY small plane, and Justin, Zach, Karen, and I took a taxi to the the Sheraton Old San Juan, where we checked in and enjoyed a HEAVENLY shower (after “boat showering” for a week) before heading into Old San Juan for dinner.
Dinner at Princesa was amazing (highly recommend!), with authentic Puerto Rican food from “old recipes.” They boasted all local, sustainably sourced produce and ingredients, incredible cocktails, and the beautiful outdoor setting made for a great last meal on the trip!
After a long flight from Puerto Rico to Houston, and another from Houston to San Francisco, we made it home, just in time to catch Grace’s CYO Basketball game that afternoon.
It had been a FABULOUS 10 days away, an incredible trip that we would surely never forget!
We created a guide to help you embark on your own journey without the stress and hassles of planning out every little details.
Simply download our guide and enjoy the ride!
We created a guide to help you embark on your own journey without the stress and hassles of planning out every little details.
Simply download our guide and enjoy the ride!
We created a guide to help you embark on your own journey without the stress and hassles of planning out every little details.
Simply download our guide and enjoy the ride!
