I love sailing. I love the beach. I love the sun. I love fishing. I love swimming. I love reading. I love napping. I love eating in the fresh air. I love making cocktails in a bathing suit. If these things sound fun to you, you might want to consider a sailing vacation around the British Virgin Islands. This trip exceeded expectations. Before I even stepped off the boat and back on land, I was planning my next BVI sailing adventure. Since this original trip in 2023, I have bareboat chartered two more times. I’m obsessed. You might be, too.
This is a little bit of a different kind of post for me. It’s definitely not a recipe post – although, as always, there will be plenty of food. And while it’s technically a travel post, it’s not exactly a guide or an itinerary to follow.
What this really is… is a collection of the words I typed into my Notes app at the end of each day during my very first sailing trip around the British Virgin Islands in February 2023 – mixed in with photos from some of my favorite places along the way.
I promise I’ll put together a more polished and practical British Virgin Islands travel guide soon. But for now, here’s the real, unfiltered version – a little brain dump from my first BVI sailing adventure.
Day 1 Trip Diary – Leaving Boston
Friday morning!! Jet Blue Flight from BOS to San Juan / 3 hour layover. 20 minute flight from SJU to St. Thomas. Walked the San Juan airport to kill some time and get some steps in and then had a drink at Margaritaville followed by Spanish olives and a charcuterie plate at a small airport restaurant. So delicious – couldn’t believe this was at an airport bar.
Super quick flight from San Juan to St. Thomas – a really quick up and down. Watched the ground crew roll two sets of stairs across the tarmac to allow us to get off the plane. Walked down the stairs and across the hot pavement to get to the terminal. So hot out!
Checked in at the Dolphin Water Taxi desk in the airport where they gave us shots of rum and bottled waters. Dolphin Water Taxi seemed pricey but worth it – so glad we did it – saved us tons of time. Waited for our bags and then took a private taxi to Red Hook. Almost immediately boarded a water taxi to West End of Tortola. This boat was FAST. Woah. Had customs at West End. We handed over our passports and $10 cash each to the water taxi driver and he brought them inside to the customs’ agents. We didn’t even need to get out of the boat. Continued to Tortola. Super windy and choppy, but glad we were able to do the entire ride via water. Initially, we were told the water was going to be too rough for any private taxi driver to want to do it.
Provisioning For A Week At Sea
We arrived at Conch Charters and found our boat – Sisterblysse. Opened it up and dropped our bags off. Took a taxi from the boat to provision at a larger supermarket – Riteway – veggies, fruit, snacks, water, beer, mixers, rum. We spent about $350 for food and drinks for the week. Best purchases were granola for morning snacks, fresh mangoes, and salted peanuts. We bought some BVI Seasoning that was absolutely amazing and we used all of it for cooking before the week was even over. We brought frozen meat with us from Boston – steaks and lamb from Previte’s and U8 shrimp from a seafood store near us in Massachusetts. Everything was portioned, shrink wrapped and frozen and then checked in a sturdy soft sided cooler on the plane.
Really my only big mistake for the week – I didn’t prepare well for morning coffee. I should have brought a French press or some way to actually brew coffee. Instead, we used instant Cafe Bustelo and powdered coffee mate creamer. Painful.
Weirdly, there was a shortage of pineapple juice at the Riteway – we found one small can in the entire store. I had grand plans to make painkillers all week so I was initially concerned. We bought other juices – pina, tamarind, and guanabana – and decided we would experiment. Guanabana was definitely the favorite of the week. We also bought crème de coconut for our mixed run drinks – essential! We bought two bottles of white rum for the week and decided to stick with just rum drinks for our cocktails because, heck, we are in the Caribbean!
After bringing back our provisions, we loaded up a cart and wheeled them to our boat. We bought ice and iced down what needed ice and then walked into town.
Finding dinner on land before we set sail
Our taxi driver had recommended we try the jerk chicken and pork at this food van tucked behind a couple of streets. He told us to follow the smoke, so we did. We literally scanned the horizon, saw a thick plume of smoke, and followed it. Ate amazing Jamaican jerk pork at Bang Good Food Truck Van. Waited 45 minutes in a long line while cars pulled into a lot and opened their trunks and started blaring music. Chickens were running everywhere. People were sitting on cars, drinking beers. Were we the only non local people there? Most likely. When it was our turn, we tried to order chicken and pork but the woman behind the window literally yelled at us, “Only pork! You eat it! Ten dollars!” It felt like the soup nazi Seinfeld episode. It was so, so good and we know we were lucky to have been directed that way – we would have never found it on our own.
Ate so late but still stopped for painkillers at Pusser’s on the walk home and bought tin Pusser’s mugs. Best purchase! We used them for our rum drinks all week.
Day 2 – Setting Sail and Heading to Norman Island
On the docks at Tortola. Slept in! No lie, we were the absolute last charter boat off the docks. We were fully embracing our vacation and clearly we needed the sleep. After getting up, we did our chart review and boat review with Bernadette and Jeremy. Organized the boat. Left Tortola at 3:30pm. Headed to Norman Island. Arrived at 4:15. Grabbed second to last mooring. Went for drinks and appetizers at Pirate’s Bight. Amazing octopus appetizer. Met Chris and Dan from Cottage Park Yacht Club – a club not too far from us back home – sitting beside us at the bar. Planned to meet up with them later at Willy T’s – a floating bar on a huge anchored boat. Dan was wearing a Hull Yacht Club t-shirt and Chris said he had one on yesterday. Small world!
Went back to the boat, tried to grill steaks but way too windy to grill and decided we probably needed to find lighter fluid somewhere. Cooked steaks and veggies in the galley instead. Delish. Headed out to the Willy T after dinner. Busy and rowdy when we arrived but all the drunk people went to bed early, apparently, so we were the last people to leave when he headed back to our boat at 11. Chris and Dan convinced us that we were all tall enough to do a shotski together. Rum, of course. I was, unfortunately, not tall enough to not get half the rum shot up my nose when the four of us did the countdown and tipped the ski. Fun anyways! Tied up the dinghy, didn’t lock it, had to rescue it later. We were warned that dinghies get mixed up all the time on the docks late at night. Oops. Lesson learned. Got back to the boat and slept well!
Days 3 and 4 – Virgin Gorda
Left Norman Island and headed for Cooper Island. Winds were 23 with high seas and gusts above 30 so we motored. Took almost 2 hours. Arrived at Cooper at 12:30 – no moorings. Fingers crossed we can get a mooring at Cooper later in the week. Decided to continue onto Virgin Gorda. Arrived to Virgin Gorda at 3:30 and easily found a mooring at the Bitter End Yacht Club mooring field. Was immediately greeted by the Rum Runner – a boat that makes frozen cocktails and delivers them to your boat – with his dog aboard! We had to have one, of course.
We made dinner – lamb and veggies – still no grill – and then took the dinghy over to Bitter End Yacht Club to explore and get ice. We had drinks at the bar and put ice in the dinghy and then headed over to Saba Rock to check it out. We had drinks upstairs at Saba. Completely rebuilt since the hurricane. Super fun vibe. Lots of families, friend groups. Good music. Good drinks. Large bar and space to hang out upstairs. I loved the big swings by the bar! There were some people really getting into line dancing. We were not those people.
Second Day At Virgin Gorda
Took the dingy to BEYC for good coffee and showers. Yay for a real shower! I even washed my hair. It took me forever to comb through all the knots. Curly hair is great, until it’s not. We had to take shelter for a little bit while there was a brief rain squall. After showering, we inquired about renting a car for the day so we could visit the Baths on the main part of the island. We were easily able to rent a car for the day for $70. The next ferry was at noon so we had some time to get ice and bring it back to the boat.
Getting To The Other Side of Virgin Gorda
We took a quick ferry from Bitter End over to Gun Creek where our car was waiting for us. We had lunch at Island Pot – chicken wings and fish tacos and enjoyed a Bushwackers – that frozen cocktail was delicious on our hot day. We continued our trip to the Baths. The total drive time from the Gun Creek ferry to the Baths was about 25 minutes.Driving is a little wild. The cars are American – so the steering wheel is on the left – but you drive on the left side of the road, not the right. It takes some getting used to – especially driving around the steep cliff edges of Virgin Gorda.
Visiting The Baths
At the Baths we paid $3 to enter because the area is part of the British National Parks. We took the hiking trail down to The Caves but left our snorkeling gear in the car. We were not quite prepared to actually go swimming through the caves after our hike. Rookie mistake. After we explored the caves, we got a fresh coconut to drink and retrieved our snorkeling gear from the car. The snorkeling on the other side of the Baths was so easy and absolutely gorgeous.
I was shivering after snorkeling. The water is warm, but you really can only stay in it for so long wearing just a bathing suit. We warmed up, had a cocktail by the pool at the rooftop restaurant overlooking the Baths and then headed to Coco Mayo for dinner. Amazing food. It was recommended to us and it did not disappoint. We did not make a reservation and almost could not get a table but the hostess took pity on us. Our favorite part of the meal was the crispy rice and pork. So unique! The sunset views from the restaurant were gorgeous. There was a wedding happening on the beach while we were eating dinner.
We headed back to the ferry – very dark and windy and driving on the left side of the road in an American style car with the steering wheel on the left. A little disconcerting! But we made it. Took the 7:30 ferry back to Bitter End and had a drink at the bar before heading back to the boat. The Bitter End was busy and fun. We probably have a handful of cocktail cups to bring home after two nights there. I am not so secretly obsessed with plastic cups from Caribbean bars.
Day 5 – Trellis Bay
Slept in. Took the dinghy from our mooring over to Bitter End for more ice and to enjoy their showers again. Took the dinghy to Saba Rock and had coffees at the bar. The bartender sighed at me – coffee?? She sighed again when we asked for a second one. $24 later, we were content with our two coffees each. We need to be better about coffee on the boat next time.
Didn’t go to Anegada because the winds were not favorable at all. Sailed to Trellis Bay instead.
Stopped at Leverick Bay for fuel, water, and ice. We didn’t need to stop at all – we had barely used any fuel or waters. Apologies for my nervousness. Rookie nerves. My fault! However, Leverick Bay was an awesome place to provision. We found lighter fluid at the grocery store and a jalapeño for pineapple salsa and some m&ms. Essentials.
We sailed Leverick Bay to Trellis Bay. Jib only, mainly downwind, and made good time. We sailed for about four hours. It was a sunny and beautiful day. The winds were much more manageable than previous days with much less sea swell.
Trellis Bay was very quiet. It was easy to get a mooring. We went ashore to get a drink and enjoyed spicy chicken wings at Loose Mongoose. Really nice facilities. We walked through the art studios and shops along the beach. Beautiful art. This area has definitely been impacted by Covid and Irma and hasn’t quite been rebuilt. There is a lot of traffic through the harbor because of the ferries and water taxis. Trellis Bay is minutes from the Beef Island Airport.
Ate fresh pineapple and drank rum drinks on our sail. Used the rest of the pineapple to make a spicy pineapple salsa for a post sail snack. Delicious. We are eating well.
Finally Got The Grill To Work!
Finally got the grill to work! Thank God for finding lighter fluid. Had ribeyes for dinner on the grill using the delicious BVI Seasoning. Amazing. Served them with Brussels sprouts and bacon. Made way too much food. Fed the fishes with some of it.
Quiet night on the boat. We entertained ourselves with backgammon.
Day 6 – Little Jost Van Dyke
Woke up and went ashore in Trellis Bay to drop off our trash and get coffee and ice. Delicious coffee. Cute coffee shop. Convinced the woman that I really did want 2 quad americanos with four shots of espresso with milk and sugar. No cream available – of course not – sad for us. Really, sad for me. I think this lack of cream is hard for me to get over. Notes for next time.
We sailed from Trellis Bay to Jost Van Dyke vía Sir Francis Drake Channel. Winds were lovely at 13-18 for most of the sail and then picked up to 22-23 so the final leg to Jost was spicy.
We reserved a mooring at Little Jost Van Dyke through Boaty Ball. I was really feisty about Boaty Ball. Possibly the only thing I got annoyed about the entire week – other than the coffee situation. Boaty Ball reservations are wild. Cane Sugar Bay and Great Harbour looked full so we opted to make a reservation. Happy we know how to do that now. When we got to Little Jost Van Dyke there were still some first come first serve mooring balls available, but it was nice to know ahead of time we had a place to stay tonight.
We boiled more shrimp and made a really delicious shrimp salad. We called it linner since we ate at 4 and hadn’t really eaten anything since our quad americanos for breakfast.
Bubbly Pools and Foxy’s Taboo
After shrimp, we took the dinghy to Foxy’s Taboo and docked at their dinghy dock and walked over to the Bubbly Pools – maybe a 15 minute walk. A little rocky, found some baby goats along the way. Adorable. It was low tide so the bubbly pools weren’t so bubbly, but they were still pretty cool. I went in them. I climbed up higher to get a look at the pools from higher up the hill. Very pretty.
We walked back to Foxy’s Taboo and ordered cocktails and sat at picnic tables on the beach until the rains came. We moved closer to the bar and met a nice family from Maine cruising for two weeks.
Jupiter, Venus, and the Moon are lined up tonight. Gorgeous.
Day 7 – Little Harbour, Jost Van Dyke
Woke up, went swimming, and cooked bacon for breakfast to go along with our fresh mango and instant coffee. Looked at the BoatyBall app and it looked like there was a lot of availability at Great Harbour so we didn’t reserve a mooring. You can imagine how this story ends…
We had a beautiful, quick sail from Little Jost Van Dyke to Great Harbour. Arrived to find no available white mooring balls and when we looked at the Boaty Ball website, all moorings had been reserved. Ugh. We looked on the website and saw all moorings were reserved at Cane Sugar Bay, too, so we decided to just go to the next harbor over, Little Harbour, and try our luck. All Boaty Balls had been reserved but there were plenty of white mooring balls still available. The first mooring ball line was shredded and unusable. The second mooring ball line was covered in oysters so there was a little bloodshed getting on our ball, but we made it.
Little Harbour is tiny. There are 20 mooring balls. Two sides. One side has Abe’s Restaurant and Bar. The other side has Sydney’s One Love shop, restaurant, and bar, and also Harris’s Place – a restaurant run by Cynthia. We stopped by to check out the menu and Cynthia gave us some rum punch as a preview to the evening. We met Easton who was rebuilding Harris’s Place following the hurricane. He showed us his progress and how high the water came up during the storm. It was wild. He also showed us the tank with the enormous Caribbean lobsters. We made plans to come back and eat one for dinner.
For lunch, we went back to our boat and grilled the rest of the lamb and boiled the rest of the shrimp to make more shrimp salad tomorrow. We made rum cocktails, ate the lamb, and met Junior, who came by on his dinghy to collect our mooring fee. We offered him some lamb and he gladly took some and stayed by our boat to chat. He asked if we had a beer – of course we did! We even sent him home with 8 more. Junior said it’s been hard to fish because the weather has been so rough. He said Little Harbour always stays pretty quiet even when Great Harbour is busy. Everyone wants Foxy’s, apparently. We are going to have to save a visit to Great Harbour and Foxy’s for our next trip.
Caribbean Lobsters – Worth The Hype?
We took the dinghy over to Harris’ Place for dinner and saw the enormous Caribbean lobsters as we walked over the docks kept in their cages. There were also huge tarpon swimming around as well.
We arrived to dinner at 7:30 and were seated at a large table with 6 other people. There were two other tables of patrons eating in the front section of the restaurant. Cynthia told us to help ourselves to rum punch and a lady from another table brought it over to us. The experience at Harris’ Place was very entertaining. The food was absolutely not good at all. I was excited to try Caribbean lobster, but it was served with overcooked broccoli and half a baked potato. The rum punch was like drinking fire.
The mood at the table was very convivial and I enjoyed hearing other people’s sailing adventures. One couple was from Indiana and was not staying on a boat – they had taken a taxi from White Bay. We have used the BVI Cruising Guide throughout this trip – it’s so useful with moorings and anchorage information- but it also has restaurant and shop info, too. We had seen Harris’ Place in the cruising guide and the friends we met our first night in Norman had also recommended it. Cynthia told us that it cost her $2300 to be put in the cruising guide. After our pricey dinner experience, I can tell you that she made that money back in 2 nights. Worth it! But, honestly, who knew that the cruising guide was taking money from people and businesses to be mentioned? I really had no idea that’s how it worked!
The night ended with fights at our shared dinner table about the best size of Maine lobster to eat and shots of rum. For real, don’t fight with Mainers. Especially about lobsters. I wasn’t fighting – just observing. Back to the boat. We slept well.
Day 8 – Cooper Island
I set an alarm for 6:57am, not to be outsmarted by the corrupt Boaty Ball system in an attempt to spend our last night on the boat at Cooper Island. I checked my login information repeatedly and clicked on a mooring ball right at 7am when the system went live for the day. My first attempt was already reserved so I quickly clicked on a second ball and this time I had success. By 7:01am, all 20 Boaty Ball moorings at Cooper had been reserved.
On Thursday, I had emailed the Cooper Island Beach Club for a dinner reservation for Friday night and they replied back that they could take us at 7:30pm. Perfect!
After getting the Boaty Ball, I took a picture of the sunrise and then, admittedly, went back to sleep knowing there was no rush to get to Cooper to grab a white mooring ball.
We slept in a little, made coffee and then took the dinghy over to Sidney’s Peace and Love to buy some more ice. We also decided to enjoy a painkiller before we started our sail. It’s our last day, might as well. We also pilfered a small piece of nutmeg from the bar so we could grate fresh nutmeg on our own rum drinks for this last day. Next time I am packing nutmeg.
We left Little Harbour before noon and headed to Cooper. Strong winds and big seas – again. We were basically heading directly into the wind for our entire trip. It was beautiful but we decided just to motor over there. We arrived by 2:30 and immediately went snorkeling. We had noticed so many people in the water when we had come through earlier in the week so we presumed it was good. The snorkeling was truly excellent. As soon as we started exploring, we were greeted by 6 squid – just staring back at us. It was wild. We snorkeled down the beach toward the dock and then back to our boat. On the way back to the boat, I looked up to see a sea turtle swimming just a foot or two ahead of me. It was an incredible experience.
Close to 5pm, we changed and took the dinghy ashore. Cooper Island Beach Club has an excellent restaurant but it also has a fun bar and a rum bar and a cute boutique. We grabbed drinks at the bar since it was still happy hour and walked down the boardwalk to the boutique. I lost my hat sailing on one of the windier days earlier in the week so I was looking for a replacement and found it. We then headed to the rum bar.
The Rum Bar is small and intimate with games to play at the bar – I learned to play Shut the Box – and great lounge chairs outside. The bartender was very knowledgeable about the rums – there are 480 of them – and we tried a few different ones.
After rum, we walked back along the beach and grabbed another drink to enjoy while watching the sun set. It was stunning.
When we finally sat down for dinner, it did not disappoint. We devoured everything we ordered – a middle eastern cauliflower steak, jerk chicken, and pork belly. We somehow managed to save room for dessert and espresso martinis. We highly recommend everything about Cooper Island. Very family friendly, but also great just for adults.
Day 9 – Last day
We slept in – shocker. We awoke to so much fog! There was a light drizzle and we couldn’t see a thing outside our mooring field. A boat had broken from its mooring the night before so there were remnants of that incident as we motored to the docks. Not exactly sure what happened. This weather has been so windy with big swells all week.
We took the dinghy to the dock to get coffees at the coffee shop and stretch our legs a little before we had to head back to return the boat:
So thankful for good coffee. I had hoped to snorkel some more before we left but the weather was bad – really our only bad weather day so far. We tidied up the boat a little and prepared to sail back.
The wind picked up and it started to rain but we were committed to sailing back – or at least I was committed to sailing back and I was indulged. We saw only two other boats sailing. Another older couple in matching foul weather gear were the most memorable sight of the morning. By the time we approached the harbor, we were soaked and decided to just motor the rest of the way.
Sailing The BVI – Wrap Up
I took this trip and wrote this trip diary in February, 2023. Since that time, I have done this trip two more times. I have been sailing since middle school and I was a college sailor so, although I absolutely love sailing, chartering my own boat around the British Virgin Islands wasn’t something I thought I could do – never mind do it almost annually. Friends who have done this already – once, twenty times – I get it. I really, really get it. As soon as we got back to shore, we were already planning our next trip back.
For the two of us, we chartered a 36 foot monohull. It was the perfect size. It cost a lot less than staying in a resort. I couldn’t believe how fun and easy and affordable a trip like this could be. If you want a sailing trip for couples, this is your trip. If you want a sailing trip with friends or family, this is also your trip, All around us we saw families, friend groups, and couples on every size of boat imaginable. Lots of catamarans! I can see the appeal of chartering a cat if you are traveling with kids or multiple couples.
Obviously, you can make this trip as fancy as you want. Do you want your own skipper? Your own chef? Done and done. Do you want to eat out every night? Completely possible. This trip is so customizable. I don’t want any extra people on my boat, but we saw a lot of charters with captains and sometimes multiple crew. I can’t wait to do this trip with my own kids basically so I can put them to work. Kids, if you are reading – I am joking! Kind of.
Friends, if you have done this trip, tell me everything! What were the best parts? What were your takeaways? We are always planning our next voyage …
