The first time I met Julian Putley, I brought him a pair of shoes. We were shooting a video on bareboat sailing, and Julian’s boss didn’t want him to be barefoot on screen. “I’ll only wear these once,” he laughed when he saw them, “and that’s for this shoot. I’ve lived in the BVI for 35 years and have yet to see a reason to own a pair!”

I knew then that I needed to get to know this guy. Over the course of an hour, Julian told me his story: he had been a world-girdling sailor before becoming a respected sailing instructor by day and a renowned island bar-hopper by night. He’d also recently published his third edition of The Drinking (and Eating) Man’s Guide to the BVIs, which he described as his “anthology of fun.” Through his “research,” he’d earned a front-row spot at all of the best watering holes in the islands. When I told him I was preparing to lead a charter of twenty-somethings, he enthusiastically gifted me a copy of his book. “It won’t lead you astray,” he promised, as we parted ways. 

With my new guidebook in hand, I made my way to TMM Yacht Charters to check out our ride: Zing, a brand new Matrix Vision 450 catamaran just in from South Africa. I also emailed my trusty first mate, Matthew, to tell him the plan: “We’ve done the BVI, right? We’ve done the extreme-sports thing and the extreme-relaxation thing. This time, what do you think about doing the extreme-party thing?” Needless to say, Matthew approved, and he and the rest of the crew arrived on Tortola buzzing with excitement. 

For the record, I would never choose to spend the first two nights of a BVI charter in Road Town. Unfortunately, the San Francisco contingent of our eight-person crew got waylaid in Miami, so we didn’t have much choice. We consulted The Guide and ended up at The Pub. 

The Pub, it told us, is Tortola’s oldest seaside watering hole, located close to the TMM charter base and a dinghy ride from anywhere in Road Harbor. The Pub’s veranda looks out over Tortola’s picturesque anchorage; it’s the perfect dining area cooled by the steady trade wind breezes. For years, The Pub has hosted its annual “Anything-that-Floats-but-a-Boat” and “Sinking Dinghy” races, in which participants must complete a course before their well-holed dinghies sink. Unfortunately, our trip didn’t align with this colorful event, but we were happy to snack on a free plate of conch fritters, courtesy of The Guide. If you go, show the book to Princess, the bartender, and ask for their specialty drink: the Pub Daiquiri. 

We spent the next day lazily provisioning and milling about town, trying to stay cool on the breezeless island as we peered longingly at the Sir Frances Drake Channel, where white sails dotted the horizon. By the time our crew arrived the sun was setting again, so it was time for round two in Road Town. 

The Guide led us to Pusser’s Road Town Pub, which Julian referred to as a “Legendary Nautical Pub.” The word “Pusser” is derived from “Purser,” referring to the person who divvied up rum rations on Royal Navy vessels. When the tradition ended in 1970, businessman and sailor Charles Tobias acquired the rum recipe and set up shop in Tortola.

Nowadays, charter guests flood to Pusser’s for its world-famous Painkiller, but Julian recommends the Nelson’s Blood. Whichever you choose, be sure to get it in a souvenir mug, perfect for bragging rights—I mean, fond memories—while back in your own boat’s galley.

Finally, with the weekend behind us, we were ready to get sailing. Matthew and I were the only two who’d sailed the BVI before, so we were determined to introduce our friends to all of our favorite spots. That morning, we got a mooring ball at the Baths, where we dinghied in and spent a few hours scampering around. The huge granite boulders, sculpted by wind, weather and waves, are haphazardly strewn along a stretch of coast interspersed with beaches and pools of water where the sun’s rays shine through crevices in the rocks. Aside from getting caught behind a line of 200 German tourists, the Baths were a hit, especially the snorkeling in Devil’s Bay. 

After lunch we sailed up to Virgin Gorda,where we picked up a Saba Rock mooring and went ashore to collect the free ice and water that comes with it. These days the restaurant at Saba Rock is famous for its all-you-can-eat buffet, but the establishment came about somewhat by accident, says The Guide. In the 1980s, a world-renowned scuba diver named Bert Kilbride built his house and dive shop there until he decided to take it a bit easier. He sold the dive business, which relocated to the Bitter End Yacht Club, but inquisitive tourists kept showing up, so Bert decided to erect a bohemian island-style bar and call it “The Pirate’s Pub.” Today, the open-air seating provides a great view of Virgin Gorda, and we treated ourselves to tasty conch fritters and a round of Painkillers. The Guide’s Saba Rock coupon is for an island classic, the Mai Tai. 

After dinner aboard, we took the dinghy to the Bitter End Yacht Club and walked straight past the fancy portion toward the Crawl Pub, the BVI’s version of a sports bar. The Crawl Pub features the largest TV screen in the BVI for those who like to watch sports and dartboards, foosball and pool tables for those who like to play them. For years, the bar has been featuring drink recipes sent in by patrons from their home yacht clubs, and The Guide recommends The Bitter End Buddy, a rum drink in honor of sailor Buddy Melges.

I could spend a week in North Sound—sailing on the BEYC’s dinghies, swimming with the tarpon, chasing the pink flamingos on Prickly Pear Island—but I had to settle for just a morning, because we were sailing for Marina Cay by 1400 hours. I have yet to have a BVI charter with less-than-stellar weather, and this was no exception. Every day, our sails were full and the sun was shining. This particular day brought a noontime sunshower, but it was certainly never cold. 

As soon as we tied up at Marina Cay, a local dinghied alongside to offer us fruit, veggies, homemade bread and local wares. It’s tough to keep fresh produce on board during a charter, so we splurged on papayas and a bag of spinach, which was the perfect appetizer before our visit to Pusser’s Marina Cay. The Guide promised us two Painkillers for the price of one, and we were happy to indulge. 

Of all the Pusser’s bars I’ve visited (four in the BVI, one in Annapolis) this is my favorite by far. The restaurant is open-air and breezy with awesome views of Trellis Bay and the Sir Frances Drake Channel beyond. We were the only patrons, but The Guide says that Beans used to play there, and Beans is a local legend: “a consummate entertainer, one-man-band and island character.” On busy nights, Pusser’s fills up with folks arriving by ferry from nearby Scrub and Beef Islands, but we had this particular peaceful, breezy evening to ourselves. 

(We later learned that Beans has relocated to Jumbies at Leverick Bay where his show has become a must-see for charter sailors. At Jumbies, in addition to the entertainment, guests can enjoy a free Bushwacker with The Guide.) 

To counter the laziness of Tuesday, Matthew and I planned an adventure-filled Wednesday. We set sail early from Marina Cay, winding our way between Little and Great Camanoe Islands, south of Monkey Point on Guana Island, and into the lee of Sandy Spit. Matthew assembled his kiteboard for a quick ride while the rest of us enjoyed the superb snorkeling. After lunch, we motored the hundred yards to Foxy’s Taboo, which offers free moorings during the day. This relatively new watering hole is the little sister to Foxy’s, the world famous party bar and restaurant on the other side of Jost Van Dyke. It’s perfect for a cold drink after a visit to the Bubbly Pool, which is a natural Jacuzzi that lies just a short hike from the moorings. At Taboo, Julian recommends a “Born ‘ere Beer,” which Foxy brews himself.

Our last stop was Sandy Cay, another small island just off Jost. The white-sand beach typically affords spectacular sunset views, but the no-see-ums were in full force. We didn’t want to watch the sunset while submerged to our eyeballs in saltwater, so decided to sail on. We dropped anchor in Little Harbor and prepared for dinner at Sydney’s Peace and Love. 

This restaurant has the cater-to-charter-guests thing down to a science. They send menus to your boat so you can order ahead, a task we assigned to our friend Jonathan. Matthew has known Sydney’s family for years, so when Sydney’s daughter, Strawberry, saw him walk in, she gave him a big hug and said “Matt-yew! So good to see you! Did ya bring two boats wit’ you dis time?” 

Matthew was confused, “Nope, just us. Why do you ask?” 

Strawberry laughed a full and loud island-style laugh, “You’ve got to be kidding. You ordered food for at least two boats!”

And she was right. Over the next few hours, the eight of us devoured bowls of conch chowder and lobster bisque, plates of seared mahi-mahi and fresh-caught lobster, and glasses of whatever hand-made drinks we poured for ourselves from behind Sydney’s honor bar. Every bite was fantastic, but we were stuffed. I guess that’s what you get when you tell a hungry 27-year-old guy to order your dinner!

All too soon, it was time to sail our friends to St. John to drop them off for a wedding. We stopped briefly in White Bay for some conch fritters at the Soggy Dollar Bar (The Guide offers a free Painkiller, but I couldn’t figure out how to swim the book ashore without ruining it), and enjoyed a picturesque sail to the west end of St. John. Because we had to clear in at Cruz Bay, we moored overnight in nearby Caneel Bay, which is close enough to dinghy to town, but much more peaceful. We enjoyed an evening with the rest of the wedding guests at the Wharfside Village in St. John and bid them farewell first thing in the morning. 

Playing host to a boat of first-time charterers can be a lot of work, especially when it’s your personal mission to make them love the BVI as much as you do. With the crew gone, Matthew and I allowed ourselves to sail casually back to Soper’s Hole to clear into the BVI, then took the dink over to Pusser’s Landing for some lunch. The Guide recommends Rotis and a Painkiller, but we stuck to a fresh-caught mahi-mahi fish sandwich and plenty of water. 

That night we anchored in Great Harbour on Peter Island. We were tickled to see a Matrix 760, our boat’s big sister, across the anchorage, and we enjoyed some wonderful snorkeling in the dwindling sunlight. 

Back at TMM, Matthew and I packed up the boat, and I picked up my no-longer-new copy of The Guide. I flipped to the back cover, and had to laugh: “Note: The authors are not responsible for hangovers or stitches, stomach cramps and heart attacks from excessive merriment and hilarity.” Excessive merriment and hilarity. That sounds about right.

Julian’s Top Three

To select the three best bars in the BVI is a true challenge, so I chose these based on what I thought would most enhance a leisurely stop during a sailing vacation.

– Julian Putley


1.One Love: In the middle of Jost Van Dyke’s White Bay, One Love has true island style. The beach bar is adorned with colorful sea detritus: floats, fishnets, discarded buoys and driftwood. Seddy, the owner, is an avid fisherman and fresh-caught fish and lobster are always on the menu. The seating is outside on the sand and the food is excellent. Try a Bushwacker, free with The Guide. 

2.Jumbies: Jumbies at Leverick Bay overlooks beautiful North Sound in Virgin Gorda. Here you can enjoy delicious lunches served under shade umbrellas and take a dip in the adjacent freshwater pool. A nearby sandy beach has loungers for public use. In season, Beans’ “Pirate Happy Hour Show” adds to an already lively ambiance and on Fridays, you can enjoy an all-you can-eat pig roast buffet accompanied by a reggae band and performing mocko jumbies. Get a free Painkiller or Bushwacker here with The Guide.

3. The Big Bamboo: In the white, powdery sand beach on Anegada’s north shore, the panorama is magnificent, with an outlying reef of breaking surf and a calm inner lagoon. This beach bar offers an array of tropical cocktails along with lobster, conch, fish and barbecued meats. Swing in hammocks under the sea grape trees or relax in shaded comfort under a palapa. The Guide offers a free rum slushie.

To see more pictures from this trip, visit the photo gallery.