Most bars and clubs around Road Town open up for the after-work crowd at about 6 p.m. (or earlier if they also double as a lunchtime restaurant). On weeknights, expect establishments to stay open until about midnight, and on Friday and Saturday nights the party often continues until 2 a.m. or later.
The Bat Cave (Administration Dr., 284/494-2270) is a popular after-work hangout located next to Jewels on Administration Drive. Head to the deck for a fun happy hour, or stay inside if you prefer a dark atmosphere with black lights and powerful air-conditioning. The clientele here is generally youthful residents and locals.
For the best Caribbean dance hall and an intense immersion into Caribbean youth culture, head to Stone’s (Long Bush, 284/494-6776), a venerable club with hot music and an even hotter clientele on Friday and Saturday nights. The party gets going late—after midnight—and goes till dawn. Don’t dare come underdressed (and for the ladies, less is definitely more).
On the waterfront you’ll find several popular watering holes, ideal for meeting up with the after-work crowd. Castaways (Sir Olva Georges Plaza, 284/494-8295, 4 p.m.–midnight Tues.–Thurs., 4 p.m.–3 a.m. Fri., 6 p.m.–2 a.m. Sat.), a second-story bar painted an eye-catching shade of purple, has the best view and is a nice place to start your evening. Cheap beer and chicken wings get the party started.
Pusser’s (Waterfront Dr., 284/494-3897) is a popular happy hour haunt, especially on Friday nights when it is downright jammed with young residents and islanders looking to wind down (or up).
Le Cabanon (Waterfront Dr., 284/494-8660) set among the trees next to Pusser’s is a popular late-night hangout especially popular with expats. During happy hour it is a quiet place for conversation. Come here for an intimate heart-to-heart with your new-found soul mate.
For a more refined nook, grab a seat at Bar Fly (67 Main St., 284/494-0313, 6 p.m. till late Tues.–Sat.), a cocktail and appetizers lounge attached to the upscale restaurant, the Dove.
If dancing under the stars is more your cup of tea, head to Cane Garden Bay , where several beach bars offer the quintessential Caribbean night out. All these establishments are open all day—from lunch (in some cases breakfast) until late-night. You can expect evening entertainment to begin at around 8p.m. and last until midnight or later.
The most famous of Tortola ’s musicians, Quito Rhymer, performs several nights a week at his Gazebo (Cane Garden Bay, 284/495-4837). Quito plays acoustic on Tuesdays and Thursdays, while on weekends he plugs in with his band, The Edge. The sound is an upbeat combination of reggae and calypso. The crowd here tends to be an equal mix of tourists and island residents, and this is a good place for dancing. Friday night is especially popular among locals, and the dance floor remains crowded well into the wee hours.
Myett’s (Cane Garden Bay, 284/495-9649) has live music Friday–Monday, and the garden atmosphere is tantalizing. There is often DJ music at other beach bars, including Big Banana (284/495-4606).
The Bomba Shack (Apple Bay, 284/495-4148) is western Tortola ’s most distinctive bar. Built of flotsam and painted an array of colors (and colorful words), “The Shack”—as it is known—is one watering hole you won’t soon forget. Bomba’s is legendary in the Virgin Islands  for its raucous full moon parties and risqué shack decor. Ladies’ underwear hangs from the rafters, often shed after imbibing Bomba’s potent rum punch or his even more potent mushroom tea, brewed from locally grown hallucinogenic mushrooms.
The tea is served at midnight during the full moon parties, which inevitably draw a huge crowd, even in the dead of summer. Bomba’s full moons feature live bands, dancing, and, sometimes, dubious attractions like wet T-shirt contests.
If you want a Shack experience that is a bit more tame, try it out on a Sunday or Wednesday night when there is live music and more mellow company. Or stop by any afternoon to benefit from the pieces of wisdom previous partygoers have scrawled on the shack’s walls over the years.
One of the most reliable places for a night out is the Jolly Roger (Soper’s Hole, 284/495-4559), a seaside restaurant that also boasts a friendly bar and live music several nights a week. Acts sometimes include rockers from the United States.