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It's a good idea to familiarize yourself with the general lay of the land in the BVIs before arriving. An online search will yield maps of both the BVIs as well as the main islands of Tortola, Virgin Gorda, Jost Van Dyke and Anegada. On Tortola, knowing general characterisitcs will be helpful. Identify the significant aspect of Tortola on your map...Road Town, East End/Beef Is and West End/Soper's Hole on the Sir Francis Drake Channel side; Smugglers Cove, Apple Bay, Cane Garden Bay, Brewers Bay, Josiah's Bay on the North Shore. This will give you a general feel for the island and help in planning your activities.
Unlike many Caribbean islands, Tortola is not resort oriented with fenced & gated compounds securing your every need. Quite the contrary, Tortola is one big resort with a very wide variety of beaches, restaurants, activities spread across the island. Crime is very low here and basic common sense will suffice to ensure your safety. You should feel free to explore the island as the people are friendly and helpful. Be certain to greet locals with "Good morning" or "Good afternoon" before asking your question as this basic courtesy is a cultural characteristic of the BVIs. It will make you feel good, too.
New visitors, especially those from the United States and Canada, should know that the British Virgin Islands, like the rest of the United Kingdom, drives on the left-hand side of the road. If you are not comfortable with this, taxis are plentiful and will get you anywhere you might want to go on the island. Ferrys and charter planes also serve well for getting between islands. Consider taking an aerial tour for that special airplane view of the BVIs. BVI-based airlines like Clair Aero or Island Birds have charter planes and helicopters with experienced pilots for hire.
It goes without saying that you came to Tortola for some quality beach time at some of the island’s pristine white sand beaches. Cane Garden Bay, Apple Bay, Brewer's Bay, Josiah's Bay and Smuggler’s Cove are great beaches with good swimming or surfing conditions. Sailing competitions are often held in these bays, so ask around (or look for announcement postings) to see if there will be a regatta while you are on Tortola.
Totrola, in fact the whole BVIs, are not big nightlife oriented destinations. If you love Cancun, you'll hate Tortola.
The "hottest nightlife" on Tortola can be found at Bomba’s Shack in Capon's Bay on the North Shore. Bomba's Full Moon Parties are legendary.
Cane Garden Bay offers live entertainment at both Myett's and Quito's Gazebo where local legend Quito Rymer & The Edge play regularly.
At West End/Soper's Hole you have The Jolly Roger for some of the best BBQ on the island and awesome live music Friday nights and Pusser's for more casual open-air dining and occasional steel pan live music. Both Restaurants draw a good crowd and are great bar spots. As this is the Caribbean, make sure to try a few of the rum drinks — particularly the famous “Painkiller” and “Bushwacker”.
Road Town offers great dining but the nightlife side is pretty much confined to the very fun Bat Cave at the Spaghetti Junction at Village Cay. A little further down the road at the East End you will find Eclipse. This is the closest thing to a club on Tortola, with closing hour TBD.
If you're considering Tortola, you will find an array of private villas and small inns for your choosing. Neighboring Peter Is Resort on Peter Is and Little Dix, Biras Creek and the Bitter End Resort on Virgin Gorda offer the high-end resort options in the neighborhood. You will find a very good representation of all of these in the listings provided here by Trip Advisor. The BVIs do not have the huge, gated resorts found in Mexico and the Dominican.
Alternatively, there is a vibrant Charter Sailing Industry offering bareboat or crewed charters for those who crave the freedom of the open water. A Google search will yield many options.
You can expect your stay in the BVIs to be very intimate, allowing for genuine interaction with a truely gracious culture.