Sail away. That probably should be the license plate motto on Tortola, the sailing center of the Caribbean's favorite cruising grounds, the British Virgin Islands. Whether you're an experienced sailor planning to "bareboat" your way from island to island, or look forward to hiring a skippered ("leave the driving to us") yacht, or just out for a day sail, the harbor at Road Town is the perfect place to start: The winds are usually steady, the sailing is easy, and there's always a buffet line of nearby islands to choose from.
But Tortola is the one island in the BVI that calls for some extended shore leave. Driving around the island's steep and winding mountain roads is not for the faint of heart, but the views are breathtaking. Some of the finest beaches in the entire island chain are here (the best, Cane Garden Bay and Long Bay, are on the north shore, where surfers also head to Apple Bay), and the restaurants are some of the most highly regarded in the Caribbean. Shopping and nightlife tend to be low-key, but you'll find a reggae-steady assortment of small clubs in Road Town (waterfront capital of the BVI) and in beach bars around the island.