Tortola, Charleston, Newport & More

San Juan, Puerto Rico’s capital and largest city, sits on the island’s Atlantic coast. Its widest beach fronts the Isla Verde resort strip, known for its bars, nightclubs and casinos. Cobblestoned Old San Juan features colorful Spanish colonial buildings and 16th-century landmarks including El Morro and La Fortaleza, massive fortresses with sweeping ocean views, as well as the Paseo de la Princesa bayside promenade.

Tortola is the largest of the British Virgin Islands in the Caribbean. It features several white-sand beaches, including Cane Garden Bay and Smuggler’s Cove. Road Town, the capital of the British Virgin Islands, has a harbor dotted with sailing boats and is known as a yachting hub. In the island’s southwest, forested Sage Mountain National Park offers trails and sweeping views over neighboring cays.

San Felipe de Puerto Plata is the capital of the Puerto Plata province on the Dominican Republic’s Atlantic north coast. The city is best known for its beaches. Playa Dorada’s lengthy beachfront is backed by resorts and an 18-hole golf course. The city’s old colonial-era center is dominated by the 16th-century Fortaleza San Felipe, a Spanish fortress that now houses historical and military artifacts.