Sitting on the south shore of Rhode Island, the town of Westerly is a quiet residential community in the winter, swelling in the summer to accommodate tourists eager to explore the local beaches, Narragansett Bay and the Rhode Island Sound. Just over the border from Connecticut, Westerly is conveniently located to the Aquarium at Mystic, as well as the Mohegan Sun and Foxwoods Casinos. Nearby, the picturesque village of Watch Hill features ocean views, ice cream shops, and craft boutiques.

Here in the heart of Rhode Island’s “Classic Coast,” you can choose your own adventure. Soak in miles of spectacular coastal scenery, study authentic Colonial and Gilded Age architecture, saunter along the wharves of the bustling waterfront, and sink your toes into the sand of stunning beaches. You can be inspired at the legendary mansions, be energized by the vibrant nightlife, and savor local flavour at our many celebrated restaurants, wineries and breweries.

From its origins as a Connecticut River trading post in 1633, Hartford has become not only the state capital but also the insurance capital of the world, with a slew of historical attractions, a thriving arts and entertainment centre, a revitalized riverfront and beautiful parks and public gardens. It was here that the lovable Huck Finn and Tom Sawyer were born in the imagination of celebrated author Mark Twain and immortalized on paper during the writer's Hartford years. Twain's home and those of fellow literary figures Harriet Beecher Stowe and Noah Webster are open to the public. The Wadsworth Atheneum, the oldest public art museum in the U.S., houses Pilgrim-Century furniture, the Amistad collection and a special treasure hunt system to entice kids to explore the museum's works. If your timing is right (end of June, beginning of July), you'll catch the Elizabeth Park rose gardens in bloom, but fall is also great for brilliant leaf colours, and spring yields colorful gardens and blossoming trees. For a bird's-eye view of the city, visit the observation deck of Travellers Tower, where you might also spot two resident falcons.

Sosua is everything you want a beach town to be. Clear waters teem with coral, perfect for snorkeling and diving. Above sea level you’ll find multicolored sands lined with beach shacks. This small enclave of the Dominican Republic was once a haven for Jewish refugees. Historic sites and synagogues offer great perspective on Sosua’s postwar identity. On a lighter note, a community of ex-pats helps fuel a boisterous, international nightlife scene.

Forget fashionable footwear, only your most comfortable shoes will cut it in Killarney. It's a walking town, and every trail is a history lesson. Journey on foot through Ireland's first national park, 26,000 acres of woodlands, sandstone mountains and low-lying lakes. When your feet wear out, take in Killarney National Park via boat from Ross Castle. And because there are more hotel beds in Killarney than in any other Irish town or city (besides Dublin), you'll always have a place to rest your head (and feet).

Thanks to its unique micro-climate, Nairn gets more hours of sunshine and less rainfall than other towns just a few miles away. Thankfully, this combination of abundant sun and no rain provide the perfect weather conditions for golf, as Nairn boasts two 18-hole championship courses. (And if you have time on your hands, there are 30 more courses within 60 miles.) Don't miss the town's jazz and film festivals, the latter of which was started by Nairn resident and actress Tilda Swinton (you'd know her if you saw her).

A patchwork of vineyards and olive groves, dotted with whitewashed hill towns and sun-bronzed beaches—Italy’s southern heel has no shortage of photogenic landscapes. There are a few surprises, too, including the baroque city of Lecce and the Itria Valley, with its UNESCO-listed trulli houses.