Coastal Slovenia’s largest town, Koper is something of a well-kept secret. Koper’s central core is delightfully medieval and rich in history. Not far from the port, the Old Town centers around Titov Trg, a plaza filled with Venetian-influenced landmarks, from its Gothic-style loggia to the Praetorian Palace and Da Ponte Fountain, a replica of Venice’s famous Rialto Bridge. The Cathedral of The Assumption, also called Koper Cathedral, features a four-story tower with sweeping bay views and houses one of the oldest bells in Slovenia.

Kirkwall is the largest settlement and capital of Orkney, an archipelago in the north of Scotland with history tracing back to Norse times in the 11th century. With history such as this, ancient archaeological sites are the highlight of a visit. The most important monuments can be found at the Heart of Neolithic Orkney, designated a UNESCO World Heritage site. The Ring of Brodgar is one of the finest known truly circular Neolithic stone rings. Other sites that are fascinating to tour are Maeshowe, the Standing Stones of Stenness and the ancient Neolithic village of Skara Brae.

Closer to Cuba than to Miami, the southernmost city in the continental United States can feel like a country all its own. Home to free spirits, scuba divers and six-toed cats, Key West is defined by its quirky charm. People go barefoot, chickens roam the streets and eclectic culture rules. Architecture lovers will appreciate classic Caribbean villas, unique Keys conch houses and Victorian and Queen Anne gingerbread homes. Shopping opportunities range from many music and book shops to trendy designer boutiques.

Of the four main British Virgin Islands, Jost Van Dyke is the smallest. Fewer than 300 residents call its three square miles home, but they extend a warm welcome to the sailors and yachtsmen who drop anchor in Great Harbour and White Bay throughout the year. Life here revolves around the surrounding seas – swimming, snorkeling, fishing and diving – and communing over a tropical cocktail and a freshly caught meal at one of Jost Van Dyke’s legendary beach bars and restaurants. The island’s rugged terrain is crossed with trails.

The site of a Puritan colony established in 1629, Providencia is a remote gem of striking topography, golden beaches and turquoise blue waters. Pirate Henry Morgan made this his base to raid the Spanish empire, and treasure is rumored to be buried here. Far from the Colombian mainland, the island feels more Caribbean than Colombian and more English than Spanish, as Creole is spoken and road signs have English town names.

Just south of La Romana is an island paradise that gives an idea of what these environs were like back in 1698 when pirate William Kidd anchored his ship offshore and fled his English pursuers. While less than six square miles in size, Isla Catalina supports diverse ecosystems including sand dunes, mangrove forests and impressive coral reefs. The entire island is a national park and rich in wildlife with numerous species of birds and tropical fish. Catalina is a haven for diving and snorkeling, and equipment can easily be rented.

The friendly village of Invergordon is your gateway to the Scottish Highlands. Visit Cawdor Castle, built in the 14th century and considered one of the most stately homes in the Highlands. The founding family, the Thanes of Cawdor, live there to this day. Next up is Dunrobin Castle, the ancestral home of the Clan Sutherland and one of the oldest inhabited houses in Scotland, featuring stunning formal gardens that run down to the sea.

One of Europe's favorite playgrounds, Ibiza boasts more than 100 miles of coastline frosted with exquisite beaches. It's a hub of sun worship, white sand, beach bars and clubs that buzz all night. And there's history too. The fortified Old Town, known as Dalt Vila, is a UNESCO World Heritage site and a spectacular example of Renaissance military architecture. Carrer del Calvari leads to Portal Nou, the entrance through the old city walls, and a walk up the hill reveals panoramic views of the city.

Super yachts crowd the harbor and waterside bars hum with wealthy vacationers and young partiers in this posh island getaway with a laid-back Mediterranean vibe. The island of Hvar is famous for its lavender fields, vineyards, year-round sunshine and nonstop nightlife, but it’s also rich in culture and history. Near the harbor stands a Benedictine convent where nuns fashion lace as part of a 150-year-old tradition recognized by UNESCO as an Intangible Cultural Heritage.