History oozes from every corner of Corfu, an island prize coveted by a succession of maritime powers since the Peloponnesian War in the 4th century BC. But who can blame them? This Ionian idyll is the greenest of all Greek islands, swathed in orange and olive groves and endless beaches bathed by a cerulean sea. A UNESCO World Heritage site, the Old Town of Corfu includes the magnificent Esplanade, where you can watch a game of cricket from a sidewalk café. There are also beautiful palaces, castles and archaeological sites to explore.

Make sure to be on deck to witness sailing into one of the Aegean’s most spectacular sights: the volcanic caldera that is Santorini’s bay. Rising from the sea, the earth transforms into a wall of stone that looms in striating hues of ochres, grays and pinks. Dotted with the island’s iconic blue-domed churches, the whitewashed village of Fira hovers in the cliffs, bustling with shops, tavernas and a fine museum while clinging to the caldera’s rim.

Named as one of Canada's 50 Places of a Lifetime by National Geographic, L'Anse aux Meadows transports visitors back in time a thousand years. Perched on the northernmost tip of Newfoundland, the ancient Viking settlement is heralded as the oldest in North America and widely accepted as evidence of European contact here prior to Columbus. Discovered in 1960, L’Anse aux Meadows was named a UNESCO World Heritage site in 1978 and now brings the struggles of early settlers to life.

San Juan, the capital of Puerto Rico, is an intriguing blend of the old and the new. Founded in 1521, the city was a key port in the Spanish colonial empire, as evidenced by El Morro, the huge fortress that guards the harbor. Behind thick stone walls, Old San Juan retains its original character of blue cobblestone streets, elegant plazas and brightly colored heritage architecture. This lively center is the city’s – and island’s – cultural hub for museums, music, dining and more.