When it comes to romance, there’s no place like Italy. You've got the history of Rome, the art of Venice, the modern vibe of Milan, the dreamy Mediterranean coastline, the wines of Tuscany, the pizza from Pisa ... Since the mid-summer weather can be scorching, try to plan your trip at the start or the end of summer so you can stroll the parks, squares, and promenades without your third serving of gelato melting faster than you can enjoy it. Where to Stay: For your own private island — on a floating city — stay at the J.W. Marriott Venice. While in Tuscany, drink your fill of wine at Castello di Casole. As for the coast? There are fabulous options on Airbnb.