Gallipoli may be best known for its wartime history, but Apulia’s island-like fortress retains a southern Italian charm all its own. Colorful fishing boats dart around the old city walls, while resilient stone churches peer across a medieval bridge to the mainland port.

A Puglia port town that’s equal parts historic and functional, Monopoli makes a splash with medieval churches and castles jutting above the Adriatic. It’s also a painter’s dream, with bright blue fishing boats adding a pop of colour against whitewashed harbour walls.

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.

Overlooking the azure waters of the Adriatic Sea, petite Polignano a Mare is home to some of Puglia’s loveliest beaches. Ringed by dramatic cliffs, the Lama Monachile Beach—also known as Cala Porte—is one of the most coveted, and most photographed, in the region.

It’s nicknamed the Eternal City for a reason. In Rome, you can drink from a street fountain fed by an ancient aqueduct. Or see the same profile on a statue in the Capitoline Museum and the guy making your cappuccino. (Which, of course, you know never to order after 11 am.) Rome is also a city of contrasts—what other place on earth could be home to both the Vatican and La Dolce Vita?

Everyone’s heard the Doors of Paradise, the Duomo, and Michelangelo’s David are captivating, but in Florence, beauty can sneak up on a traveller unexpectedly. You’ll duck into a random church to escape the heat only to spend two hours staring at an impossibly pure blue in a fresco. Or you’ll consider writing a sonnet about pear gelato. It’s just that kind of place. Don't miss the sunset over the Arno and the famous wines of the Chianti region just south of town.

This resort town, with its great beaches, has a bit of a Spring Break atmosphere (the parties start in the late afternoon and go all night). If dancing in a bikini is not your thing, though, no worries—you can explore a mediaeval monastery or enjoy cruises on the lovely blue water. Families will want to visit Water World, the biggest theme waterpark in Europe.

Portimao is a sailor’s delight, thanks to its calm waters and beautiful conditions. Plenty of elite international competitions happen here, but you don’t have to be a professional to set sail. Cruising the coast on the double-masted Santa Bernarda pirate ship is a family favorite. On dry land, you can wander the lovely Alvor boardwalk, enjoy a succulent seafood meal or zip around the go-kart track at the Autódromo Internacional do Algarve.

With the dramatic backdrop of 12,200-foot Mount Teide towering behind the resort, Adeje makes an unforgettable holiday destination. Adeje is less than two miles from the boisterous nightlife of Playa de las Americas, allowing visitors to choose whether to take it easy or to party. Bake in the sun on black volcanic sands before cooling down at a water park, such as popular Siam Park, or out windsurfing. Barranco del Infierno, Hell's Gorge, is a lush oasis, perfect for hiking.