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?

Founded by the Berbers in the 2nd millennium BCE, the city of Tunis has been controlled by Phoenicians, Romans, Arab Muslims, the Ottomans, the Spanish, the French and the Germans, finally achieving independence as the capital of Tunisia in 1956. This history has made Tunis a mélange of ancient and modern cultures. The medina is a network of narrow alleyways, mosques, mausoleums, palaces and a souq where shoppers haggle over the price of everything from filigreed gold to inexpensive souvenirs.

Over the centuries, many cultures have added their mark to this prized piece of land. Today, you can experience those influences firsthand by exploring Istanbul’s mahalles (neighbourhoods). From the holy sites of Sultanahmet and the 19th-century European elegance of Beyoğlu to the high fashion of Nişantaşı, the vibrant café society of Kadıköy and the football-loving streets of Beşiktaş, it’s easy to see why travellers say that Istanbul isn’t just one city, but many cities within one.

Cairo’s an ancient city that also happens to be a modern metropolis—it’s one of the biggest cities in the Middle East and has the traffic and noise issues to prove it. But as long as you’re not looking for solitude, Cairo—the City of the Thousand Minarets—is a splendid place to explore Egyptian history and culture. (Editor's note: Our list was compiled before political unrest prompted many countries to issue travel warnings for Egypt. If you're currently planning a trip to Egypt, please consider the risks and monitor your government's travel alerts.)

The beach town of Kololi is one of Gambia’s most popular vacation spots. Spend a day lolling on the golden sands, then explore “the Strip,” Kololi’s main throughfare, lined with restaurants, hotels and nightclubs. Brave the bush on a guided safari, chatter with the monkeys of Bijilo Forest Park and bargain for handmade treasures at the Senegambia Craft Market.