Vilamoura, Portugal

This sprawling tourist complex on Portugal's Algarve coast is one of the largest in Europe, covering 2,000 hectares of land. With a 1,000-berth marina, five golf courses, and a casino, Vilamoura caters to a well-heeled crowd seeking luxury. But beneath the veneer of opulence lies a persistent administrative headache - the town is privately owned, so navigating its bureaucracy can be a challenge.

The area was once an important Roman fishing outpost, and remnants of ancient baths and ruins still dot the landscape. Today, tourism dominates, with a glut of 3-5 star resorts and ample nightlife options. Chartered boats offer access to the region's picturesque caves, while bird-watchers can spot over 20 species in the 271-hectare nature preserve.

If you can handle the red tape, Vilamoura offers a polished, resort-style lifestyle. But those seeking a more authentic Portuguese experience may find this enclave a bit too manicured and insular.