As one arrives in Key West via the Overseas Highway from Miami, it’s very easy to be struck by just how unimpressive the island seems at first sight. The marinas, shopping centers, and fast food joints that are your first introduction to the “Conch Republic” are largely charmless. This is what’s known as New Town; it’s in the historic district called Old Town that has the romance and fun of Key West.

Historic buildings, tropical landscaping, quirky residences (and residents), and a deep sense of individuality combine to create a powerful atmosphere that’s quite welcoming but that must be met on its own terms.

Denizens of Key West are fiercely libertarian; from the grizzled mariners who live on houseboats in the historic marina to the flamboyant drag queens beckoning tourists into nightclubs, people here are strongly encouraged to be themselves. That extends to visitors as well, as long as you manage to be respectful of the fact that Key West is home to 25,000 people who were there before you arrived and will still be living there when you leave.

Getting to Key West

The 160-mile, two-hour drive to Key West from Miami is the ideal way to decompress in preparation for a relaxing vacation in the Conch Republic, and directions couldn’t be easier: just drive. The narrow Overseas Highway that connects Key West and the rest of the Keys to the mainland is a mostly two-lane road with very few connecting roads. There is absolutely no chance that you will get lost, as any substantial wrong turn will find you in either the Gulf of Mexico or the Caribbean Sea.

Key West does have an airport: Key West International Airport (EYW, 3491 S. Roosevelt Blvd., Key West, 305/296-5439), where American, Delta, Continental, and US Airways flights land after connecting through other Florida airports.

Another option is to take the Key West Express (888/539-2628, www.seakeywestexpress.com), a high-speed ferry with daily departures from Fort Myers on Florida’s southwest coast. The ferry ride is about 3.5 hours (compared to the five-hour drive), with round-trip fares costing $139 for adults and $75 for children.