NEWS FLASH: If you're a U.S. citizen, traveling to Cuba is every bit as illegal as it's been since the passage of the Trading with the Enemy Act in 1963. Exceptions may be granted to journalists, students, government officials, and athletes (if you're game for the bureaucratic hassle, contact the Office of Foreign Assets Control at 202-622-2520 or www.treas.gov/ofac), but most folks opt to slink in through a third country. Cubana, Cuba's national airline (514-871-1222; www.cubana.net), has regular flights between Havana and Toronto, Montreal, Mexico City, or Cancún, as well as points in Europe, the Caribbean, and Central America. Just be sure to keep your tickets for the Havana leg separate, since Americans showing an airline reservation with a connection to Cuba won't be allowed on the flight out of the States. And when entering Cuba, make certain that your passport does not get stamped. Commit this to memory: "Por favor, no me selle el pasaporte." Officially, U.S. citizens need visas, but a tourist card will suffice. Get one through your airline or the Cuban consulate in Ontario (613-563-0141).

GUIDED TRIPS: A few American companies have been authorized to offer so-called "study tours" of Cuba, but don't be frightened: The phrase is merely a foil for the bureaucrats. San Francisco–based Global Exchange (800-497-1994; www.globalexchange.org) has ten-day cycling tours through Havana and beyond for $950. Canada's MacQueen's Bicycle Tours (800-969-2822) offers one- and two-week bike tours through the island's mountains and villages, as well as trips that let you choose among diving, fishing, or cycling each day. Or you can simply have MacQueen's book your flight, hotels, and rental car and create your own itinerary. Tours range from $869 to $2,000.

ON YOUR OWN: If you know Spanish and have the fortitude to deal with impromptu hairy eyeball interrogations, getting around is a cinch. Bus service is available throughout the island (Empresa Omnibus Nacionales is the state agency—reservations are recommended; 011-7-70-6155), rental bicycles abound, and car rentals (no, they're not all junkers) cost what they do back home (Havanautos is the largest agency in Havana, 011-7-33-2369). And though sea kayaking is risky and camping is not allowed, there's plenty of adventure to be had. Some of the best diving in the Caribbean is off the northwestern coast of Cuba on Isla de la Juventud. The International Scuba Diving Center offers a certification course, beginner lessons, and gear rentals ($30–$200; 011-61-9-8282). For something more remote, consider the El Salton eco-lodge, which sits at the base of a 65-foot waterfall nestled in the Sierra Maestra Mountains northwest of Santiago. The hiking, horseback riding, and jasmine-scented air make it well worth the trek. Rooms start at $65 a night; call 225-33-6336 in Cuba, or contact MacQueen's Bicycle Tours.

For further DIY details, try Cubanacan in Toronto (416-601-0343) or Informacion Nacional in Havana (011-7-32-1269). —CHRISTIAN NARDI