Bermuda
Bermuda has a leg up on most other islands because it is further north and thus closer to continental North America; the drawback is that, unlike its Caribbean neighbors, Bermuda does not experience tropical weather year round, with a climate more like that of the Carolinas.
Bermuda is just 693 miles south of New York (and 770 miles southeast of Boston and 729 miles south of Halifax, Nova Scotia), with direct air service from these cities as well as Atlanta, Charlotte, Chicago, Detroit, Ft. Lauderdale, Miami, Philadelphia, Toronto, and Washington, D.C. Airlines serving Bermuda include Air Canada, American Airlines, Continental, Jet Blue (as of May 6, 2006), United, USA 3000, and US Airways.
So, if you catch American Airlines' 9 a.m. daily flight out of New York/JFK, you'll touch down in Hamilton in just over two hours -- about as long as it takes to drive from New York to Philadelphia. You could leave home on a chilly spring morning and be curling your toes in some pink Bermuda sand by lunchtime. Bermuda is just 20 square miles, meaning that no matter where you stay, you'll find all of the island's attractions just a short taxi or scooter ride away.
If you have slightly more than a weekend, Royal Caribbean offers five-night cruises from New York and Baltimore to Bermuda between May and October.
San Juan is a popular weekend getaway destination thanks to its myriad of nonstop flights from the U.S., including service from low-cost carriers at prices that can make a few days in San Juan a reasonable alternative to a weekend on the Jersey Shore or Myrtle Beach. And once you touch down at Luis Munoz Marin International Airport, beach resort areas like Condado and attractions like Old San Juan are literally minutes away. San Juan accommodations range from budget to luxury, so you won't have to overspend for a quick getaway.
Jet Blue and Spirit Airlines compete with the major airlines like Alaska Airlines, American, Continental, Northwest, United, and US Airways. A nonstop from New York will have you in San Juan in 4 hours; a flight from Chicago takes just 40 minutes longer.
The Bahamas offer a pair of tempting destinations for weekend getaways and short trips. Nassau, home to Atlantis and the other resorts of Paradise Island and Cable Beach, is just three hours from New York and is well served by both traditional and low-cost airlines, including AirTran Airways, American, Air Canada, Air Jamaica, Continental, Delta, JetBlue, Spirit Air, and US Airways.
Atlantis can be a bit pricey for a weekend away, but you'll find options like the Comfort Suites Paradise Island at about half the price.
Many travelers also don't realize that the Bahamas are as close as 50 miles to the Florida coast, making sea travel another popular option, particularly from Miami and Fort Lauderdale. Discovery Cruise Line, for instance, takes more than 200,000 passengers each year to Grand Bahama Island, partnering with the Our Lucaya resort for stays as short as one and two nights (the cruise line also does same-day roundtrips from Fort Lauderdale for those who want just a taste of island life).
Our Lucaya is perhaps a 20-minute drive from the airport in Freeport, but once you are at the resort you won't have to leave: beaches, casino, restaurants, nightlife, and even a small straw village are just steps away. The Westin and Sheraton resorts at Our Lucaya offer rooms at various price points, and the small, independent eateries at the straw market mean you don't have to go broke paying resort restaurant prices every night.
American Eagle is now flying nonstop on weekends from Chicago/O'Hare to Freeport; Continental has three-hour nonstops from Newark, and AirTran flies nonstop from Baltimore.
Cancun, Punta Cana and Cozumel
The Mexican Caribbean is just 3 to 4 hours by air from the East Coast of the U.S. (5-6 hours from the Midwest), making it a viable weekend getaway destination, especially for bargain-hunters who can take advantage of low rates on Mexican all-inclusive resorts. If sleeping on the beach by day and partying all night is your idea of a Caribbean weekend blowout, head for the Riviera Maya!
