ISLA MUJERES, MEXICO
No fewer than 30 U.S. cities (Seattle, Chicago, and, in 2013, Minneapolis, St. Louis, and Dallas) offer nonstop flights to Cancún. Isla Mujeres, a dialed-down Caribbean island and one of Jacques Cousteau’s old haunts, is just a 20-minute ferry ride away. Stay at the Ixchel Beach Hotel (from $139), which sits smack on Playa Norte’s pristine beach, and snorkel the nearby Manchones Reef.
RINCON, PUERTO RICO
Warm winter surf is easy to get to in Puerto Rico. Fly nonstop from New York City (JetBlue), Newark (Continental), or Atlanta or Ft. Lauderdale (Spirit Air) to Aguadilla, a 30-minute drive from Rincón. The charming Casa Islena Inn (from $125) is reasonable and on the beach. Surfing instruction is ubiquitous here, with Surf 787 ($90 for a two-hour lesson) and Surf Lessons Puerto Rico ($175 per day) topping the list.
Nearly on the shore of Venezuela, Tobago is reachable nonstop with a four-hour Caribbean Airlines flight from New York. Stay at the relaxed Kariwak Village (from $165), bask at the secluded beach at Englishman’s Bay, dive Buccoo Reef, or hire Newton George to show you some of the island’s 470 bird species.
With direct flights from San Francisco and Los Angeles (United and American), Phoenix (America West), and, starting this month, Portland, Oregon (Alaska Airlines), Kauai is closer than you might think. Stay at the boutique Koa Kea hotel ($369) at Poipu, on the island’s sunnier south shore. But explore the stormier north shore’s surf breaks—like Hideaways and Tunnels Beach in Hanalei—and the wild Na Pali Coast, on a guided sea-kayaking trip with Na Pali Kayak Tours ($200 per day).
Three hours nonstop from Miami on InSel Air or five-plus from Newark on Continental Airlines lands you in Bonaire, a divers’ island in the Dutch Antilles, just off the coast of Venezuela. Dive at Angel City or windsurf at Taylor Maid. The owners of the six-room Coral Paradise Resort (from $1,886 per week for two, including dive package and vehicle) can make it all happen for you.