From ornate mansions to ocean views, this charming city - the largest in Maine - will enchant you. Saunter down the brick sidewalks and cobblestone streets of the revitalized Old Port District, where you can browse through bookstores, explore craft shops and eat to your heart's content. Visit the Portland Head Light, which dates back to 1791, and is the oldest lighthouse still in continuous use in the U.S. The great poet Henry Wadsworth Longfellow is the city's native son, and you can visit his childhood home, the Wadsworth-Longfellow House. With kids in hand, enjoy the highly interactive Children's Museum of Maine. And then go next door to the calmer Portland Museum of Art, a small, but eclectic museum with Impressionist works, Maine landscapes by Homer and Wyeth and other collections. Land or sea is an option here, so if you're tired of the street life, take one of the popular scenic cruises or whale watches, or hop on a ferry to the islands in Casco Bay. At the end of the day, and without kids in hand, unwind and rest your tired feet at one of the city's brewpubs.

It took George H.W. Bush to make Kennebunkport known to most of the country, but New Englanders have enjoyed this quiet coastal Maine town for years. In hot weather, beaches are a major draw, but Kennebunkport's many small boutiques, art galleries and restaurants make a visit fun at any time of year. Inveterate shoppers may want to combine a visit to Kennebunkport with a trip to nearby Kittery, where dozens of outlets and factory stores offer plenty of bargains.

Crystal clear waters beckon from the south part of this tranquil Caribbean islet, a hundred miles south of Havana and known for its17 miles of stunning white sand beaches, mangrove forests and scuba diving to the black coral reef. The largest of the 300 keys and islets in Los Canarreos Archipelago, waters in the north are much cloudier. Cayo Largo also offers excellent deep sea fishing. Rent a jeep to explore the islet’s few roads and paths or trot across coral sand beaches on horseback.