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WINNER WONDERLAND
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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.
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    *Prices are based on 1-21 day travel. These are the best fares found by travelers who searched TripAdvisor and a select group of our fare search partners in the past 72 hours. Ticket prices and seat availability change rapidly and cannot be guaranteed.