The best time to go to the Hamptons is earlier than the crowds descend and right after they go away. Alexandria’s Old Town is full of canine lovers and dog-loving venues, and the Lorien Hotel & Spa, on one of its most charming brick-lined streets, welcomes breeds of all sizes. The rooms’ outside terraces are ideal for four-legged vacationers, and there’s a dog-friendly park a block away at the finish of Harvard Street. With outsized home windows overlooking the town and Lake Michigan, The Ritz-Carlton in Chicago’s swanky Gold Coast neighborhood is for canine who expect five-star service. When the climate is nice, friends can stroll their pets to many of the city’s best shops or hang around on Navy Pier. In colder climate, they may choose to stay in and revel in their spacious room or suite together.
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