This former 17th-century convent mixes elements of its past (exposed wood ceilings, beautiful arched walkways) with modernity in a very graceful way: Rooms are either contemporary or colonial-style, and while the newer ones offer views of the pool or the Caribbean, colonial suites have antique furniture and overlook the Old Town or interior gardens. To play at being pious, check out Restaurant 1621, once the Clarist nuns’ dining room, which now serves French-inflected cuisine.
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At the No. 2 Best Hotel in Maui, guests are greeted with panoramic views of Wailea Beach and the Pacific Ocean. Accommodations are spacious (each room measures at least 600 square feet) and include lanais, locally inspired art, deep-soaking tubs and Nespresso coffee makers. On the resort grounds, travelers will find three saltwater pools, two tennis courts and a spa, but this resort's best attribute is its kid-friendly atmosphere. One of the island's most family-friendly properties, the Four Seasons Resort Maui offers everything from a game room to a waterslide to the brand's complimentary Kids For All Seasons activities program. (Courtesy of Four Seasons Resort Maui at Wailea)