An Old Town icon, the Sofitel Legend Santa Clara is a smart pick for travelers who appreciate high-tech modern conveniences as much as colonial architecture. The 123 French-influenced rooms and suites are spread between two 17th- and 19th-century wings separated by gardens and courtyards; the former includes parts of a former convent replete with original crypts, confessionals, and secret windows. Accommodations lean on the contemporary side with signature MyBed mattresses, Nespresso machines, and Lanvin toiletries. True to Sofitel form, the property also offers the full range of luxury amenities, from a large outdoor pool and nearly 9,000-square-foot spa with solarium to a sun-drenched poolside bar, 24-hour room service, and three on-site restaurants. Opt for clubby El Coro Lounge to dine on tapas and sip mojitos with a live-music backdrop.