19 Unexpected Honeymoon Destinations in the U.S

Gasparilla Island, FL

Coined as the “preppiest place on earth,” Boca Grande, the heart of Gasparilla Island, offers travelers a taste of Florida’s yesteryear. Clustered around the old train depot that brought industry to this pint-sized village, this small, intimate locale has evolved into a playground for discerning travelers. Here, you’ll find vibrant, patterned clothing (think Vera Bradley meets Lilly Pulitzer) along with vintage shops and restaurants. Gracing the outskirts of town is the century-old Gasparilla Inn & Club, an iconic resort with trellis-patterned carpets, shell-encrusted décor, and old hardwood floors that evoke a classic, vintage Florida charm. Katherine Hepburn even rented a house on Gasparilla Island for several years. From there, island hop to other barrier islands within the Southwest Florida destination, including Sanibel, a world-class shelling locale and ideal spot for nature-loving couples (plenty of kayaking and home to the expansive J.N. Ding Darling Nature Reserve); Captiva, an artist community where you’ll find the private home of renowned American painter and graphic artist Robert Rauschenberg; and quirky dining options like the Bubble Room, a three-story venue decked out in nostalgic decor from the '30s, '40s, and '50s.

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