Boca Grande on Gasparilla Island, Florida, Is America's Best Small Beach Town

"I stop at this island-favorite ice cream shop—opened in 1988 by the manager’s grandfather—for hand-dipped Amish ice cream, sorbets, specialty sundaes, shaved ice, all-fruit smoothies, açaí bowls, and coffee; they also sell snacks, beer, wine, bagged ice, and souvenirs, and there’s Tortuga, an outdoor walk-up window behind the storefront serving authentic Mexican food. The Pink Pony is a generations-old Boca Grande tradition that reopened soon after Hurricane Ian, embodying the community’s resilience." - Skye Sherman Skye Sherman Skye Sherman is a travel writer based in West Palm Beach, Florida. Aside from traveling, she's also a pilot, scuba diver, bookworm, and fourth-generation Floridian. Her work has appeared in Travel + Leisure, USA Today, Palm Beach Illustrated, Atlas Obscura, and more. Travel + Leisure Editorial Guidelines