Café Marquesa photo
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If you know us, you know we’re passionate about Key West. There’s a special kind of magic down in the Southernmost City beyond the buzzy Duval Street scene lined with bars and dives. There are wonderful restaurants scattered throughout the town that are intimate, charming, and serve dishes that feel as though they were home-cooked. At these special restaurants, the service is spectacular, the seafood is fresh, and the people are warmly welcoming in that genuine, down-to-earth Key West way. So, it’s no surprise to us that this paradise at the very end of U.S. 1 is now shining in the spotlight for romance, too.
According to Tripadvisor’s 2025 Travelers’ Choice Awards, where fewer than one percent of its eight million listings earn the “Best of the Best” trophy for each category, a pair of Key West restaurants have snagged national honors in the coveted Date Night category. And one has been honored as the best date night restaurant in the entire country.
Why does this matter, especially for us here in Miami? The fall and winter months bring out the best of Key West: softer light, gentle breezes, abundant fresh-seafood menus, and a mood that’s relaxed yet refined. And by early December, almost every street light and charming house will be decked out in Christmas cheer. It’s only about a three-and-a-half to four-hour drive from Miami, so an overnight escape or a slow-moving weekend feels completely doable. Therefore, get ready to plan your next date night (or full weekend getaway) without hesitation.
Red Shoe Island Bistro photo
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No. 1 Red Shoe Island Bistro in Key West
Red Shoe Island Bistro earns its title as the best date night spot in the U.S. for all the right reasons. This cozy Key West gem serves up fresh Florida seafood in a laid-back, romantic setting that feels effortlessly special. From yellowtail snapper and Key West shrimp to creative daily seafood specials, every dish feels one-of-a-kind and made with care. The restaurant is also known for its gluten-free options and its award-winning Key lime pie, the perfect sweet ending to a perfect evening. It’s the kind of place where time slows down, the food shines, and every date night feels unforgettable. P.S. – Order the seafood special of the day and don’t forget to end the night with one of their great desserts. 411 Petronia St., Key West; 305-509-7271; instagram.com/redshoeislandbistro.
Café Marquesa photo
No. 5 Café Marquesa in Key West
Café Marquesa is the perfect mix of upscale dining and classic Key West island charm – it’s truly one of our favorite spots for a double date or intimate dinner on the island. Café Marquesa snagged the No. 5 spot on Tripadvisor’s list of the most romantic restaurants in the U.S., and honestly, we couldn’t agree more. It’s the kind of place that makes you fall in love with Key West all over again. It’s tucked inside the beautiful Marquesa Hotel in the heart of the Historic Seaport area, where every corner feels warm, elegant, and picture-perfect. The menu is a dream, featuring velvety lobster bisque (or whatever the seasonal version happens to be), perfectly seared seafood, and entrées plated so beautifully you’ll hesitate to take the first bite (don’t miss the crispy duck breast if it’s there in season). The espresso martinis are just as flawless — smooth, strong, and the perfect way to cap off the night. Café Marquesa somehow manages to feel both sophisticated and cozy, making it one of those rare spots where romance, great food, and old-school Key West charm come together effortlessly. If you’re looking for fine dining in Key West, look no further. 600 Fleming St., Key West; 305-292-1244; marquesa.com/cafe-marquesa.
