Having spent lots of time in Key West and dining at so many restaurants...here are a few of our absolute favorites for dining recommendations. We are foodie, sommelier-level wine connoisseurs. You will DEFINITELY need reservations for these top spots, but it is so worth the effort!: 

• Flaming Buoy: divine food, awesome Star Wars motif, fun art. Very on-point for Key West.
• Santiago's Bottega: fabulous tapas, good vibe.
• Red Shoe Island Bistro (via OpenTable): OMG the food here was amazing. Their house specialty, Yellowtail fish, is out of this world.
• Lola's Bistro: this is BYOB...so grab a great bottle of wine or your preferred alcohol...and dine in this small, intimate bistro where the chef prepares your DELISH meal right in front of you.
• Louie's Backyard (Outdoor patio): cannot top the ocean views, sunset and balcony...exactly what you dream about when thinking about KEY WEST.
• Viv Wine Bistro: Intimate wine bar with hundreds of FABULOUS wines (even including Yalumba's tawny port!) with the option to order a very worth it charcuterie platter, supplied by the neighbouring french cafe. Gorgeous wine selection.
• Cafe Marquesa: Michelin-starred, white table cloth...impeccable dining.
• Better than Sex dessert lounge: Bring your R-rated audience to this charming, swanky loungy dessert bar...sexy and fun!! The menu will have you and your guest(s) ROFL>! Great late-night treat. We booked for 10p and the place was hopping!
• Gardens Hotel: D'Vines wine gallery and jazz daily 5-7p: This off-the-beaten-path wine gallery features a gorgeous metered wine bar where you can sample 1, 3 or 5 ounces of 50+ wines while live jazz wafts through the air...it's a terrific experience.