Skip the endless searching: this is the definitive list of romantic things to do in Key West, Florida. 6 editor-curated spots, ranked by distance from downtown — Campiello for dinner — with practical date ideas and what-to-do highlights for every stop.
Planning the trip itself? Browse tours and experiences in Key West, Florida →
Romantic Dining109 mi1177 3rd St S, Naples, FL 34102
Old Naples' Tuscan landmark — a lantern-lit courtyard on Third Street South where the town's best-dressed evenings begin.
Romantic Dining109 mi1180 3rd St S, Naples, FL 34102
A raw bar and forty salts of the world — crudo, oysters, and handmade pasta on Third Street's most elegant corner.
Romantic Dining110 mi605 5th Ave S, Naples, FL 34102
Fifth Avenue's crown of Mediterranean seafood — Dover sole carved tableside, a deep champagne list, and candlelight under the palms.
Romantic Dining110 mi698 5th Ave S, Naples, FL 34102
Naples' palm-lined showcase street — candlelit patios, courtyards, and wine bars steps from legendary Gulf sunsets.
Romantic Dining112 mi9891 Gulf Shore Dr NW, Naples, FL 34108
Toes-in-the-sand fine dining at La Playa — candlelit tables on the sand, Gulf sunsets, and champagne at the water line.
Classic Romance< 1 miMallory Square, Key West, FL 33040
Every evening the island gathers for one of the most spectacular sunsets on earth with street performers.
Outdoor Adventures127 mi8700 Estero Blvd, Fort Myers Beach, FL 33931
Paddle hand-in-hand through emerald mangrove tunnels where manatees glide, then shell a nearly-empty beach at sunset — pure Old Florida romance.
Classic Romance129 mi3251 S Miami Ave, Miami, FL 33129
An Italian Renaissance villa and formal gardens on Biscayne Bay — Miami's most breathtakingly romantic backdrop.
Scenic & Sunsets130 mi100 Estero Blvd, Fort Myers Beach, FL 33931
The beach town's beating heart — a palm-lined pedestrian square where the fishing pier meets the sand, with live music, barefoot bars, and the Gulf's best people-watching.
Romantic Dining131 mi3201 Rickenbacker Cswy, Miami, FL 33149
The definitive Miami view — floor-to-ceiling glass with the downtown skyline glittering across the bay, and champagne poured as the light goes gold.
Classic Romance132 mi112 Periwinkle Way, Sanibel, FL 33957
World-famous shelling beaches and Gulf sunsets beside a historic lighthouse — the quietest, most romantic island evening in Florida.
Scenic & Sunsets134 mi100 Ocean Dr, Miami Beach, FL 33139
Where dunes, boardwalks, and the pier meet the Atlantic — golden-hour walks with cruise ships on the horizon.
Yes — Key West, Florida is one of our 167 curated romantic destinations, with candlelit dining, sunset views, and quiet corners for two. This guide covers our editor-vetted favorites, sorted by distance from Key West.
Couples come to Key West for sunset strolls, special-occasion dinners, and scenery worth sharing. Start with the places listed above — each entry is curated, described, and easy to reach from Key West.
Romance here is year-round, but shoulder seasons mean smaller crowds and easier reservations. The seasonal picks on our home page help you time the trip.
Pick your favorites from this guide, add them to your itinerary with the My Itinerary tool, and browse local tours and experiences for the splurge-worthy part of the day.
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