Romantic Things to Do in St. Augustine
Why honeymooners and couples keep coming back to America’s Oldest City.
St. Augustine has been drawing couples for generations, and it is not hard to understand why. The city has everything romance requires, beautiful water, centuries of history that feel genuinely alive, exceptional dining, unhurried pace, and the kind of atmospheric streets that make people slow down and pay attention to each other. Whether you are honeymooning, celebrating an anniversary, or just escaping, here is how to do St. Augustine as a couple.
Where to Stay
The historic district bed and breakfasts are in a league of their own for romantic stays. Casa de Sueños on Cordova Street specializes in couples and offers that rare combination of genuine character, excellent breakfast, and a location that puts you steps from everything. St. Francis Inn, consistently rated among Florida’s top bed and breakfasts, has been hosting romantic getaways since 1791, complimentary lighthouse tickets, bicycles, and an innkeeper who actually knows the city are included.
For oceanfront romance, First Choice Florida Vacation Rentals books beachfront condos and cottages direct, no platform fees, and a kitchen means private dinners with the sound of the ocean outside. Ask specifically for Anastasia Island properties with balconies facing the water.
Sunset on the Water
A sunset cruise on the Matanzas River is the quintessential St. Augustine romantic experience. The light on the Castillo at golden hour, the Bridge of Lions backlit against the sky, and the Matanzas Bay turning copper, it is genuinely beautiful and not something you see from land the same way. Several operators run dedicated sunset cruises ranging from sailing vessels to party-boat options. For couples, the sailing cruises are the right call, smaller, quieter, and more intimate than the larger vessels.
Sunset Sailing Cruise
Two-hour shared sunset sail along the historic bayfront. The view of St. Augustine from the water at golden hour is one of the best in Florida. Small group size keeps the experience intimate. Some operators include wine and appetizers.
Private Boat Charter
Several operators offer private vessel charters for couples, your own boat, your own pace, your own itinerary on the water. More expensive than shared cruises but genuinely private. Some operators accommodate special occasions including proposals with advance notice.
The best free romantic experience in St. Augustine: walk Avenida Menendez along the bayfront after dinner, when the crowds thin and the Castillo is lit against the night sky. The Bridge of Lions glowing over the Matanzas River is genuinely beautiful and costs nothing.
Dining for Two
Columbia Restaurant on St. George Street is the occasion dining choice, 1905-era Spanish recipes, tableside salad preparation, and flamenco dancers on weekend evenings. Reservations are essential, particularly on weekends. The Floridian was a local favorite that has unfortunately closed, but the dining scene continues to evolve with strong options along the waterfront and throughout the historic district.
For something more casual but equally atmospheric, Cathedral House Garden has courtyard seating in a historic setting that most tourists walk right past. Ask a local rather than trusting the obvious tourist-district recommendations.
Experiences Worth Booking Together
Horse-Drawn Carriage Tour
A private horse-drawn carriage through the historic district at dusk is deeply romantic and genuinely atmospheric. The clip-clop through centuries-old streets while the city lights come on is one of those experiences couples mention years later. Evening departures are significantly better than daytime ones.
Ghost Tour for Two
St. Augustine ghost tours are excellent date experiences, intimate, atmospheric, and genuinely interesting. The city’s paranormal history is well-documented and the guides are typically very good. Evening walking ghost tours through the candlelit streets of the historic district are a St. Augustine tradition worth experiencing together.
- Book sunset cruises and carriage tours at least a week ahead in peak season, these sell out
- The Nights of Lights holiday display runs November through January, the most romantic version of the city
- Vilano Beach north of town is quieter and less crowded than St. Augustine Beach for romantic beach mornings
- Several historic inns host small wedding ceremonies and elopements in their courtyards, worth inquiring if that is your plan
Plan Your Romantic Getaway
St. Augustine rewards couples who slow down. Book the sunset cruise, make the dinner reservation, and let the city do the rest.
Plan your romantic St. Augustine getaway: