The most ROMANTIC Things to Do in St. Augustine, Florida


Start your romantic night with champagne and charcuterie at Michael’s, 25 Cuna St., downtown St. Augustine.

Let’s face it, St. Augustine is just plain romantic. From the historic streets and buildings to the gorgeous beaches, the area is a ROMANTIC destination — for weddings, weekend getaways, holiday celebrations and so much more! Here’s a list of the Top 6 most Romantic Things to Do in St. Augustine:


Take a stroll in downtown St. Augustine, also known as the historic district. While Saint George Street is the main thoroughfare for foot traffic (vehicles are not allowed), there are endless other little streets to discover. Aviles Street is the oldest mapped street in the U.S. — filled with art galleries, shops and restaurants. Cordova Street also is lined with fun shopping spots and eateries, old cemeteries and even a love tree (a palm growing through an oak tree), which is believed to give good luck to happy couples when they kiss under the entangled trees! Cuna Street is also lined with boutiques, art galleries and restaurants. Just park downtown and EXPLORE.

For more on St. Augustine’s love trees:

How to pay LESS for PARKING:

Self-guided walking

St. Augustine Lighthouse & Maritime Museum courtesy of the nonprofit museum.


The top of the St. Augustine Lighthouse is a romantic spot, with breathtaking views of the St. Augustine area. Couples often climb in the evening just before sunset. The Lighthouse tower is also one of the most popular spots for marriage proposals! Hours are 9 a.m. to 6 p.m. seven days a week. Details at

Bayfront Marin House has amazing views of the Matanzas bay in downtown St. Augustine.


Bed and Breakfast Inns are the most popular choice for a romantic stay in St. Augustine. Staying at the B&B locations in the historic district is best when you want to experience the city by foot. Here are two good resources for finding the inn that fits your expectations — The St. Augustine Inn Association, and the Inns of Elegance,

Catch 27 offers innovative dishes and amazing fresh seafood.


There are dozens and dozens of romantic restaurants in St. Augustine in downtown and at St. Augustine Beach. Here’s our Top 10 dining list:

Catch 27, 40 Charlotte Street, downtown St. Augustine

Collage, 60 Hypolita Street, downtown St. Augustine

Old City House Inn & Restaurant, 115 Cordova Street, downtown St. Augustine

Michael’s St. Augustine, 25 Cuna Street, downtown St. Augustine

Black Fly The Restaurant, 108 Anastasia Boulevard, St. Augustine (on the island)

The Ice Plant, 110 Riberia St., downtown St. Augustine (Lincolnville)

The Reef, 4100 Coastal Highway, St. Augustine (north of Vilano Beach)

Cap’s on the Water, 4325 Myrtle Street, St. Augustine (north of Vilano Beach)

Costa Brava (formerly 95 Cordova), 95 Cordova Street, downtown St. Augustine (inside the Casa Monica Hotel)

The Raintree, 102 San Marco Ave., uptown St. Augustine

The St. Augustine Amphitheatre plays host to outdoor concerts year round.


St. Augustine has some of the most talented musicians performing in area venues every night of the week! Acoustic solo shows are popular at restaurants, while full bands play at bars and other venues throughout St. Augustine. Jazz, folk, country, rock ‘n roll, classical — there’s a genre for all tastes. If you are strolling in downtown, you can often see and hear the music at locations along St. George Street including the Colonial Oak Music Park and Prohibition Kitchen. Stop in for a drink and a few songs! For an even more romantic evening, the St. Augustine Amphitheatre, the Ponte Vedra Concert Hall, and Lewis Auditorium at Flagler College (EMMA Concert Association) offer concerts by big names in music — from international orchestras to the Avett Brothers and Santana. The music scene is THRIVING here!

The San Sebastian Winery offers free tastings.


Horse-drawn carriage tours, food & wine tours, helicopter tours, chocolate-tasting tours — there are DOZENS of ROMANTIC tours in St. Augustine! Here are some of the tours offered:

FREE tours (and often tastings):

Other tours:

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