Most Romantic Things to Do in St. Augustine

By Renee Unsworth

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 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 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 tour:


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

La Pentola, 58 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 Tasting Room, 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)

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

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


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’re strolling in downtown, you can often see and hear the music at locations along St. George Street and 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 Billy Idol and Sarah McLachlan. The music scene is THRIVING here!

Here’s the Music News list that is posted each week featuring St. Augustine musicians and bands:


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 

  • Fort Matanzas National Monument (free ferry to the Fort), 8635 A1A South, 904-471-0116,

OTHER tours


The art of live theatre is ROMANTIC — “bringing you all that is passionate, exuberant, profound, deep and dangerous in the human spirit!” Limelight Theatre offers year-round shows on two stages, while A Classic Theatre, Inc. stages classic and original plays in various venues throughout St. Augustine. In addition, Flagler College Theatre Arts  offers productions in downtown St. Augustine.

Limelight Theatre, 11 Old Mission Ave., uptown St. Augustine

A Classic

Flagler College Theatre Arts, 14 Granada St., downtown St. Augustine


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