St. Augustine’s Top 6 ROMANTIC Things to Do

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Start your romantic night with champagne at Michael’s Tasting Room, 25 Cuna St., downtown St. Augustine. Photo by Renee Unsworth

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 Top 6 most Romantic Things to Do in St. Augustine:

1. HISTORIC DISTRICT STROLL

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 joined 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: www.simplystaugustine.com/romantic/st-augustine-love-trees

How to pay LESS for PARKING: staugustinegovernment.com/sites/park

Self-guided walking tourwww.citywalkingguide.com/staugustine

2. ACCOMMODATIONS

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, www.staugustineinns.com and the Inns of Elegance, www.innsofelegance.com

3. DINING

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

  • 904-829-0055
  • collagestaug.com

    Bread with roasted garlic, olive oil, and balsamic vinegar is a romantic start to a meal at Old City House, Photo by Renee Unsworth

    Bread with roasted garlic, olive oil, and balsamic vinegar is a romantic start to a meal at Old City House, 115 Cordova St., downtown St. Augustine. Photo by Renee Unsworth

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)

Seafood pasta and other specialties are available nightly at The Raintree Restaurant, 102 San Marco Ave., the perfect spot for a romantic date in St. Augustine. Photo by Renee Unsworth

Seafood pasta and other specialties are available nightly at The Raintree Restaurant, 102 San Marco Ave., the perfect spot for a romantic date in St. Augustine. Photo by Renee Unsworth


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

4. LIVE MUSIC

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. 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 Duran Duran  and Aretha Franklin. The music scene is THRIVING here!

The Music News list is posted each week featuring St. Augustine musicians and bands: oldcity.com/music-news

5. ROMANTIC TOURS

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):

  • San Sebastian Winery (daily tours and wine tastings), 157 King St., 904-826-1594, www.sansebastianwinery.com
  • St. Augustine Distillery Company (free tours and tastings), 112 Riberia St., downtown St. Augustine (Lincolnville), 904-825-4962, staugustinedistillery.com  
  • Fort Matanzas National Monument (free ferry to the Fort), 8635 A1A South,  904-471-0116,  www.nps.gov/foma
Free tours of the St. Augustine Distillery, 112 Riberia St., include a tasting of St. Augustine-made vodka and gin. Photo by Renee Unsworth

Free tours of the St. Augustine Distillery, 112 Riberia St., include a tasting of St. Augustine-made vodka and gin. Photo by Renee Unsworth

FREE self-guided tours

OTHER tours

6. LIVE THEATRE

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 by students. Other live theatre and music shows are held in the Pioneer Barn at Old Florida Museum.

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

A Classic Theatrewww.aclassictheatre.org

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

 Pioneer Barn at Old Florida Museum, 259 San Marco Ave., St. Augustine

Take a romantic stroll on St. Augustine's streets in the historic district. Photo by Renee Unsworth

Take a romantic stroll on St. Augustine’s streets in the historic district. Photo by Renee Unsworth

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