A weekend in St. Augustine, FL

Palm trees and sunset in St. Augustine.

St. Augustine, the oldest European settlement in the United States, was founded by the Spanish explorer Pedro Menendez de Aviles in 1565. It was originally called La Florida (“Land of Flowers”) by Spanish explorer Juan Ponce de Leon, who claimed the land in the name of Spain on March 27, 1513. The Land of Flowers still seems to fit this beautiful old area of Florida.

Growing up in America’s northeastern seaboard, I recall someone jokingly referring to Florida as “a sunny place for shady people”and I avoided the state for other southern destinations such as New Orleans, Savannah or Charleston, with rich culture and history and comparably warm climates. Yet, St. Augustine, Florida has been on my American bucket list for a number of years and now I finally got to see it. It was worth the wait as I found the city to be charming, historic, full of good restaurants and genuinely friendly, welcoming people.  Here is a brief weekend itinerary for anyone interested in visiting.

When to go: 

Living in New York City, I would highly recommend going during our cold months (January, February, or March) when you want to get out. The summers in Florida are too hot and humid for me. So anytime from December-March is ideal.  I had the luck of visiting during a festival called “Lincolnville Porchfest” which is a grassroots neighborhood festival featuring local artists at different porches in the Lincolnville section of St. Augustine over President’s Day weekend.

Friday:

Get settled into your accommodations and go out for dinner either at one of the many seafood places along Avenida Menendez with views of the Matanzas River, or go over the Bridge of Lions and try one of the popular restaurants on A1A Beach Boulevard. Having just arrived in St. Augustine, I chose Sunset Grille, arriving at the peak of Friday Night Happy Hour.  I admit that I chose the Sunset Grille based solely on the name and the proximity to St. Augustine Beach, which is across the street. Unfortunately, there are no ocean views due to tall buildings and a berm being in the way. While the Sunset Grille had no romantic sunset views, it had a really lively Happy Hour attended by friendly, ebullient locals who were celebrating the end of the work week and the beginning of the weekend. In sum, while the food was okay, and there are no sunset views, the Sunset Grille is a fun place to kick off the weekend.

Saturday:

Grab some fresh,local produce and rub elbows with the locals at the St. Augustine’s Farmers Market.

Drive over to the St. Augustine’s Amphitheater Farmer’s Market (1340C A1A S). Open Saturday 8:30-12:30pm.

Late morning: Window shopping Aviles St and St Georges St (both of which cater to tourism), check out the Cathedral, the main square, and the gardens at the LIghtner Museum.

Try to get a table outdoors and enjoy a healthy brunch at the Floridian Restaurant.

Afternoon: take a tour of Flagler College (74 King St, historical tours are offered at 10:00AM and 2:00PM and last about an hour).  This elegant college campus was formerly the Ponce De Leon Hotel, built in the late 1800s as a winter resort by Henry Morrison Flagler with the interior designed by Louis C. Tiffany. Flagler was an industrialist, railroad pioneer and oil magnate. The school store doubles as the ticket office and the college students who run the store also serve as the tour guides, so the school store/ticket office is closed from 10-11 AM and 2-3 PM while the tours are going on. Try to get tickets ahead of time because in high season they sell out. The engaging tour guides are very knowledgeable and humorous.

An artist at Lincolnville’s Porchfest.

We stayed at an airbnb in the historic Lincolnville neighborhood near downtown St. Augustine during porchfest, so we walked around Lincolnville and enjoyed the music and banter with the neighbors. Lincolnville is an historic black neighborhood where Martin Luther King, Jr., spoke and stayed over during the Civil Rights Movement.

Evening:

Rose on the rooftop of San Sebastian Winery after the end of a “long” day of window shopping.

Get a happy hour drink  at San Sebastian Winery (157 King St, Monday-Saturday, 10 AM – 6PM and Sunday, 11 AM – 6PM). San Sebastian Winery is in Henry Flagler’s East Coast Railway Building. They have complimentary tours and wine-tasting starting every 20 to 25 minutes. The highlight was making it to the rooftop bar that offers live music most nights.

The charming restaurant called Preserved (102 Bridge St) is housed in a renovated Victorian house. If possible try to get seating outside on the patio. They serve locally sourced ingredients at this southern restaurant.

Sunday

Brunch at Maple Street Biscuit Company or Blue Hen Cafe.

 Spend an hour checking out the beautiful Mission of Nombre de Dios (Saturday 9:00AM- 5:00PM, Sunday 12-4:00PM) and the great cross. The beautiful mission and its grounds present a nice place to enjoy a morning stroll.

A few blocks from the Mission of Nombre de Dios is the beautiful Magnolia Avenue. Definitely worth the two block hiatus from the Mission to drive, bike, or walk down.

Get a coffee fix from Crucial Coffee Cafe before heading to the Castillo de San Marcos National Monument (9:00 AM – 5:00 PM) They do cannon reenactments on the top level. Try to sit close to where the cannon, so you can hear the history lesson, but you may want to block your ears for a moment as the cannon is fired.

For Sunday night dinner, I highly recommend that you try the large Columbia Restaurant. Call ahead for reservations.  This old-time restaurant has been in the same family for over 100 years. The wait-staff, ambiance and food are phenomenal. I recommend the sangria, paella and the salad.  In my group, we ordered varied entrees, did some sharing and found the food to be consistently excellent.

If you are based on the east coast and are looking for a weekend getaway consider looking at my Barcelona, Cotswolds, Mexico City, or San Diego itineraries.

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