City Guide: St. Augustine Florida

St. Augustine

Rent a beach condo (we use Home Away), especially if it's a family vacation.

For a small getaway: Hilton has a gorgeous location in the historic bayfront, 
right in the heart of everything.

St. Augustine Beach. DMD Travel Guide
Beach is an absolute must

The Pirate Museum
An amazing collection of pirate history. The museum owns the only Jolly Roger flag in the United States, one of only three left in the world. Take the guided tour if available, and don't forget to hug your pirate on the way out.
They also have awesome kids camps, check to see if some fall during your vacation time: you gain four hours of adult time, they get to hold a gator.

St. Sebastian Winery, St. Augustine, Florida
St. Sebastian Winery

Castillo de San Marco. St. Augustine.
Castillo De San Marco

St. Augustine.
Walk around the Old Town

Stroll through the fine art galleries on First Friday of every month from 5-9 pm. 
Wine, hors d' oeuvres, and live music provided. 

Sail the Schooner Freedom*.

After hours: St. Augustine has quite the lively night life (it is a college town after all). Neon lit cabs with mohawk-haired drivers, twinkling lights and torches, and live music in every bar included. There is something for everyone. Highly recommend as an 'adults only' experience.

Serenity Blue for fabulous beach-inspired unique jewelry.

Alvin's Island (on A1A) for beach and spring break kitsch. 
And an occasional shark in a bottle.

St. Sebastian Winery
Yes, they ship to most states. Christmas shopping completed in one go.

St. Augustine Premium Outlets
Yes, they have them. If the airline lost your luggage, I guess you can go...

Publix is what grocery store dreams are made of. 

Columbiaan institution. Spanish and Cuban cuisine. White tablecloths and amazing service. Tableside sangrias. Reservations highly recommended.

Preserved recently opened in 2016 by a James Beard Award Nominee chef. Off the tourist path, Southern cuisine with emphasis on local ingredients.

Harry's authentic New Orleans fair.

Sunset Grille (on A1A across the beach) southern home cooking. Great for families. Best piña colada I have ever tasted. Don't forget to Instagram and tag them while eating. You might get a treat.

Salt Life Food Shack (on A1A directly across from the pier) best raw oysters.

Nalu's Tropical Takeout a seafood truck. Permanently parked in Surf Station parking lot on A1A. Taco truck with Hawaiian flavor. Tuna poke, seafood tacos, homemade tuna jerky, need I say more?

Kookaburra an Aussie-American espresso bar. Multiple locations. Come for an amazing coffee (including all the Cuban options), hot baristas, and Aussie meat pies.

Flying: Jacksonville airport is less than and hour away and quite delightful.
Driving: From Chicago to St. Augustine is about 17 hours. Stop at Chattanooga overnight on the way down and Nashville on the way up. Or with multiple drivers just drive through.

*these places have been featured on DMD. Click on the item to view, or check Archives.