A Quirky Tropical Weekend in Historic St. Augustine

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Advisor - Caroline Eubanks
Curated By

Caroline Eubanks

  • Arts & Culture

  • City Travel

  • Food & Wine

  • Weekend Getaways

  • St. Augustine

  • Florida

  • Local Food

A Quirky Tropical Weekend in Historic St. Augustine
Curator’s statement

I've visited St. Augustine several times, including as a budget traveler road-tripping the state, but this time around, I was here to check out a local music festival. During this trip, I was able to visit new-to-me spots like a local record store, a tropical-inspired bar, and a coffee shop that also functions as an antique store—two of my favorite things. This trip report highlights spots sure to be enjoyed by millennial travelers.

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Where to stay in St. Augustine

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St. Augustine has fantastic shopping, especially just outside the historic district. I started my visit on San Maroc Avenue, with its abundant shops and boutiques. My favorites were Cool and Collected, Antiques & Things, and Hilaman and Co. From there, it was easy to pop into Spinster Abbott's, which is a bar, coffee shop, bodega, and antique store. It hosts live music and even has guest rooms.

Spinster Abbott's

I'd visited many of the top attractions on a previous visit, including the Fountain of Youth and Castillo de San Marcos. But I joined a golf cart tour with Pineapple Ride and Tour, which provided historic details I'd never learned about, including stories about early European settlers in the then-Spanish city. I also returned to the Lightner Museum, housed in a historic hotel built by Henry Flagler, filled with oddities and relics.

The former pool area at the now Lightner Museum

The campus of Flagler College, built on the site of another former railroad hotel

The city is chock-full of great places to eat and drink, but when I'm in Florida, I seek out seafood and a tropical setting. Boat Drinks specializes in both, with oyster happy hour and frozen cocktails. The Conch House is classic old Florida, with tiki-style dining huts and a dockside bar, both offering fresh seafood. My one exception is Llama, helmed by a young Peruvian chef, which has some of the most beautiful dishes around.

Sought-after seating at The Conch House

Minorcan clam chowder, a local delicacy

Most of the accommodations in St. Augustine are historic inns. This trip, I stayed at The Collector Inn, an adults-only garden paradise made up of several historic homes, with a bar, daily breakfast, and a pool. The inn even offers tours of the property to learn about its origins.

Guest room at The Collector Inn

Gardens at The Collector

Need to know

Parking can be at a premium in St. Augustine's historic district, so plan on walking or biking to get around. Many hotels and inns offer rentals.

For more inspiration and insider recommendations, visit our St. Augustine page.

Advisor - Caroline Eubanks

Travel Advisor

Caroline Eubanks

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