This year Florida is celebrating the 500th anniversary of Juan Ponce de León's arrival on Florida's east coast… what a perfect time to visit our oldest city!

St. Augustine was founded in 1565 by Spanish admiral Pedro Menéndez de Avilés, and subsequently served as the capital of Spanish Florida for two hundred years. Today, that romantic Spanish influence still weaves its way through the architecture, some still standing, including Castillo de San Marcos, the oldest structure of its kind in the continental United States. Completed in 1695 and now managed by the United States National Park Service, the nearly 450-year-old fort is open to the public from 8:45am to 5:15pm every day of the year except December 25. Tickets are $7 and are valid for seven consecutive days.

Where to Stay

If you’re going to visit the country’s oldest city you really ought to stay in the city’s oldest inn. St. Francis Inn was built in 1791, although you’d hardly know it since this boutique bed and breakfast has been well cared for and renovated through the years. Unlike local hotels, the St. Francis Inn’s rates, which start from $139/night, include an unbelievable number of delightful free amenities and surprising treats.

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Besides the gourmet hot breakfast served in the dining room with coffee (including complimentary lattes and cappuccinos by request!), homemade granola and apple butter, the 17-room inn also serves a happy hour snack and drink spread daily from 5pm – 6pm featuring warm, freshly-made appetizers and well as complimentary bottled beer, red and white wine. Then from 8pm – 9:30pm, the inn serves an evening dessert in the dining room complete with complimentary homemade treats, coffee, tea, hot chocolate, and iced tea.

They have free bicycles for you to borrow, free WiFi, free parking (a huge perk!), and they are one of just two B&Bs in St. Augustine with a swimming pool, something you’ll really appreciate after a long, hot day of touring the city. Oh, and they are dog friendly in case you need to bring Fido along with you on your getaway.

For rooms, I highly recommend the Garden Hideaway suite, a private unit with its own two-person whirlpool tub and electric fireplace. Very romantic!

What to Do

One of the best ways to ‘do’ St. Augustine is to take a tour. I know, I know… tours can be cheesy and can feel so canned. I’d agree with you if we were talking about another city, but St. Augustine is filled with so much history and so many landmarks of such historical significance and interest that you really need an expert guide to make sure you drink in as much of this city as possible.

The trolley tours are fun (I recommend Old Town Trolley Tours) especially since you can typically hop off and on at your whim, but I think a walking tour is the way to really peel back the layers of this city. St. Augustine City Walks takes visitors on specialized excursions including the St. Augustine’s Historic Chocolate Tour, a 2-hour trip that includes stops at handful of chocolate shops, and St Augustine Savory Faire Food Tour featuring tastings at about 5 or 6 stops, plus an optional wine pairing you can tack onto the experience.

A great way to spend a few hours is to simply wander through the main commercial district, where you’ll find a ton of eclectic boutiques and creative cafes. While much of the activity centers on St. George Street, don’t be afraid to veer off down one of the side streets. That’s where I found The Hyppo, an artisanal ice pop shop on Charlotte Street. There are actually four Hyppo shops in St. Augustine so if you walk around long enough, you’re bound to stumble upon one. Inside you’ll find a gourmet array of popsicles made with atypical flavor concoctions such as Pineapple Cilantro or Riesling Pear. Such a wonderful treat on a hot day!

Where to Eat

If you’re sticking with the Spanish theme for dinner, check out Columbia or The Tasting Room; both offer fabulous Spanish cuisine including lots of shareable tapas. Although it’s not Spanish, I also recommend Bistro de Leon, a cute little bistro serving authentic French cuisine made by Chef Jean-Stephane Poinard, who originally hails from Leon, France. If you don’t mind dining early, the chef runs an unbelievable deal daily from 5:50-6:30pm. For just $24.95 you’ll receive a chef’s choice of an appetizer, entrée, dessert and a glass of wine!

There are more than 100 restaurants and cafes in St. Augustine; part of the fun is simply wandering around town and picking what floats your boat.

Where to Drink

One of the best little gems I discovered on a recent visit was The Backyard at Meehan’s Irish Pub. After the sun goes down, this is one of city’s best outdoor patios to sit and enjoy some beers and pub grub with a Caribbean twist. Another favorite of mine is Sangria's Wine & Tapas Bar where you can try seven different types of sangria while sitting on the outdoor porch perched over St. George Street. Great people watching.

Getting There

It takes less than two hours to get to St. Augustine, an easy drive on Interstate 4 and then I-95 North. Once you’re there, you’ll park your car at your B & B and you probably won’t need it again until you leave; this city is as walkable as it is romantic.