Splurge in Saint Augustine

When Henry Flagler was developing Saint Augustine in the late 1800s, his goal was to make the waterfront city the New Port of the South. He dreamed of making the oldest city in the country a playground for wealthy northerners looking to escape the harsh winters. While Saint Augustine isn't exactly known for it's rich and famous visitors today, there are still remnants of Flagler's luxurious touches all over town. Museums, restaurants, shopping centers and even schools now reside inside buildings that were once fine hotels. However, you can still enjoy a stay in a luxury hotel, fine dining and upscale shopping along Saint Augustine's historic streets.

Casa Monica Hotel

The Casa Monica Hotel is actually one of the only hotels in town that was not built by Henry Flagler. It was built by Bostonian architect Franklin W. Smith right next door to a Flagler property. A few months after its opening, Flagler purchased the failed hotel from its original owner and soon turned it into a thriving business. Yea... More >

San Sebastian Winery

Do everything you'd expect to do in a winery: take a tour, enjoy a wine tasting, and purchase your own bottles to take home. This winery is especially known for its table, sparkling, and dessert wines. Worried about drinking driving? Not a problem - this location is included on both of the trolley tours in town! Hop off, spend a fe... More >

Although it's listed as a splurge, the prices aren't unreasonable for the quality of the meal and the experience.

St. Augustine Sightseeing Trains

Purchase one ticket and enjoy the convenience of being hauled around town for three days. The trolley drivers are very knowledgeable about the area and give a running narration of the sights you're driving by. You get hop-on and hop-off service with most stops having a trolley go by every 15 minutes. This is a great way to see a lot of the historic sites without wearing yourself out and then you can stop and investigate further if an area really interests you.

Ghost Tours of St. Augustine

A guided ghost tour of Saint Augustine isn't exactly inexpensive, but it's something you have to do at least once. The town has been featured on numerous national television shows for its spook factor and a ghost tour will take you to all the spookiest places and give you the background story. Of course, the only time to take a ghost tour is after dark, which makes the eerie tales all that more believable. Ghost Tours of St. Augustine includes a visit to two cemeteries and a trip to the Castillo de San Marcos, which was featured on Ghost Hunters.

Columbia Restaurant

Enjoy Spanish and Cuban cuisine that gives a nod to the first people to settle Saint Augustine. The Colombian is known for it's gorgeous atmosphere, exceptional service, great wine list and - of course - delicious food. Although it's listed as a splurge, the prices aren't unreasonable for the quality of the meal and the experience. If you're lucky (or ask nicely), you'll be seated next to the gorgeous fountain in the courtyard. Of course, like any old building in town, rumor has it that Columbia Restaurant is haunted.

This winery is especially known for its table, sparkling, and dessert wines.

St. George Street

Saint George Street is a narrow, cobblestone road that doesn't allow vehicles of any kind, which makes it perfect for a stroll and shopping. It's lined with historic buildings, art galleries, antique shops and restaurants. You'll find beautiful art and unique gifts (for yourself or someone else). You can also find really great homemade fudge and a tiny courtyard perfect for enjoying a slice of that homemade fudge. The s... More

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