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Trips to the beach are often meant to be times of relaxation, an opportunity to allow the salt to smooth your skin, the breeze over the water to wash away your worries and the sun to give a boost of vitamin D we have been so desperately needing. But St. Augustine isn’t your typical beach town — or your typical beach vacation. Although the city is lined with 42 miles of beautiful beaches, it is the historic district that makes St. Augustine so special. History and culture collide in the heart of The Ancient City, where cobblestone streets fill with pedestrians, buildings date back to the 1700s and the oldest wooden school house stands. St. Augustine has a noticeably slower pace than other cities, but a visit is defined by learning and exploration, perhaps more so than relaxation and rejuvenation.

We had the opportunity to spend a few days in St. Augustine last month, and it was just what the doctor ordered. During our three-day trip, the oldest city in the United States left a mark on us. We were delighted by the bright colors and textures in the city’s architecture, the rich history that is celebrated in all facets of life in the city and the warmth of everyone we encountered. If you are looking to add a little sunshine to your days, make the trip to St. Augustine and follow our SB-approved itinerary to experience most of what this Florida city has to offer.


1 p.m. — Check in at The Collector Inn & Luxury Garden

Formerly the site of the Dow Museum of Historic Houses, The Collector Inn & Luxury Garden is a one-of-a-kind setting for your weekend away. The homes date back to 1790, and with any luck, you will be put up in the Murat House — the oldest of the bunch. Check in, drop your bags and familiarize yourself with the grounds, as you will be calling them home for the next 48 hours. Read our rave review of The Collector here.

48 Hours in St. Augustine, Florida

Welcome home (for the next 48 hours!).

48 Hours in St. Augustine, Florida

The historic homes are picture perfect.

2 p.m. — Late Lunch at The Floridian

Once you are settled, make your way to The Floridian for a late lunch. A walk down the famous St. George Street will lead you to the restaurant set on Spanish Street. It was recommended by just about every local we encountered. If like us, you are from a landlocked state, revel in the abundance of seafood and opt for a shrimp remoulade po’ boy or a salad with the fresh catch if you are looking for a lighter option.

48 Hours in St. Augustine, Florida

This looks like the perfect place for lunch. Image: The Floridian

3 p.m. — Explore St. George Street

After a long morning of travel and a late lunch, you are likely in need of a good stroll. Make your way back to St. George Street for a closer look at what it has to offer. This pedestrian-friendly street is in the Historic District of St. Augustine. You will get a bit of history and, thanks to the nation’s oldest wooden schoolhouse and the state’s oldest houses, you will also get a closeup look at the city’s architecture. And you might be tempted by a sweet shop, or 10! Duck into any store that strikes your fancy, and don’t overlook the side streets, as they each have something to offer as well.

48 Hours in St. Augustine, Florida

St. Augustine’s downtown is centered around St. George Street. Stroll the main street for shops, restaurants and historic sites that define the city’s character.

48 Hours in St. Augustine, Florida

The Oldest Wooden School House is a site worth seeing. The structure, which was made by hand in the early 18th century, is still standing tall today.

48 Hours in St. Augustine, Florida

The Hyppo Gourmet Ice Pops are natural ice pops that have become famous in St. Augustine. Treat yourself to one of their many flavors — you’ll find The Hyppo in downtown St. Augustine.

6 p.m. — Drink at The Well at The Collector Inn

Head back to the hotel and get ready to start your evening. The Well is housed in St. Augustine’s first two-car garage, which has been converted into the on-property bar. You’ll find Sonny Wallace behind the bar and ready to create a drink that is sure to wow you. You can order from the menu, or you can tell him a little bit about what you typically drink, and he will concoct something special just for you. Take your drink outside to enjoy views of the property.

48 Hours in St. Augustine, Florida

Cheers to a great first day in the oldest city in the United States!

7: 30 p.m. — Dinner at Catch 27

Another favorite for locals and tourists alike, Catch 27 serves some of the freshest seafood in town. Everything you eat (shrimp, clams and fish) was locally caught from Florida water that very day. Start with seacuterie (beet and peppercorn cured salmon, smoked Florida fish mouse, chef’s daily selection and accoutrements) before pondering what to order for your entrée. The gumbo and fish tacos are two items that had our mouths watering.

After dinner, it’s time to turn in — you have an exciting day coming up tomorrow!

48 Hours in St. Augustine, Florida

Fish tacos for dinner, please! Image: Catch 27


9 a.m. — Breakfast at The General Store

This morning, you won’t have to travel far for breakfast. In the hotel’s main lobby, The General Store, breakfast is served to guests. A selection of pastries, breads, cereals, fruits and smoked salmon is sure to keep you satisfied until lunchtime. If you can, snag a table outside to soak in as much of that Florida sunshine as possible.

48 Hours in St. Augustine, Florida

Breakfast at the inn is convenient and delicious.

10 a.m. — Property Tour with Melissa Stewart

Melissa Stewart has a wealth of knowledge that she is more than willing to share. This docent at the Dow Museum of Historic Homes leads property tours each Tuesday, Thursday and Sunday at 10 a.m. Spend an hour with her to learn every last detail of the property that is now The Collector Inn, and we promise she will leave you with facts about the property itself, as well as the city of St. Augustine, that will fascinate you. Learn how The General Store got its name, learn which writers frequented the Howells House (one of the buildings on the property), learn what they discovered when digging out the swimming pool and so much more.

48 Hours in St. Augustine, Florida

Each corner of The Collector Inn holds a piece of history.

48 Hours in St. Augustine, Florida

Melissa knows a thing or two about the property!

48 Hours in St. Augustine, Florida

The view from St. George Street shows the Murat House, the oldest home on the inn property.

11:30 a.m. — Hop on the Red Train Tour

I am not one to regularly suggest guided tours, as I find the beauty in freely exploring a new place. But, I will make an exception for the Red Train Tour. With so much to see in St. Augustine, I welcomed an educated guide to take me through the city. This tour is attractive to many because of the ability to re-board as many times as you like. We claimed our seats on the trolly and didn’t move until the 90-minute tour was complete. The driver showed us more than 20 sites, including the Castillo de San Marcos, Ponce de Leon’s Fountain of Youth, Villa Zorayda, St. Augustine Distillery and Flagler College, and gave us a brief overview and history of each.

48 Hours in St. Augustine, Florida

See the streets of St. Augustine.

48 Hours in St. Augustine, Florida

Flagler College showcases some amazing Spanish architecture. The small liberal arts college was once the site of the Hotel Ponce de Leon. The hotel closed in 1967 and the college open in 1968.

48 Hours in St. Augustine, Florida

Catch views of the water as the trolly takes you across town.

1 p.m. — Lunch at O.C. White’s

Hop off the train and head to O.C. White’s for lunch, and a bit more history. Don Miguel Ysnardy constructed the building, which served as one of the first hotels in St. Augustine. The structure was moved from its original location to where it sits now, on Avenida Menendez with views of the water. Call us crazy, we but can’t seem to order anything that isn’t seafood. An appetizer of coconut shrimp and crab spinach dip was followed by O.C.’s homemade blue crab cake sandwich.

48 Hours in St. Augustine, Florida

We are more than happy to have seafood for breakfast, lunch and dinner.

2:30 p.m. — Anastasia State Park

A short drive from the inn, Anastasia State Park offers 1,600 acres with four miles of beach. Head to the park and walk the four miles to the tip of the Matanzas Inlet. Take note of the wildlife you encounter, and take in the beautiful views of Florida’s East Coast.

48 Hours in St. Augustine, Florida

Here is a view of the inlet from the water.

6: 30 p.m. — Drinks and tapas at Columbia

At this point, you are sure to be starving. Make Columbia Restaurant your first stop for shared tapas and a mojito. The restaurant was founded in 1905 by Cuban immigrant Casimiro Hernandez, Sr.. It is Florida’s oldest restaurant and is still family-run more than 100 years since its opening. Drenched in rich colors and patterns, this lively restaurant is a delight for the eyes and the stomach.

48 Hours in St. Augustine, Florida

Grab a mojito at the colorful Columbia Restaurant!

7:45 p.m. — Dinner at Michael’s Tasting Room

Enjoy dinner in yet another historic building, one that was built in 1764 and converted into the restaurant it is today in 2006. The menu at Michael’s Tasting Room combines Spanish and Puerto Rican-inspired cuisine, resulting in thoughtful, seasonal dishes. You can order from the seasonal menu, which during our visit featured everything from tuna cruda and grilled oysters to braised beef short ribs and sea scallops. If you would like to let the chef take the reins, make a reservation for a date night menu that includes an amuse bouche and sparkling wine, a seasonal salad, entree with wine pairing and dessert.

48 Hours in St. Augustine, Florida

Is your mouth watering yet? Image: Michael’s Tasting Room

9:30 p.m. — Nightcap at The Well

After dinner, it is time for a drink to toast a stellar visit to St. Augustine! There are plenty of bars in the city’s downtown district, but if you are looking for something more low-key, grab a drink from The Well and take a seat around one of the inn’s fireplaces. Reminisce on the past 30 hours and celebrate the fact that you still have a few hours left in this wonderful, historic city.

48 Hours in St. Augustine, Florida

The last night calls for a toast to St. Augustine at The Well.


10 a.m. — Brunch at Preserved

Set in historic Lincolnville, Preserved serves a weekend brunch that is centered around locally sourced ingredients. Leading with roasted oysters is the best way to start any brunch. After oysters, the shrimp and grits, banana nut French toast and duck and potato hash are all worthy entrées. Go ahead and indulge! It is your last meal in St. Augustine, after all.

48 Hours in St. Augustine, Florida

A farewell brunch at Preserved | Image: Preserved

11 a.m. — St. Augustine Eco Tours

A trip to the coast is not complete without getting on a boat. A two-hour trip with Eco Tours will get you on the water and give you a glimpse at the ocean’s ecosystems. Your knowledgeable guide will help you identify the creatures in and around the water, including oysters, birds, plants and dolphins. This tour will leave you with the last piece of a well-rounded understanding of St. Augustine — from the history to the food to the water.

48 Hours in St. Augustine, Florida

The views of the city from the water are quite spectacular.

48 Hours in St. Augustine, Florida

Wildlife abounds!

48 Hours in St. Augustine, Florida

The Great Cross stands at 208 feet tall and was erected by the Bishop of Diocese of St. Augustine. It was completed in fall of 1965 and celebrated the 400-year anniversary of Christianity and the founding of St. Augustine.

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