WHAT TO DO
Saint Augustine is a city located on the Atlantic coast of northeastern Florida. It lies on the Matanzas River, forty miles south of Jacksonville. The first European known to have explored the coasts of Florida was the Spanish explorer and governor of Puerto Rico, Juan Ponce de Leon, who likely ventured in 1513 as far north as the vicinity of the future Saint Augustine, naming the peninsula he believed to be an island, La Florida or 'place of flowers' and claiming it for the Spanish crown. Founded in 1565 by the Spanish conquistador Pedro Menendez de Aviles, Saint Augustine is the oldest continuously occupied settlement of European origin in the United States. The 1763 Treaty of Paris, signed after Great Britain's victory over France and Spain during the Seven Years' War, ceded Florida to Great Britain. The vast majority of Spanish colonists in the region left Florida for Cuba - Florida became Great Britain's fourteenth and fifteenth North American colonies (East Florida and West Florida), and because of the political sympathies of its British inhabitants, Saint Augustine became a Loyalist haven during the American Revolutionary War. The 1783 Treaty of Paris, which recognized the independence of the Thirteen Colonies as the United States, ceded Florida back to Spain.
During the Second Spanish period (1784-1821) of Florida, Spain was dealing with invasions of the Iberian peninsula by Napoleon's armies in the Peninsular War and struggled to maintain a tenuous hold on its territories in the western hemisphere. The royal administration of Florida was neglected, as the province had long been regarded as an unprofitable backwater by the Crown. The United States, however, considered Florida vital to its political and military interests as it expanded its territory in North America. The Adams Onis Treaty, negotiated in 1819 and ratified in 1821, ceded Florida and Saint Augustine to the United States. Henry Flagler, a co founder with John D Rockefeller of the Standard Oil Company, spent the winter of 1883 in Saint Augustine and found it enchanting. He had the idea to make the town a winter resort for wealthy Americans from the north, and to bring them south he bought several short line railroads and combined these in 1885 to form the Florida East Coast Railway. Today, Saint Augustine's distinctive historical character has made the city a major tourist destination. With wonderful art and architecture, fantastic food and pristine beaches, charming Saint Augustine is a traveler's delight.
Most of the city sights are in and around the National Historic District (Old Town). Start your journey in the center of town at Plaza de la Constitution. This grassy square, the oldest public park in the United States and a former marketplace for food (and slaves), has an attractive gazebo, some cannons, the remains of the town well, a monument to the Spanish Constitution of 1812 and a statue of Juan Ponce de Leon. Next to the plaza is the Cathedral Basilica of Saint Augustine. With its magnificent bell tower, this Spanish mission style cathedral was designated a United States National Historic Landmark on April 15, 1970. Its congregation, established in 1565, is the oldest Christian congregation in the country. Nearby on Aviles Street (the oldest road in the nation), is the Spanish Military Hospital Museum. The original structure was built during the Spanish Colonial period and the authentically reconstructed building is on the same site, recreating the hospital as it would have been in 1791. Guided tours introduce visitors to displays of antique medical equipment and surgical instruments. There is also an apothecary where you can learn about traditional medicines and the herbal origins of modern medications.
From there, make your way back across the plaza to the most popular thoroughfare in town. Saint George Street is a pedestrian mall that runs north from the cathedral to the city gate. The cobbled lanes are lined with endless eateries, boutique shops, historical structures and quaint courtyards. Stroll the entire length of the street to enjoy the true local vibe as outdoor musicians fill the air with a cheerful ambience. Saint George Street will take you to the Saint Augustine City Gate. When the Spanish walled the city in the 1700s this gate was the only way in and out of the city to the north. The original gate was constructed out of palm tree logs - the current coquina (sedimentary rock composed almost entirely of sand size fossil debris) pillars were built in 1808. Around the bend from the city gate is the Pirate & Treasure Museum. More like a theme park, this kid friendly spot encourages guests to let out their inner pirate by transporting them back more than three centuries to the zenith of Caribbean pirate activity. As well as genuine historical treasures (including real gold) there's plenty of animatronic pirates, blasting cannons, artifacts from shipwrecks and Captain Jack Sparrow's sword.
Next door is the Colonial Quarter. See how they did things back in the 18th century at this living history museum of Spanish Colonial Saint Augustine, complete with craftspeople demonstrating blacksmithing, leather working, musket shooting and all sorts of historical stuff. A replica Spanish caravel (ship), the kind used by Juan Ponce de Leon and other explorers of his time, is among the items on display. Note: I would like to add that there is no denying the presence of some tacky tourist traps in town, but it's all part of the fun. Across the street is the Castillo de San Marcos. This photogenic fort, strategically positioned on the Matanzas River, is an atmospheric monument to longevity: it is the country's oldest masonry fort, completed by the Spanish in 1695. They used the native beach stone coquina to construct thick fireproof and impenetrable walls that were able to withstand multiple attacks from British troops, including the massive fire in 1702 that wiped out the rest of the city. In its time, the fort has been besieged twice and changed hands between nations five times - from Spain to Britain, back to Spain, to the USA, to the Confederate States of America and back to the USA again. You can walk around the exterior of the fort for free, but for the best experience you should take a tour guided by a park ranger to learn about why this structure was essential to the protection of the Florida coast.
North of the fort is Ponce de Leon's Fountain of Youth Archaeological Park. As the story goes, Juan Ponce de Leon came ashore here in 1513 and considered this freshwater spring the possible legendary Fountain of Youth. This fifteen acre park along the Matanzas River is a working archaeological site, which focuses not only on the first Spanish settlers but also on the native Timucuans. Parts of a replica village were constructed on the original site, including a home and a meeting house. Artifacts from excavations are on display and reenactments depict native life and traditional crafts. There are beautiful views from the watchtower and throughout the park you can mingle with the colorful peacocks. Not far away are the Saint Augustine History Museum and Old Jail. The museum of history is a combination of historical displays and private collections that bring over 400 years of Florida history to life. You can visit the Spanish sunken treasure room, a Timucuan Indian village, a Florida Cracker (pioneer settler) trading post and Henry Flagler's Florida East Coast Railway exhibit. The jail museum is listed on the National Register of Historic Places and has many interesting stories relating to its history and the infamous prisoners that were housed here in the 19th and 20th centuries. The Old Jail was financed by Henry Flagler to help free up land that he wanted in Saint Augustine to build one of his luxury hotels. The stories about the prisoners and the time period come to life with costumed performers who share the important history of the jail in an entertaining way.
From there, hire an Uber ride and take the Bridge of Lions over the Matanzas River to the Saint Augustine Lighthouse & Maritime Museum on Anastasia Island. Note: the name Bridge of Lions comes from the two lions that are on display at the approach to the bridge on the Saint Augustine side. Named Firm and Faithful, they were sculpted from Carrara marble (the same quarry that Michelangelo used). The tall spiral striped lighthouse is the city's oldest standing brick structure, built in the 1870s to replace the original wooden watchtower. During the Second World War, the Coast Guard used it to keep watch over the shore, and it is considered the first permanent navigational aid in North America. In 1986 the lighthouse and its original Fresnel lens, made of 370 glass prisms cut by hand, were restored, and the museum's proceeds make its upkeep possible. Atop the 219 steps, standing at 165 feet above sea level, the beacon light is still in operation and uses the original beehive shaped prism, which stands at 12 feet tall and 6 feet in diameter. After a steep climb to the top of the lighthouse you are rewarded with commanding views of Saint Augustine and beyond. Be sure to check out the light keeper's house and one of the only field schools for underwater archaeology at the Maritime Museum.
Back in town is Flagler College - the campus is a great place to take a stroll to soak in the stunning landscaping and historic buildings. The centerpiece of the campus is Ponce de Leon Hall. In 1888, Henry Flagler built the Spanish Renaissance structure as the Hotel Ponce de Leon, one of several resorts he built in Florida. The building is now a National Historic Landmark and one of the most impressive pieces of architecture in the city. Note: you can take a Historic Tour of Flagler College with the purchase of a ticket. There are two tours per day, where you will learn behind the scenes details about Henry Flagler and his contributions to Saint Augustine and see intricately restored details in the historic hotel, like the dining room that is decorated with 79 Tiffany stained glass windows. Across the street is the magnificent Lightner Museum. One of the country's best collections of 19th century decorative and fine arts is displayed in the four floors of the former Gilded Age resort Hotel Alcazar, also built by Flagler in 1888. The collections are eccentric and although they include Tiffany glass, fine furniture and porcelains, sculpture and paintings, they also include shrunken heads, mechanical musical instruments, a mummy and cigar box labels. Flagler's hotel was the marvel of its era, filled with fashionable guests who danced in its grand ballroom and swam in the world's largest indoor swimming pool. Outside the museum, walk the beautiful manicured gardens and courtyard with a koi pond and stone walking bridge.
Close by is the Lincolnville Museum & Cultural Center, which chronicles 450 years of African American history in Saint Augustine. This cultural museum is in the city's Lincolnville Historic District, which was settled by emancipated slaves after the Civil War. The building housing the museum is the former historic Excelsior High School, founded in 1925, which was the first public high school for African American students in town. There are several rooms of exhibits, including a Civil Rights room and a Cultural room featuring artifacts from prominent African Americans who spent time in Saint Augustine, including Martin Luther King Jr and Ray Charles. Saint Augustine has long been a Mecca for artists. There are numerous galleries throughout the city, many of which are on King Street. On the first Friday of every month the town hosts Art Walk when galleries are open later in the evening. Also enticing are the San Sebastian Winery and the Saint Augustine Distillery. The winery is located at 157 King Street - one hour tours are capped with wine tastings and a video about Florida wine making since the 1600s. The distillery can be found around the block at 112 Riberia Street. Opened in 2013, it too offers educational tours and tastings of its yummy handcrafted spirits - bourbon, rum, gin and vodka.
For more deliciousness, head to Whetstone Chocolates at 139 King Street. Henry and Esther Whetstone began their business in 1966 when they opened a homemade ice cream shop on Saint George Street. They entered the chocolate market when they created a fudge recipe. The following year they were selling 13 different flavors of fudge along with an increasing assortment of hand dipped chocolates. Tours of the factory are offered daily and reservations are recommended. Note: they have two additional locations, one in the Historic District and another on Anastasia Island. One more chocolate store that should not be missed is Claude's Chocolate at 6 Granada Street. Opened in 2005 by Claude Franques, this boutique shop introduced European style bonbons and truffles to the neighborhood. Conclude your tour of Saint Augustine with a relaxing sailboat ride or a visit to the beach. A sail on board the Schooner Freedom is one of the best ways to see Saint Augustine and experience the city from the water. Besides feeling the ocean breeze on your face as you quietly sail through the water, you will enjoy seeing the marine life, including dolphins and sea birds on the trip. A sail on the Schooner Freedom is unique because it is a replica of a 19th century blockade runner, built to exact specifications - it is a 76 foot long, double masted, topsail schooner. As Christopher Cross sang, 'if the wind is right you can sail away and find tranquility.' The soft, white sand of Saint Augustine Beach almost gets lost in the historical mix, but it's Florida, so a visit would not be complete without some fun in the sun and a swim in the ocean.
WHERE TO EAT
Saint Augustine has several great places to eat and enjoy a drink or two. Start your day at Maple Street Biscuit Company, located at 39 Cordova Street. The name of this place delivers on its promise - they do biscuits that wow (the Southern flaky kind) and they do them right. There's plenty of variations, I destroyed the Sticky Maple which comes with fried chicken, maple syrup and bacon. Be sure to add a side biscuit with sausage gravy and wash it all down with a glass of fresh squeezed Florida orange juice. Nearby at 69 Hypolita Street is Schmagel's Bagels. This cozy, counter service spot does New York style bagels. Do try an everything bagel with taylor ham, egg and cheese, and enjoy it with a cup of coffee outside on the patio. For a wee bit of European flare and a darn good pastry, head to Parfait Pastry Shop at 142 King Street. They do delicious chocolate croissants and pastelitos (Cuban pastries with guava, cheese and coconut), that pair nicely with a lavender vanilla latte.
For lunch, make your way to Harry's at 46 Avenida Menendez. This popular spot in the heart of the Historic District is known for its tasty seafood dishes and New Orleans inspired grub. You can't go wrong with the signature crab cakes, jambalaya or the red beans and rice with smoked sausage. To wet your whistle, Harry's Hurricane packs a punch. Not far away at 72 Spanish Street is a locals favorite, The Floridian. This laid back joint does 'innovative Southern fare for omnivores, herbivores and locavores.' A few comfort food highlights on the menu include the fried green tomatoes, meatloaf sandwich and the shrimp po boy with house pickled vegetables. They have a solid selection of refreshing ciders to quench your thirst. Close by is Columbia Restaurant, located at 98 Saint George Street. In business since 1905, this pretty place serves traditional Spanish and Cuban cuisine. Me gusto the Spanish bean soup with smoked ham, chorizo and potatoes. The original Cuban sandwich (roasted pork, ham, pickles, cheese and mustard served on pressed Cuban bread) was named 'best sandwich in Florida' by Food & Wine Magazine.
Saint Augustine Fish Camp can be found at 142 Riberia Street. This relaxed harborfront restaurant features local seafood specialties and terrace dining. Start with a dozen chilled oysters on the half shell then move on to the salt and pepper seared tuna, and be sure to save room for the Florida key lime pie. Just across the Bridge of Lions at 9 Anastasia Boulevard is Gas Full Service. This funky retro gas station cafe is famous for its burgers. I devoured the Half Tank burger - 1/2 pound chargrilled burger topped with house made pimento cheese, full service slaw, applewood smoked bacon, fried pickles, lettuce, tomato and onion. For dessert, I polished off the fried green tomatoes with buttermilk ranch dressing because I had to. Up the road at 205 Anastasia Boulevard is O'Steen's Restaurant. Locals claim this seafood shack has the best shrimp on the East Coast. This family institution opened in 1965 and little has changed. You would be silly if you did not order the famous Saint Augustine fried shrimp platter. Note: the restaurant is cash only.
For dinner, head to Michael's at 25 Cuna Street in the Historic District. Set in a building that dates back to 1764 and run by acclaimed chef Michael Lugo, this elegant restaurant has a menu that changes seasonally. It focuses on steaks and coastal Spanish inspired cuisine with influence from the finest local ingredients. Standouts include the Spanish mushrooms with garlic confit, sea scallops with saffron corn puree and the 60 day wet aged filet mignon with seared foie gras. The wine list is impressive and the service is top notch. Note: the restaurant is closed on Monday. Chef Michael recently opened La Nouvelle Bistro at 102 Bridge Street in the historic Lincolnville neighborhood. You get to enjoy classic French bistro fare with an elevated edge in the cozy dining room, on the wrap around porch or in the lush garden patio of this restored home. I began with the Burgundy escargots then moved on to the duck leg confit with duck fat potatoes. To satisfy my sweet tooth, it was the lavender creme brulee. Note: the restaurant is closed on Sunday and Monday. An additional spot for classic French food is The Drunken Horse, located at 56 Charlotte Street in the Historic District. This welcoming restaurant and wine bar offers pan seared foie gras, fine cheeses and charcuteries along with a superb selection of wines.
The fabulous Catch 27 is down the road at 40 Charlotte Street. It derives its name from the seafood caught in our nation’s 27th state, Florida. The food, the drinks and the vibe are all awesome. They cook everything from scratch with seasonal ingredients and local produce. My meal involved the deviled egg blt with Southern fried oyster (crispy corn fried oysters, house made tomato bacon jam and local micro greens) and the rustic catch (grilled mahi mahi with glazed carrots, rice and lemon garlic compound butter). My beverage of choice was the Catch 27 G&T - Saint Augustine gin, thyme tonic, pink peppercorn and blossoms. Note: the restaurant is open daily from 5p and reservations are recommended. Collage Restaurant can be found at 60 Hypolita Street. This upscale restaurant is renowned for its impeccable service, intimate atmosphere and the consistency of its cuisine. The menu makes the most of Saint Augustine's seaside locale and nearby local farms. I enjoyed the sweet corn chowder topped with basil oil and the house favorite homemade lobster ravioli with sauteed shrimp in a pesto cream sauce, topped with a 5 oz Maine lobster tail. A bottle of Sancerre from the Loire Valley was the perfect complement to the food. Note: the restaurant is open daily from 5p and reservations are highly recommended.
My most memorable dining experience was at Llama Restaurant, located at 415 Anastasia Boulevard on Anastasia Island. This lovely spot features artful presentations of Peruvian specialties in a charming setting with an intimate feel. Owner and chef Marcel Vizcarra takes you on a journey that allows you to explore the rich culture, ingredients and tastes of his homeland. I started with the ceviche Lima (fresh catch marinated with lime juice, cilantro and limo peppers served with Peruvian giant corn and glazed sweet potatoes). My main was the mar y tierra (Lomo Saltado stir fry hanger steak, onion and tomatoes with a nice smoky finish over a shrimp tagliatelle pasta with creamy Huancaina sauce) - yum. The celebration ended with the luna llena (lavender honey tres leches, white chocolate yeast ice cream, butterfly snow pea and shortbread ground). They also have an excellent selection of cocktails, wine and beer. Note: the restaurant is closed on Sunday and reservations are strongly encouraged.
Conclude your evening in Saint Augustine with a drink or two. The super cool Ice Plant Bar is located above the distillery at 110 Riberia Street. The hottest spot in town, it flaunts exposed concrete, raw brickwork and soaring windows surrounding a vintage dual facing centerpiece bar all carved out of a former ice factory from 1927. Savor some of Florida's finest cocktails, mixed by overall clad bartenders and snack on farm to bar bites. I knocked back more than a few of the Moonage Daydream - London dry gin, aloe, snap pea, grapefruit, black pepper and lemon - I'm an alligator David Bowie. Another rad spot is Odd Birds, found at 200 Anastasia Boulevard on Anastasia Island. This watering hole embodies just about everything one could want in a quirky, totally unique craft cocktail bar: innovative, imaginative, often playful drinks and a casual setting that is unpretentious. Finish up back over the Bridge of Lions at the Tradewinds Lounge, located at 124 Charlotte Street. Smelling of stale beer, this classic dive bar with a tropical theme has live music, mostly Southern rock or '80s hits. Note: the bar is open daily until 2a.
WHERE TO STAY
Saint Augustine offers a number of places to call home during your stay and there are 2 that I especially enjoyed. Both are in prime locations and provide exceptional service, modern amenities and comfort. The first is Casa Monica, located in the center of the Historic District at 95 Cordova Street. This grand Spanish and Moorish styled hotel, built in 1888, has an ornate lobby with frescos, fountains and chandeliers. Elegant rooms include custom designed interiors with classical furnishings featuring gold accents, free WiFi, flat screen TVs and Bose sound systems. Upgraded quarters add wet bars, antiques, balconies and stained glass windows. Amenities include the upscale Cordova restaurant, a lounge, a rooftop pool and sundeck, plus the Grand Bohemian Art Gallery and Poseidon Spa.
A second option is The Collector Inn, located just up the road at 149 Cordova Street. Occupying a group of nine late 18th century houses set around a lush, landscaped courtyard, this adults only hotel is a short walk from the Lightner Museum and Flagler College. Warm, traditional rooms have period furnishings and come with complimentary WiFi and flat screen TVs, plus granite kitchenettes and stylish bathrooms with subway tiles. Upgrades add sitting areas and patios overlooking the courtyard. Other perks include continental breakfast and loaner bikes on the house, a heated outdoor pool and fire pits, plus the welcoming Well Bar.
Saint Augustine is full of remarkable history, amazing architecture, wonderful art and fabulous cuisine. It treated me well and I look forward to returning.
