The oldest city in America is a must-visit for boaters. St. Augustine is old meets new, loaded with Spanish revival architecture and a fun festive coastal vibe. This northeastern Florida destination offers historic charm, plus beautiful waterways and beaches, trendy cuisine, and a lively music scene.
St. Augustine was first flagged by Spanish explorer, Juan Ponce de León who proclaimed he’d found the fountain of youth here in 1565. You’ll find plenty of “youthful” entertainment in this very walkable town, with an ancient city skyline of towering terracotta rooftop spires, an imposing 1600s fortress and marble lions guarding a beautiful bridge.
Just a mile from the Atlantic inlet, follow the ICW south, under the bascule Bridge of Lions, to St. Augustine Municipal Marina, MM 779, on the western shore. This well-staffed marina has stunning views of St. Augustine, overlooking Matanzas Bay, in the shadow of the 1924 Lions drawbridge. You know you are in “nauti” company when you spy the pirate ship and mega-yachts.
The marina is just steps to the Spanish moss-draped Plaza de la Constitución. Passing the Governor’s House, head up St. George Street to experience the half-mile brick pedestrian zone. This colonial-era avenue is lined with coquina walls, cafés, shops, a serene Greek shrine and America’s oldest wooden schoolhouse. Stroll all the way to the 1808 City Gates.
Enjoy lunch with river views at Sainte-George Restaurant on the balcony, or at River & Fort on the top deck. Pop into City Gate Spirits for a free distillery tasting tour of their clever boozy concoctions — Apple Pie Moonshine, Salted Carmel Whiskey, Limoncello.
Tour the 1672 Castillo de San Marcos fort, a U.S. national monument along the waterfront with a fascinating legacy of occupations and preservation due to its unique coquina construction. Your visit may coincide with cannons firing. Afterward, stroll back along Avenida Menendez riverfront promenade watching boats ply the Matanzas (ICW) and occasional dolphins bobbing and blowing.
For dinner, stop at O.C. White’s Seafood & Spirits in the arbored courtyard near the marina. This was St. Augustine’s first hotel, established in 1790. Today, O.C. White’s serves delicious daily catch, crab, shrimp and Key lime pie, with a side of spirited stories (yes, it’s haunted!). An easy walk from the marina are Collage and Catch 27 that feature more upscale global cuisine.
After dinner, live music may draw you into A1A Ale Works taproom, Tradewinds (a local crowd), or back to St. George Street to Prohibition Kitchen, Pierre’s Pub, Milltop Tavern or Colonial Oak Music Park.
With so much to see and do in St. Augustine, you might want to stay two nights at the municipal marina in the heart of everything.
After coffee at Kookaburra in the grand 1920s Treasury on the Plaza, board the Old Town Trolley open-air narrated tour to explore St. Augustine’s highlights. Ride the circuit to learn how St. Augustine was founded, fought over by the Spanish and British, and how Henry Flagler made this a Gatsby-style winter retreat at the turn of the century.
The Flagler College tour presents a perfect opportunity to go inside Henry Flagler’s lavish 1887 Ponce De Leon, Florida’s first luxury hotel. Now turned into a college, it was state-of-the-art back in the day with stained glass crafted by Louis Comfort Tiffany and electricity installed by Thomas Edison. Flagler had all the right friends including Roosevelts and the well-to-do from Newport, Philly and New York, who came to his vacation haven for the season.
Across King Street is Flagler’s second masterpiece: the 1888 Alcazar Hotel, now called the Lightner Museum. The world’s largest indoor swimming pool is the impressive centerpiece. You can no longer swim here, but you can have an elegant lunch in the pool’s deep end at Café Alcazar, where a pianist fills the magnificent space with incredible acoustics. Or dine at a cozy café, Gaufre’s & Goods on historic Charlotte Street, where they dish up authentic Greek and Polish dishes such as hunter stew, gyros, pierogies and buttery baklava.
Stroll Lincolnville, St. Augustine’s post-Civil War African American neighborhood, a charming district established by freed men. Shaded by moss-draped trees, colorful Victorian homes are listed on the National Historic Register. Signposts depict legendary spots including the home where Martin Luther King Jr. wrote his “I Have a Dream” speech. Here you’ll learn how St. Augustine played a pivotal role during the Civil Rights movement.
Your wandering brings you to St. Augustine Distillery, North America’s #1 whiskey tour, and it’s free! Visit the distillery in a renovated Ice Plant and taste hand-crafted spirits and the award- winning barrel-finished gin. Visit San Sebastian Winery, just a block north, for another free tasting tour, don’t miss the rooftop Cellar Upstairs for fabulous city views. Nearby on King Street is Whetstone Chocolates, this tour will cure any sweet cravings.
Aviles Street, just off King Street by the marina, is the oldest street in the oldest city in America. The cobble and brick alley is lined with art galleries and local jewelers’ shops. Dine here at Forgotten Tonic, grab a seat at the bar or out on the lovely sidewalk. Discover live music happening around town or simply head back to the docks to watch the sunset light up the Bridge of Lions and the picturesque city skyline.
Take a leisurely boat ride 3.8 NM north, watching for dolphins as you pass the fort and cruise under the Vilano Bridge. Caps on the Water is an ideal dock and dine lunch on the ICW Tolomato River. Arrive at 11:30 a.m. to secure a coveted dock slip. Sitting along Cap’s waterfront deck, shaded under mossy branches, savor smoked fish dip, grouper, gator — all ideal for sharing with a drink and view of your boat.
Boat 3.8 NM south to the eastern shores of Anastasia Island, with St. Augustine Lighthouse as your beacon. Your destination, the Conch House Marina, is a fun full-service marina with a relaxed tiki bar restaurant, and pool for marina guests. Live bands play at “The Conch” (locals’ nickname) Thursday to Sunday afternoons on the Pier Deck. It’s fun to watch charter fishing boats return and filet their catch on the docks below.
From the Conch Marina, you can walk .8 miles to climb the 1874 St. Augustine Lighthouse, where its 219 circular steps award you with an amazing 360-degree view of the Atlantic. Don’t miss the Maritime Museum to learn of lighthouse keeping and the hauntings of this glorious light. If you love gators, snakes and birds, nearby St. Augustine’s Alligator Farm Zoological Park will fulfill your reptile fantasies (or fuel nightmares if you are phobic).
Anastasia State Park is also in this neighborhood, a pristine four-mile Atlantic beach park, home to the original Coquina quarries that built the Fort. St. Augustine Ampitheatre. Just over a mile from The Conch House is a fantastic outdoor concert venue hosting popular bands. Or just kick back on your boat enjoying the island vibe and the Conch’s free band.
A great in-town location on the ICW and Matanzas Bay, southwest of the Bridge of Lions (opens on-demand every half hour for over 25’ clearance), this marina offers 151 slips, fuel, showers, laundry and a lounge.
This full-service marina is just off the ICW in Salt Run, with a fun tiki bar and live music, a casual restaurant and motel. The Conch has 200 protected dock slips, fuel, pump-out, showers, swimming pool and laundry for marina guests.
Located just two miles from St. Augustine’s Historic District, this full-service marina boasts 230 wet slips, high-speed fuel pumps and a service yacht yard. Enjoy amenities such as a pool, fish cleaning station and on-site dining.