What to Do in St. Augustine: Activities When Not Sailing With Us

St. Augustine isn’t just a destination, it’s a feeling. The moment you step off our dock after a full-day charter, a glowing dinner sail, or your very first sailing lesson with St. Augustine Sailing, the city wraps around you like Spanish moss in the breeze. Founded in 1565, America’s oldest city somehow feels both frozen in time and vibrantly alive. Cobblestone streets, candlelit forts, dolphin-filled waters, and some of the best sunsets on the East Coast are all waiting for you.

You came for the sailing (and we’re flattered), but you’ll stay for everything else. Here’s your ultimate guide to what to do in St. Augustine when your feet are back on dry land, plus a few irresistible reasons to get right back on the water with us tomorrow.

The Historic Heart: Landmarks That Define St Augustine

You can’t fully answer “what to do in St. Augustine” without diving into the history that makes this city unlike any other in America.

Castillo de San Marcos National Monument

This 17th-century star fort is the oldest masonry fortress in the continental U.S., and it has never been taken by force. Built of coquina shell-stone that literally absorbs cannonballs, it withstood sieges by pirates and the British Navy alike. Walk the gun deck at golden hour, watch weekend cannon and musket demonstrations, and look out over the very waters you just sailed. Fun fact: on calm days you can see our sails gliding past from the seawall.

Lightner Museum and Flagler College

In the late 1800s, railroad tycoon Henry Flagler decided St. Augustine should be America’s premier winter resort. His opulent Hotel Ponce de León is now the breathtaking campus of Flagler College. Take the free daily tour and stand inside the rotunda where Tiffany stained-glass windows and hand-painted murals still dazzle. Across King Street, the Lightner Museum occupies Flagler’s former Alcazar Hotel and houses one of the wildest Gilded Age collections you’ll ever see, think Victorian shrunken heads, antique mechanical instruments, and a mummy or two

St George Street & The Colonial Quarter

The pedestrian-only St. George Street is the bustling soul of downtown. Duck into centuries-old buildings that now hold art galleries, fudge shops, and taverns pouring local craft beer. A few blocks away, the Colonial Quarter is a two-acre living-history museum where costumed interpreters fire muskets, forge iron, and even let you try your hand at 18th-century leatherworking. It’s immersive without being cheesy, perfect for kids and history buffs alike.

"Only-in-St Augustine" Experiences

Some activities are so uniquely St Augustine that they belong on every bucket list.

St Augustine Lighthouse

Climb 219 spiral steps to the top of Florida’s oldest lighthouse (built 1874). On a clear day you’ll see Anastasia Island, downtown, and the exact sailing grounds we use every day. The keepers’ house museum dives deep into shipwrecks, WWII coastwatching, and the ghosts that supposedly still climb the tower after dark.

St. Augustine Distillery

Housed in a restored 1917 ice plant, this award-winning distillery offers free 45-minute tours ending with generous tastings of bourbon, gin, vodka, and rum, all made in-house. Stay for dinner or cocktails at the Ice Plant Bar upstairs, where bartenders chip ice by hand and the Datil Pepper Old Fashioned will wake up your taste buds.

Ghost Tours

St. Augustine is consistently ranked one of America’s most haunted cities. Evening walking tours, hearse rides, and haunted pub crawls recount tales of yellow-fever graveyards, pirate executions, and restless spirits along the bayfront. Many of the stories take place on the exact waterfront you’ll recognize from your charter.

Whetstone Chocolatiers

Free factory tours let you watch sea-salt caramels and key-lime truffles being made, then load up on samples. Pro tip: the dark-chocolate bourbon pecan “barks” travel well as souvenirs.

Nature Breaks When You Need Sand and Solitude

Anastasia State Park – Four miles of untouched Atlantic beach, kayak rentals, and shaded trails just across the Bridge of Lions.
Fort Matanzas National Monument – Free ferry to a tiny 1740s fort on Rattlesnake Island; perfect half-day history-and-nature combo.
Guana Tolomato Matanzas Research Reserve (GTM) – Boardwalk trails, birdwatching, and peaceful kayak launches if you still crave paddling.

Your Perfect St Augustine Itinerary Starts on the Water

St. Augustine delivers history, haunts, beaches, and world-class food, but nothing ties it all together like the moment our sails fill and the city slips away behind you. Whether you’re still buzzing from a full-day private charter chasing dolphins, toasting a sunset on a dinner sail, or proudly trimming the jib after your first ASA lesson, one thing is clear: the best answer to “what to do in St. Augustine” always involves more time on the water.

Don’t leave without the highlight of your trip. Book your private charter, romantic dinner sail, or sailing lessons today and make memories that outshine even the lighthouse beam.

Fair winds await — see you on deck!

Keep the Nautical Vibes Alive

Let’s get the obvious out of the way first: the single best answer to “what to do in St. Augustine” is… book another sail with us. Our guests do it all the time because no two trips are ever the same.

Half or Full Day Private Charters

Imagine having a luxurious 40-foot sailing yacht all to yourself and up to 12 of your favorite people. That’s exactly what our full-day private charters deliver. We’ll glide across Matanzas Bay, venture out into the open Atlantic Ocean, or slip under the Bridge of Lions, and cruise the Intracoastal Waterway while bottlenose dolphins surf our bow wave. Spread out a picnic (BYO or let us provision) and let the autopilot of life take over. Morning departures catch the calmest seas; afternoon trips chase the golden hour. Either way, you’ll return to the dock sun-kissed, salty, and already planning the next one.

Romantic Dinner Charters

Sunset in St. Augustine is spectacular from land but it’s cinematic from the water. Our evening dinner charters turn the Matanzas into your private dining room for up to 12 guests, made even more memorable with Chef Wes of Khloe’s Kitchen, who curates a menu around your tastes and preferences. Every menu is uniquely designed for each guest, whether you’re craving a luxe grazing spread, chilled prosecco, fresh seafood towers, or a full surf-and-turf experience. As the sky explodes in pinks and oranges behind the lighthouse, you’ll understand why so many couples choose this moment for proposals, anniversaries, or simply saying “I love you” without words. Add soft music, warm blankets if the breeze picks up, and zero distractions, just your favorite people, Chef Wes’s personalized dining, and the sea.

ASA - Certified Sailing Lessons

Vacation is great, but coming home with a new lifelong skill is better. Our American Sailing Association courses are world-class. Start with Basic Keelboat (101) and learn to harness the wind in just one or two days. Already have experience? Move up to Basic Coastal Cruising, Bareboat Chartering, or even Coastal Navigation. We offer private lessons, small-group classes, kids’ weeks, and women-only clinics. By the end of your trip you won’t just be a passenger, you’ll be the one trimming the sails while your friends cheer.

Book one experience or stack all three. The water will still be here tomorrow, and so will we.