Have Your Best Besties Trip to St. AugustineSt. Augustine is the kind of city that turns a weekend into the story you and your friends are still telling years later. Historic, walkable, full of great food, ghost tours, and beaches that make it very easy to stay one more day.Authorskerrieturcic
DestinationsSt. AugustineItinerary

Day 1

The Blue Hen Café
This is the spot locals actually go, and the line proves it. Get the chicken biscuit with peach butter — it's the thing everyone talks about. The blue crab quiche and pumpkin pancakes are both worth ordering too, especially if the group is splitting plates. On West King Street, closed Tuesdays and Wednesdays.
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Heritage Walk
An indoor market at 162 St. George St. with a genuinely eclectic mix of independent shops, including a pirate outfitter, a hat shop, leather goods, and an old-time portrait studio where you can get a full sepia photo in period costume! Easily one of the more memorable stops of the trip, and way more fun than the standard souvenir shops.
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Castillo de San Marcos National Monument
The oldest masonry fort in the U.S., built between 1672 and 1695, still standing because the coquina walls absorbed cannonballs instead of shattering. Walk the ramparts together, look out over the bay, and catch a cannon demonstration if it's a weekend visit. $15 adults and no cash at the gate.
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Columbia Restaurant
Five generations of the same family have operated this St. George Street institution since 1983. The dining rooms are stunning, with hand-painted tiles and a Spanish fountain setting the mood. The tableside 1905 Salad is prepared right in front of you with garlic, oregano, wine vinegar, and Spanish olive oil, while a pitcher of mojitos or white sangria keeps the night going. The paella, roast pork, and Cuban sandwich are some of the standout dishes on the menu.
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A Ghostly Encounter
The perfect thing to do together after a good dinner when no one wants the night to end. Operating since 2001 and still the best ghost tour in the city, with guides who are genuinely knowledgeable and entertaining rather than theatrical about it. Options go from a walking tour to a pub crawl to a full paranormal investigation with K2 meters in actually haunted locations.
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Day 2

O'Steen's Restaurant
Cash only, no reservations, line out the door most days, and worth every bit of the wait. Been here since 1965 and the fried shrimp is the reason. Order the Minorcan clam chowder too, a local specialty made with datil peppers that you're not going to find anywhere else.
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St. Augustine Lighthouse & Maritime Museum
219 steps and the view at the top with the coast in one direction and the city skyline in the other makes every one of them worth it. It's a great photo moment together up there. The restored keeper's quarters and maritime exhibits at the base are genuinely interesting and right next door to Anastasia so the afternoon flows naturally.
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Anastasia State Park
Four miles of Atlantic beach with real dunes and no development crowding the shoreline, voted a Top 10 Florida Beach by USA Today in 2025. Anastasia Watersports inside the park rents kayaks, canoes, and paddleboards on the calm Salt Run with lighthouse views and a solid chance of spotting dolphins.
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Catch 27
Fresh-catch Florida seafood at 40 Charlotte Street, whatever came off the boat that day and cooked from scratch. Start with the deviled egg BLT with southern fried oysters and tomato-bacon jam because everyone at the table is going to want it. Mahi, snapper, triggerfish, and flounder all rotate on the menu with the season. The courtyard patio on a Saturday night is the place to be.
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Saint Augustine Distillery
Free tours and tastings in a beautifully restored 1907 ice plant where they make small-batch bourbon, vodka, rum, and gin on-site. The bourbon is the one to try. It's also an Old Town Trolley stop so no one has to worry about navigating.
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Day 3

The Boathouse St. Augustine
The Boathouse sits right on the intracoastal and a short drive from the historic district. The outdoor deck has water views, boats going by, and live music most Sundays — the kind of brunch spot where two hours pass without anyone noticing. Order the lobster Benedict or shrimp and grits, get a round of Bloody Marys or hibiscus mimosas, and let the morning stretch out.
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St Augustine Beach
Wide open Atlantic shoreline with easy parking at St. Johns County Ocean Pier Park, no state park entry fee, and plenty of room to spread out. Different feel from Anastasia, a little more laid back, and a great place to just be in the water together before the afternoon picks up.
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Anastasia State Park & Watersports
Two great operators right next to each other near the lighthouse. Anastasia Watersports puts the group on the Salt Run, calm protected water with lighthouse views and dolphins likely making an appearance. Kayaking St. Augustine is directly across the street with the same setup. Both rent kayaks, canoes, and paddleboards and both are by reservation only, so lock in Sunday slots before the trip.
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Lightner Museum
Lightner Museum occupies Henry Flagler’s 1888 Alcazar Hotel and is now one of the best museums in the city. The building alone is worth the visit, with grand arches, an enormous converted indoor pool, and ornate staircases throughout. Inside, you’ll find Tiffany lamps, Victorian mechanical musical instruments that still play, and Gilded Age fine art spread across three floors. Aim to arrive by 3:30 if the water sports run long.
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Churchill & Lacroix, Antiquaire
Right in the Lightner Museum courtyard at 75 King Street, the kind of shop where everyone finds something they can't leave without. Estate jewelry from the Victorian, Art Deco, and Edwardian periods, Tiffany Studios glass, Baccarat crystal, Lalique, Meissen, hand-signed paintings, and fine porcelain. The owner has been sourcing pieces for over 45 years and the staff knows every item in the room. A genuinely special last stop.
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The Options Don't Stop

Airboat Adventure in Saint Augustine with a Guide
Strap in — this 90-minute airboat ride through the freshwater tributaries of the St. Johns River is the kind of thing nobody on the trip will stop talking about. Gators, manatees, bald eagles, wild boar, and more, all up close along Trout Creek and Six Mile Creek with a guide who knows exactly where to find them.
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St. Augustine Hop-On Hop-Off Trolley Tour
Twenty-two stops, live narration, and a conductor who actually makes the history interesting. Ride the full loop first to get the lay of the land, then hop off wherever the group wants to dig deeper. Your ticket includes the St. Augustine History Museum and a free beach shuttle, so it pulls more weight than it looks like on paper.
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Sunset Cruise of St. Augustine
Cold drink in hand, water under you, and the St. Augustine skyline doing its thing at golden hour. Pick your vessel based on the vibe — the Osprey is 21 and up with a full beer and wine bar on board, while the Island Breeze is BYOB and the Great Blue Heron has a bar if you'd rather not haul your own.
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