What is the perfect 3-day itinerary for St. Augustine?
The perfect three-day St. Augustine itinerary includes exploring Historic Downtown, St. George Street, Castillo de San Marcos, local restaurants, the beaches, water adventures like dolphin cruises or parasailing, and ending with a sunset dinner overlooking Matanzas Bay. Staying in Historic Downtown allows you to walk to many of the city’s most popular attractions.
If you’re anything like most visitors, you’ve probably spent hours reading travel blogs trying to figure out the best way to experience St. Augustine.
Some tell you to spend all your time downtown.
Others say head straight for the beach.
Some recommend twenty attractions in one day, while others leave out some of the city’s best experiences entirely.
After living here and exploring nearly every corner of America’s oldest city, I’ve learned something important…
The perfect St. Augustine vacation isn’t about seeing everything.
It’s about experiencing the city the way locals enjoy it.
That means slowing down.
Enjoying your morning coffee.
Walking historic streets instead of rushing through them.
Watching dolphins swim through Matanzas Bay.
Finding incredible restaurants tucked away in hidden courtyards.
Watching the sunset from places most visitors never discover.
That’s exactly what this itinerary is designed to do.
Whether you’re visiting for the first time, celebrating an anniversary, bringing the family, or simply escaping for a long weekend, this guide will help you experience the very best St. Augustine has to offer.
Let’s start your vacation.
Before You Arrive
Where I Recommend Staying
If you’re only visiting for three days, I strongly recommend staying in Historic Downtown.
Yes, you’ll probably spend a little more on your hotel.
It’s worth every penny.
One of the biggest mistakes visitors make is staying fifteen or twenty minutes away because the room is cheaper.
They end up spending half their vacation driving, paying for parking, or walking much farther than expected.
Stay somewhere within walking distance of St. George Street.
Some of my favorite options include:
• Casa Monica Resort & Spa
• Hilton Historic Bayfront
• The Collector Luxury Inn & Gardens
• St. George Inn
• Bayfront Marin House
If you haven’t already chosen a hotel, be sure to read my complete guide:
➡ Where to Stay in Historic Downtown St. Augustine
Local Tip
Here’s something many visitors don’t realize…
You don’t need to rush.
Downtown St. Augustine is surprisingly compact.
Most of the places you’ll visit over the next three days are within walking distance of one another.
Park your vehicle.
Forget about it.
Walk everywhere.
You’ll notice details you’d completely miss from behind a windshield.
DAY ONE
History, Coffee & Hidden Courtyards
7:30 AM
Coffee Like a Local
Forget Starbucks.
Head to The Kookaburra Coffee on St. George Street.
Order their famous Australian-style flat white or an iced coffee if you’re visiting during the warmer months.
Local Tip
Go early.
Around 8:30, the line starts growing quickly, especially on weekends.
Grab your coffee and walk toward the Plaza de la Constitución.
Sit on one of the benches beneath the giant oak trees.
Watch the city slowly wake up.
It’s one of my favorite moments in St. Augustine.
8:30 AM
Walk St. George Street Before Everyone Else
This is one of my favorite local recommendations.
Most visitors experience St. George Street in the middle of the afternoon when it’s packed.
Don’t.
Morning is magical.
The brick streets are quiet.
Shop owners are opening their doors.
The smell of fresh pastries drifts from nearby bakeries.
Take your time.
Walk every side street.
Peek into the hidden courtyards.
Some of the prettiest places in St. Augustine are tucked behind gates that most tourists walk right past.
9:15 AM
Castillo de San Marcos
Now head toward the Castillo.
Morning is the perfect time.
The sunlight illuminates the front of the fort beautifully, making it one of the best times for photographs.
You’ll also beat many of the larger tour groups.
Plan on spending about an hour exploring the oldest masonry fort in the continental United States.
Local Tip
After leaving the Castillo, don’t immediately head back toward St. George Street.
Walk along Avenida Menendez beside Matanzas Bay.
You’ll often see dolphins swimming surprisingly close to shore.
Many visitors completely miss this.
10:45 AM
Explore the Colonial Quarter
After leaving Castillo de San Marcos, don’t rush to the next attraction.
Cross the street and spend some time wandering through the Colonial Quarter.
Many visitors simply walk past it, but it’s one of the best places to understand what life was like in St. Augustine hundreds of years ago. You’ll find demonstrations, historic buildings, beautiful wooden walkways, and excellent photo opportunities.
Take your time exploring.
One thing I love about St. Augustine is that there really isn’t a wrong turn. Some of the best photos you’ll take aren’t planned—they’re found while wandering down a quiet brick street or stumbling across a hidden courtyard.
Local Tip
Don’t worry about trying to see every museum.
One of the biggest mistakes first-time visitors make is trying to cram ten attractions into one day.
Slow down.
The atmosphere is what makes St. Augustine special.
12:00 PM
Lunch at Prohibition Kitchen
By now you’ve probably worked up an appetite.
One of my favorite lunch stops downtown is Prohibition Kitchen.
The burgers are excellent, but if you’re visiting on a weekend, check to see if live music is playing upstairs.
It’s one of those places where you’ll find both locals and tourists enjoying the afternoon together.
If burgers aren’t your thing, another excellent option is Catch 27 for fresh local seafood.
Either choice is within easy walking distance.
Local Tip
If there’s a wait, don’t stand outside.
Walk a block or two.
Downtown is incredibly walkable, and you’ll almost always find an interesting shop, art gallery, or historic building while you’re waiting.
1:30 PM
St. Augustine’s Oldest Jail
Now it’s time for one of my favorite historic attractions.
The Old Jail isn’t just another museum.
The guided tours are entertaining, funny, and surprisingly informative.
You’ll learn about famous prisoners, attempted escapes, and what life inside the jail was actually like.
Even if you don’t normally enjoy history museums, this one tends to surprise people.
Local Tip
The jail sits just outside the busiest part of downtown.
If you’re feeling tired, this is a great opportunity to hop aboard the Old Town Trolley instead of walking back.
The trolley lets you rest your feet while learning even more about the city.
Reserve Your Trolley Tickets Here
3:30 PM
Wander Without A Plan
This might sound strange…
But one of the best things you can do in St. Augustine is stop following the itinerary for an hour.
Seriously.
Walk.
Turn down streets you’ve never heard of.
Browse the art galleries.
Watch the artists working.
Listen to street musicians.
Grab homemade fudge.
Sample olive oils.
Step inside bookstores.
Walk through hotel courtyards.
Some of my favorite memories in St. Augustine happened when I wasn’t trying to get anywhere.
My Favorite Hidden Walk
Here’s something I recommend to friends whenever they visit.
Start at King Street near Casa Monica.
Walk toward Flagler College.
Continue to the Lightner Museum.
Then wander through the quiet residential streets behind the museum before making your way back toward St. George Street.
Most tourists never explore this part of town, but it’s full of beautiful Victorian homes, massive oak trees, and peaceful streets that feel completely different from the busy shopping district.
It’s one of the most relaxing walks in the city.
5:30 PM
Rooftop Drinks at Casa Reina
As the afternoon starts turning into evening, make your way to Casa Reina.
Even if you don’t plan on eating dinner here, it’s worth going upstairs.
The rooftop views overlooking Matanzas Bay are fantastic.
Order your favorite drink, relax for a while, and watch downtown begin to come alive.
If timing works out, this is one of my favorite places to watch the golden hour before sunset.
Local Tip
If you can, grab a table facing the bay.
You’ll have a front-row seat as horse-drawn carriages roll by, sailboats drift across the water, and people stroll along Avenida Menendez.
It’s one of those moments that reminds you why people fall in love with St. Augustine.
7:00 PM
Dinner
For your first night, I’d choose one of these:
For a Romantic Evening
• Casa Reina Rooftop
• Collage
• Michael’s Tasting Room
Fresh Seafood
• Harry’s Seafood Bar & Grille
• Catch 27
Fine Dining
• La Nouvelle
No matter which you choose, make reservations ahead of time if you’re visiting during weekends or holidays.
8:45 PM
End Your Evening With A Ghost Tour
St. Augustine is considered one of the most haunted cities in America.
Whether you believe in ghosts or not, the tours are an incredible way to experience the city after dark.
The streets become quieter.
The historic buildings take on a completely different feel.
The stories become even more captivating.
This is one attraction I recommend doing after you’ve spent the day exploring downtown because you’ll recognize many of the buildings and landmarks featured throughout the tour.
One Last Stop Before Bed
If you’re not quite ready to head back to your hotel, walk over to Kilwin’s.
Grab a scoop of homemade ice cream or a piece of freshly made fudge from Kilwinn’s.
Then take a slow walk along the bayfront.
There’s something special about downtown after 10:00 PM.
The crowds have thinned.
The lights reflect off the water.
The breeze coming off Matanzas Bay cools everything down.
It’s quiet.
Relaxing.
And the perfect way to end your first day in America’s oldest city.
Day 2: Beaches, Dolphins & Life on the Water
If Day One introduced you to the history and charm of St. Augustine, Day Two is all about experiencing what makes Florida one of the world’s great vacation destinations. The Atlantic Ocean, miles of beautiful beaches, incredible wildlife, and the waters of Matanzas Bay all become the backdrop for a day that’s equal parts relaxing and adventurous.
One thing I always tell first-time visitors is this: don’t spend your entire vacation downtown. The historic district is incredible, but some of the most memorable experiences happen just a few minutes away along the coast.
7:00 AM – Start the Day with a Sunrise
If you’re willing to set your alarm a little early, you’ll be rewarded with one of the most beautiful sunrises you’ll ever see.
Head to St. Augustine Beach or Vilano Beach before the crowds arrive. Bring a cup of coffee, take off your shoes, and simply enjoy the moment. Locals know that sunrise is when the beach feels its most peaceful. The air is cooler, the shoreline is quiet, and you’ll often see people walking their dogs, surfers paddling out, and shorebirds running along the water’s edge.
If you’re staying downtown, the drive is only about fifteen minutes. Trust me—it’s worth it.
Local Tip
If you’re looking for the perfect sunrise photograph, walk a little farther away from the public beach access points. A five-minute walk down the shoreline often gives you wide-open views without another person in your frame.
8:30 AM – Breakfast at Beachside
After sunrise, it’s time for breakfast. If you’re near St. Augustine Beach, head over to Beachside Diner. It’s one of those local spots that has earned its reputation by consistently serving excellent breakfast without trying to be trendy.
If you’re staying closer to Vilano Beach, another great option is to enjoy breakfast at your hotel before heading out for the day.
Either way, don’t rush. One of the best parts of vacation is enjoying a slower morning.
10:00 AM – Dolphin Tour or Parasailing
This is where your day becomes unforgettable.
If you’re traveling with young children or simply want a relaxing experience on the water, I highly recommend booking a dolphin and wildlife cruise. Dolphins are frequently spotted in Matanzas Bay, and it’s not unusual to see ospreys, pelicans, and even the occasional manatee depending on the season.
If you’re looking for something a little more adventurous, book a parasailing trip with Fury Water Adventures.
There’s nothing quite like floating hundreds of feet above the Atlantic Ocean while looking back at the coastline, Anastasia Island, and Historic Downtown St. Augustine. On a clear day, the views stretch for miles, and it’s one of those experiences you’ll still be talking about long after your vacation ends.
Reserve Your Dolphin Tour Here
Local Tip
Morning departures usually offer calmer water and more comfortable temperatures, especially during the summer months. If you’re planning to parasail, I almost always recommend choosing one of the earlier trips.
12:30 PM – Lunch with an Ocean View
After your morning on the water, you’ve earned a great lunch.
Salt Life Food Shack has become a favorite for both locals and visitors thanks to its relaxed atmosphere and excellent seafood. Grab a table outside if the weather cooperates and enjoy lunch while looking toward the beach.
If you’re craving something a little quieter, there are several excellent restaurants on Vilano Beach where you can slow down and enjoy the afternoon without feeling rushed.
2:00 PM – Spend the Afternoon at the Beach
This is one part of the itinerary where I intentionally don’t schedule anything.
You’ve spent the morning exploring and adventuring. Now it’s time to enjoy why so many people vacation in Florida in the first place.
Rent a beach chair and umbrella if you didn’t bring your own. Walk along the shoreline collecting shells. Let the kids build sandcastles. Take a swim if the weather is warm. Read a book under the shade of an umbrella while listening to the sound of the waves.
Sometimes the best vacation memories come from doing absolutely nothing.
A Local Recommendation
If you’re visiting with children, St. Augustine Beach is usually my first recommendation because of its wide sandy shoreline, nearby restaurants, and convenient facilities.
If you’re looking for something quieter and a little more relaxed, drive a few minutes south toward Crescent Beach. The atmosphere is noticeably more peaceful, and you’ll often find long stretches of sand with far fewer people.
5:30 PM – Sunset Cruise on Matanzas Bay
There’s no better way to end your second day than out on the water.
As the sun begins to sink toward the horizon, the light reflecting off the Castillo de San Marcos and the Bridge of Lions creates one of the most beautiful scenes in the city. Watching downtown slowly light up while enjoying a sunset cruise offers a completely different perspective than you’ll ever get from land.
If you’re celebrating an anniversary, honeymoon, or simply enjoying a romantic getaway, this is one experience I would absolutely recommend booking in advance.
Reserve Your Sunset Cruise Here
Local Tip
Bring a light jacket, even during the warmer months. Once the boat gets moving and the sun begins to set, the breeze over the water can be surprisingly cool.
Dinner at Cap’s on the Water
If you don’t mind a short drive, end your evening at Cap’s on the Water.
This restaurant has become one of my favorite places to recommend because it feels like Old Florida. Sitting outside beneath the towering oak trees while watching boats glide through the Intracoastal Waterway is an experience that’s difficult to duplicate anywhere else.
If you’re fortunate enough to arrive just before sunset, you’ll understand why locals continue coming back year after year.
Order fresh seafood, slow down, and enjoy your evening.
After all, vacations aren’t measured by how many attractions you checked off a list—they’re measured by moments you’ll remember years from now.
Day 3: Experience St. Augustine Like a Local
By now you’ve seen the historic streets, explored the waterfront, enjoyed the beaches, and hopefully discovered why so many people return to St. Augustine year after year. Today is different. Instead of trying to check attractions off a list, spend your final day enjoying some of the places and experiences that locals recommend to friends and family when they come to visit.
8:00 AM – Breakfast at Maple Street Biscuit Company
If you haven’t made it here yet, today is the day.
Maple Street Biscuit Company has become a downtown favorite, and for good reason. Their biscuits are made fresh, the portions are generous, and it’s one of those places where you’ll hear both visitors planning their day and locals catching up over breakfast.
One thing I appreciate about Maple Street is that it feels relaxed. Nobody is rushing you out the door. Order a coffee, enjoy breakfast, and take your time. Vacation shouldn’t feel like you’re racing from one attraction to the next.
If you’re looking for something lighter, The Blue Hen Café is another excellent choice, although it’s a short drive from Historic Downtown and can have a wait on busy mornings. Many locals will tell you it’s worth it.
Local’s Tip
If you’re staying downtown, consider leaving your car parked one last time. Walking through the historic district in the morning has a completely different feel than it does in the afternoon. Before the crowds arrive, you’ll hear church bells, see horse-drawn carriages making their first trips of the day, and notice details in the architecture that are easy to miss later.
10:00 AM – Climb the St. Augustine Lighthouse
No visit to St. Augustine feels complete without seeing the city from above.
The climb to the top of the lighthouse is a workout, but the panoramic view is one of the best in Northeast Florida. You’ll see the Atlantic Ocean stretching toward the horizon, Matanzas Bay winding through the city, Anastasia Island, the Bridge of Lions, and the rooftops of Historic Downtown.
Take your time on the observation deck. It’s one of those places where you realize just how much water surrounds St. Augustine and how closely the city’s history has always been connected to the sea.
After exploring the lighthouse grounds, spend a few minutes walking around the property. The maritime museum and exhibits are well worth your time, especially if you enjoy learning about Florida’s coastal history.
12:30 PM – Visit the St. Augustine Alligator Farm
If you’re traveling with children, this may become their favorite stop of the entire trip. Even adults who aren’t usually interested in zoos often leave impressed by the variety of wildlife and the beautifully landscaped grounds.
Of course, the alligators are the stars of the show, but you’ll also find crocodiles from around the world, exotic birds, giant tortoises, monkeys, and educational exhibits throughout the park.
If you’re feeling adventurous, consider adding the Crocodile Crossing zip line experience. It offers a unique perspective of the park as you zip above alligator habitats and scenic boardwalks.
Local’s Tip
Plan to arrive around lunchtime or shortly afterward. Many families head there first thing in the morning, so the crowds often begin to thin by early afternoon. Don’t forget sunscreen and comfortable shoes because you’ll spend more time walking than you might expect.
3:30 PM – One Last Walk Through Historic Downtown
Before heading home, give yourself one more opportunity to wander downtown without an agenda.
This is the perfect time to revisit a favorite shop, pick up souvenirs, or simply enjoy one final stroll along St. George Street. Stop by an art gallery that caught your eye earlier in the trip, browse a local bookstore, or grab a handmade chocolate from Peterbrooke Chocolatier.
One thing I always tell visitors is this: don’t feel like you have to buy something everywhere you stop. Some of the best memories come from simply walking through the city, listening to street musicians, watching artists at work, and soaking in the atmosphere.
5:00 PM – Dinner to Remember
For your final evening, choose a restaurant that captures the spirit of St. Augustine.
If you’re celebrating a special occasion, Collage consistently delivers one of the city’s finest dining experiences. The intimate atmosphere and thoughtfully prepared dishes make it a wonderful choice for anniversaries or romantic getaways.
If you’re in the mood for fresh seafood and waterfront views, Cap’s on the Water is hard to beat. Sitting beneath the sprawling oak trees while boats drift along the Intracoastal Waterway is one of those experiences that feels uniquely Floridian.
For visitors who want one last evening in Historic Downtown, Michael’s Tasting Room offers exceptional steaks and Spanish-inspired cuisine, while Harry’s Seafood Bar & Grille remains a favorite for visitors looking to enjoy New Orleans flavors in the heart of the city.
One Final Recommendation
Before you head back to your hotel, take a slow walk along the bayfront.
Watch the lights reflecting off Matanzas Bay.
Listen to the sound of the horse-drawn carriages passing behind you.
Take one last look at Castillo de San Marcos illuminated against the evening sky.
It’s a peaceful way to end your visit, and it’s often the moment people remember most. St. Augustine has a way of slowing life down just enough to remind you that the best vacations aren’t about how many places you visited—they’re about how those places made you feel.
Before You Leave
Three days is enough to fall in love with St. Augustine, but it’s rarely enough to experience everything the city has to offer. There are still quiet beaches to discover, hidden courtyards to explore, live music venues to enjoy, and restaurants waiting to become your new favorite.
If you’re already thinking about your next visit, you’re not alone. It’s one of the reasons so many people return year after year.
And if you’re still planning your trip or want help creating an itinerary that’s tailored specifically to your interests, I’d be happy to help. Whether you’re looking for the perfect romantic getaway, a family vacation, a golf trip, or a relaxing beach escape, I can help you build a personalized St. Augustine itinerary with recommendations based on how you like to travel.
After all, the best vacations aren’t accidental—they’re thoughtfully planned.
Frequently Asked Questions About Spending 3 Days in St. Augustine
Is three days enough time to visit St. Augustine?
Yes. Three days is the perfect amount of time for most first-time visitors. It gives you enough time to explore Historic Downtown, relax at the beach, experience the city’s history, enjoy local restaurants, and fit in a few unforgettable activities like a dolphin cruise, ghost tour, or sunset sail. While you certainly won’t see everything, three days allows you to experience the very best of St. Augustine without feeling rushed.
What is the best time of year to visit St. Augustine?
St. Augustine is beautiful year-round, but my favorite times to visit are spring and fall. The weather is comfortable, outdoor dining is enjoyable, and you’ll generally find smaller crowds than during the peak summer months. If you don’t mind cooler evenings, Nights of Lights during the holiday season is one of the most magical times to experience the city.
Should I stay in Historic Downtown or near the beach?
If this is your first visit, I almost always recommend staying in Historic Downtown. You’ll be able to walk to many of the city’s most popular attractions, restaurants, shops, museums, and the bayfront without worrying about parking. If your vacation is centered around relaxing by the ocean, surfing, or spending most of your time on the sand, St. Augustine Beach or Vilano Beach are excellent alternatives.
Do I need a car during my visit?
If you’re staying in Historic Downtown, you’ll spend much of your trip on foot. Many attractions, restaurants, and shops are within easy walking distance of one another. You’ll likely only need your car for visiting the beaches, the lighthouse, or a few attractions outside the historic district.
What are the absolute must-see attractions in St. Augustine?
If it’s your first trip, I recommend visiting Castillo de San Marcos, St. George Street, the Colonial Quarter, the St. Augustine Lighthouse, the Old Jail Museum, and taking either a dolphin cruise or a sunset cruise. Together, these experiences offer a great balance of history, scenery, and coastal adventure.
Is St. Augustine a good destination for families?
Absolutely. Families will find plenty to enjoy, including beautiful beaches, dolphin tours, the St. Augustine Alligator Farm, pirate attractions, trolley tours, miniature golf, and museums designed for all ages. The city offers a nice balance of educational experiences and fun outdoor activities.
Is St. Augustine a romantic destination for couples?
Very much so. Couples love St. Augustine for its historic streets, horse-drawn carriage rides, rooftop restaurants, waterfront dining, charming bed-and-breakfasts, sunset cruises, and beautiful beaches. It’s one of Florida’s most popular destinations for anniversaries, proposals, and weekend getaways.
What should I pack for a three-day trip to St. Augustine?
Comfortable walking shoes are essential since you’ll spend a lot of time exploring downtown on foot. I also recommend bringing lightweight clothing, sunglasses, sunscreen, a reusable water bottle, a swimsuit, and a light jacket for evenings on the bayfront or while enjoying a sunset cruise.
Are the beaches close to Historic Downtown?
Yes. St. Augustine Beach is approximately a 15-minute drive from Historic Downtown, while Vilano Beach is even closer. Many visitors spend the morning exploring downtown before relaxing at the beach in the afternoon.
Is it worth taking a dolphin cruise or sunset cruise?
Without question. Seeing St. Augustine from the water offers a completely different perspective of the city. Dolphin cruises are a favorite for families, while sunset cruises are especially popular with couples looking for a relaxing evening on Matanzas Bay.
What are some local tips for first-time visitors?
Arrive at popular attractions early in the morning whenever possible, especially Castillo de San Marcos. Take time to wander beyond St. George Street into the quieter side streets and hidden courtyards. Don’t overbook your itinerary—some of the best memories come from simply exploring. And if you’re planning dinner at a popular restaurant, make reservations well in advance during weekends and holidays.
Can someone help me plan my St. Augustine vacation?
Absolutely. If you’d like personalized recommendations based on your travel dates, interests, budget, and who you’re traveling with, I’d be happy to help. Whether you’re planning a romantic getaway, family vacation, golf trip, or long weekend, I can recommend the best hotels, restaurants, attractions, and experiences to help you make the most of your time in St. Augustine.
Continue Planning Your St. Augustine Vacation
I hope this itinerary helps you make the most of your time in America’s oldest city. If you’re still planning your trip, these guides will help you dive even deeper into the places, restaurants, beaches, and experiences that make St. Augustine such a special destination.
🏨 Find the Perfect Hotel
Not sure where to stay? My local guide breaks down the best hotels and inns within walking distance of Historic Downtown, St. George Street, and the bayfront.
→ Where to Stay in Historic Downtown St. Augustine
🏖️ Discover the Best Beaches
From the family-friendly shores of St. Augustine Beach to the quieter beauty of Crescent Beach and Vilano Beach, here’s where locals go to relax.
→ Best Beaches in St. Augustine
🍽️ Eat Like a Local
Skip the tourist traps and discover some of my favorite restaurants, hidden gems, rooftop dining, fresh seafood, and local breakfast spots.
→ Best Restaurants in St. Augustine
🌙 Experience St. Augustine After Dark
Looking for live music, rooftop cocktails, ghost tours, or waterfront dining? Here’s how to spend an unforgettable evening in the Ancient City.
→ St. Augustine Nightlife Guide
🚤 Get Out on the Water
Whether you’re interested in parasailing, dolphin tours, paddleboarding, fishing charters, or a relaxing sunset cruise, these are some of my favorite ways to experience St. Augustine from the water.
→ Best Water Activities in St. Augustine
🌴 Explore More Outdoor Adventures
Love being outside? Discover scenic biking trails, championship golf courses, kayaking, pickleball, surfing, hiking, and more.
→ Best Outdoor Adventures in St. Augustine
🎢 Take an Easy Day Trip to Orlando
Visiting for a few extra days? Here’s how to plan the perfect day trip to Orlando’s world-famous theme parks and attractions.
→ Best Orlando Day Trips from St. Augustine
Ready to experience St. Augustine like a local?
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