A Weekend in St. Augustine | Ultimate Romantic Itinerary

St. Augustine is one of those small towns where you could go back a million times and never tire of it. It’s incredibly walkable, beautiful, and filled with vibrant culture. 

The moment you and your better half walk through its old city gates, you’ll be in awe of the Spanish colonial architecture that adorns its historic buildings and the sweeping views of the Atlantic Ocean. 

Need a thorough itinerary for St. Augustine that is exclusively for couples?

We’ve got you. This article was curated from our own experience of spending a romantic weekend in this charming city. We’ll cover everything from where to stay, what to do, and where to eat so you can worry less about planning and spend more time getting totally amped for the romantic weekend of your dreams!

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As America’s oldest city, Saint Augustine is the perfect place for a romantic weekend getaway. Its rich history, remarkable scenery, and utterly charming people make it unforgettable.

Whether you and your partner are history buffs, foodies, beach bums, night owls, or adventure seekers, a weekend in St. Augustine will forever hold a place in your heart.

History & Facts

Around every corner of the historic city of St. Augustine is a fascinating story of the past. There is simply too much to go over in this article alone, but we’ll give you a brief summary — we wouldn’t want to spoil too much anyway!

In 1513, the Spanish explorer Juan Ponce de León discovered the coast of Florida and claimed the territory for the Spanish crown. Despite many failed attempts, it was Pedro Menéndez de Avilés who eventually succeeded in establishing the first permanent European settlement in Florida in 1565. This event marked the beginning of Spain’s influence and rule in Florida for over 200 years.

As important as this piece of history is, it is equally important to acknowledge that this settlement was built on the backs of enslaved local natives and Africans. Do remember this when walking through its streets and admiring this special place!

Now, we fast forward to the 1800s, when Henry Flagler transformed St. Augustine, a once sleepy town, into a hot resort destination. His romantic hotels, extravagant buildings, and transportation system brought tourism to the city and greatly contributed to its preservation as a historic city today.

St. Augustine is a melting pot of cultures and influences, from Spanish and British to African and Native American. As you walk through its streets, you’ll see the remnants of these diverse cultures in its architecture, food, and traditions. It’s a truly special place!

When to Visit

St. Augustine is honestly a delight any time of year. But if you want to maximize your experience, we recommend visiting between March and May. This is when you’ll experience the best weather and the least amount of tourism, so you and your sweetie can enjoy your romantic weekend to its fullest.

The summer months (June to August) are the most crowded, and the chilliest time of year is between December and February. Either way, you’ll find that St. Augustine has something special to offer in every season.

In this Article:

  • The interesting historical facts about St. AUgustine so you can fully appreciate the culture when you’re there.
  • The best time of year to go along with the easiest ways to get there and our favorite places to stay.
  • A detailed 3-day itinerary that covers all the top romantic activities, places to visit, and dining options.
  • A breakdown of what you don’t want to miss and an easy-to-read list of things to do.
  • What to pack for a seamless romantic vacation in St. Augustine.

Where to Stay

You may be staying in the nation’s oldest city, but that doesn’t mean the accommodations are outdated. There are plenty of amazing places to stay in St. Augustine. From quaint little guest rooms to luxury hotels, you and your beau will find the perfect spot to rest your heads.

Our personal favorite is the St. George Inn, a boutique hotel nestled in the heart of downtown St. Augustine. This great place features a wine bar, semi-private balconies, and al a cart-style breakfast at no additional charge. 

The rooms are over top of the shops of the famous St George Street for amazing views of shops below or out to the Castillo de San Marcos and yet at night, they get quiet enough for a peaceful evening sleep.

With everything in walking distance, you and your sweetie can explore the downtown area by day and relax in your cozy room at night. Not to mention, the hospitality is phenomenal! 

How to Get There 

There are a few different ways to get to St. Augustine, depending on the direction you’re coming from. If traveling from the north or south, you can take Interstate 95, U.S. Highway 1, or Florida’s scenic A1A highway.

Visitors coming from the west have access to Interstate 10, while those coming from central and southwest Florida can take Interstate 4 or Interstate 75.

If flying in is more your style, St. Augustine has a small airport (St. Augustine Regional Airport) that services private and charter flights. The closest major airports are in Jacksonville, Orlando, and Daytona Beach.

St. Augustine 3-Day Itinerary 

Day 1:

Arrive at St. Augustine and check into St. George Inn or your favorite hotel or Airbnb of choice. Make sure you’re both in comfortable shoes and clothing before heading out on the Old Town Trolley Tours. 

There are so many historical sites, museums, quirky shops, and popular restaurants to explore! So, this is a great way to get a feel for what looks interesting to explore further later as you two lovebirds take in all the sights. 

Right on St. George Street, stop for lunch at St. Augustine Seafood Company. Then, spend the rest of the day taking advantage of your trolley pass. You and your sweetie can stop at places like the Colonial Quarter and the Ximenez-Fatio House before having a romantic dinner at the Columbia Restaurant. 

Don’t forget to watch the sunset at Wander Ponte Vedra before heading back to your hotel! The beautiful views are sure to get the sparks flying.

Day 2:

Just like the sunsets, you can’t beat a St. Augustine sunrise. Wake up early with your love and take a stroll along the Bayfront Walk for a special morning. Stop by The Kookaburra, a local coffee shop, and grab breakfast before venturing off for the day.

Take a drive out to Washington Oaks Garden State Park to immerse yourself in the stunning Florida landscape. You and your one and only can pack a picnic for lunch and spend some quality time together in picturesque scenery.

After your romantic picnic, have a splash at Crescent Beach. You can rent chairs and umbrellas and soak up the sun before heading off to dinner at La Floridian.

Day 3:

Now that you’ve got your bearings at this point, day 3 is a great opportunity for you and your partner to explore anything else you’d like to see that you haven’t gotten to yet. The Lightner Museum, Flagler College, St. Augustine Lighthouse, and San Sebastian Winery are all must-sees.

For a truly romantic evening, end your trip with a private sailboat ride with St. Augustine Sailing. Enjoy an adventure out on the water, taking in the sights and sounds of this beautiful city from a different perspective while cuddling close to your love.

Once you’re back ashore, head over to The Ice Plant (which was literally an Ice Plant in the 1920s). Savor a craft cocktail or two and indulge in some farm-to-table food before a cozy night in or night out on the town, enjoying local live music at the Saint Augustine Amphitheatre. 

There really is no better way to end your romantic weekend getaway!

Things You Don’t Want to Miss

Make sure to check the calendar of events. St. Augustine has a TON going on all year long. 

For one, the Asado Life dining experience is a must-try for foodies. Located across the river from downtown St. Augustine, this open-fire cooking experience combines traditional Argentinian techniques with top-notch culinary skills to create a dining experience like you’ve never experienced before!

Another not-to-miss event is the annual Night of Lights festival, a holiday tradition that lights up the entire city for the ultimate romantic ambiance. You also want to check out the Castillo de San Marcos National Monument, a historic fort that offers guided tours and amazing views of the city. 

Best Places to Eat

St. Augustine is full of culinary delights, so expect nothing but the best wherever you decide to go. Even so, you can’t help but have your favorites! We highly recommend trying out Asado Life, Llama Restaurant, Michaels, Catch 27, Rainforest Cafe, and Floridian. 

As mentioned previously, Asado Life is a must-try for foodies. But make sure to check their schedule in advance and plan your trip around one of their dinners for the ultimate experience. 

Llama Restaurant is another top-rated spot that offers some of the best Peruvian cuisine in town, and for a more upscale dining experience, check out Michaels. This fine-dining restaurant features creative dishes made with local ingredients and an extensive wine list. If you’re in the mood for seafood, Catch 27 is the place to be.

For a classic white tablecloth ambiance, head to Rainforest Cafe. This iconic restaurant has been serving up delicious meals in downtown St. Augustine for decades. Lastly, Floridian is a must-visit for its Southern charm, delicious drinks, and amazing fried green tomatoes. Make sure to save room for dessert and try their famous key lime pie!

Insider tip: Cafe 11 has the best happy hour on the island! With a wide selection of drinks and delicious tapas-style dishes, this cozy cafe is the perfect spot to unwind after a day of exploring for both locals and tourists alike.

Things to Do

With only 3 days to explore St. Augustine, you’ll want to make the most of your time and see all the must-see attractions. Here are some top picks for things to do during your stay:

  • Take a tour of Flagler College
  • Climb to the top of the St. Augustine Lighthouse 
  • Zipline at the Alligator Farm 
  • Visit the St. Photios Greek Orthodox National Shrine
  • Step in the footprints of Andrew Young at the central plaza
  • Check out the Lincolnville Museum
  • Grab a bite at the Village Garden Food Truck park 
  • Kayak or hike at Anastasia State Park


What is the prettiest street in St. Augustine?

Magnolia Avenue takes the number one spot for scenic streets in St. Augustine. The road is lined with majestic oak trees and is a popular spot for photos.

How long is the trolley ride in St. Augustine?

The trolley ride is approximately 80 minutes long. However, guests can get on and off at various stops throughout the city to explore at their own pace. Your pass is good all day.

What part of St. Augustine is best to stay in?

This all depends on the kind of environment you and your partner prefer! If you’re looking for a romantic and historic vibe, staying in the Historic District is your best bet. For a more laid-back and beachy feel, check out Vilano Beach or Saint Augustine Beach.

What to Pack 

With warm temperatures year-round, packing for St. Augustine is pretty easy. Be sure to bring plenty of swimsuits, sunscreen, and comfortable walking shoes as you’ll be exploring the city on foot. 

Other essentials include a hat, sunglasses, light layers for cooler nights, and an umbrella or rain jacket just in case. Don’t forget to pack your camera or phone charger to capture all the special moments during your trip. And if you’re planning on dining at any upscale restaurants, be sure to pack a nicer outfit or two!

Pack Your Suitcase….. 

Now that you have all the necessary information for your romantic weekend getaway in St. Augustine, it’s time to pack your bags and get ready for an unforgettable trip with the love of your life.

Don’t forget to include any special items or surprises for your partner, whether it’s a favorite snack, a small gift, or anything else that will make their experience even more special! And most importantly, don’t forget to pack your sense of adventure and love for each other as you explore this unbelievable city together! 

Was there anything we missed? Feel free to share with us your favorite parts of your romantic weekend in St. Augustine! And for more travel tips and itineraries, subscribe to my newsletter

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