A Romantic Weekend Itinerary in St. Augustine For Couples

If St. Augustine isn’t the number-one romantic destination in Florida, it surely comes close. We love the ancient city atmosphere, the crisp cool ocean breeze, and the dazzling Nights of Lights celebration. We adore St. Augustine and are eager to share it all with you. Below we cover an amazing romantic weekend itinerary, from the morning of Saturday’s day one to the closing evening hours of Sunday night. 

Once you book one of our top-rated St. Augustine condo rentals, you are ready to plan your adventure. So, what’s in store for you?

Day 1

Grab Breakfast and Coffee at Kookaburra

While St. Augustine is home to many wonderful coffee and breakfast shops, we recommend the Kookaburra. Kookaburra is primarily a coffee shop, but you can find a selection of handmade special pies. Kookaburra is also a great choice because there are three locations in the city. You can easily visit the beachside location, just a few miles from our St. Augustine oceanfront condos for rent. But there is also a town location and a historic district location. 

Eco Tour Boat Excursion

Before you get too deep into the day, we highly recommend setting aside some late-morning time for an eco-tour. Before the weather is too warm and the crowds pick up, you can cruise the local waters seeking dolphin and even manatee. The aptly-titled St Augustine Eco Tours offers 1.5 nature trips for all ages.

Grab Lunch at O.C. Whites

O.C. Whites sits right on the Matanzas River (and is right across from our favorite eco-tour provider). This seafood restaurant is the quintessential stop for Florida seafood lovers. It’s outdoor patio space hosts music most weekend afternoons.

Tour the Distillery or Winery

We think the St. Augustine Distillery is one of the area’s best attractions- and it is free to visit! Tours come with no charge, and you even get to try a little whiskey while you are at it. Stop by this recently-rescued former ice plant for a fun and romantic little trip.

Sunset Dinner at Aunt Kate’s

If Aunt Kate’s is famous for anything, it is its exquisite view. Stop by Aunt Kate’s to indulge in one of the city’s all-around best evening dinners by the water. 

Grab drinks at Prohibition Kitchen

If you still have some energy, be sure to head back downtown for some drinks at Prohibition Kitchen. When this authentic steampunk bar and restaurant settled in St. Augustine, it changed the game. Its dazzling aesthetic is a treat all on its own, but its unique drinks really make it a must-see.

st augustine couple holding hands
Photo from Pexels

St. Augustine Condo Rentals

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Day 2

Explore the Lighthouse and Museum

You can’t go on any trip to St. Augustine without seeing the views from the top of the St. Augustine Lighthouse. It truly is something special, with its views of both downtown and the marshland.

Take a Sip from the Fountain of Youth

Head just past downtown and have a romantic walk through the Fountain of Youth. What it lacks in bold attractions it makes up for in quiet and simple beauty.

Join a Food Tour for Lunch

St. Augustine is home to literally hundreds of possible places to eats. So why not get a taste of a few restaurants in one day with the tasting tour flight. Check out a hand-picked selection of local restaurants and get a small taste of the city’s wide spectrum of eats. We recommend Tasting Tours.

Grab Gelato and Explore the Shops

We highly recommend an afternoon romp from one end of St. George Street to the other. On the way, be sure to stop at Gelato Time, next to the very famous Pizza Time. 

End the Day with Dinner at the Floridian

Since you are already downtown for the evening, be sure to see the city’s finest organic and local restaurant. The Floridian is simply dazzling. The dishes change seasonally. Be sure to get a peek at the Shrimp and Grits.  

Undoubtedly, The Ocean Gallery condominium is one of the best beachfront St. Augustine resorts for couples. You can have an amazing weekend escape for two in the cozy nook of St. Augustine.