Florida couples hoping to escape the hustle and bustle of the city for a few days on a weekend getaway or midweek trip should consider heading from Orlando to St. Augustine—an idyllic destination steeped in history and romance. Located just two hours from Orlando, this historic gem provides the perfect backdrop for romantic dinners, immersive sightseeing tours, and days on the white sand beach.
The journey is part of the charm, featuring a scenic route covering beautiful tropical landscapes and coastal views from the historic AIA. Heading from Orlando to St. Augustine via this historic highway only adds to the memories with stunning views of the sparkling water as you make your way to the Nation’s Oldest City. Aside from all of the great things to do in St. Augustine, which we’ll fill you in on below, there are so many great places to stay!
Many of these lodging options are small boutique properties with elegant accommodations, historic stories, and welcoming service. Two of these bed-and-breakfast-style choices are our very own intimate Casa de Sueños and our sister property, the St. Francis Inn. If you’re heading from Orlando to St. Augustine with romance in mind, Casa de Sueños is your best bet, as it’s designed to cater to couples looking to reconnect, relax, and spend that quality time together. Book your room at our St. Augustine Bed and Breakfast today!
Romantic Getaway From Orlando to St. Augustine, Florida
St. Augustine, the nation’s oldest city, exudes old-world charm and a romantic ambiance without even trying! This makes it an ideal destination for couples seeking both relaxation and adventure. As you wander through the cobblestone streets, you’ll be transported back in time, surrounded by the stunning architecture of ancient buildings and ocean breezes.
Here are the best things to do on your romantic getaway from Orlando to St. Augustine:
- Carriage Ride For Two: Explore the beauty of St. Augustine with a horse-drawn carriage ride through the historic district offered by Old Town Trolley Tours. This romantic experience is perfect for snuggling up with your partner.
- Shop and Stroll the Historic Downtown: Explore the charming boutiques, galleries, and historic buildings along St. George Street, a pedestrian-only thoroughfare. Take a leisurely stroll and soak up the vibrant atmosphere of this ancient street.
- Visit Castillo de San Marcos: Discover the oldest masonry fort in the continental US, Castillo de San Marcos. Enjoy panoramic views and step into history on a guided tour from one of the knowledgeable historians.
- Wine Tasting and Fine Dining: Experience a romantic night at one of the exquisite St. Augustine restaurants. Savor a candlelit dinner featuring fresh seafood, local delicacies, and a fine wine selection—a must on any romantic getaway from Orlando to St. Augustine.
- Take a Sunset Cruise: Embark on a sunset cruise along the Matanzas Bay or the Intracoastal Waterway with St. Augustine Boat Tours. Enjoy breathtaking sunset views over the water while sipping champagne and savoring each other’s company.
- Hit the Beach: Take a short drive to one of the nearby beaches, such as St. Augustine Beach or Anastasia State Park. Spend a relaxing day sunbathing, swimming, or exploring the rolling sandy dunes.
- Explore the Lightner Museum: Discover the grandeur of the Gilded Age at the Lightner Museum, housed in the former Alcazar Hotel. Admire the extensive collection of art, antiques, and curiosities, and appreciate the stunning architecture of the building.
- Spa Day: Pamper yourselves with a couples’ massage or a rejuvenating spa treatment at one of the luxury spas in St. Augustine. Salt Spa is one of our favorite spas in St. Augustine. If you’ve booked the Pampered Package, you’ll be all set for a massage!
Book Our Romantic Bed and Breakfast in St. Augustine
Our Inn is one of the most romantic places to stay in Florida on your getaway from Orlando to St. Augustine! It has seven beautifully appointed guest rooms and en suite spa-like baths to make your time here the most memorable and full of relaxation possible. Each room at our St. Augustine Bed and Breakfast is unique, with a different floor plan, decor, and special touches. A few rooms have double French doors that open onto a private balcony with seating, the perfect space for your morning coffee or mimosa.
Each morning, you can enjoy breakfast service in your room or join us in the dining space to mingle with other guests. It’s the best way to start the day before heading out to downtown historic St. Augustine, romantic sailing tours, or a day at the beach. In the afternoons, join us in the drawing room for social hour, featuring house-made appetizers and an excellent selection of wines, beer, and non-alcoholic beverages. It’s the perfect activity after a siesta and before you head to St. Augustine for a romantic night out.
If you’re looking to up the romance, we have a great selection of special packages like “Pampered Romance.” This option includes massages at the nearby Salt Spa, Champagne with flutes, chocolates, and a voucher towards dinner at one of the most romantic restaurants in St. Augustine: Collage Restaurant. We can’t wait to host you on your getaway from Orlando to St. Augustine; book your lodging today!
