Things to Do

Places to Eat

Places to Stay


Romantic Weekend Itinerary in St. Augustine

Escape the hustle and bustle of everyday life and immerse yourself in the charm and romance of St. Augustine, Florida. 

Here’s a curated itinerary to make the most of your romantic weekend in the nation’s oldest city.

Whether you’re celebrating an anniversary, planning a surprise for your loved one, or simply craving a romantic escape, St. Augustine has something for every couple.

Day 1: Arrival and Sunset Stroll

Check-in at a Charming Bed and Breakfast: Start your romantic weekend by checking into one of St. Augustine’s quaint bed and breakfasts, such as the Casablanca Inn or the Bayfront Marin House. These historic accommodations provide a cozy and intimate atmosphere.

Sunset at Castillo de San Marcos: Head to the iconic Castillo de San Marcos for a romantic evening. The historic fort offers stunning views of the sunset over the Matanzas Bay. Bring a blanket, enjoy a leisurely stroll, and revel in the beauty of the changing colors.

Dinner at The Columbia Restaurant: Conclude your evening with a romantic dinner at The Columbia Restaurant, located in the heart of St. Augustine’s historic district. Indulge in Spanish and Cuban cuisine while basking in the warm, dimly lit ambiance.


Day 2: Exploring the City

Breakfast at The Blue Hen Café: Start your day with a delicious breakfast at The Blue Hen Café, known for its farm-to-table offerings. Fuel up with a hearty meal before exploring the city.

St. Augustine Lighthouse and Museum: Climb to the top of the St. Augustine Lighthouse for panoramic views of the city and the Atlantic Ocean. The lighthouse grounds also provide a picturesque setting for a romantic stroll.

Lunch at The Floridian: Enjoy a casual lunch at The Floridian, a restaurant committed to using locally sourced and sustainable ingredients. The laid-back atmosphere and creative Southern-inspired dishes make it a delightful choice for a midday meal.

Horse-drawn Carriage Ride: Embark on a horse-drawn carriage ride through the historic district. Let the rhythmic clip-clop of hooves create a romantic soundtrack as you explore St. Augustine’s charming streets and hear stories of its rich history.

Wine Tasting at The Gifted Cork: Unwind with a wine tasting session at The Gifted Cork, a boutique wine shop offering a curated selection of wines. Choose a bottle to enjoy back at your accommodation or as a delightful keepsake.

Day 3: Relaxation and Departure

Breakfast at Maple Street Biscuit Company: For your final morning, savor breakfast at Maple Street Biscuit Company. Known for its mouthwatering biscuit creations, it’s the perfect way to kickstart your day.

Relaxing at St. Augustine Beach: Spend your last few hours in St. Augustine at the beautiful St. Augustine Beach. Whether you choose to dip your toes in the Atlantic Ocean or simply bask in the sun, it’s a serene way to wrap up your romantic weekend.

Farewell Lunch at A1A Ale Works: Before heading home, savor a farewell lunch at A1A Ale Works, a waterfront restaurant offering a diverse menu and picturesque views of the Matanzas River.

St. Augustine, with its historic charm and romantic ambiance, provides the perfect setting for a weekend getaway with your loved one. From breathtaking sunsets and historic landmarks to intimate dining experiences, every moment in this enchanting city contributes to a memorable and romantic escape. Create lasting memories as you explore the cobblestone streets hand in hand, savor delicious meals, and immerse yourselves in the rich history and beauty that St. Augustine has to offer.