Planning a romantic escape to Northeast Florida? St. Augustine is the ultimate couples destination, with historic charm, cozy coastal vibes, and unforgettable experiences just minutes from the beach. Whether you’re celebrating an anniversary, planning a Valentine’s getaway, or simply craving quality time together, this weekend itinerary blends the best of St. Augustine with dreamy day trips nearby.
And when you stay with Joseph Ellen Properties, you’ll enjoy boutique vacation rentals designed for romance, relaxation, and unforgettable memories.
Friday: Arrive + Set the Mood
Check In to Your Joseph Ellen Properties Stay
Kick off your weekend by checking into your Joseph Ellen Properties vacation rental. From historic downtown cottages to waterfront retreats, each home is thoughtfully designed with comfort and romance in mind. Expect cozy bedrooms, spa-like bathrooms, and spaces perfect for slow mornings and late-night conversations.
Pro Tip: Ask us to add on champagne, chocolates, or a surprise welcome gift for your partner to make your arrival extra special.
Featured Property: Southern Wind Inn is the ideal couples getaway stay in Saint Augustine. A historic inn with updated interior design, a coffee bar, balcony and porch to sit coffee in the mornings and wine in the evenings AND walking distance to all of the best date night spots in town.
Sunset Stroll Through Historic Downtown
Head to St. George Street for a golden-hour walk through cobblestone streets, art galleries, and charming shops. Grab a glass of wine at a cozy bar, then wander hand in hand past the Lightner Museum and Plaza de la Constitución as the city glows at dusk.
Romantic Dinner for Two
Reserve a table at one of St. Augustine’s most romantic restaurants:
- Collage Restaurant – Intimate, candlelit fine dining
- Llama Restaurant – Global flavors in a historic setting
- The Floridian – Elevated Southern cuisine
End the night with dessert and nightcaps, then head back to your Joseph Ellen Properties stay to unwind under the stars.
Saturday: Day Trip + Coastal Magic
Morning Coffee & Breakfast
Start your morning slowly with coffee and pastries from Kookaburra Coffee or Dos Coffee & Wine, then enjoy breakfast at Maple Street Biscuit Company or Blue Hen Café.
Scenic Day Trip: Washington Oaks Gardens State Park
Just 30 minutes south of St. Augustine, this hidden gem features formal gardens, oak-lined paths, and one of the most romantic beaches in Florida, famous for its coquina rock shoreline. Pack a picnic and explore together.
Optional Day Trip: Marineland Dolphin Adventure
For a once-in-a-lifetime experience, swim or snorkel with dolphins at Marineland, located between St. Augustine and Daytona Beach. Perfect for adventurous couples.
Afternoon at the Beach
Head back toward town and spend the afternoon at Anastasia State Park. Rent bikes, relax on the sand, or kayak the tidal marshes before heading back to freshen up.
Date Night in the Oldest City
Enjoy sunset drinks at Ice Plant Bar or The Tini Martini Bar, followed by dinner at Preserved Restaurant or Michael’s Tasting Room. End the evening with a moonlit walk along the waterfront.
Sunday: Slow Morning + Sweet Goodbyes
Brunch With a View
Savor brunch at The Blue Hen Café or Sunday Gathering Table, then enjoy one last stroll along the St. Augustine Waterfront.
Sweet Treats & Souvenirs
Stop by Mayday Ice Cream, Claude’s Chocolate, or Hyppo Popsicles for a final taste of St. Augustine before heading home.
Why Stay with Joseph Ellen Properties for Your Romantic Getaway?
- Boutique-style vacation rentals designed for couples
- Prime locations in St. Augustine, Jacksonville, and the Beaches
- Fire pits, hot tubs, balconies, and spa-like amenities
- Local hospitality with thoughtful touches that elevate your stay
Book Your Romantic St. Augustine Getaway
Make February unforgettable.
Enjoy 15% off your stay when you book with code: LOVE
Browse available properties and book your couples escape today at josephellenproperties.com.
Your romantic weekend in St. Augustine starts here.