St. Augustine Adventure and Romance Itinerary

Day 1: Historic Exploration

St. Augustine, FL

8:00 AM

Breakfast at Blue Heaven

Start your day with a delicious Floridian breakfast featuring homemade key lime pie pancakes at Blue Heaven, tucked within the historic district.
Walk or drive to the historic district.
USD15, 1 hour

9:30 AM

Castillo de San Marcos

Explore the oldest masonry fort in the continental U.S., taking in engaging history and panoramic views of the Matanzas Bay.
5-minute walk from Blue Heaven.
USD15, 2 hours

12:00 PM

Lunch at The Columbia Restaurant

Indulge in authentic Spanish and Cuban cuisine as you enjoy a lively atmosphere at this local gem.
10-minute walk from Castillo de San Marcos.
USD30, 1.5 hours

2:00 PM

Historic District Stroll

Wander the charming streets of the historic district, taking in colonial architecture and local shops.
Walking through the historic district.
Free, 2 hours

4:30 PM

St. Augustine Lighthouse

Climb to the top of the iconic lighthouse for breathtaking views of the coastline and surrounding area.
20-minute bike ride or 10-minute drive from the historic district.
USD12, 1 hour

6:00 PM

Dinner at O'Steen's Restaurant

Feast on their famous shrimp and grits in a cozy setting, perfect for a romantic evening.
15-minute drive from the lighthouse.
USD25, 1.5 hours
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Day 2: Nature Retreat

St. Augustine, FL

8:00 AM

Breakfast at The Kookaburra

Enjoy a fresh Australian-style breakfast and grab some coffee to fuel your adventurous day.
5-minute drive from your hotel.
USD15, 1 hour

9:30 AM

Anastasia State Park

Spend the morning soaking in nature, kayaking, or relaxing on the beach within this beautiful park.
15-minute drive from The Kookaburra.
USD8 (per vehicle), 3 hours

1:00 PM

Lunch at The Beachcomber

Savor some fresh seafood right on the beach, with a fantastic view to accompany your delicious meal.
5-minute drive from Anastasia State Park.
USD20, 1.5 hours

2:30 PM

Join a Dolphin Watching Tour

On this memorable tour, you’ll encounter playful dolphins and scenic coastal views, making for a perfect honeymoon delight.
15-minute drive to the marina.
USD45, 2.5 hours

5:00 PM

Relax at the Beach

Spend the late afternoon unwinding on the sandy shores, taking in a romantic sunset together.
Walk to the nearby beach.
Free, 1.5 hours

7:00 PM

Dinner at Catch 27

Enjoy a unique farm-to-table dinner focusing on fresh, locally sourced seafood selections.
10-minute drive from the beach.
USD40, 2 hours
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Day 3: Cultural Delights

St. Augustine, FL

8:00 AM

Breakfast at The Salt Life Food Shack

Start your day with a hearty breakfast burrito or omelet while enjoying ocean views.
10-minute drive from downtown.
USD15, 1 hour

9:30 AM

Visit the Lightner Museum

Explore a re-vamped hotel turned museum, housing an eclectic collection of art and antiques.
15-minute drive.
USD15, 2 hours

12:00 PM

Lunch at the Gypsy Cab Company

Savor a classic Cuban sandwich or their famous gypsy ragu in a quirky atmosphere.
Walking distance from Lightner Museum.
USD20, 1.5 hours

1:30 PM

St. George Street Shopping

Stroll the charming pedestrian street filled with boutiques and local artisans for unique souvenirs.
5-minute walk from lunch.
Free, 2 hours

4:00 PM

Old Jail Tour

Take a fascinating guided tour of the historic Old Jail, complete with stories of the past and tales of its infamous inmates.
10-minute drive from St. George Street.
USD12, 1 hour

6:00 PM

Dinner at The Reef

Enjoy dinner with a view on the beach, famous for their fresh catch and tropical cocktails.
15-minute drive from Old Jail.
USD35, 1.5 hours
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Day 4: Romantic Experiences

St. Augustine, FL

8:00 AM

Breakfast at The Blue Hen Cafe

Start your day off with a fresh, farm-to-table breakfast featuring their renowned blueberry pancakes.
5-minute drive from your accommodation.
USD15, 1 hour

9:30 AM

Explore the Fountain of Youth

Discover this historic park where legend says Ponce de Leon found the fountain of eternal youth, while enjoying beautiful grounds.
10-minute drive.
USD18, 2 hours

12:00 PM

Lunch at Pizzalley’s Chianti Room

Indulge in their famous lobster bisque and handcrafted pizza under twinkling lights.
15-minute drive from the Fountain of Youth.
USD25, 1.5 hours

2:00 PM

Horse-Drawn Carriage Tour

Enjoy a romantic carriage ride through the charming streets, experiencing the history and beauty of St. Augustine.
10-minute walk from lunch.
USD40, 1 hour

4:00 PM

Relax at a Spa

Pamper yourselves with a couples massage or spa treatment to unwind and rejuvenate.
10-minute drive from the carriage tour location.
USD150, 2 hours

7:00 PM

Dinner at The Prince of Wales

Savor an upscale dining experience and try their traditional Fish & Chips amidst cozy English decor.
5-minute drive from the spa.
USD40, 2 hours
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Day 5: Beach Day

St. Augustine, FL

8:00 AM

Breakfast at Dune’s Cafe

Enjoy breakfast with a beach view, featuring their famous breakfast bowls and fresh juices.
10-minute drive to Anastasia Island.
USD12, 1 hour

9:30 AM

Visit to Vilano Beach

Relax and take in the sun at this scenic beach, perfect for a full day of beach activities.
5-minute drive from breakfast.
Free, 4 hours

1:30 PM

Lunch at The Smoothie King

Refuel with refreshing smoothies or light snacks while still enjoying the beach vibes.
Short walk along the beach.
USD10, 1 hour

2:30 PM

Water Sports Rental

Opt for exciting water sports such as paddleboarding or jet skiing for an adrenaline rush on the water.
Close to the beach entrance.
USD60 (per person), 2.5 hours

5:00 PM

Sunset Beach Walk

Stroll along the beach at sunset, capturing beautiful moments together.
Stay at the same location.
Free, 1 hour

7:00 PM

Dinner at The Atlantis Restaurant

Finish your day with exquisite seafood while enjoying views of the Intracoastal Waterway.
15-minute drive from Vilano Beach.
USD35, 2 hours
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Day 6: Farewell St. Augustine

St. Augustine, FL

8:00 AM

Breakfast at Café Alcazar

Enjoy a delightful breakfast in a historic setting overlooking the swimming pool.
5-minute drive.
USD15, 1 hour

9:30 AM

Shopping at St. Augustine Premium Outlets

Spend your morning shopping for souvenirs to commemorate your magical stay.
15-minute drive from breakfast.
Free, 2 hours

12:00 PM

Lunch at The Honey Baked Ham Company

Grab a delicious sandwich from this quick and tasty stop before heading back.
10-minute drive from the outlets.
USD15, 1 hour

1:30 PM

Explore the Spanish Quarter

Take a leisurely walk through this historical neighborhood, enjoying the architecture and local shops one last time.
10-minute drive back to downtown.
Free, 1 hour

3:00 PM

Relax at your hotel

Take a moment to unwind and reminisce about your beautiful adventures in St. Augustine.
Return to your hotel.
Free, 1 hour

5:00 PM

Farewell Dinner at The Capital Grill

Conclude your trip with fine dining that celebrates the tastes of Florida and its seafood delicacies.
15-minute drive from your hotel.
USD60, 2 hours
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