Enchanted 6-Day Honeymoon Escape to Historic St. Augustine

3 Days Trip in Jersey, Channel Islands

7 Days Trip in St. Augustine, Florida

St. Augustine is America’s oldest city, known for its historic charm, beautiful beaches, and rich Spanish colonial heritage.

Take Your Itinerary With You

Download this complete 7-day St. Augustine travel guide as a PDF for offline access during your trip.

Plan Your Trip

Day 1 – Arrival & Historic Charm

Morning

Jacksonville & St. Augustine
Arrival & Check-in
Arrive at Jacksonville International Airport (JAX) and drive to St. Augustine. Check into your mid-range hotel or vacation rental near the historic district.
arrival check-in
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Light Lunch at The Kookaburra
Enjoy delicious Australian coffee and light fare. A great place to start the trip with tasty snacks and refreshing drinks in a friendly setting.
dining coffee
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Afternoon

Historic District
Self-Guided Walking Tour
Explore St. George Street, Castillo de San Marcos (exterior only this day for budget), and the charming side streets at your own pace.
walking tour historic
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Flagler College
Take a self-guided tour of the beautiful Flagler College, formerly the Ponce de Leon Hotel. Marvel at the stunning architecture and history.
architecture college
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Evening

Bridge of Lions & Downtown
Sunset Stroll on the Bridge of Lions
Enjoy a relaxing walk across the Bridge of Lions for stunning sunset views over the Matanzas River. Perfect photo opportunity.
sunset photography
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Dinner at Columbia Restaurant
Experience authentic Cuban cuisine in a historic setting. Try the Paella a la Valenciana for a flavorful culinary experience.
dining Cuban cuisine
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Pro Tip: Wear comfortable shoes for walking, as you’ll be doing a lot of exploring on foot! Hydrate throughout the day, especially in warmer months.

Day 2 – Spa Day & Coastal Views

Morning

The Collector Inn
Spa Day at The Collector Inn – Gardens, Ales & Spirits
Indulge in a couple’s massage or other spa treatments for ultimate relaxation. Book in advance to secure your preferred time and treatments.
spa relaxation
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Relax by the Pool
After your spa treatments, unwind by the pool at your hotel or vacation rental. Soak up the sun and enjoy some quiet time together.
pool relaxation
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Afternoon

Anastasia State Park
Anastasia State Park Exploration
Head to Anastasia State Park. Enjoy the beach, take a leisurely walk on the nature trails, or rent kayaks for a peaceful paddle.
state park nature
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St. Augustine Lighthouse
Tour the lighthouse and maritime museum. Climb to the top for panoramic coastal views. Consider going later in the afternoon to avoid peak crowds.
lighthouse museum
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Evening

Beach Area
Casual Dinner at The Beachcomber
Enjoy fresh seafood and casual beachside dining at The Beachcomber. Known for its relaxed atmosphere and tasty food.
seafood beachside
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Bonfire on the Beach (if permitted)
Check local regulations and enjoy a bonfire on the beach. Bring blankets and enjoy the stars with your group. (Permits may be required).
bonfire stargazing
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Pro Tip: Book spa treatments and water activities in advance, especially during peak season. Check the weather forecast and pack accordingly.

Day 3 – History & Serenity

Morning

Castillo de San Marcos
Castillo de San Marcos National Monument
Explore the historic fort, Castillo de San Marcos. Learn about its history and enjoy the waterfront views. Arrive early to beat the crowds.
fort history
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Light Breakfast & Coffee at City Perks Coffee Co.
Enjoy a light breakfast and delicious coffee at City Perks Coffee Co. Great for a quick and tasty start to the day.
breakfast coffee
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Afternoon

Museums & Distillery
Lightner Museum
Explore the eclectic collection of Victorian-era artifacts at the Lightner Museum. A great way to spend a rainy afternoon or escape the heat.
museum Victorian
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St. Augustine Distillery Tour
Take a free tour and tasting at the St. Augustine Distillery. Learn about the process of distilling spirits and sample local products.
distillery tasting
Google Maps

Evening

Downtown
Dinner at Catch 27
Enjoy fresh, locally sourced seafood at Catch 27. Reservations are recommended. Try the grilled fish tacos or the shrimp and grits.
seafood fine dining
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Ghost Tour (Optional)
If you’re feeling adventurous, take a ghost tour of St. Augustine. Many different tour companies offer walking or trolley tours.
ghost tour entertainment
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Pro Tip: Wear comfortable shoes for walking around the fort and museum. Stay hydrated and take breaks as needed.

Day 4 – Art, Nature & Relaxation

Morning

Beach & Art District
Morning Yoga on the Beach
Find a quiet spot on the beach and enjoy a self-guided yoga session. Start the day with mindful movement and fresh air. Bring your own mat.
yoga beach
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Art Galleries on Aviles Street
Explore the art galleries on Aviles Street, the oldest street in the United States. Browse local artwork and enjoy the charming atmosphere.
art galleries historic street
Google Maps

Afternoon

Washington Oaks Gardens
Washington Oaks Gardens State Park
Visit Washington Oaks Gardens State Park. Explore the formal gardens and the unique coquina rock formations on the beach. Pack a picnic lunch.
gardens state park
Google Maps
Relaxation Time
Enjoy some relaxation time by the pool or in your hotel room. Read a book, take a nap, or simply unwind. Recharge before dinner.
relaxation rest
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Evening

Fine Dining & Stargazing
Fine Dining at Michael’s Tasting Room
Enjoy a special dinner at Michael’s Tasting Room. Experience a fine dining experience with creative dishes and excellent service. Reservations required.
fine dining tasting menu
Google Maps
Stargazing
Find a dark spot away from city lights and enjoy stargazing. Download a stargazing app to help identify constellations.
stargazing astronomy
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Pro Tip: Bring sunscreen, a hat, and insect repellent for outdoor activities. Check the park’s website for hours and admission fees.

Day 5 – History & Local Flavors

Morning

Colonial Quarter
Colonial Quarter
Explore the Colonial Quarter and learn about the history of St. Augustine during the Spanish, British, and American periods. Interactive exhibits.
colonial history interactive
Google Maps
Shopping on St. George Street
Browse the unique shops and boutiques on St. George Street. Find souvenirs, gifts, and local crafts. Take your time and enjoy the atmosphere.
shopping souvenirs
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Afternoon

Pirate Museum & Treats
St. Augustine Pirate & Treasure Museum
Discover the world of pirates at the St. Augustine Pirate & Treasure Museum. See real pirate artifacts and learn about their history.
pirates museum
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Ice Cream at Kilwins
Indulge in delicious ice cream at Kilwins. Choose from a variety of flavors and enjoy a sweet treat while strolling through the historic district.
ice cream treats
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Evening

Dining & Live Music
Dinner at The Floridian
Enjoy Southern comfort food with a modern twist at The Floridian. Try the fried green tomatoes or the shrimp and grits. Reservations recommended.
Southern cuisine comfort food
Google Maps
Live Music at A1A Aleworks
Enjoy live music and local craft beer at A1A Aleworks. Relax and unwind after a day of exploring. Check the schedule for live music performances.
live music craft beer
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Pro Tip: Be aware of your surroundings and keep your belongings safe. Take advantage of free activities and events in the historic district.

Day 6 – Scenic Drives & Beach Time

Morning

Coastal Drive
Scenic Drive Along A1A
Enjoy a scenic drive along A1A, the coastal highway. Stop at scenic overlooks and enjoy the ocean views. Take your time and explore the coastline.
scenic drive coastal views
Google Maps
Marineland Dolphin Adventure
Visit Marineland Dolphin Adventure (Drive South on A1A). Consider a dolphin encounter or a show. Check show times and book in advance.
dolphins marine life
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Afternoon

Crescent Beach
Beach Day at Crescent Beach
Spend the afternoon relaxing on Crescent Beach. Enjoy the soft sand, clear water, and peaceful atmosphere. Pack a picnic lunch and beach gear.
beach relaxation
Google Maps
Beachcombing
Walk along the beach and collect seashells. A relaxing and mindful activity. Bring a bag or container to collect your treasures.
beachcombing seashells
Google Maps

Evening

Waterfront Dining
Dinner at Aunt Kate’s
Enjoy waterfront dining at Aunt Kate’s. Dine outdoors with beautiful views of the Tolomato River. Try the Minorcan clam chowder.
waterfront dining seafood
Google Maps
Relaxation
Relax at hotel or rental. Reflect on experience and prepare for departure.
relaxation reflection
Google Maps
Pro Tip: Bring sunscreen, a hat, and beach towels for your beach day. Check the tide schedule and plan your activities accordingly.

Day 7 – Departure

Morning

Final Morning
Breakfast at Maple Street Biscuit Company
Enjoy a hearty breakfast at Maple Street Biscuit Company. Known for its delicious biscuits and friendly atmosphere. A great way to start your final day.
breakfast biscuits
Google Maps
Last-Minute Souvenir Shopping
Visit any shops you missed and grab some last-minute souvenirs. Consider buying local products or artwork to remember your trip.
shopping souvenirs
Google Maps

Afternoon

Departure
Check out of Hotel
Check out of your hotel or vacation rental. Allow plenty of time to pack and say goodbye to St. Augustine.
check-out departure
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Departure from JAX
Drive back to Jacksonville International Airport (JAX) for your flight home. Allow ample time for traffic and airport security.
airport departure
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Pro Tip: Allow plenty of time to get to the airport. Check transportation schedules and flight status in advance.
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