7-Day Family Friendly Relaxation & Foodie Itinerary in St. Augustine, Florida

Day 1: Drive to Charleston

Charleston, West Virginia

7:00 AM

Departure from Essexville, MI

Start your day early to make the most of your drive with plenty of stops along the way.
Drive south on I-75 and then onto I-64.
Free, 7 Hours

1:00 PM

Lunch at The Blue Grass Kitchen

Stop in Charleston for a hearty local lunch featuring seasonal dishes.
Located in downtown Charleston, easily accessible off I-64.
USD25, 1 Hour

2:30 PM

Check-in at the Four Points by Sheraton Charleston

Relax and take a moment to settle into your hotel accommodations for the night.
A quick drive from the lunch spot.
USD120, 1 Hour

4:00 PM

Explore the State Capitol and Grounds

Visit the beautiful state capitol building and stroll around its scenic grounds.
A short drive from the hotel.
Free, 1.5 Hours

6:00 PM

Dinner at The Olive Garden

Enjoy family-friendly Italian cuisine that everyone will love after a long drive.
Located nearby, easy to access.
USD30, 1.5 Hours

8:00 PM

Evening Relaxation at Hotel

Unwind with family in your hotel room or check out hotel amenities.
Return to your hotel for the evening.
Free, Varies
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Day 2: Drive to St. Augustine

St. Augustine, Florida

7:00 AM

Breakfast at the Hotel

Enjoy the complimentary breakfast provided at your hotel before checkout.
On-site at Four Points by Sheraton.
Free, 1 Hour

8:00 AM

Departure from Charleston, WV

Hit the road again, this time heading straight toward St. Augustine!
Take I-64 E and merge onto I-75 S.
Free, 8 Hours

12:00 PM

Lunch Break at a Rest Area

Pack lunches or stop at a rest area for a picnic-style lunch to break up the trip.
Planned break along your route.
Free, 1 Hour

4:00 PM

Arrival in St. Augustine

Check-in to your chosen hotel, ready to unwind after your long journey.
Select from hotels such as Hilton St. Augustine Historic Bayfront or Guy Harvey Resort.
USD150, 1 Hour

5:00 PM

Dinner at The Conch House

Enjoy a delicious seafood dinner with a fantastic view of the marina.
A quick drive from your hotel.
USD35, 1.5 Hours

7:00 PM

Evening Stroll along the Bayfront

Take a relaxing evening stroll along the waterfront to soak in the beautiful scenery.
A short walk from The Conch House.
Free, 1 Hour
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Day 3: Welcome to St. Augustine

St. Augustine, Florida

8:00 AM

Breakfast at The Blue Hen Cafe

Start your day with a hearty breakfast featuring local favorites like shrimp and grits or their famous blueberry pancakes.
Walk to the café, located in downtown St. Augustine.
USD20, 1 Hour

9:30 AM

Visit Castillo de San Marcos

Explore the majestic coquina fortress, the oldest masonry fort in the continental US, and learn about its history.
A short 10-minute walk from the café to the fort.
USD15, 2 Hours

12:00 PM

Lunch at Columbia Restaurant

Savor delicious Cuban and Spanish cuisine famous for its 1905 Salad and paella.
A 15-minute walk from Castillo de San Marcos.
USD25, 1.5 Hours

2:00 PM

Stroll through the Historic District

Wander through the beautiful streets, shop for souvenirs, and enjoy the local architecture.
Explore by foot in the Historic District.
Free, 2 Hours

4:30 PM

Ice Cream at The Hyppo

Cool down with gourmet popsicles made from fresh, local ingredients.
Located nearby in the Historic District.
USD5, 30 Minutes

6:00 PM

Dinner at O'Steen's Restaurant

Indulge in St. Augustine’s famous fried shrimp, a true local delicacy.
A short drive or a 10-minute ride-share from the Historic District.
USD30, 1.5 Hours

8:00 PM

Relax at the Hotel

Spend your evening unwinding at your accommodation, preparing for the adventures ahead.
Return to the hotel by walking or a quick drive.
Free, Varies
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Day 4: Beach Day!

St. Augustine, Florida

8:00 AM

Breakfast at Cafe Alcazar

Enjoy a delicious breakfast in a unique setting inside the historic Lightner Museum.
Located in the hotel area, just a short drive.
USD15, 1 Hour

9:30 AM

Visit St. Augustine Beach

Spend the morning soaking up the sun and enjoying the ocean waves at the family-friendly beach.
A 15-minute drive from Cafe Alcazar.
USD0 (Parking fees may apply), 3 Hours

12:30 PM

Lunch at The Beachcomber Restaurant

Grab a casual beachside lunch featuring fresh seafood and tasty sandwiches.
Right on the beach, easy walk from your beach spot.
USD25, 1 Hour

2:00 PM

Visit the St. Augustine Lighthouse and Museum

Climb the 219 steps of the historic lighthouse for breathtaking views of the coastline.
A quick 10-minute drive from the restaurant.
USD12, 2 Hours

4:30 PM

Relax at the Lighthouse Park

Enjoy a leisurely stroll through the park surrounding the lighthouse, perfect for family pictures.
Right next door to the lighthouse.
Free, 1 Hour

6:00 PM

Dinner at Salt Life Food Shack

End your day with casual dining offering a variety of seafood, burgers, and salads.
A short drive from the park.
USD30, 1.5 Hours

8:00 PM

Evening Stroll on the Beach

Enjoy a peaceful walk along the shore as the sun sets, providing a perfect end to your day.
Walk down to the beach from the restaurant.
Free, 1 Hour
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Day 5: Cultural Exploration

St. Augustine, Florida

8:00 AM

Breakfast at The Kookaburra

Enjoy some of the best coffee and Australian pastries in a cozy setting.
Located nearby in the Historic District.
USD10, 1 Hour

9:30 AM

Visit the Lightner Museum

Explore the museum’s impressive collection of fine and decorative arts from the 19th century.
A short stroll from your breakfast spot.
USD10, 2 Hours

12:00 PM

Lunch at The Cellar

Experience fine dining in a historic setting, with an excellent selection of Italian dishes.
Just a quick drive away.
USD40, 1.5 Hours

2:00 PM

Explore the Fort Matanzas National Monument

Take a scenic boat ride to this beach fort and learn about its historical significance.
A drive followed by a boat ride from downtown.
Free (Boat ride might have nominal fee), 3 Hours

5:30 PM

Return to the Hotel

Unwind and relax after a busy day of exploring and fun.
Return by boat and drive back to the hotel.
Free, 1 Hour

7:00 PM

Dinner at The Q

Savor a fantastic Southern BBQ meal, perfect for families.
Located just a short drive away.
USD25, 1.5 Hours

9:00 PM

Evening Relaxation at the Hotel

Enjoy some family time in your room or lounge area.
Back at your hotel.
Free, Varies
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Day 6: Adventure and Nature

St. Augustine, Florida

8:00 AM

Breakfast at Maple Street Biscuit Company

Start your day with their famous biscuits and comfort food in a family-friendly atmosphere.
Around a 10-minute drive from downtown.
USD15, 1 Hour

9:30 AM

Visit Anastasia State Park

Enjoy outdoor activities such as hiking, birdwatching, and beach-combing.
Only a short drive from breakfast.
USD8 (Vehicle fee), 3 Hours

1:00 PM

Lunch at Beachside Diner

Enjoy a casual beachfront lunch with great seafood options.
Located near the beach entrance of the park.
USD20, 1 Hour

2:30 PM

Kayak Tour at Ripple Effect Eco Tours

Experience a family-friendly eco-kayaking adventure, exploring the rich ecosystems of the marshlands.
A quick drive from Beachside Diner.
USD45 per person, 2.5 Hours

5:00 PM

Return to Hotel

Rest and refresh after your kayaking adventure.
Drive back to your hotel.
Free, 1 Hour

6:30 PM

Dinner at Hurricane Patty's

Enjoy tasty Caribbean-inspired dishes overlooking the water.
A short drive from your hotel.
USD30, 1.5 Hours

8:00 PM

Leisurely Evening at the Hotel

Have a relaxing evening enjoying games or movies together.
Back at the hotel.
Free, Varies
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Day 7: Farewell St. Augustine

St. Augustine, Florida

8:00 AM

Breakfast at The Sweet Spot

Indulge in pastries, coffee, and light breakfast options before heading out.
Located near your accommodations.
USD15, 1 Hour

9:30 AM

Visit the Mission of Nombre de Dios

Explore Florida’s first mission and its beautiful grounds.
A quick drive from breakfast.
Free, 1.5 Hours

11:00 AM

Stroll through the Fountain of Youth Archaeological Park

Discover the fascinating history and enjoy the lush gardens.
A short drive from the mission.
USD15, 2 Hours

1:00 PM

Lunch at The Riff

Enjoy modern American eats with a fresh twist in a laid-back atmosphere.
Easy drive from the park.
USD20, 1 Hour

2:30 PM

Last-minute shopping at St. George Street

Pick up souvenirs and enjoy last glimpses of the historic area.
A quick drive from lunch.
Varies, 1.5 Hours

4:00 PM

Depart St. Augustine

As you leave, cherish the memories made during this delightful trip.
Drive to your departure point.
Free, Varies
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