Two Days in St. Augustine: A Jeep Wrangler or Mustang Convertible Road Trip to Florida's Oldest City
- miamiconvertibles
- May 27
- 3 min read
Ready for a blast from the past with a salty breeze? Pack your sunscreen and hit the road—because we’re taking the ultimate two-day road trip from Miami to St. Augustine, the oldest city in the U.S. Yes, it’s a bit of a trek, but when you break it up over two days, it turns into an epic Florida adventure.
The Drive: Miami Beach to St. Augustine
You’re looking at a solid 5 to 6-hour drive (around 320 miles), so plan to leave mid-morning or even early afternoon if you're not rushing. Take I-95 North most of the way—cruise-friendly and scenic if you love seeing that classic Florida coastline.
Now here’s the fun part: choose your ride.
🛻 The Jeep Wrangler:
Perfect for groups of 3–5 who want the rugged, top-down Florida freedom experience. The extra room and elevated view make long drives a breeze—and yes, you can even roll onto certain beaches.
🚘 The Mustang Convertible:
Ideal for couples or solo adventurers looking for that open-road thrill and a sporty ride. Cruising the coastline in a drop-top Mustang? Now that’s a vibe.
Day 1: Road Trip & Arrival
Morning: Hit the Road
Start your journey to St. Augustine around 10 AM with your favorite snacks and road trip playlist queued up. There are great spots to stop for a bite along the way—like West Palm Beach or Vero Beach—for a scenic break and some lunch.
Afternoon: Arrival & Beach Time
Arrive in St. Augustine around 4–5 PM. Head straight to St. Augustine Beach to shake off the drive and enjoy the ocean breeze. If you’re in a Wrangler, roll onto Vilano Beach and catch the sunset from the comfort of your ride.
Evening: Dinner & Walk Downtown
Head into town for dinner at The Floridian, a cozy and creative Southern-inspired eatery with dishes like fried green tomatoes and shrimp & grits. Then walk off dinner with a casual stroll through the Historic District—the vibes at night are romantic and peaceful, with twinkle lights and Spanish colonial charm.
Overnight: Stay Downtown or Beachside
Stay overnight at a cute inn downtown like Casa Monica Resort & Spa or book a beachside Airbnb for that laid-back coastal feel.
Day 2: Explore the City
Morning: Castillo de San Marcos 🏰
Start your day with a quick breakfast and then head to the Castillo de San Marcos, a 17th-century Spanish fort. Entry is $15 per adult and you’ll want at least 1–1.5 hours to explore the fort and enjoy the views.

Coffee Break at Kookaburra ☕
Grab a latte and snack at The Kookaburra nearby. It's a funky Aussie-American coffee shop and a local favorite.
Midday: Historic District Walking Tour
St. Augustine’s Historic District is full of charm—think narrow cobblestone streets, Spanish architecture, and hidden courtyards. Don’t miss:
St. George Street – Shops, art, and some quirky boutiques
Flagler College – Gilded Age architecture and Insta-worthy shots
Cathedral Basilica – Beautiful Spanish cathedral
Lunch Stop: Columbia Restaurant 🍽️
Head to the Columbia Restaurant in the heart of town for classic Spanish cuisine. Their Cuban sandwich and 1905 salad are iconic.
Optional Stop: Lighthouse or Alligator Farm 🗼🦎
If you have time before heading home, check out the St. Augustine Lighthouse & Maritime Museum or the St. Augustine Alligator Farm for some lighthearted fun.
Afternoon: Head Back to Miami
Start your return trip in the late afternoon—around 3 or 4 PM—and expect to be back in Miami Beach by 9 or 10 PM, just in time to share your stories over a nightcap.
What to Pack for the Trip:
Sunscreen & sunglasses
Comfy shoes for exploring on foot
Refillable water bottle
Portable phone charger
Swimsuit & towel (optional beach detour!)
Camera or smartphone for all the history & beach shots
Overnight bag with clothes, toiletries, and chargers
Why the Mustang or Wrangler Is Perfect for This Trip
Whether you’re craving a rugged adventure or cruising in style, both the Jeep Wrangler and Mustang Convertible deliver in spades. Tight city corners, highway stretches, or a beachside breeze—these rides are made for the magic of Florida road trips.
Need a Jeep or Mustang for your St. Augustine trip? Miami Convertibles has your perfect road trip ride. Rent a fully loaded Wrangler or a sporty Mustang Convertible and make your Florida getaway a ride to remember.
📞 Contact Us — Let's Get You in the Driver’s Seat!
Got questions? Want to lock in your dream ride? We’re here to help!
📍 Miami Convertibles📧 Email: info@miamiconvertibles.com📱 Phone: (305) 799-7892💬 WhatsApp: Chat with us
🌐 Website: www.miamiconvertibles.com
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