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.

Rent a convertible and take a trip to the oldest city in the US, St Augustine

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.