Scenic Small Town Road Trip from St. Augustine to Denver in 5 Days

Day 1: Historic Coastal Journey

St. Augustine, FL to Pensacola, FL on June 26, 2025

8:00am

Breakfast at The Blue Hen Café

Start your day with a delightful southern breakfast in this cozy spot known for hearty biscuits and local flavors. It opens early at 7:00am, perfect for a morning start.
USD15, 1h

9:00am

Explore Historic St. Augustine

Visit the Castillo de San Marcos and stroll through the old town square to admire Spanish colonial architecture and museums. It opens at 9:00am and offers a deep dive into the oldest city in the US.
USD15, 2h

12:00pm

Drive to Pensacola, FL

Set out on the roughly 6-hour drive northwest along I-10 W, enjoying scenic views and small town stops along the way such as Tallahassee for a stretch.
USD0, 6h

6:00pm

Dinner at McGuire's Irish Pub, Pensacola

Dine in a lively, traditional Irish pub offering great steaks and seafood in a unique setting perfect for relaxing after a long drive.
USD30, 1.5h
View Hotels

Day 2: Gulf Coast Charm

Pensacola, FL to New Orleans, LA on June 27, 2025

8:30am

Breakfast at The Ruby Slipper Cafe

Enjoy southern-style breakfast classics with excellent coffee in this popular local spot open from 7:00am.
USD20, 1h

9:30am

Pensacola Beach Walk

Take a relaxing morning stroll along Pensacola Beach, admiring the white sands and emerald waters. Free and open any time.
USD0, 1h

11:00am

Drive to New Orleans, LA

Travel west along I-10 W, passing through wetlands and small towns like Gulfport for a break. Approximately a 3-hour drive.
USD0, 3h

2:30pm

Lunch at Coop's Place, New Orleans

Discover authentic Cajun and Creole dishes in a lively, casual atmosphere. Popular for jambalaya and gumbo.
USD25, 1h

4:00pm

Explore French Quarter

Wander through iconic French Quarter streets, including Jackson Square, with its vibrant street life and historic architecture. Best explored late afternoon to evening.
USD0, 2h

7:00pm

Dinner at Brigtsen's Restaurant

Enjoy upscale Creole dining in a cozy historic house, offering seasonal and refined dishes. Reservations recommended.
USD50, 2h
View Hotels

Day 3: From Bayous to Texarkana

New Orleans, LA to Texarkana, TX on June 28, 2025

7:30am

Breakfast at Café Du Monde

Start early to enjoy famous beignets and café au lait at this open-air café in the French Market, opens at 7:00am.
USD10, 1h

8:30am

Drive towards Texarkana, TX

Depart northwest via I-49 N and US-71 N through small towns and forested areas, with a pleasant drive of about 5.5 hours.
USD0, 5h 30m

2:15pm

Lunch at Gaslight Coffee Roasters, Texarkana

Relax with quality coffee and sandwiches at this local favorite, perfect for a refreshing midday break.
USD15, 1h

3:30pm

Visit the Texarkana Post Office and Federal Building

Check out this unique building bisected by the state line between Texas and Arkansas, a fun photo opportunity and local landmark.
USD0, 30m

5:00pm

Dinner at Unique Eats & Drinks

Dine on modern American cuisine with a cozy ambiance just before settling in for the night.
USD35, 1.5h
View Hotels

Day 4: Texas Panhandle Adventure

Texarkana, TX to Amarillo, TX on June 29, 2025

7:30am

Breakfast at Bleu Monkey Coffee Company, Texarkana

Enjoy fresh coffee blends and light breakfast fare in a local café that opens at 7:00am.
USD15, 1h

8:30am

Drive to Amarillo, TX

Head west on I-40 W for roughly 8 hours, passing through small Texas towns like Shamrock and McLean, known for Route 66 Americana charm.
USD0, 8h

4:30pm

Check in and Rest

Arrive in Amarillo and take some rest after the long drive before dinner.
USD0, 1h

6:00pm

Dinner at The Big Texan Steak Ranch

Experience the famous Texas steakhouse known for its 72 oz steak challenge and authentic cowboy atmosphere.
USD40, 1.5h
View Hotels

Day 5: Final Stretch to Denver

Amarillo, TX to Denver, CO on June 30, 2025

7:30am

Breakfast at Ye Olde Pancake Station

Fill up on classic pancakes and breakfast favorites in Amarillo, opening at 7:00am.
USD15, 1h

8:30am

Explore Cadillac Ranch

Visit this iconic public art installation of half-buried spray-painted Cadillacs, a quick must-see on the outskirts of Amarillo, open all day.
USD0, 30m

9:00am

Drive to Denver, CO

Travel approximately 6 hours northwest on I-25 N, passing through scenic towns including Raton and Pueblo.
USD0, 6h

3:30pm

Arrive in Denver and Check-in

Settle into your accommodation and begin exploring the Mile High City at your leisure.
USD0, N/A

6:00pm

Dinner at Rioja

Enjoy Mediterranean-inspired cuisine in a warm ambiance located in downtown Denver. Reservations suggested for dinner service starting at 5:00pm.
USD45, 2h
View Hotels