Route 66 Roadtrip Itinerary | Winslow to Williams, AZ

Steve and I have been wanting to take Honey Bee (our Jeep) on a roadtrip up to the Grand Canyon. Spending Valentine’s Day on the South Rim sounded like an excellent plan. We also happened to rent out our home for Super Bowl so it’s the perfect opportunity to cross off some items on our 2023 Arizona Bucket List. 

Honeybee in Winslow, AZ
She’s a beauty.

I’ve been researching all the cool places to stop along the way. The following is our itinerary for a 7-day, 6-night Northern Arizona Road trip. We will update you with all the amazing sites after our trip. This time of year you still have to pay attention to the weather forecast as Northern Arizona can still get lots of snow. Lucky for us our forecast is for clear and chilly days. I had to dig out our coats and hats so we don’t freeze.

One of my favorite apps for planning is Roadtrippers. I find their free version to be perfect for what I need to plan. Once we are on the road I activate the Sights & Attractions function so that we don’t miss a giant ball of string. 

AZ Route 66 Itinerary

Besides the Roadtrippers app, I also use Hotel Tonight, Booking.com and HotelsCombined to find the best deals on hotels and accommodations.  

Day 1: Surprise to Winslow, AZ | 194 miles, 3h 6m

Sights: The World’s Largest Kokopelli. Added bonus: it’s in the Starbucks parking lot so if you need a little pick-me-up you can grab a cuppa joe when you stop.

Hotel: La Posada Hotel, 2 nights, Best rate was booking direct through the website, $139/night

The History of La Posada: A Tale of Two Visions

La Posada embodies the visions of both Mary Elizabeth Jane Colter, the hotel’s renowned architect, and Allan Affeldt, its current owner. But the story really begins with Fred Harvey, who “civilized the west” by introducing linen, silverware, china, crystal, and impeccable service to railroad travel. (He was so legendary that MGM made a movie called The Harvey Girls starring Judy Garland.) Harvey developed and ran all the hotels and restaurants of the Santa Fe Railway, eventually controlling a hospitality empire that spanned the continent.

In the 1920s, Harvey decided to build a major hotel in the center of northern Arizona. “La Posada”—the Resting Place—was to be the finest in the Southwest. Construction costs alone exceeded $1 million in 1929. Total budget with grounds and furnishings was rumored at $2 million (about $40 million in today’s dollars). They chose Winslow, then (as now) the Arizona headquarters for the Santa Fe Railway. Winslow was ideally situated for a resort hotel since everything to see and do in northern Arizona is a comfortable day’s drive. They asked Colter to design the new hotel.

Colter worked for the Fred Harvey Company from 1905 until her retirement in the 1950s. Although famous for her magnificent buildings at the Grand Canyon, she considered La Posada her masterpiece. Here she was able to design or select everything from the structures to the landscape, furniture, maids’ costumes, and dinner china. Many people consider this the most important and most beautiful building in the Southwest.

www.laposada.org

The Turquoise Room is their onsite restaurant and tops all the Must Eat Arizona lists. The menu looks amazing. I might have to have breakfast, lunch and dinner here. Reservations are recommended.

Read all about the history of La Posada here.

Day 2: Winslow, AZ

Little Painted Hills

Day 3: Winslow to Strawberry, AZ | 72 miles, 1h 27m

Hotel: The Strawberry Inn | Booked the Airstream directly through their website

The Strawberry Inn is a small boutique hotel and cabins located in Strawberry, Arizona. We are so excited because we rented the Airstream. So fun!

Day 4: Strawberry to Sedona, AZ | 71 miles, 1h 25m

Hotel: Sky Rock Inn of Sedona | Booked directly through

I just can’t help adding Sedona to every roadtrip we go on. Those red rocks just pull me in.

Day 5: Sedona to Williams, AZ | 62 miles, 1h 24m

Hotel: Grand Canyon Railway Hotel

The Grand Canyon Railway is both a train adventure and a hotel. Their website is very user friendly and has a ton of information but when it came to reservations I couldn’t get the online system to do what I wanted. I called and received amazing help. I booked the package deal that included:

  • Hotel room at the Grand Canyon Railway Hotel
  • Dinner at the Fred Harvey restaurant at the hotel
  • Breakfast at the hotel before the train leaves
  • Our train tickets. The ride is 2 1/2 hours each way. I booked the Luxury Dome for the ride to the GC and coach home.
  • 90-minute bus tour at the GC
  • Hotel at the Maswik Lodge, Grand Canyon

Day 6: Williams to Grand Canyon via The Grand Canyon Railway

Itinerary
  • 8:00AM Breakfast at Fred Harvey Restaurant
  • 9:00AM Cowboy Shootout in Williams
  • 9:30AM Board The Grand Canyon Railway Train | We purchased the luxury dome tickets for the trip up to the canyon and then coach tickets for the way back.
  • 12:00PM Arrive at the Grand Canyon, 90 minute bus tour (included in our package)
  • 2:00PM Explore

We leave the following day at 3:30PM so we have lots of extra time for making our own adventure.

Hotel: Maswik Lodge

Day 7: Grand Canyon Railway back To Williams & Home to Surprise

3:30PM Train ride back to Williams

Williams back to Surprise will be under a starlit sky. It should be beautiful. We will update you all after our roadtrip is over.

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