There’s never been a better time to rediscover the spirit of the open road. In 2026, Route 66 turns 100—marking a century of unforgettable journeys across the heart of the United States.

It’s the kind of vacation where the journey matters just as much as the destination—where every mile brings a new view, a new story, and a moment you’ll want to revisit long after you return.

From retro diners and neon signs to desert landscapes and vibrant cities, Route 66 is more than a drive. It’s a celebration of American history, culture and adventure. And with Pleasant Holidays®, planning your vacation is simple, flexible and designed around you.

Why Route 66 Still Captivates Travelers

Route 66, known as the "Main Street of America," stretches from Chicago to Santa Monica—linking iconic cities with hidden gems along the way.

What makes this journey so unforgettable:

• See more in one vacation with a true cross-country experience
• Step into classic Americana, from roadside attractions to historic small towns
• Travel at your own pace with flexible getaway options
• Discover something new every day, whether it’s a local café or a scenic overlook

Sip a milkshake at a classic diner, stop for a photo beside a vintage neon sign or take in sweeping desert views as the road stretches ahead.

Whether you’re planning your first road trip or returning to relive the magic, Route 66 offers a vacation filled with character, connection and discovery—perfect for couples, families and explorers alike.

Celebrate the 100-Year Anniversary in 2026

A milestone like this only happens once. As Route 66 marks 100 years, interest is already building—making now the ideal time to plan your vacation.

With heightened demand expected throughout 2026, booking early helps secure your preferred hotels, travel dates and itinerary.

With Pleasant Holidays, you can bring every detail together in one convenient booking:

• Handpicked 3- to 5-star hotels and resorts
• Rental cars for freedom and flexibility
• Tours and activities to enhance your journey
• Expert support before and during your journey

Enjoy the value and ease of booking everything together—so you can spend less time planning and more time enjoying the drive.

Three Route 66 Itineraries to Inspire Your Travels

Not every road trip has to span the entire route. These “mini adventures” highlight some of the most memorable sections of Route 66—each offering a unique perspective on this historic journey.

Chicago to St. Louis – A Nostalgic Midwest Start

Begin in Chicago and head toward St. Louis, with easy stops in charming towns along the way.

Highlights:

• Historic Route 66 landmarks
• Quirky roadside attractions and local museums
• The Gateway Arch

Where to stay:

• Four Seasons Hotel Chicago
• The Royal Sonesta Chase Park Plaza St. Louis

Why go: An easy, nostalgic introduction—perfect for a long weekend or your first Route 66 getaway.

Albuquerque to Flagstaff – Southwest Scenery at Its Best

Travel through New Mexico and Arizona for wide-open landscapes and unforgettable views.

Highlights:

• Route 66 Diner
• Petrified Forest National Park
• Meteor Crater

Where to stay:

• Hyatt Regency Tamaya Resort & Spa, Santa Ana Pueblo
• Hilton Sedona Resort at Bell Rock

Why go: Dramatic scenery, red rock landscapes and endless photo opportunities make this a must for nature lovers.

Santa Fe to Santa Monica – From Culture to Coastline

Start with art, history and wellness in Santa Fe, then end your journey at the Pacific Ocean.

Highlights:

• Santa Fe’s vibrant arts scene
• Desert landscapes and spa experiences
• Santa Monica Pier at sunset

Where to stay:

• Hilton Santa Fe Historic Plaza
• Fairmont Miramar Hotel & Bungalows, Santa Monica or Regent Santa Monica Beach

Why go: The perfect blend of culture, relaxation and a memorable coastal finish.

Don’t Miss These Stops Along the Way

• Chicago – Where your journey begins
• Tulsa – Arts, culture and local flavor
• Dallas – Big-city energy and standout dining
• Santa Fe & Albuquerque – Rich heritage and Southwest charm
• Flagstaff & Sedona – Stunning natural beauty and outdoor adventure
• Santa Monica – A scenic ending by the sea

Tips for Planning Your Route 66 Vacation

• Plan your route—but leave time for spontaneous stops
• Book early to secure the best options for 2026 travel
• Combine city stays with scenic drives for balance
• Pack for changing weather and landscapes
• Work with a Travel Advisor to make planning easy and seamless

Travel Your Way With Pleasant Holidays

A road trip is about freedom—and planning it should feel just as effortless.

Pleasant Holidays brings everything together in one convenient booking experience, from flights and hotel stays to rental cars and activities. With a vetted portfolio, flexible options and trusted expertise, you can travel with confidence every step of the way.

Customize your itinerary, choose your pace and enjoy a vacation designed around you—with added value and support you can rely on.

Start Your Route 66 Adventure

The road is calling—and the 100-year anniversary is your perfect reason to answer.

Connect with your Travel Advisor to book your Route 66 vacation with Pleasant Holidays and secure your preferred travel dates for this milestone year.

Start planning a road trip filled with unforgettable moments.