Fancy a holiday that will take in eight US states and give you access to awe-inspiring landscapes, stunning National and State Parks and quaint towns with retro motels and diners? Then Route 66 holidays will be for you – and our guide to Route 66 holidays can help you pick the best road trip for you.

Route 66 is the holiday road trip of legends. Winding its way over 2,278 miles (3,665km), it stretches from Chicago across eight states to Santa Monica on the Californian coast. Route 66 is a road rich with diversity, taking in sprawling cities, eye-popping vistas, National Parks and iconic landmarks. It’s also a journey through small-town America, with its main streets that seem untouched from the 50s, replete with drive-throughs, diners and shopping. Along the way, you’ll travel through three time zones and it’s one the longest road trips you can take in the world.

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There are lots of Route 66 holidays that offer you the chance to travel the iconic route from Chicago to Santa Monica – so it pays to make sure that you plan carefully to make sure that you get the best from your trip.

We’ve pulled together advice on when to go, where to start and finish, and tips of budget and accommodation along the way.

Want to know more about Route 66 tours? Read our guide to Route 66 tours – travel choices for Route 66 holidays.

Route 66 holidays – when to travel

Timing is everything when planning to drive Route 66 and, as with most holiday destinations, Route 66 has both high and low seasons.

During the summer months, and it can get very busy with lots of traffic on the road. Summer heat can be an issue too – especially along the western part of Route 66 – so make sure you choose a car with reliable air conditioning for a comfortable ride. September sees Americans back to work and school, so traffic is reduced.

Winter is not the best time for Route 66 holidays. Snow and ice may cause road closures and sheet ice makes for dangerous driving conditions. It’s also worth keeping an eye out for tornados during March to June, despite being a rare weather event.

Anytime from May to October is good for a Route 66 holiday.

For the budget-conscious, motels and hotels are cheaper off-season and outside the summer vacation period when finding rooms can be more difficult. A top tip is to use online hotel booking websites to pre-book accommodation in advance.

Route 66 holidays – how long to travel

It takes a long time to drive Route 66. You’ll need at least two weeks, and that’s with some serious daily driving. Ideally, three or four weeks will be enough to really experience all that Route 66 holidays have to offer.

Plan your drive time sensibly. Think about how many hours you’ll want to drive each day compared to stopping and enjoying the sites. Even at 50mph, you’d need to drive over two hours each day to get through the entire route in three weeks. Less holiday time means more time behind the wheel, and that means less time available for sightseeing.

If you’ve less time, be selective about your itinerary. Stick to the major attractions and use the Interstate to travel at a quicker pace, as well as bypasses and toll roads to scoot around major cities and downtowns. You also don’t need to drive Route 66 in its entirety: some Route 66 holidays allow you to instead travel just section of it.

Route 66 holidays – route planning

Most people planning Route 66 holidays generally head east to west – starting surrounded by the towering skyscrapers of Chicago and ending on the shores of California’s coastline.

Chicago is easier to fly to and ending up on Santa Monica’s beaches or heading to Los Angeles is a great endpoint to any Route 66 journey.

However, you don’t have to follow this route, and can even just focus on segments such as Amarillo to Saint Louis or Los Angeles to Albuquerque. Where you plan to fly into and out of the US plays a role in determining your route. Flying into and out of both Chicago’s O’ Hare and Los Angeles International Airport are convenient.

It’s worth planning where gas stations are along the route. Finding a gas station on Route 66 isn’t usually an issue but there are some western stretches such as Arizona where gas stations can be up to 100 miles apart. It’s worth topping up with fuel often and aiming to keep the tank at least half full.

Route 66 holidays – Grand Canyon, State Parks and Monument Valley

There are lots of sights to see along the way on Route 66 holidays. List all the ‘must-see’ attractions and decide how long you’d like to spend at each. Allow plenty of time for stopping for food, and also ensuring you visit each site at the right time of day. For example, while the Grand Canyon is a bit of detour, if you’re planning to go it is best experienced in the early morning or late evening to catch the light from the rising or setting sun. Accommodation at the Grand Canyon South Rim books up early – as much as 9-12 months in advance – so plan ahead.

In addition to the Grand Canyon, there are many other sites fairly close to Route 66 that are worth taking a detour to visit, such as the Hoover Dam or Monument Valley. There are also State Parks and National Parks offering plenty of amazing views sights and outdoor recreation. Sometimes it pays to get off the beaten track, take a side road to explore a small town.

Using Google Maps’ directions feature, identify the major towns and stopping points, and use the directions tool to gauge how long it will take to travel between stops. You can set specific times and dates, too, and Google Maps will look at historic traffic levels to provide a more accurate estimate of your journey time. Research the towns you’ll be passing through, so you can find places to visit from museums and landmarks to quaint towns and antique shops, vintage diners and classic service stations.

Accommodation on Route 66 holidays

Plenty of accommodation options exist along Route 66 – from historic motels, B&Bs, large hotels, campsites and even wigwams and tents.

You can stay in hotel chains along the route, such as those by Best Western, Super 8 and Comfort Inn. For a more authentic feel, opt for smaller independent hotels and motels. There are classic Route 66 motels and must-see hotels all along the road. The glory of a self-drive route 66 holiday is you can stop at any motel or hotel that catches your eye.

However, it’s best to book a room in advance, especially during summer holidays and other key vacation periods. Some lodging may be fully booked months in advance, so pinpoint these places and reserve with plenty of time. Look at booking websites such as Booking.com or research towns to find suggested lodging, as well as visiting sites such as Tripadvisor.

If you book well in advance of your trip, remember to confirm your reservation closer to your departure date and carry confirmation of your reservation with you when you travel.

To avoid the hassle and cost of staying in hotels, choose an RV (stands for Recreational Vehicle) instead. RVs are like mobile homes and can offer a luxury way to travel. There are plenty of RV parks that offer power and water, and parking up is inexpensive. RVs do provide lots of flexibility but take confidence to drive and can be restricted from accessing places off-the-beaten-track.

Route 66 holidays – planning your trip and budget

You can spend as little or as much as you’d like when driving Route 66. While everyone’s budget can vary, there are some costs that you’ll need to research.

Flights – One of the biggest costs, flight prices vary and tend to be cheaper the earlier you book. Look for sales in January by airlines such as Virgin Atlantic and British Airways – and remember you can fly different airlines in and out of the US from your different start and endpoints.

Car hire – Most of us dream about driving a convertible Ford Mustang along Route 66 but there are plenty of options when it comes to car hire. A convertible can be very impractical. In the summer months, the top will need to be up more than down to take advantage of the air conditioning, and the constant wind and noise can get wearying. A mid-size SUV, for example, will offer more comfort for a long trip and has plenty of space for luggage.

Car insurance – Make sure your car insurance covers Unlimited miles, Collision Damage Waiver with zero excess, Basic roadside coverage with the ability to upgrade, local taxes and theft protection with zero excess. You may want to throw in satnav hire as well as additional driver cover to help split the driving load. However, most modern mobile phones offer cheap satnav apps that download the maps for your journey before you head off. Factor in the one-way drop off fees, which bump up costs considerable or look for car hire companies that wavier this fee.

Petrol / Gasoline – Work out how many miles you’ll be driving and add 10% to be on the safe side, then estimate the average mileage per gallon of your car, work out how many gallons of fuel you will need.

If you’ve not driven in the US before, be aware that you pay for your fuel before you fill-up. And it’s best to avoid paying with your credit card as the gas station may pre-authorise several hundred dollars to cover the cost of the transaction. While this clears after a few days, it may impact how much credit you have on your card available to spend.

Route 66 holidays – accommodation, food and activities

Accommodation – How much will you need to spend on lodgings. You can stay in cheap motels or spend hundreds of dollars a night on suites in larger hotels. Using online booking sites such as Trivago to compare accommodation prices. Many hotels will offer the best rate if you book direct via their own website in the US.

Food – Consider how much you’ll need to cover food each day. Think about whether you’ll be eating at restaurants or diners? Does your motel or hotel offer free breakfast – if so, this can be a cost-effect start to the day? There are plenty of fast food joints along the route.

Attractions – Don’t forget to factor in the entrance fees to National or State Parks, Museums, and other attractions and events. These can vary according to time of year, and there are various discounts, such as for seniors and students.

Miscellaneous – Put aside some cash for tips, souvenirs and emergencies. You can always access your UK bank account using an ATM, and credit cards bearing the Visa or Mastercard logo are widely accepted. Be aware that there is usually a fee to withdrawing cash from an ATM – usually around 2-3%. A prepaid currency card such as that offered by Caxton is worthwhile, often offering a better exchange rate and the ability to top it up with dollars using a free app on your smartphone.

Travel insurance – Make sure you’ve adequate travelling insurance. You must have sufficient cover for USA health and accident and it should cover you for cancellations or other travel mishaps.

Get the best over 50 travel insurance with our money-saving guide to travel insurance over 50: buying the best policy.

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