How to Book Travel: A Step-by-Step Guide to Planning Your Next Trip

For most people, the dream of jetsetting off to a bucket list travel destination is quickly canceled out by thoughts of actually booking and making travel plans. This is especially true if you're hoping to visit a far-off place and experience a variety of cool, interesting things.

Turns out, booking travel doesn't have to be overwhelming—we're here to help you learn how to plan a trip. Whether you're traveling solo or you've got the entire squad in tow, this article will cover everything you need to know about picking flights, booking accommodations, planning for tours, and more. Ready to start planning that dream vacation? Read on.

Booking Flights

Plenty of websites can help you score cheap flights. Google Flights is my favorite, but I've also used Dollar Flight Club, Skyscanner, and Kiwi, in a pinch. If your travel dates are flexible, this can rack up the savings even more. In fact, it's one of my top tricks for finding cheap flights.

Understanding how airlines operate can help you save money, too. Oftentimes, a flight from A to B only takes off three times a week, so if you’re trying to get from A to B on a date the flight isn't offered, you’ll see it reflected in the price tag. Play around with your dates—even by just a day. You’d be surprised at how much you can save by adjusting for a day or two.

If you’re serious about traveling more, it may be worth it to stay loyal to an airline. I take at least three or four trips a year, but I am not loyal to an airline. I’m loyal to the price tag (and flight times).  As a solo traveler, this has worked out to be easier for me, but I realize that staying loyal to an airline can be beneficial in the long run.

Booking Lodging

Finding a great place to stay is key to making your vacation memorable. One of the biggest mistakes I see travelers make is booking a hotel (or Airbnb) that’s too far away from public transportation, the downtown scene, tour pick-up areas, etc. Don’t get me wrong, there’s something to be said about booking a place on the outskirts where you won’t deal with city noise, but it’s a balancing act. 

Think twice before forgoing a rental car, especially if your accommodations are far from the airport or other major attractions. Those ride-share fees can really add up, and the city bus might only drop you off six blocks from your Airbnb—all mistakes I've made and lessons learned!

When booking lodging, check Google Maps to make sure you're staying at a location that's close to things you want to see and do. If you choose to stay further away, take note of the bus routes and taxi situation before you book. (One of my worst travel mistakes involved booking a hotel over a mile away from the train station, forcing me to walk with my duffel bag over my shoulders after 18 hours of travel... my own personal IronMan race.)

I'd also argue that hotel chain loyalty is more effective than airline loyalty. You can climb the membership ranks with major hotel chains faster than you think, and before you know it, you'll have enough points saved up for a free night or two. Plus, hotel members tend to get perks like free upgrades, late check-outs, and more. Just make sure you're joining a hotel chain that has locations where you'd normally go.

Booking Tours

The first thing I do when planning a trip is check sites like GetYourGuide and Viator to check for interesting tour options. I’m always going to do at least one activity that requires a helmet, and online marketplaces like Viator are set up perfectly to see your options. 

I see a lot of rumors about these online marketplaces (Viator and GetYourGuide), so let me be clear: both of these marketplaces show you what tours/activities/experiences you can have with tour companies—they do not offer the tours. Just like how Priceline and Booking.com will show you hotels and flights, but there is no Booking hotel or Priceline airline. You can always check which tour company is running the tour and do your own research. I’ve written a guide to Viator recently, and it’s worth checking out if you’re new to booking tours through them.

Using Travel Search Engines

Travel search engine sites like Kayak are underrated tools. Kayak, for example, is a one-stop shop for booking flights, hotels, and even rental cars. It lets you compare deals so you can find the best one for your needs. I've used Kayak both domestically and internationally, and have always been happy with my results. Some wholesale retailers, like Costco, also offer travel package deals to select destinations that you can customize and compare.

One of my favorite ways to use Kayak is the “explore” tool. This nifty feature allows you to plug in your budget, duration, and type of trip, and it will reveal all of the destinations that fit your criteria—including flights. You can even set your filter to include just nonstop flights, one-stop only, or you can ping pong across the country if you really want a cheap flight. These travel search engines are perfect for those hoping to pinch some pennies.

Checklist for Planning a Trip

Once you’ve decided on your destination, here are the steps you should take to book the travel. I would strongly recommend you do them in this order:

• Research the destination for the month you'll be traveling
• Book the flight
• Book the rental car
• Book the hotels
• Book tours

Always do your research. Specifically, check for the month you’re planning to visit. Want to visit New Orleans in August? Well, it’s going to be hot with a side of hurricane watch. Or, maybe you want to see the puffins in Maine, but you can only visit in March. Well, puffin season in Maine is from May through August, so no puffins for you.

Check the average temperatures, average rain (or snow) fall, etc, before you book the flight. Ask yourself this question: What do you want to do in [destination]? Then, do a quick Google search to see if that’s possible for the time of year of your visit.

Book your flights before the hotel and rental car. (A booked hotel won't matter if you have no way to get there!) From there, reserve your rental car and then book your hotel. It’s easier to book your hotel once you know the kind of car you’ll have—you’ll know parking rates, how far of a drive the hotel is from the airport, etc. Heck, you'll even have an idea of what type of car you'll need. Will a normal sedan be sufficient? Or do you need all-wheel drive for your adventures?

I would wait to book tours and activities for as long as you can. Why? Weather! The one uncontrollable throughout your entire vacation is the weather. Of course, the weather can change, but if the forecast shows that day three of your trip might be rainy, you can easily switch up your itinerary and use that day for indoor activities like museums.

Ultimately, there's no "one size fits all" way to plan a trip. Whether you're hoping to stay in unique Airbnbs, conquer amazing hiking trails, or explore charming small towns, planning the perfect itinerary takes practice. If you need some help getting started, try out Only In Your State's itinerary planner. Just plug in your destination and how long you're planning to go, and it'll gather some ideas for you.