The Ultimate Guide to Your Next Trip: Successful Booking Tips

There are a lot of things that go into planning a trip. Deciding where to go, when to travel, and how to get there can be very stressful, even for the veteran traveler. There are a lot of options to get where you are going. Different airlines, airports, connections, nonstop, and ground transport options all need to be taken into consideration when booking your next vacation, and that’s all before booking a place to stay.

Luckily there are a lot of great tools out there to help you book your next vacation. If you go through a site like Tripadvisor it is possible to do all of the necessary destination research, book your flights, hotels, and set up a comprehensive itinerary for the trip. Tripadvisor is a one-stop shop for your next vacation! I also like using booking sites like Expedia, especially for bundle deals and cruises, or if all you need are accommodations.

Check out the best travel resources here! 

Regardless of which booking method you decide to look at first, I always recommend cross checking prices between different sites to see if one will offer a better deal. It is always a good idea to check directly with the company that will be operating the flight, or cruise as well. Airlines, cruise lines, and hotels will often offer the best price for customers when they book directly through them, and you may get some extra amenities out of the deal.

Get Your Airline Contact Info Here!

Even if you’re only cross checking one site you will have a good idea of what the best price will be for your trip. If I am booking a trip I typically check at least five different booking options before making my decision. It doesn’t take that long to do a few extra searches, and I almost always end up with the best deal possible. I have saved thousands over the years by doing just a little bit of extra research.

Aside from doing some extra searching for the best travel deals there are a lot of factors that you should be considering before booking and boarding your next flight. Remember that the lowest price is not always the best value, especially when it comes to air travel. Airline fees and extra connections can cause you lots out of pocket and end up being a waste of your time. Don’t get caught on a bad flight just because you saved a few bucks on the base fare.

I have outlined some of the key points that your should consider the next time you fly. Travel interruptions and delayed flights are sometimes unavoidable, but if you use these tips you will have a higher probability of making it to your destination with no hassle.



Smart Booking

  1. Try to fly nonstop

If you are not making a connection then you will have no chance of getting stuck in a city where you don’t want to be. When you miss a connecting flight due to a delay then the airline will rebook you on the next available flight, this will sometimes be hours away, and in some cases you may need to wait overnight. Missed connections always cost you time, and may end up costing you lots of money if you need to pay for a hotel and buy meals when you’re delayed overnight. Take the nonstop option when it’s available!

  1. Travel on Tuesday, Wednesday, or Saturday

Airlines often have cheaper flights on these days. Sunday, Monday, and Friday are very travel days for obvious reasons. Most people’s vacations start on the weekends so they are likely to travel Sunday to Sunday, or book a weekend trip Friday to Sunday. Business travelers usually leave on a Monday and return Thursday or Friday. Tuesday, Wednesday and Saturday often have more open seats and the airlines will be offering them at lower prices.

  1. Give yourself an extra day

Especially when you’re going on a cruise or excursion. These companies will not wait for you if your flight is delayed and you miss embarkation time. Fly in the day before. Even if there is a delay or cancellation you’ll have time to rebook and make it to your destination.

  1. Get a long Connection

There are many situations when you will not be able to fly nonstop into your destination from your origin. When you are forced to make a connecting flight, make sure there is enough time in between flights. The airlines have cut down significantly on several of their connecting times lately. If you have less than one hour between flights that is not enough. Even a slight delay at your origin could cause you to miss your next flight. I like to make connections with at least two hours in between flights. This gives you enough margin for a delay on your originating flight.

If you get in early and there is another flight before your scheduled flight to the same destination then the airline may accommodate you on the earlier flight.

  1. Fly early

You will want to book morning flights when available. Most airline delays occur in the afternoon and evening. The early morning flights are usually on time. The aircraft is usually ready at the gate, and your flight crew will be fresh with almost no threat of timing out. You’re better off getting up early for your flight then getting delayed later in the day.

  1. Understand the Fees

Check out the airline’s policies for checked baggage, carry on luggage, seat assignments, and in flight amenities. A slight difference in price between two similar flights could turn into a large gap if the cheaper airline is going to pummel you with fees once you try to check in. Some airlines are even charging passengers to print boarding passes! (Spirit)


Before You Check In (days leading up to your trip)

  1. Sign up for the mileage program

Almost every airline has a mileage rewards program. It’s free to sign up and you may get some perks for being a member. Check on the airline’s website for the form you need to fill out. It should just take a few minutes.

  1. Seats

Once you have bought your ticket try to pick your seat for the flight. Holding a seat in advance will save you from getting whatever is leftover when you check in for the flight. Many airlines allow you to pick seats online, or you could always call them and see what’s available.

Some airlines will charge you to pick a seat even if it’s not a premium seat; hopefully you realized this before booking. Your preferred seat may cost you a few bucks.

If you’re flying Southwest you will not be assigned a seat at any time. They board their aircraft by group numbers. When aboard the passengers select whatever seat they want as long as no one else is occupying it.

  1. Get the App

Most airlines have a comprehensive travel app. You’ll be able to review your reservation, view boarding passes, (after check-in) get flight and gate information, and get general airline info. It’s a great tool to keep with you when flying.

  1. Get an Airport Plan for Each Direction

How are you getting to the airport? I prefer to get a ride; parking at airports can be very expensive.

Where is the Check-In counter? TSA? Airline gates? Especially for large airports you will need to know where to go when you get there. You don’t want to end up at the wrong terminal before your flight. Most airports will have a website that you can visit to get this information. If you are renting a car at your destination you’ll want to know where to go to pick it up. Using public transportation? Check out the bus/train schedules before you depart. If you get in late at night there may be nothing available until the next day.

  1. Check the Conditions

Know the weather at your destination. You will want to pack accordingly.

  1. Make sure you have everything you need.

I always think I’m forgetting something when I leave for a trip. If you forget something then odds are you’ll be able to buy it when you remember that you left it, but it’s still a pain. Make a checklist of the items that you want to bring with you and make sure they get into your bags. Here are some key things you may need:

  • Cell Phone
  • Phone Charger
  • Medication
  • Wallet
  • Passport
  • Airline Confirmation Info
  1. How’s Your Bag?

You’ll want to check your luggage and make sure it’s in good condition for travel. All of the zippers and straps should be in good working order. Look out for big holes, loose stitching, and weak material. You don’t want your bag bursting at the seams on your trip. You’ll be stuck lugging everything in a garbage bag!

  1. Get Security Compliant

Know what you can and can’t carry through airport security. Check out for a list of items you won’t be able to bring through the airport. Leave the full size shampoo at home! You can buy TSA approved toiletries at most grocery stores and pharmacies. Remember, nothing more than 3.4 ounces liquid per bottle.


Day Of the Flight (up to24 hours out)

  1. Check In

Most airlines will let you check in 24 hours in advance. Checking in early will give you the best selection of seating (if available) and will make you less likely to be pulled off of the flight in cases of oversales and weight restrictions. You can use the airline’s app or go on to their website to check yourself in. You will probably need your confirmation number handy to do this.

  1. Flight on Time

Get the most up to date information from the airline app, or through their website. Make sure your flight is running on time. If you have a connection then you will want to check the status of that flight too. If either is delayed then you may want to contact the airline about alternate options. You also don’t want to be hanging out at the airport for a couple extra hours if your first flight is significantly delayed.

  1. Dress Comfortably

You’re going to be stuck on a tin can for a number of hours, make sure you are comfortable. Leave the flip-flops and high heels in your bag. Wear closed toed shoes that are good for walking (or running) some airports have longs concourses that will require a lot of walking between gates. If your inbound flight was late then you’ll have the footwear necessary to run to the next flight if need be.

  1. Baggage

Hopefully you’re carrying everything on and you can skip this step. When you carry everything you can go straight through security with your boarding pass and avoid the counter all together. Carrying on gives you several other advantages; check out my post about baggage here. If you must check your bag then make sure to arrive at the counter two hours before your flight. Airlines have strict cutoff times for checking bags; if you arrive after the cutoff then you won’t be able to travel.

  1. Get The Gate

Get your gate information either on the airline app, departure boards at the airport, or from an airline employee. You need to know where your flight is departing from. If you don’t know how to get there then ask someone!

  • If you’re sitting at a gate 30 minutes prior to scheduled departure time and you don’t see a gate agent, a plane, or signage indicating that your flight is leaving from that gate you should be concerned. It is likely that your flight has switched gates. Time to talk with an airline representative and find out what’s going on. I’ve seen many people miss their flight because they were waiting in the wrong spot.


Now that you have checked in and gotten to the airport the hard part is over. Now you just need to get through security and to your gate. Hopefully everything will be running on time and you’ll make it to your destination with no issues. If you followed the above steps then you are well prepared, and odds are you will have no problems with your travel. Of course there are scenarios where you will do everything right and a flight will still get delayed. That is just part of the airline business. In a delay situation, travelling early, carrying your luggage with you, and limiting connections will give you the best opportunity to make your destination.


Click here for tips to deal with the airline in delay situations or if you have missed your flight.

Are you dealing with a creeping delay? If your flight time keeps getting pushed back with no end in sight you need to take action to avoid getting cancelled and stuck. Check out my creeping delays section here!


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