How to Plan a Trip from A to Z: Cheap Flights, Destinations, Hotels and More

Planning a trip isn’t brain surgery but there are a few things you need to know. The most important: Get organized ahead of time. That’s what this list is all about.

You travel pros may find some of this very basic, but sometimes it’s the basic stuff that’s easy to overlook. If anyone would like to add to this list, be my guest.

LISTEN: Travel expert Rick Seaney never misses a detail. At least not lately.

How to Plan a Trip

Please note: FareCompare does not endorse any of the sites listed below (we do not endorse any product); they are included for informational purposes only.

1. Choose a destination

If you know where you want to go, skip ahead to #2. Otherwise, keep reading.

  • Do some fun research: Ask yourself what you want. If it’s a beach, there are beautiful spots in Florida, the Caribbean, all over the world (including some lovely secluded beaches). Look at ‘best of Europe’ lists or whatever takes your fancy.
  • Look at cheap destinations: In the U.S., good value cities include Austin, Boston, Dallas, Denver, Ft. Lauderdale, Seattle and Washington, D.C. In Europe, check out Dublin, Copenhagen, Oslo, Stockholm and though it’s not exactly cheap, we’ve been seeing decent deals to Paris.

2. Choose a place to stay

If you’re lucky, you can cut costs by staying with friends or family. If it’s a hotel you want, look for rooms within your budget on TripAdvisor,, Trivago, Yelp and more, but also try less traditional options like HomeAway, Airbnb and super-budget alternatives like Couchsurfing or HostelWorld. You might save money and make a new friend.

Tip: When looking at reviews toss out the best and worst. Be sure the places that sound good to you are in suitable locations and offer the amenities you want.

3. Find the cheapest flights

First, read the tips in our guide to finding cheap flights (it’s a quick read). It tells you the cheapest days to fly, best day to shop, and other useful information, but the bottom line is, you must compare airfares because no airline always has the best prices.

If you want to fly a favorite carrier to redeem miles, start this process early. Getting awards seats is not as easy as it used to be, see this information on Frequent Flyer miles programs.

Tip: If you’re close to the miles you need, it might pay to top-off with purchased miles.

4. Find local transportation

How will you get around once you’ve reached your destination?

  • Rental cars: Sign up for any discounts ahead of time with your favorite agency.
  • Taxis: This can be an expensive option but may be your only alternative to/from the airport.
  • Uber and Lyft: Sign up ahead of time because all fares are paid electronically.
  • Apps: There are plenty out there (like HopStop) which offer info on public transportation including routes and timetables for subways, buses and trains in cities around the world.
  • Shuttle buses: Contact your hotel to see if they have airport shuttle service and if you have to pay for it.

5. Tie up those last-minute loose ends

Useful things to do that are easily forgotten.

  • Phones: If you’ll be traveling internationally, get in touch with your mobile provider to find out what you need to do to avoid getting hit with overseas charges; AT&T, for example, has ‘passport’ packages for international vacationers with a one-time charge from $30 to $120. If you’re an extremely heavy device user, consider investing in a local SIM card.
  • Credit cards: If traveling internationally, let the bank/credit card folks know you’ll be out of the country to avoid frantic calls asking why you’ve suddenly gone nuts with the spending.
  • Passports: Again, if traveling abroad, start the application process now – or make sure your current passport is up to date. Note: Standard processing time for passports is four to six weeks but you can pay extra for expedited service.
  • Speedier security: Now is the time to sign up for the TSA PreCheck program or Global Entry for international travelers (it includes PreCheck). There is a brief in-person interview and costs range from $80-$100 but membership is good for five years and you can’t put a price on speedier airport lines.
  • Contacts: Put every useful contacts you can think of in your phone, from airline to hotel and rental car plus embassy/consulate info if traveling outside the country. Consider adding numbers for credit card contacts, auto insurer (if you’ll be renting), the kennel you put your dog Sparky in, and whatever else you think you might need.
  • Packing: If at all possible, use a carry-on to avoid the $50 round-trip bag fee. Here’s a list of what you should pack, and a list of what you should not pack.

Tip: Southwest still offers two checked-bags for free but a carry-on can’t get lost and makes for a faster exit from the airport.

See more in Rick’s latest ABC News column. See all columns here.


Updated: August 26, 2015