Trip Planning Checklist – Step-By-Step Guide to a Problem-Free Vacation

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You’ve decided to take a vacation.  Yay!  You’re excited, right?  If you’re planning to book your own travel online, there is no shortage of sites to get information from and help you do that.  But after spending a few hours online researching, does it suddenly seem like a daunting task?  Probably.  Bottom line is – you need to use a trip planning checklist.

Traveling is complicated these days.  And planning your travel is even more complicated.

Using a trip planning checklist will give you a sort of roadmap of what to do and when to do it.  And most importantly, you won’t forget a vital piece of the puzzle that could cause your trip to turn into a disaster.

So don’t invite travel mishaps. Here is a simple step-by-step trip planning checklist to help you get on your way to a problem-free vacation.

Trip Planning Checklist

Trip Planning Phase

trip planning checklist

1. Choose Your Destination

This may seem like an obvious first step, but sometimes your destination isn’t necessarily set in stone and solid when you first decide to plan a trip.

Sometimes the destination can depend on other factors like the seasonality of the places you’re considering, special activities you might want to experience when you’re there, or special events that may be happening at certain times of the year.

In fact, whether you choose your destination first, or your travel dates first, or simultaneously, depends on your specific situation.  This is something that varies from person to person.

If you’re uncertain about where you want to travel to, then narrow down your choices to a solid 2 or 3 options and do a little further research on things on weather, cost, and activities and then make your final choice depending on which destination suits you the best.

2. Choose Your Dates

This also may seem obvious.  But you’d be surprised at the number of people that don’t actually specify their exact dates.  If you’re traveling, you need a starting and an ending date.  End of story.  That’s the day you leave home, and the day you plan to return home.

Only then, after you have those specific dates, can you realistically plan your trip.

As mentioned above, your own specific situation will determine whether you need to choose your destination first or your travel dates first.  If, for instance, you only have specific vacation time off from a job or business, then you obviously will have to choose your travel dates first, and then decide what your destination is.

3. Choose Type of Experience

Here’s where things start getting fun!

And this is a step that is often missed.

What is it that you want from your vacation?  What type of experience do you want?   Are you looking for a beach vacation?  Do you want to relax by a fabulous resort pool the whole time?  Or are you instead looking for more of a cultural experience?  For example, a European vacation with plenty of historical sites and museums?  Do you want to be completely on your own or with a group?  Do you want to travel internationally, or stay within your own country?  A cruise?  A Riverboat?  A package tour, or piece everything together on your own?  An adventure tour of some sort?  Hiking, biking, backpacking, or another active tour?

The possibilities are really endless, and only you can decide what type of travel experience you want.

These are all things that you need to think about in order to finally craft the perfect vacation for yourself.

4. Set A Realistic Budget

Now that you’ve decided on a destination, it’s time to get down to the nitty-gritty. 

Money.

You need to think about what your realistic budget is.  If you don’t have a clue as to how much things cost, then you need to do a little research first to figure out how much you may need to spend on a trip to the destination you have chosen.  That’s not always easy, but you should be able to come up with some idea. 

Alternatively, you can work with a travel agent to help you plan your vacation.  One conversation with an experienced travel agent is all it will take to find out approximate costs for your chosen destination.  There’s a reason they are called travel industry professionals!

So either work with a pro or do it on your own.

The bottom line here is – you should now have a budget for your trip, which should include everything from your departure day to your return day.

5. Check Your Travel Documents

Stop!

Before going any further with trip planning, you must check to see what documentation is required for the destination you have chosen, and make sure that you either already have the required documents or that you can get them in time for your departure.

  • Do you need a passport?
  • How long does your passport need to be valid after return to your home country?
  • Do you need a visa?
  • Are vaccinations required?
  • Must you provide a recent Covid-19 test result?

The subject of vaccinations and testing has become front and center with the arrival of Covid-19, and there are many rules and restrictions in place for almost every country now.  And those restrictions are changing and evolving very quickly.

The point here is, you need to make sure you can produce all of the required documents before you book your trip, especially if you are booking a last-minute trip.

Check out these 11 Best Trip Planning Apps For Travelers in 2021 for some help you accomplish all of the tasks on your trip planning checklist.

Trip Booking Phase

Image of laptop, smartphone and airplane model

6. Day-By-Day Itinerary

Once you have your specific travel dates and destination, plan out a day-by-day itinerary.

This is not so much necessary for things like beach vacations where all you intend to do is lounge around the pool and walk the beach for your entire vacation.

But planning out a day-by-day itinerary is especially critical for more complicated trips where you will be visiting more than one destination, or moving from city to city during your vacation.

By planning out your itinerary, I mean that you should actually write it down.  Day-by-day.

For example, here is a sample 7-night Italy itinerary and this is what a day-by-day itinerary would look like:


Day 1 – Depart home.  Overnight flight to Rome.

Day 2ARRIVAL DAY. Arrive in Rome in AM.  Hotel Overnight Rome.

Day 3 – Sightseeing Rome.  Hotel Overnight Rome.

Day 4 TRAVEL DAY. Travel to Florence.  Depart 10:00 AM, Arrive 3:00 PM.  Hotel Overnight Florence. 

Day 5 – Sightseeing Florence.  Hotel Overnight Florence.

Day 6TRAVEL DAY. Travel to Venice.  Depart 11:00 AM, Arrive 4:00 PM.  Hotel Overnight Venice.

Day 7 – Sightseeing Venice.  Hotel Overnight Venice.

Day 8DEPARTURE DAY. Depart Venice for home in AM.


On a day-by-day itinerary, you want to be sure and list every single day with the place you are stopping and traveling to next. That way you’ll be able to see where you are supposed to be at any given time and what bookings or services you will need for that day.

By looking at this day-by-day itinerary, you can immediately see that you have need hotel reservations for 6 nights. 2 in Rome, 2 in Florence and 2 in Venice. Also, you can clearly see that you have 2 travel days in the middle of your itinerary, not including the arrival and departure travel days. Which means you probably can’t schedule anything else on those days.

Alot of times people forget that they have to allow time for traveling from place to place in their itineraries. This is one of the most common mistakes when planning out a multi-stop itinerary like this.

I’ve worked inside the travel industry creating custom itineraries for clients for over 30 years (and still do). This is a real request I got:

“I would like to go to Rome, Florence, and Venice, but I can only be gone for 5 days. Can you plan the itinerary?”

Do you see any problem with that request?

The problem, of course, is that if you actually did 3 cities in 5 days (logistically it’s possible!), you would be doing nothing but traveling. You wouldn’t actually have time to stop and see anything.

If you’re planning your own itineraries, don’t make these mistakes! Make a day-by-day timeline so you can see what you’ve got to work with.

7. Book Flights

My favorite sites for getting good deals on airfare are:

Skyscanner – One of my tops choices. It works great for searching more than one destination at a time.

Momondo – A pretty good site for finding cheap airline tickets.

Kiwi – Sometimes you can find flights on more obscure routes and airlines with Kiwi.

8. Book Accommodations

Before searching for accommodations, you need to give some thought as to what type of accommodations you want. Hotels, a vacation rental like a house or apartment, B & B? Here are my favorite accommodation booking sites to use.

Booking.com – This is a great site to get good deals on hotels. They also have some vacation rentals as well as smaller inns and boutique hotels.

Airbnb – My favorite vacation rental site. Offers house and apartment rentals around the world for both short-term and long-term stays.

VRBO – More vacation rentals. This is my second stop after searching Airbnb.

9. Local Transportation

Once you get to your destination, will you need to travel around? If so, you need to plan how you’re going to do that.

Planes, trains, and automobiles? They could all factor into your transportation needs. But you may need to plan some of them in advance.

For short distances, are you renting a car? Taking a train? Using a taxi? A bus? A rideshare service like Uber or Lyft?

For longer distances perhaps a train? Or a plane?

Which way will be most cost efficient?

What about transfers from the airport to a city center or wherever your final destination is when you arrive in a new place? Sometimes airport transfers are expensive. Best to solve this problem before it becomes a problem.

These are all questions you should be asking yourself during this phase of the trip planning so as not have a last minute surprise with either no transporation or transporation that is too expensive.

10. Sightseeing and Activities

At this point your itinerary should really be taking shape.

Now is when you want to think about what sightseeing and activities you’re interested in for your chosen destination.

Make a list! You don’t want to miss out on seeing something worthwhile.

If you’re traveling to popular, busy tourist spots and plan to visit major attractions, you may want to think about doing two things:

  1. Taking a tour with a guide
  2. Booking the tour in advance

Taking a guided tour is just a great way to see many important sites, and means that you will get the most out of your visit.

Not sure exactly what you want to see and do yet where you’re going? You can check out a variety of Things To Do, Attractions, and Tours at Get Your Guide.

BONUS TIP: Don’t pre-plan activities every single day without allowing any free time. Once you arrive at a destination, you want to give yourself some time to soak up the ambiance and culture at a leisurely pace and be able to decide on the spur of the moment to do something that catches your fancy!

11. Purchase Travel Insurance

As soon as you purchase any of the components of your vacation, especially those with the larger cost like airline tickets and accommodations, you need to purchase your travel insurance.

Travel Insurance is technically optional (except in a few cases post-Covid where certain countries have required it).

But you should never consider Travel Insurance optional. Factor it in to the cost of your trip and consider it a necessity.

Travel Insurance protects you against more than just getting a refund if you cancel your trip. If you have the correct insurance, it will cover you if you become ill or incapacitated in some way while you’re traveling, require emergency medical care or hospitalization. And it can even cover minor unexpected expenses like lost or delayed baggage or trip delay expenses.

And while you may be thinking that these things may happen to other people but won’t happen to you, think again! In my 35+ year career in the travel industry I’ve seen all of these situations and more happen to clients in all corners of the world.

Have you ever heard the term “Up a creek without a paddle?” That’s exactly where you’ll be if you have a serious mishap or illness while abroad and you have no travel insurance.

Here are the best places to get your travel insurance:

Insure My Trip

World Nomads

Travel insurance prices wil vary depending on your age, where you’re traveling and how long you’re staying.

Pre-Travel Phase

trip planning checklist

For me, I consider the Pre-Travel phase to be within 1-2 weeks before travel begins. That’s when I personally kick into high gear and complete some of these very last minute tasks. You can, of course, complete some of these even earlier if you wish. Or later! That’s a personal choice.

12. Pack

Not much further to be said about this! Use a packing checklist to make sure that you’ve packed everything you need.

13. Prepare Your Home

If you are leaving your home empty while you’re away, then there are most likely some things that you need to do to properly prepare your home for your absence. Use a checklist for this too.

14. Plan For Remote Bill Bay

Many people already rely on remote bill pay, but if you don’t regularly use it make sure you’re organized well ahead of time on what bills will be due while you’re traveling and how you’re going to pay them remotely.

15. Plan For Remote Banking

Remote banking really goes with remote bill pay. However, what I’m really referring to here is accessing your money while you’re traveling.

The best way to get local currency if you’re traveling abroad is by using local ATM machines. You’ll need to make sure you’ve got an ATM card that works wherever you’re traveling to. Check with your bank for information on where you can use your card.

16. Foreign Currency Exchange

Although getting local currency abroad is very easy by using a local ATM machine, it’s not a bad idea to start off your trip by having some local currency in hand the moment you arrive.

There are ATM machines in most airports, however, things happen! Sometimes the machines don’t work or they’ve run out of currency or whatever.

To avoid being in a situation where you need some cash and can’t find a machine upon arrival at your destination, be proactive and order a small amount of local currency from your own bank before you travel. Depending on the type of currency, they may already have it on hand at the branch you use, or they may have to order it. It’s best to get this done a few weeks before travel to make sure you have enough time if your bank has to order the currency.

17. Advise Credit Cards Companies

Be sure and advise your credit card companies as well as your bank if you’re using an ATM card of where you’re traveling and when.

If you don’t do this and they see unusual charges from places that you usually don’t use your cards, they will most likely decline the charges. Once you advise them of what your travel plans are they will honor the charges with no problem.

Post-Travel

trip planning checklist

18. Rinse and Repeat.

OK, this is not really a step on your travel planning checklist! But I do hope this information will help you plan many perfect getaways in the future! When and where is your next trip?

Travel safe, travel often!

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Mary Emmer
Mary Emmer

About the Author

Mary is an online entrepreneur here at Still en Route where she uses her knowledge from a travel industry career beginning in 1984 to write about everything travel-related, sometimes with a baby boomer twist!  Read more.

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