39 Step Guide to Planning for a Vacation (Checklist & Timeline PDF)

Planning for a vacation can feel overwhelming, especially if you are traveling with kids. Luckily travel planning is my superpower and over the years, I’ve gotten my process and timeline down to a science. To help others, I’ve boiled down my 20-plus years of trip planning experience into this trip planning checklist.

Since travel planning gives me joy, along with the anticipation of the trip, I tend to start planning as early as possible. Therefore, this vacation planning timeline and checklist is spaced out over a 12 month period, which is ideal for international trips. It also allows you to tackle just a few tasks at a time and not be overwhelmed with the planning process.

However, I realize everyone is not an advance planner like I am, so you can always compress this vacation planning timeline to suit your trip.

Download the Vacation Planning Checklist

Planning for Vacation Checklist

If you are planning an international trip, especially if you are traveling during peak season or to a very popular destination, you need to start planning quite early. The preliminary stages should begin as far out as 12 months to decide on a destination, budget, and timeframe.

There are destinations, such as National Parks in the summer or Caribbean resorts during Festive Week, that can book up as early as nine to twelve months in advance.

Here is my step-by-step guide for planning a vacation:

Pick Your Destination

The first step to planning a vacation is figuring out where you are going. It sounds easy, but sometimes it takes a lot of work to figure out when, where, and how much. Start by discussing your vacation preferences and how you will make a decision. Will your choice be influenced by budget? Finding a flight deal? Will everyone in the family get a vote?

This process usually requires a bit preliminary research into a various destinations such as how much a trip costs, popular things to do, and the best time of year to visit.

Determine Your Trip Budget

We all have dream destinations, but there is a reason why there is something called a “bucket list”. Not every destination is affordable to us at this time. Sometimes we need to save up for years to afford a trip. Maybe we need to strategize about earning points and miles to make travel more affordable. Other times we need to wait for a flight sale. The whole reason we went to Morocco and Vienna was because we found a flight sale (although those destinations were ones that we were considering.)

When planning your trip budget, be sure to include airfare (if needed), accommodations, local transportation, activities, food, and other expenses such as gratuities, travel insurance, visas, etc. I have many guides to help you understand the trip cost for many destinations including Europe, London, Paris, Italy, Portugal, Amsterdam, Scotland, Iceland, Ireland, Japan, Morocco, and more.

Decide on Dates

Many times, especially when it comes to family travel, we don’t have a lot of flexibility when it comes to travel. Even so, you need to decide if you are traveling for spring break, summer vacation, or over the December holiday break. If you have more availability, you may want to research weather and trends to visit destinations during shoulder seasons or off-season when things are more affordable. Once you decide on a general time frame, you can start to research flight prices.

Research Airfare and Set Alerts

Note: This post contains affiliate links. If you click a link and make a purchase, I may receive a small commission at no cost to you.

Once you have determined your destination and dates, it is time to start planning in earnest. I recommend using an app such as Hopper to see the cheapest times to fly. You can also set alerts and the app will let you know when they think it is a good time to buy.

I also subscribe to Going, which is a flight deal service that lets you set your preferred home airports and destinations and they will send out flight deal alerts.

Lastly, if you want to find the best way to accumulate points and miles through credit card spending and sign up bonuses, I’d suggest downloading the Travel Freely app to track your credit cards and learn how to earn points.

Request Paid Time Off

Before you book anything, especially anything non-refundable, be sure to request time off from your employer and get the approval on record.

Book Flights

Once the above steps are complete, you have a bit more breathing room. I typically try to book my international flights about six to eight months in advance for the most availability of reward seats and the best rates. Domestic flights should be booked about three to six months if possible, or at least four to six weeks in advance.

This is a good time to start paying attention to those flight deal alerts and look for sales around major events like Black Friday or Travel Tuesday. Some airlines also offer anniversary sales (JetBlue) or seasonal sales (Southwest.)

Book Accommodations

If you are traveling during a particularly busy time, you will want to start looking for accommodation early. National Park lodges book up very quickly after reservations open for the following year, generally nine to twelve months in advance. Other destinations that have limited availability and book up at least six months in advance include the Amalfi Coast, Greek Islands, and anywhere that you don’t have a large inventory of rooms and there is a limited season. Remember that you can always try Airbnb and these competitors too for alternatives to hotels.

For other trips, look to book accommodations anywhere from six months to three months in advance.

Purchase Travel Insurance

Purchasing travel insurance as soon as you book your trip has a few advantages. First, it protects you in case something comes up that forces you to cancel before you leave (for included reasons.) Also, if you are purchasing cancel anytime or cancel for any reason coverage, you generally need to purchase this within 14 days of your first trip deposit.

Having a travel insurance policy on your whole trip will typically also protect you against trip interruption, baggage loss, theft, and, importantly especially when traveling internationally, medical coverage.

Double Check Passport Validity

Remember that many countries require your passport to be valid for at least six months after your arrival. Double check the expiration dates of all of your travelers’ passports if traveling internationally. Also research your destination’s validity requirements and make sure that you are within that window. Be sure to give yourself a minimum of eight weeks to get a passport renewal and remember that things like government shutdowns can make this time frame much longer.

Check Visa and Vaccination Requirements

When traveling internationally, research if you require any visas or additional vaccinations including yellow fever, Covid-19, and others. If vaccinations are required, you may need to book an appointment at a travel clinic. Some visas can be purchased on arrival but others require paperwork to be completed in advance.

Start to Research Activities and Things to Do

Around three to six months out, you will want to begin to research your activities and things to do. I have some suggestions on how to do this and other ways to prepare kids for an international trip. You need to do this in advance because some attractions require advance reservations that sell out as soon as they open up (such as the Eiffel Tower in Paris or the Anne Frank House in Amsterdam).

You don’t need to create your full itinerary yet, but what I do is open a Google Doc and when I find something I’m interested in, I copy the website, opening days/hours, and any relevant information (e.g. advance tickets required) into the document so that I can go in later and start to organize by day. I also open Google Maps and star/save each location on the map so that I can start to visualize where everything is in relation to each other and where I am staying (or would like to stay.)

Create An Itinerary Outline

By three months out, you need to really dig into your vacation planning. That is, unless you want to be disappointed when things you want to do or places you want to stay are booked. Start by putting together a skeleton outline.

Go back to the document that you started when researching things that you want to do. Refer to the hours and days they are open and the map to see which things are near each other. You will also want to make sure you have a balance of activities and downtime.

When traveling with young kids, I try to make sure that we only have one organized activity a day, two at most. You can also look to incorporate at least one thing a day that the kids chose to do. Plan the more physical activities and tours in the morning when everyone is fresh and take into consideration the weather as well.

Book Tours & Activities

Start booking your tours, classes, private guides, and activities between three months and one month out. Keep in mind, as mentioned above, some attractions have tickets that go on sale at very specific times and they sell out very quickly. Other attractions, such as the Louvre Museum and many others, require timed entry tickets.

If you are visiting National Parks, keep in mind that some require reservations (such as driving the Going-to-the-Sun Road in Glacier National Park) and others require permits for specific hikes.

As you book your activities, put the confirmation numbers, contact information, cancellation policy, meeting place, and meeting time in your itinerary and/or your calendar (for the appropriate time zone!) Print any tickets or save them to your mobile wallet. You may also want to file or upload any confirmations or documentation to the Cloud so it is accessible at any time.

Book Your Other Transportation

If you require a rental car, try to book one between three to six months out for international trips, especially if you require an automatic transmission. Since there is usually limited inventory, those tend to book up fast and car rental prices increase the closer you to get to the date.

Trains can also book up, especially if you want an assigned seat in a premium cabin (which makes it easier for storing luggage.) Often trains start taking reservations from about 90 days in advance, but others open earlier.

Book Dining Reservations

Between four and two weeks out, it is time to start researching and booking dining reservations (earlier if you are looking for Michelin Star restaurants.) When reading blogs, I usually make a note about restaurants that they recommend and add them to my Google Doc and Map. I also use Yelp, TripAdvisor, OpenTable, The Fork, and Resy. Because I’m a bit of a research nut, I don’t just look at reviews, I also look at the restaurant websites to get a sense of formality, menu, and price.

I then consider the other activities we have planned for the day and where we will be for lunch and dinner time. If we are exhausted, I know we will want to stay close to the hotel for dinner and have something informal. For days with more downtime, or maybe the last night of the trip, we might want more of a splurge or special meal. When booked, add the reservation time and address, along with the booking method in case you need to cancel, to the itinerary.

Finalize Your Itinerary

Once everything is booked, it is time to finalize the itinerary. I usually keep this as a Google Doc and set it to be available offline. This means that I can edit it and access it on the road. I also print out at least one copy to carry with me and sometimes I’ve given a copy to my daughter too so she can easily see what we are doing each day. When she was younger, we would review the itinerary each night to discuss what we would do the next time. This helps a lot with sensitive kids.

It is a good idea to also send a copy to friends or family in case of an emergency.

Obtain an International Driving Permit

If you are renting a car in another country, you should research whether or not that country requires an International Driving Permit. Note that car rental companies are not very good about providing this information. You can get one at AAA offices, just call ahead to see if you need an appointment.

Order Foreign Currency

It is possible to get foreign currency from a local ATM when you arrive in-country, but then you need to pay additional fees if the bank doesn’t have a partnership with your home bank. And, the ATMs in airports tend to have higher fees. Just in case I have trouble finding an ATM or getting my card to work if I don’t have a PIN, I like to have some currency in my pocket when I arrive. You can usually get a pretty decent exchange rate from your local bank.

I know with Bank of America, you can place your order online and either have it shipped to you or you can pick it up at your local branch. This is a good time to take care of a few other money-related things:

• Let your bank know that you will be traveling so that they don’t put a hold on any transactions;
• Make sure your credit card(s) of choice don’t charge foreign transaction fees;
• Make sure you have a PIN for your chip-enabled credit cards, as some international terminals require a chip and PIN;
• Also notify your credit card provider to let them know about any international travel plans so they don’t trigger fraud alerts or deny transactions.

Arrange Pet Sitting or House Sitting

If you have pets, make sure you arrange pet sitting or kennel boarding. You may also want to consider house sitters for someone to take care of your plants, bring in the mail, and make sure your house isn’t empty. You can find house sitters on sites such as TrustedHouseSitters.com and other resources if you don’t have someone already.

Determine International Cell Plan

Make sure you know what your cell carrier’s international plan options are. Is some data included, like T-Mobile, or do they charge a daily fee, like Verizon? A cheaper option is often to purchase an e-SIM for unlocked, compatible phones. I use Textr because it is much cheaper than using my Verizon international plan. If you are interested, you can sign up using this link to save $3.00 off your data plan.

Purchase Travel Items

This is a good time to look through your closet and see if you need anything for your upcoming trip. Do you have good walking shoes? A lockable day bag? A good packable sunhat? Are you suitcases in good working order? Do you need a travel umbrella? An international adapter? Make sure to give yourself time to shop and for order to deliverable.

Download Apps, Maps, and Entertainment

While you are on your home WiFi, be sure to download all the mobile apps that you might need on your trip including transit apps, phrasebook apps, airline apps, etc. Also go into Google Maps and download maps for the destinations you are visiting.

Make sure all your mobile tickets are saved in your mobile wallet and download any books, movies, or shows that you might want to use on the trip including on the plane.

Arrange for Mail to Be Held

Call the post office and arrange for your mail to be held while you are away (unless you hired a house sitter.) You may also want to ask your neighbors to keep an eye out for any package deliveries.

Alert Your Alarm Company or Police

If you have a home alarm monitoring service, you should reach out to them and let them know that you are traveling and give them alternate ways to contact you. You could also let the local police know so that they can schedule patrols.

Back Up Your Computer and Phones

If you are traveling with your computer, make sure it is backed up before you leave, same with your phone. Phones are a prime target for theft and computers have a way of getting stolen, broken, or left behind.

Arrange Parking and Airport Transportation

At least 24 hours before departure, figure out how you are getting to the airport and make your transportation arrangements or reserve your airport parking. If using a ride share service, you can schedule a pick up in advance to ensure a driver will be availability.

Pack!

Packing for a big trip requires some thought so don’t leave it until the last minute. Make sure you are aware of your airline’s luggage weight and size restrictions. Also remember a clear, quart-size bag for your carry on liquids. Don’t forget your important documents, Passports, tickets, medications, etc.

See my tips for packing for a long flight.

Check In and Download Boarding Passes

Check in to your flight, double check your seat assignments, and download your boarding passes. You want to make sure your passport information and Known Traveler Numbers are all saved in your airline profiles before you check in.

This brings you up to your departure day and that last race to get things done before you leave for the airport!

Set Your Out of Office Message

Enjoy your paid time off! Set your out of office message to let people know that you will be on vacation.

Change Your Voicemail Message

If you are going out of the country and won’t be able to get voice calls, let people know by changing your voicemail message. You can suggest they contact you on FaceTime to WhatsApp instead.

Reset Your Thermostat

Before you leave the house, reset your thermostat so that you aren’t paying to heat or cool your house more than you need to while you are gone.

Empty Perishables from Refrigerator

No need to come home to a stinky fridge! Empty your refrigerator of all perishables before you go away.

Take Out Garbage

Now that your fridge is empty, time to take out the garbage. If you don’t want to bring it all the way to the curb, ask your housesitter or neighbor to bring it out for you on garbage day.

Unplug Appliances

Make sure you unplug appliances such as hairdryers, curling or flattening irons, toasters, or other devices that could catch fire.

Put Lights on a Timer

You can easily turn your lights into smart devices and either set timers or use the app to turn the lights on and off at appropriate times so that your house doesn’t look deserted while you are away.

Secure Valuables

Thieves prey on houses when people are on vacation, that is why it is important to not post on social media until you get home and have the lights go on and off to make it look like you are home. Even still, secure your valuables such as jewelry and computers in a safe location, such as an in-home safe.

Add Last Minute Items to Suitcases

Don’t forget all those last minute items that need to go into your suitcase and carry-on bag…toiletries, brush, wallets, money, chargers, etc.

Double Check Tickets / Passports / IDs

Before you jump in the car, make sure you have your IDs, passports, and any tickets or documents that your trip requires.

Set Alarm

Set the house alarm (if you have one) and off you go…have fun!

Download the Trip Planning Checklist PDF

Find this useful? Share it!