How to Easily Plan Your Next Vacation

Planning a vacation can be daunting.  I remember planning my six month trip overseas and how overwhelmed I felt.  There is so much information on the internet and so many guide books, I just didn’t know where to start. Where do I go?  How do I get there? How much will it cost? During the past few years of traveling extensively, I’ve created a checklist that has made planning trips easier for myself.  In this post I will share a step-by-step process that will help you easily plan your next vacation.


Deciding where to visit, when to travel and how long to stay is the most important step when planning a vacation.

  • Where to go: When it comes to deciding where to go you should think about the experience you’d like to have. Think about the landmarks you would like to see, the foods you would like to eat and the activities you would like to experience. Are you looking for a long weekend on a sandy beach to recharge or a 10 day trip to explore ancient ruins?
  • When to go: Your next choice would be when to leave. Are you traveling during peak season or will you venture out during the shoulder season? This decision will impact your experience (more/less crowds, weather) and budget.
  • How long: How long will your vacation be? 4 days? 14 days? How many vacations days do you have? What’s your budget like? The answer to these questions will affect how long you’re away.

Plan & Research Budget

The next step in the planning process is coming up with a budget. Are you a luxury or budget traveler? Are you an adventurer, foodie or a sightseer? As much as I love to travel, I don’t want to go into debt because of it. Doing your research and coming up with a budget will ensure your trip will not break the bank.

  • Flights: There’s no magical day or formula when it comes to booking a cheap flight. Once you figure out your itinerary start looking for flights. Sign up for price alerts, play with the dates and times. If you’re hopping on a long-haul flight and want some more comfort, try using travel reward points to book your seat. For more information on how to book a cheap flight, read my blog post Simple Ways to Save Money on Travel.
  • Accommodations: Nowadays, there are many options when it comes to accommodations. Hotels, Airbnb, hostels, home stays, etc. all offer different experiences for any type of traveler. My favorite sites to research and book accommodations are, and Reserve your accommodations as soon as you have your dates set.
  • Food: Your food expense can really eat into your budget (no pun intended) and if you’re a foodie, like me, then that’s half the reason you travel!  If you really don’t care what you eat then a sandwich on-the-go will suit you.  Either way, you’ll want to research the cost of food.  If you venture to Southeast Asia, food is relatively cheap.  If you’re going to big cities in the United States or Europe, food can be pricey and you’ll want to budget for that.
  • Activities: Start looking into any activities you’d like to do as soon as you have your travel dates set. Tours tend to sell out especially during the weekends.

Start Saving

Now that you have your itinerary and budget set, it’s time to start saving for your vacation. So let’s say your trip is 6 months away and you have a budget of $3,000. Simple math says you need to save $500/month. During this saving period there are a couple of things I like to do:

  • Travel Reward Cards: This step is optional but it’s a great way to save money while traveling. Applying for travel reward credit cards can earn you free flights and hotel rooms which allow you to spend more on activities or a nice meal! You can apply for cards that have a large amount of partners like the Chase Sapphire Preferred or even a specific airline’s travel card. For more information on travel hacking you can visit my Weekend2Wander Pinterest board Top Travel Hacking Tips.
  • Loyalty Programs: If you already know who you will be flying with, why not sign up for their free loyalty program. That way, when you purchase your flights, you’ll earn rewards. If they have a shopping portal or dining program, you can earn rewards towards your flights as well.
  • Open up a Travel Account: This account will solely be for everything travel related; hotels, flights, activities, etc. I prefer Charles Schwab for their no-ATM fees, zero foreign transaction fees debit card. Put all of your extra money into this account and start to get inspired for your upcoming journey.

Start Booking

It’s time top start booking your vacation! Look for any last minute flight deals or hotel deals. Websites like Scott’s Cheap Flights will show you recent cheap flight deals in your region. My personal favorite tools for flights are Google Flights and Skyscanner. Usually between these two tools, you can find the cheapest flight available for your trip.

When it comes to accommodations I find and Trivago work pretty well for finding the cheapest hotel rooms available. If you’re traveling with a group and want to stay together in a more cozy setting, I love Airbnb. You can request to stay at a home that will fit your whole group and that everyone will be comfortable in. Or if you’re solo and on a budget, give Hostelworld a try.

Also at this time you’ll want to start planning and booking your activities as those can sell out pretty quickly, especially on weekends and holidays.

So you thought you were done.  And you might be but if you’re heading overseas (and even if you’re not) then you might want to keep reading…

Important things to do before your vacation:

1. Make a copy of your passport

2. Check the visa requirements of the country you are visiting

3. Set up an e-mail folder for all of your booking confirmations

4. Make a copy of your travel plans – Digital. Save to phone.

5. Alert your credit cards/banks of your travels


If you have to blow the dust off your passport, most likely it’s expired or close to it. Many countries won’t accept your passport if you’re entering their country with less than 6 months before your passport expires. This is easily fixed, especially if your planning for a trip well in advance. If there is no rush you’ll be able to mail in your passport with the correct forms, a passport picture and a check. You’ll usually receive your new passport within 6 weeks. You can find more information here (for U.S. citizens).


Depending on where you’d like to visit you might have to apply for a visa in advance. Visas are a country’s way of giving you permission to visit and documenting who is in the country. If you’re visiting Europe you won’t need to apply for a visa. U.S. citizens get a 90-day visa upon arrival for countries in the European Union, specifically the Schengen Region. If you’re visiting, let’s say, China you will need to apply for a visa in advance. Usually you will need to provide proof of arriving flight, departure flight and hotel stay. Some countries, like India, you can apply for your visa online days before your arrival. Every country has different rules on how far in advance you can apply, how long the visa is valid, etc. So once you choose your destination you’ll need to do some research. A good quick source for passport/visa info is Passport Index. This will let you know what countries you may need a visa for with your particular passport.


Once you’ve chosen a destination you’ll want to check if you’ll need any vaccination or immunization shots. Your general physician should be able to give you advice on which shots to receive. Another great resource is Passport Health. They specialize in travel medicines and immunizations.  The nurse provided a customized list of everything I needed based on the countries/regions I was visiting.


My advice to all travelers is do yourself a favor and learn some of the culture and language of the country you will be visiting before you get there.  Obviously, I wasn’t able to do that for all of the 26 countries I visited but I did for many of them.  I never came across a rude person and I like to think that’s because people could see I was making an honest effort to speak the language and learn the customs.  Learning simple phrases like “Hello”, “Good-bye”, “Please”, “Thank You”, “How Much”, “Beer”,  etc. goes a long way with locals.  Learn the phrase “Do you speak English” in the local language and you won’t get dirty looks.  I promise.  Download Google Translate to your phone and download the language you need so you’re able to use it offline.  You’ll be speaking like a local in no time.  Well kind of.

So that’s it! You should feel confident that everything you need to be done is done. Now all you have to do is wait and enjoy your trip! If you enjoyed this checklist please share it with your friends and family on social media!

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