How I Planned 12 Trips in 12 Months – and You Can Too!

For the last three years, I have had a schedule packed with travel doing 12 trips or more each calendar year! My 12 trips in 12 months campaign started in 2015, and I am proud to be doing it again in 2017. This adventure has been exciting, exhausting and rewarding all at once, and I have learned A LOT about what it takes to make travel a regular part of your routine.

I am a planner by nature but with some practical tips, anyone can turn their year into a year filled with short and long trips. Check out the variety of trips I’ve got coming up below!

  • January — Raleigh, NC for vacation with my husband
  • January — Kansas City, MO to visit a friend
  • February — Breckenridge, CO for a family ski weekend
  • February — Cuba for solo vacation
  • March — New Orleans, LA for work retreat
  • March — Naples, FL for couples trip
  • April — Naples, FL for Easter weekend
  • April — Milwaukee, WI for Women in Travel Summit
  • May — San Miguel de Allende, MX for a wedding
  • May — London, England to visit my sister
  • June — Detroit, MI for a wedding
  • July — Costa Rica for work trip
  • August — Alaska for a family vacation

Planning one trip in one year is hard enough, but consider planning 12 trips in 12 months. It’s a lot to keep organized and prepare for. I understand why it is a daunting & overwhelming task for some people. I might be a little crazy for doing this much travel, so it’s understandable if you want to set your goal of annual trips a little bit lower than 12 to start off with. I was chatting with a friend a few days ago and she had planned 7 trips in 2017. I was so proud of her! That’s a great goal!

Regardless of how many trips you  might want to accomplish in one year, below are practical tips and tutorials for what goes into planning 12 trips in 12 months.

Dream Big….

By nature, I am a dreamer, especially when it comes to travel. My destination bucket-list is ever growing, and looking at my calendar, I tend to get a little over ambitious. But hey, you can never attain something that you don’t dream of, so let your imagination run wild. Spend some time daydreaming about those trips you’ve always wanted to go on and see if you can make them a reality this year. Is Antarctica  your last continent? Have you always dreamed of seeing the Great Wall of China? Why not make it happen this year! A little bit of wanderlust inspiration goes a long way, especially as you watch frequent flier miles start to flow in. I find a great way to daydream about new destinations is by looking through my favorite travel bloggers on Instagram and see what inspires me!

… But Tailor Your Expectations

When I originally thought up this idea of 12 trips in 12 months in 2015, I honestly wasn’t sure I could actually follow through on it. I only had half of the trips already planned, so I was concerned about where the other destinations would be and how I would afford them. If I didn’t achieve a goal I had made so publicly, I was worried that I would look & feel like a failure. But I pushed forward on my goal continually adding new destinations to the list and sure enough, I managed to achieve my goal!

Having “learned” from my overambitious mistakes of 2015 & 2016, I vowed to myself that in 2017 I would not schedule back-to-back travel weekends because they get exhausting. I grew to miss my cats and my husband when I was gone for several weekends in a row. And yet again, I did it do myself again… in February this year, I was out of town every weekend. I have a tendency to prioritize travel and work above my own personal health, and that is something I continue to struggle with. It’s all a learning process, and I would encourage anyone thinking about making frequent travel a part of their routine to understand the realities of stretching yourself thin.

You may learn more about your own limits than you thought. For me, I noticed that my energy levels and mental health really took a hit and I was constantly distracted or creatively uninspired. I lost sight of a lot of the things that made me happy like blogging or exercising. While having lots of new adventures is really fun & exciting, giving yourself time for relaxing weekends at home or on a beach can be much needed restoration periods.

Take Time to Plan

It’s important for me to sit down and plan my travels at the beginning of the year. I like to look at all the elements — time off, budget, flight options, dates,etc — before I even put anything on my schedule. I usually spend a weekend early in the year to look at my calendar and think about where and what I want to accomplish. Below are my best planning tips for making the most of your year:

  • Block of Time for Mandatory Trips: I start by locking in the dates of any “must complete” trips, especially work-related trips. Those tend to be non-negotiable and you’ll need to make sure you’ve got the dates locked in before planning anything else. Those are dates that you need to work around, and should avoid any scheduling conflicts.
  • Utilize Holiday Weekends: I like to think about trips that can line up with holidays or pre-arranged time off so that I can conserve my precious vacation days. Holidays like Columbus Day, President’s Day and MLK Day are the perfect opportunities to take long weekends around your home country because they fall on Mondays. If you wait until last minute for holiday weekends, you typically won’t do anything because prices will be expensive. But if you plan for those to be travel weekends ahead of time, you can really optimize limited vacation time.
  • Coordinate with your calendar: Another very important tool for my planning process is a calendar. I like to have a physical calendar on hand because it helps me to visualize the months and lengths of stay a little bit better than doing it online. Once my travel details are finalized, I will transition the final plans into my Google calendar where I can input the exact dates and locations. What I love about Google Calendar is it syncs up with your email to add on any flights you reserve, hotels booked, etc. You’ve got all your logistics in one mobile cloud based location! Plus it is easily sharable with family & friends who might want to know what you’re up to.
  • Leave your schedule a little open to last-minute trips: You never know when an amazing flight detail might show up or a last-minute work trip will present itself. Having a few open weekends on your calendar over the course of the year allows you to be spontaneous when you want. That’s what happened for me with the Raleigh trip I took this year! Need help planning a last minute trip somewhere? Check out my tips! 

Plan Your Budget

A lot of people have this perception that traveling is incredibly expensive and is only an option for the wealthy. Let me tell you, I work for a non-profit with a small salary and I’m on track to take 13 trips this year, 3 of which are international. Obviously I understand that I am in a privileged position because my job allows me to travel professionally while also giving me generous time off to honor our staffs’ interests in travel.

Regardless of my personal situation, I can’t stress enough that it is absolutely possible to make travel part of your annual routine, even for people who have limited vacation time off. My husband Sam is one of those people — he has the standard 10 vacation days and 5 holidays — and yet we still make traveling a big part of our lives and marriage. That doesn’t come without sacrifices. You have to understand going into travel planning that being diligent about saving money and vacation days are important steps you’ll need to achieve this dream.

By listing out as many of your trips as you can ahead of time, you are able to anticipate certain expenses and create a budget for each. In order to make this work, you have to commit yourself to your travel plans and stick to your decision. 

By making a few minor adjustments to your routine (ex: making coffee at home instead of Starbucks, packing a lunch instead of going out, cut out cable and opt for only Netflix), you can save hundreds of dollars per month. I, for example, stopped buying newly produced clothing completely and only shop at thrift stores, especially ones where I can sell clothes for credit. I looked at my spending this year over last year, and I’ve already saved $1450 from my spending (yes, I know, I was buying too many clothes but that is a separate conversation). All of this has been reallocated to travel expenses, covering the cost of several of my trips.

Another step you can take to make travel more affordable is signing up for airline/hotel reward programs. Many companies offer credit cards with bonus miles or frequent user programs that give you cheap benefits and ways to take free trips. By taking advantage of these programs, you can make traveling a lot cheaper by strategically planning your spending based on the timing of your trips, sign ups and rewards programs. Read more about how you can optimize travel credit cards to get the most bang for your buck or take this example:

  • Last year Sam & I planned our honeymoon to Portugal and a few weeks before departing for our trip, we ordered a new Chase Sapphire card from our joint account (Sam already had this card and loved it). By getting this new line of credit ahead of our trip — a time when we knew we’d be spending a decent amount of money — we were able to book all our flights, hotels, etc on that card. This helped us automatically qualify for the new user bonus threshold of $2,000 spent in 3 months. We also signed up for the free frequent flier miles program on United Airlines which we flew to Portugal, so we could log points while we were on the trip. Then when we came back home, we were able to use the miles we had accrued from our honeymoon spending to book free 3 flights to different US destinations.

Research Logistics

Once you’ve dreamed up a few locations, organized your calendar and planned for the costs, it’s time to start thinking about the logistics of making your trip happen. You’ll need to research flight itineraries, accommodation options, restaurants, things to do, etc. Need help with food research? I’ve got you covered! 

There are certain times of the year that are “off-peak” or “shoulder” seasons for travel, which are perfect for keeping on a budget. Typically rates are discounted since demand is low, and you can score some good deals! Checking off-peak schedules is a perfect way to plan your long weekend trips, since they are usually at obscure times like February or October. Let the destination choose itself based on what is cheapest.

You’ll also discover that there are good days and routes to use your frequent flier miles on. Each airline is different so it will require a little bit of research. I personally think Southwest makes it super easy on their website, and would highly recommend them! I’ve learned to love scouring through airlines terms & conditions and searching on their reward programs to find the best deals for mile redemption. You’ll need a few hours to research all the different options, and Google Flight Matrix is a huge help.

Create an Excel Sheet & Custom Google Map

When you’ve got lots of trips going on, all of a sudden you’ll find that you have 15 tabs of internet searches open on your computer and it’s overwhelming. Sometimes you might lose track of a URL or accidentally close a browser window that was particularly useful.

To keep everything organized, I like to use Microsoft Excel. It’s a great and widely available tool for listing all the necessary information for trips in one convenient format. Plus with Google Drive, you can easily share your findings with other people. On my excel sheet, I like to put information such as:

  • Dates
  • Actual days (Monday, Tuesday, etc)
  • Location
  • What the purpose of travel is?
  • Who will be going on the trip?
  • How much time off (if any) is required
  • How you plan to pay for it?*
  • Estimated costs & types
  • Actual Costs & types (to be added afterwards)

Below, you can see an example of the excel sheet I used to plan my 2015 trips. This is a great way to get all the really important information in one place, and then you can add additional details as the trips firm up.

As many of my readers already know, I can’t sing the praises for Google Maps enough. It is one of my favorite travel planning resources because it is really simple. Before taking off for any trip, I make use of Google’s custom “My Map” feature by creating a customized map of the activities, restaurants and neighborhoods to explore.

Don’t know how to create a Custom Google Map yet? Follow my step by step directions here

Because researching tends to take a few hours and often utilizes multiple websites, I like to save all the information I discover on my Google map by pinning my favorite finds to my map. Once you pin something to your map, you can add personalized notes about it by clicking on the little pencil icon you see in the info box. This allows you to take notes on restaurants, for example, to remind you what the food is or what their best dish is.

Since Google Maps is already an app that I use regularly, having all my research saved in one convenient place makes simple to explore! As I mentioned above, I like to utilize multiple layers & icons on my map to indicate different activities. Check out an example of what I mean below:

Now I’m a little more neurotic about planning and it’s ok if you’re not as crazy as I am. By applying a few of these steps and principles I listed above, you can be more methodical and meaningful about your travel planning, which in the end, will help you travel more often and more comfortably.

Are you considering doing extensive travel this year? Share your itinerary ideas below!

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Author: Megan Arz

I am a travel and food obsessed Midwesterner living in Chicago and dreaming of the world. I work as a full-time program manager for Greenheart Travel, but I am also committed to integrating the travel lifestyle into my every day routines. I am passionate about ethical travel, meeting new people, creating unique memories and eating local cuisine!

4 thoughts

  1. 12 trips seems like a lofty goal, but it’s so much easier than people think! It definitely doesn’t mean 12 exotic overseas destinations. I love how you balance international trips and local adventures, business and pleasure.
    Oh – and of course you know that I love that DETROIT is on the list! 🙂

    1. Thanks Amanda! It definitely is a lofty goal, but more than achievable when you mix in adventures close to home and far away. People tend to be their own worst roadblock when it comes to travel by believing the myth that it isn’t achievable. It was so fun meeting you this weekend!!

  2. While you’re in Detroit, pop across the border to Windsor, Ontario Canada. It’s an easy trip across the Bridge or through the Tunnel (or one on the way in and a different one on the way out) and it’s got a great view of downtown Detroit from the river front. It’s a really easy way to add one more country to your list!

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