By Christine Song

How to Plan Vacations and Trips All Year Long with Ease

Smart planning strategies from an experienced traveler.

I don’t know about you, but I love planning a vacation. A trip somewhere, anywhere. A short trip or a long one, to a new destination or one frequently visited.

I have planned trips that ultimately didn’t happen, but I still enjoyed the process and mental respite it provided to just imagine getting away. Of course, going on the trip and having those experiences is awesome, but figuring out all the cool places you’ll visit, where you’ll stay, and the amazing food nearby can be just as exciting.

This makes sense when you think about it, and studies actually show that the key ingredient in this scenario is the anticipation and excitement of this positive thing you’re looking forward to doing.

Anticipating a positive event like a vacation (or in this 2015 study, a funny cartoon) causes positive emotions which improve stress coping and well being. And a 2010 study specific to holiday vacationers found that those going on vacation reported higher degrees of happiness compared to those who were not before the planned trip, suggesting vacationers positively anticipated the time off.

What’s even more evident from the research though is that people derive more happiness from anticipating experiential events versus a consumable, material product. So putting your money towards a trip that you can anticipate going on will be more rewarding and bring you more happiness than going on a shopping spree for example.

So today’s post provides inspiration to help you plan a future trip using your planner, building up the anticipation and excitement of a getaway, plus shortcuts for planning amazing trips at the last minute.

Organize your imagination

Imagine your next vacation…where do you want to go and what do you want to do with your precious time off?

Brainstorm and let your imagination run a little wild, and then start to write down your thoughts in your planner or travel specific spreadsheet. This is a great activity to do at the beginning of the year or in between trips to plan for your future time off, including last minute getaways!

There is no need to start getting practical yet. Right now, imagine you have unlimited funds and unlimited time. What would you do if there were no restrictions? What matters most to you in a trip?

Knowing your dream trip can help you stay on track with things you’ll still love to do, even as you get reigned in by money and time restrictions during your actual planning process.

Now start sorting and organizing your thoughts using these suggested parameters:

Sort destinations and activities by how long you need or want to spend in a place

Where would you go if you only had 3 days or a week to explore? Or if hiking part of the Appalachian trail is something you’ve always wanted to do, how much time do you need for a trip that big?

Next, break out headers like the examples below and add the destinations that you want to go to that fit under each category. Include activities that are associated with that destination and/or time period:

  • Weekend = 1-2 days/overnight. Add to this list places that are local or within a few hours drive. Places you would want to do a staycation in. For example, in my list I include activities like local hikes, adventures, restaurants or stores, and specific cities that are at most a few hours away from me.
  • Long weekend = 2-3 days. These destinations could be local like above or a short flight away. Depending on your travel preferences, the destination shouldn’t be more than a 4-5 hour drive away. For me, these are places that also include cities that are a 1-2.5 hour flight away to take into account time spent at the airport.
  • Week = 5-7 days. Add destinations that are out of state or a short plane trip away that you want more time to experience. International travel to another continent could be hard, but possible depending on which one you choose.
  • Weeks = 8+ days. For me, this list includes international destinations, but out of state cities or regions in the United States are fair game too.
  • Month(s) = month(s)! If you have the opportunity to take a sabbatical or many weeks off at a time, you’re set to explore a region, multiple countries or travel across the country (road trip anyone?!). Add destinations or types of trips like a road trip or backpacking trip that you would want and need to spend this much time exploring.
Create a list of accommodations by type

As you flip through travel magazines or follow someone’s travel blog, you might find that you keep noticing or liking certain types of accommodations. To make sure you make good choices about where to stay (since it can be easy to get swayed by a good deal or a hip recommendation, even if it’s for a place you wouldn’t really actually enjoy staying), keep a list of those favorite places, sorted by type.

For me, I’ve got a list of cabins sorted by region, so that if I ever have a last minute reason to get away, I have a list of go-to spots at the ready, depending on how far and long we go for.

Here are some ideas for different types of places to stay; depending on what you like, make a list of your top favorites places based on what you find.

  • Campsites with or without amenities
  • Glamping spots you want to try, like Airstream sites, treehouses…
  • Unique/one-of-a-kind cabins with or without amenities
  • Luxurious, top-of-the-line hotels for splurge-worthy or special occasion destinations
  • Bed and breakfasts
  • Timeshares
  • Resorts or other all inclusive accommodations
  • Cruises

This is not necessarily a checklist or bucket list of places to stay at, but rather an assortment or menu of options to pick from based on likes, preferences, etc.

Next, read through reviews and accommodation websites to collect more information. Make a note of:

  • What amenities do you like at each place, and what is/is not included. This will help you tease out the places you don’t like at all, in addition to the ones you’ll love.
  • Is it good for a group, a trip with family or close friends, or better for just one or two? Make sure to note this on your spreadsheet or planner.
  • Add which room/suite/cabin you like the most so that when you have specific dates, you’ll quickly be able to tell if that Meadow Cottage is available or search for dates it is available and plan your trip around that.
  • Specials or promotions, and seasonal amenities.
  • Times of the year it’s best to stay to take advantage of a pool, snow, or fire pit, etc.
Start creating a master list of where to travel, when, and where to stay

This is perfect for last minute travel, as well as long term planning. When you already have options researched and organized, all you have to do is open your spreadsheet or planner when you have time for a spontaneous trip!

You can keep these two lists (spontaneous options vs. bigger planned trips) separate or combine them, the one based on trip length with destinations and activities, with the accommodation type, into one for example:

  • Weekend Trips
    • City/Activity
      • Accommodations
      • Activities
  • Weeklong Trips:
    • City/State 1
      • Accommodations in City/State 1
      • Accommodations in City/State 1
      • Activities
    • City/State 2
      • Accommodations in City/State 2
      • Accommodations in City/State 2

Another idea to keep track of cool stories or ideas about the destinations and activities you find, is to keep a list of travel sites and resources. Come across an  interesting blog focused on travel on the east coast? Add if to your list of resources for future reference. This will streamline your travel planning when your trip is actually a go.

Enjoy anticipating your next trip

If you’ve got dates for your next trip on the horizon, time scheduled off from work, and feelings of anticipation building and building, you’re ready to fill in the blanks.

You may have collected notes through the above process, but now’s the time to drill down into more details based on what you feel like doing, the season, who you’re traveling with, and what’s available.

Use your planner or a spreadsheet format like the example below to organize specific information about your next trip.

How to Plan Vacations and Trips All Year Long with Ease

The goal is to fill in the blanks in the categories for accommodations, eats, adventures, and any others you’d like to add with ideas and options. You can then block out time on a specific day to do an activity or try a restaurant; how much you fill out depends on you and your trip. An entire block of time from noon to 5 PM could just be the name of the city or you can fill in smaller chunks of time with specific activities, destinations, or foods.  Just avoid overscheduling if you can. It’s better to assume you’ll need more time; if you ultimately have extra time, that’s when you can refer back to your list of ideas on the right.

Give these ideas a try to plan a fun and memorable vacation that won’t feel stressful. You can still be spontaneous and flexible, even while having a great plan in place!

Planning can be the beginning of the fun of travel, even while you’re still sitting at your desk at home. We hope these tips will help you enjoy the process of researching, planning, and anticipating your next trip — before you have the time of your life while away!