How to make the most of your summer vacation
A simple but surprising technique that works every time

A simple but surprising technique that works every time
It’s almost time for summer vacation. For me, taking time off during the summer is a non-negotiable necessity, not a luxury. Holidays are crucial to my mental health and my relationships. This precious time is not something I am willing to waste due to a lack of planning.
A few years ago, I learned a surprising but straightforward technique that transformed how I design my vacations. Whether you’ve planned your vacation or not, it’s not too late to use this technique.
It all boils down to one question. Are you ready? Here goes…
How do I want to feel this summer vacation?
Not what you expected, right? I’m guessing you might need more convincing.
After reading The Desire Map, I realized that I was planning my vacations the wrong way. First, I focused on when the vacation would happen. Scheduling my next break in advance gave me peace of mind. After thinking about budget, I then decided where I wanted to go. Then I dealt with all the nitty-gritty details like transportation and accommodations. Sometimes I also planned and book activities in advance.
Don’t get me wrong. Using this old method, I have had some enjoyable and memorable vacations. But I’ve also had other holidays where I didn’t feel the way I wanted to feel before, during, or after the trip. Or I couldn’t put my finger on it, but something about the vacation was off.
Flip the process: Start with feelings and then make summer vacation plans.
But now I understand why. I hoped a vacation would help me be happy, have fun, or relax. Hope without planning didn’t always work. But when I flipped the process, my holidays became much more satisfying.
A few summers ago, my husband, son, and I traveled to England. Here’s how I planned a trip that even writing about it still makes me feel wonderful. Reliving vacations can make us feel as good as the vacation itself.
First, I ask: How do I want to feel during my vacation? In the case of this trip, I wanted to feel connection, curious, and relaxed.
Now the fun part, fantasize about your summer vacation.
I imagine my vacation and try to make the images as specific as possible. Where am I? What am I doing? With whom? At this point, I allow myself to dream and enjoy fantasizing about it.
I wish I could…
It would be great if….
Ask more questions to make your summer vacation fantasy a reality.
Now, I begin to move from fantasy to reality by asking myself questions and doing research online.
What place or places will make me feel how I want to feel?
England (London for sights, Windsor and Litchfield to connect with family)
How long do I need to achieve that feeling? A weekend, a week, a month? Two weeks
What activities or choices will make me feel that way?
To feel connection: Visit my relatives in the cities where they live. Connect with England by having tea and scones, eating fish and chips in a pub, drinking Pimms, and visiting historic sites.
To feel curious: Explore locations I haven’t visited before, especially Wimbledon. Research the trip in advance to heighten my anticipation.
To feel relaxed: I will not book any red-eye flights or schedule super early departures. I will stay in locations for more than one night. I won’t jam in too many activities in one day or micromanage every detail. Instead, I want to linger and relish the present moment as much as possible.
Top priorities for your next summer vacation
Next, I figured out between one and three top priorities activities for every member of the trip. When you travel with others, you may need to compromise to make sure everyone’s needs get met.
Priorities for my family trip to England:
- I wanted to connect with my aunt and cousins, enjoy a cream tea, and visit Wimbledon.
- My son wanted to go on a tour of the Harry Potter Warner Brother’s studio tour, see Platform 9 3/4, and visit a castle. The timing of the trip coincided with his obsession with Harry Potter phase.
- My husband’s top priorities were seeing a friend from college, drinking at a pub, and seeing a show.
As these activities formed the anchors for the trip, I scheduled as many of these in advance as possible. I made arrangements in advance with the people I wanted to see. Plus, I booked the Harry Potter tour and purchased tickets to a West End show. Also, we decided to stay in a hotel close to Platform 9 3/4 on our first night in England.
My family and I enjoyed anticipating these activities almost as much as doing them.
Ditch the idea of a perfect summer vacation
Figure out how you want to feel on vacation, but please don’t try to have a perfect one. Planning and having a perfect vacation is too much pressure and stress.
Plus, things will inevitably go wrong. In the case of my trip to England, I miscalculated the number of nights we needed to stay at a hotel. My husband saved the day by finding a new hotel for us to stay in for one night. That lousy hotel became a family joke that we can now laugh about in retrospect.
Now, time to plan my next vacation. Where will you go?
Kelsey Cleveland helps smart women in transition design their lives and set goals based on how they want to feel using the Desire Map method. She is also a freelance writer who writes articles, essays and blog posts and is working on a book-length memoir.
Originally published at Kelsey Cleveland LLC.