Simple Vacations: 7 Steps to Your Dream Holiday (Even When You Don’t Think You Can Make It Happen)

Depending on your personality, planning a vacation can be stressful or it can be fun. You dreamers out there love browsing through all the possibilities. The planners love the details: where you’ll stay, what you’ll do, how you’ll get around… right down to the train schedule. But regardless of your approach, it’s easy to get overwhelmed and believe that a vacation is beyond your reach. My advice?

Break it down into smaller steps.

I’ve found that it helps to choose a focus. Your focus can be a theme or a hobby or specific feature. Love baseball? You might plan your vacations around visits to ball parks. Like playing golf? You can plan your vacations near all the best golf courses. Enjoy hiking? There are a gazillion peaks all around the world. Or maybe your focus are the locations themselves; maybe you want to see all 50 US States.

I’m a bit of a dreamer. I want to travel to every corner of the world and I want to see and do just about everything. This can make it difficult to choose a vacation. Even if I can narrow it down to a place, there never seems to be enough time or money to do what I want to do. So, I choose a focus.

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British Summertime Festival – Hyde Park, London (2014)

My significant other and I have had success planning vacations around one of our favorite activities, attending concerts. We have a shared love for live music. Here’s the process we use to plan our vacations. Perhaps you’ll find it useful.


STEP 1: Consider what you enjoy the most. Hobbies, activities, people, places… When you can spend your time anyway you like, how do you like to spend it? If you expect to have a travel companion, talk to them about these things as well. You’ll likely find some common themes.

STEP 2: Choose the focus. Once you have an idea about your interests and priorities, choose one focus. Ours is live music.

STEP 3: Prioritize the locations. Though we want to travel just about everywhere, each year we narrow the list to a few locations that we’d most like to visit. This list is very fluid and tends to change year to year. Right now, France, Italy, and the California coastline are high on our list.

STEP 4: Do some research. Look for opportunities to do your focus thing in the locations you prioritized. In our case, we might look for concerts and music festivals in France, Italy, and California next year.

STEP 5: Find your target. After doing some research, you’ll probably have a few options. Choose one. We settled on the Hellfest music festival in France.

STEP 6: Build your vacation in the chosen location around your focus. Say we choose Hellfest in France. We know we’ll need to be in Clisson June 16-18 for the festival. Then we look at our options. What other things are nearby that we’d like to see or do? Maybe we fly into Paris a few days before the festival and see the Louvre, the Eiffel Tower, and the Palace at Versailles. Maybe after the festival we travel to the French Riviera to enjoy some time in the cafes, stroll through Nice’s Vieille Ville, or relax on the beaches. After you decide on the big picture, dig into the details. What’s off the beaten path in the areas that you’re visiting? Then you can decide on the details.

STEP 7: Determine what you need to do to make it happen. Will you need to request time off from work? Will you need someone to care for your pet while you’re away? What resources do you have? Do you have a friend or family member in the location that you’re visiting who would let you sleep on their couch? Do you have any credit card rewards or gift cards that you could use to cover some of your costs? Can you split costs with friends? The cost of hotel rooms and cabs can be split between four or more people. The more friends you have, the less you’ll end up paying. And how much money do you actually need? I’m often surprised to find that it was less than I expected. Search the internet to learn how others have done it.

STEP 8: Set the date and buy the tickets. Yes, I know this feels risky if you don’t already have all the money you need or you don’t have all the details worked out. But I must tell you, that in all the times I’ve done this, I’ve never failed to come up with the money or work out the details by the time the departure date arrived. There’s something about committing to the trip that makes it a priority, and helps everything else fall into place.

STEP 9: Allocate your resources to what’s most important. We carefully consider the value of each option. We fly coach and use public transportation whenever it’s available, and we usually choose the cheapest, most basic accommodation. We know that we aren’t going where we’re going for the transportation or the accommodation so we don’t spend extra money on those things. Besides, public transportation is a great way to get to know a city.

 STEP 10: Prioritize! I’m not independently wealthy and I don’t have an inheritance. I save away small amounts of money whenever I can, but every vacation I take still requires an evaluation of my resources and subsequent sacrifices to come up with the money. I’ve been known to cut restaurants and movies, internet and streaming services at home, and I’ve pretty much survived on eggs and rice in the months leading up to a big trip. If you find that after evaluating your resources and cutting costs you’re still coming up short, you might be able to make extra cash by working overtime, taking side jobs, or selling the stuff you have lying around.


Choose where you want to go and what you want to do and then make it happen! Weeks and months and years will pass, whether or not you’re working toward your dream vacation. In a year, you could still be dreaming about the trip, trudging through your days, or you can be living your dream. And even if you don’t make it there in a year, if you start now, in a year you’ll be that much closer to getting there.

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Coonoor, Tamil Nadu, India

 

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