Planning Your Next Vacation is Easy

Silhouette of a traveler standing in the ocean gazing out at the sunset

For months you’ve worked your butt off to earn it: your vacation. If you aren’t excited to tell the world what you’ve got planned, you need to keep reading. You didn’t take two weeks off for anything less than fantastic.

It’s possible for every vacation to be incredible and it’s easier than you think. While working a full-time job, my vacations have included visiting Morocco, scuba diving in the Galapagos, and touring Central America through Guatemala, Honduras and Belize. Keep reading to find out how I made the most of my two to three weeks off per year and how you can too.

3 Considerations:

Yes, there are only three things to think about when you’re squeezing the most fun out of your vacation time.

    1. Where you want to go
    2. How much time you have
    3. How much money you have to spend

We’ll use these considerations as steps, so you can plan your best vacation ever.

Before starting to plan, you’ve got some prep work. Grab your bucket list. What? You don’t have a bucket list? Now’s a good time to start. If you don’t know what a bucket list is, please get out from under your rock and pay attention: a bucket list is a list of things you want to do before you die. Or as I like to think of it, a list of things for achieving happiness. What have you dreamed about doing? Put it on your bucket list.

Here’s an example of a bucket list:

Bucket List Ex (pic)

Tip: You can use pen and paper for your bucket list and planning, but (NERD ALERT) I prefer Excel.

Stuck for inspiration? Check these out:

    • Pinterest
    • travel websites
    • recommendations from friends
    • guidebooks
    • magazines
    • movies
    • books

Tip: Get specific for your bucket list, choose a goal and start big, then get smaller rather than starting small and building up. Example: ‘go to Egypt’ can be narrowed down to ‘see the pyramids’.

Take a look at your bucket list. Does it look intimidating? Good, that’s the point. Accomplishing these things can take a lot of work, but you can do it. Let’s get started.

#1: Where do you want to go? (And what do you want to do when you get there?)

Now that you’ve got a bucket list, take a good hard look at it. Choose what you want to tackle on your next vacation, and see if you can cross two things off at once (ex. learn to play guitar + visiting Mexico). Choosing from your list takes time, but once you make a choice things get easier.

You’ve decided where you want to go, now figure out what you want to do when you get there. Be specific, and be honest. What do you like to do at home? You won’t change into a different person as soon as you leave your house.

Some ideas to get you going:

  • Food
  • Theatre
  • Museums
  • Adventure
  • Shopping
  • Beach
  • Meet people
  • Music
  • Walking
  • Driving
  • Meeting up with friends
  • Learning a language

#2: How much time do you have?

From a four-day weekend to a three-week trip, every vacation can benefit from planning. In this step you need to do some research and make an itinerary. It can be extremely detailed or not, it’s up to you. Some people – like my mother – prefer hour-by-hour schedules, others – like my brother in law – a rough outline. If you’re spontaneous write ‘TBD’ for each day, but remember there are a few things that could make or break your good time:

  • Travel time: Flying and driving are both great, but too much of either could cut a four-day vacation into two.
  • Opening hours: Events, museums, restaurants aren’t open every day. Don’t miss out because you didn’t check ahead.
  • Reservations: Do you need to rent a car for a day trips? Or take the train from one country to another? Do you need accommodation during high season? Figure out what to reserve in advance.

Once you’ve built a day-by-day schedule, build in some slack so you don’t get stuck if you miss a connection. Transit strikes, unexpected holidays, and crappy weather can all keep you in one place longer than you planned.

If you plan like me, by now you can’t fit everything into your vacation. What to cut and what to keep? Again, think about what you like to do at home. If you’re normally busy, planning seven days of ‘beach time’ won’t be enough.

Once you’ve got your plan filled with things you want to do, and it includes travel time and some slack, you’re ready to move on to the next step.

#3 Budget: What can you afford, what are you comfortable with, and what can you get for free?

This part has the most uncertainty. I’ve made a budget and then been totally wrong (both over-estimating and under-estimating). Depending on the research and reservations you do beforehand, your budget will be more or less accurate. This is where your money goes:

  • Accommodation
    • Are you a pampered prince / princess, or are you on the low-dough-show? Is a private bathroom important to you? Are pillow-mints necessary? Be honest with yourself, don’t plan for something you know you aren’t going to enjoy.
  • Food
    • Local food or expat restaurants? Can your stomach handle street food? Will you be heading to the nearest KFC? Do you enjoy sitting down to eat or are can you handle buying pizza out of a hole in the wall? (Literally. I actually did this in Cuba.)
  • Transportation
    • Public transit or private? In Las Vegas you can get a three-day pass for the Deuce bus, or you can take a taxi whenever you want for considerably more. The bus is a cheap option, but when it’s 40 degrees Celsius, a taxi might be worth it.
  • Fun
    • Tickets, tours, and tips. Private Scuba guide, or braving the cattle boat to save a few bucks? Private tour of the Vatican, or waiting in line at dawn to get close to St. Peter’s Basilica?
  • Souvenirs
    • You’ll want to remember your trip when you get home because it’s going to be freaking awesome, but where do you draw the line with souvenirs? Just buying for yourself, or do your five brothers and seven sisters all expect something? Be sure to put this into your budget (and leave enough room in your luggage).

Take a look back at the day-by-day itinerary you made. You’ve already got your days filled in with fun and relaxation, now it’s time to add your costs (you’re following my tips and using Excel right?). Once you’ve put in what you think you’ll be spending each day, add it all up. If you’ve got the money to spend, then book it. If not, decide what you can cut to meet your budget.

Tip: pad your budget so you don’t run out of money. You’ll want to try things on the spur of the moment, try restaurants you didn’t plan on, and spot souvenirs you didn’t count on. I usually add 10% to my final number.

Helpful hints

  • Most basic planning info can be found in the first section of a guidebook or in the intro. The ‘basics’ chapter in a guidebook can answer high-level questions before you start to plan (average costs, transportation, vaccinations, etc).
  • You’re probably a member of several points rewards programs (Aeroplan, Airmiles, Hilton Honors, etc.). If not, what are you waiting for? This shit pays off! Anyways, check your points and see if you can get a free flight or a free hotel. There may be travel promotions or discounts for members (just be wary of ‘deals’ that seduce you into spending too much).

You should now be looking at a plan for the best vacation of your life. But wait, there’s one more thing to remember: don’t fall into the over-planning trap. After every step, think about the time you’ve put in and ask yourself if it’s worth it. It shouldn’t take three months to plan a three-day weekend. You’ll get better at this, I promise.

Congratulations, you’ve learned the three steps for planning your best vacation ever! You decided where you wanted to go, what you wanted to do with your time, and how much it’s going to cost. These steps can work with any length of vacation, for any destination in the world.

Goodbye mediocre long weekend, hello accomplishing your dreams.


Considerations to make your trip more awesome:

  • Time of year (summer or winter)
    • China in the winter is fantastic, hardly any crowds and small tour groups. Disney World in the summer is stupidly crowded.
  • Festivals or events you don’t (or do) want to miss
    • Antigua during Easter: prices are jacked up and it’s crazy packed with people for a huge celebration. Sound awesome? Reserve. Sound like a headache? Skip it.
  • Food for thought
    • Going to Korea and you don’t like Korean food? Seoul could be a mistake. Hate spicy food? Thailand might not be the place for you. Things will be a lot easier if you enjoy the local food.
  • Do you speak the language, or do you need to?
    • English is widely spoken on Earth, but French and Spanish can come in handy. Will you be comfortable trying to converse in Spanish/Italian/German/sign language/whatever?
  • Book ahead for events, tickets, transportation, etc.
    • You can’t buy tickets at the gates of Machu Picchu, you NEED to buy them in town in advance. Sucks to find out too late.
  • Take a day to recover at home before going back to work
    • Especially if you’re going to be jet lagged this is a VERY GOOD idea. Take a rest day if you can, you can catch up on sleep and run some errands. After all, you probably ate all the food in your house before you left so you’ll need groceries.
  • Vaccinations and medications
    • To Dukoral or not to Dukoral? Some swear by it, some don’t, but the good news is you have a choice. Medications that aren’t optional: Yellow fever is a big deal in a lot of countries, and you could be asked for your card at immigration. Without it you can be denied entry. Find out before you go.
  • Foreign VISAs (if necessary)
    • Plan ahead for a Chinese VISA; some countries only accept USD for their VISAs.
  • Currency: before or when you arrive?
    • Have USD no matter where you go, it’ the closest thing to a world currency, and can be changed just about anywhere in the world. You can get money at official currency exchange spots, or possibly on the black market. We’ve changed money at some shady spots, but we’ve never been gypped more than $20 CAD (I think).
  • Arriving at night? Make a reservation.
    • We’ve done both: we arrived late at night in Thailand and everywhere was full, but we reserved in advance (thankfully). We arrived in Morocco and asked the cab driver to find us a ‘cheap’ place, and we got it. Both strategies were successful, but estimate your stress tolerance for this type of situation.
  • Travel points programs
    • Can you get a free flight? Free hotel? This is why you’ve been saving your points after all.
  • Do you need to be connected?
    • When traveling solo you’ll want to check in with friends and family frequently.
    • Can you live without Facebook? Be honest.

What do you think?

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