Trip Planning 101: How to Build Your Itinerary

So one day in the near(?) future, travel will once again be safe and you’ll have broken free from your pod. You’ll decided to take a trip. Maybe it’s across town or across the country or across the ocean. There’s so much to see and do in preparation that it can start to feel a bit overwhelming, especially if you’re travelling somewhere you’ve never been before. Where to start planning?

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1. Determine your budget

This is not the fun part of trip planning, but it is the most essential. Your budget- how much you have saved for the trip, how much you plan to spend on it- determines virtually everything else on this list, like the flights you take and the things you plan to do. Sit down and be honest with yourself; determine your budget and stick with it no matter what.

2. Pick your dates

Once you have your budget, think about when you want to travel. A couple different things may go into this decision: is there a particular event or season you want to be at your destination for? Are you hoping to go during the off-season to avoid crowds or score cheaper flights? Do you have to work around something going on at your job? Get your pen and calendar out, and put in your vacation request as soon as you know when you want to go.

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3. Select your destination

The beginning of the fun! You’ll have to factor in your budget, of course, but then it’s time to get dreaming. Start doing some research on your options- what appeals to you about each place? Do you want to do a city trip or a countryside getaway? Are you okay with using one place as a home base the whole time you’re there, or are you looking to travel from place to place? Will you rent a car? Consider all the logistics when looking at potential vacation destinations, then hone in on the one that’s right for you. Of course, in this day and age, you may also have to consider a locale’s coronavirus transmission rates, entry requirements, or quarantine rules.

4. Find your flights

There’s plenty of advice out there (see here and here, for starters) about the best way to buy flights. Browse flights in an incognito-mode browser. Book on Tuesdays. Try to fly in and out on a weekday. Stick with one airline as much as you can when you travel to amass points and miles you can put towards upgrades and other flights. Not all of these tips and tricks will work for everyone, but you may find one or two you can put to use. I personally like to watch flights on Hopper or Skyscanner, although I like to book through the airline itself. (This makes it easier if you want to change seats, purchase additional checked luggage, etc.)

5. Make a master list of everything you want to see and do

This is your “blue sky” list: if you had unlimited time and money, zero security concerns, and an infinite amount of energy, what would you do? Do not limit yourself with this list. Do a deep dive into everything you might be interested in- places you’d see, activities you’d do, experiences you’d engage in. Put it all on paper so you can see what you’re working with.

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7. Research lodging options

Everyone prioritizes different characteristics in their lodging. Decide what’s important to you: do you plan to spend a lot of time in your room? Do you prefer a luxury boutique hotel, a no-frills hostel, a homestay with a local? If your lodging situation ranks high on your list of priorities, take the time to read amateur reviews, articles on the property in travel magazines and blogs, so you really get a sense of the place. Even if you’re not really fussed about where you stay, it’s still a good idea to do some research before putting down your credit card. The last thing you want is to be scammed or end up at hotel for spring breakers when all you wanted was a romantic getaway with your spouse.

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8. Cull your dream list

The next thing is to trim that list from step #6. Unlike your master list, your new one has to be based in realism. Consider your finite resources, namely time, money, and possibly logistics, and narrow it down from there. The sad truth is you can’t do it all, and you’ll have to be judicious about what you want to eliminate from your itinerary. Identify your “must-sees” or “must-dos” first, and build your other plans around there. Check out local transit options if you’re not renting a car- how will you get to these places? Pull out Google Maps or a good old-fashioned atlas and look to see if there is a way you can group activities into days based on their proximity to one another. You’ll probably see pretty quickly that you have some outliers- stops that you can’t group with any others or that are tricky to get to. Weigh how badly you want to see or do these things, then methodically go down your list and cross off the ones you’ll regrettably have to miss.

9. Decide what to pack

Now that you know where you’re going, for how long you’ll be travelling, what you’ll be doing, and where you’ll be staying, it’s time to think about what you’ll be bringing. Again, packing for a holiday boils down to personal preference. You may love to pack light and plan to get by with the bare minimum. You may be a chronic overpacker who brings three outfits per day. Once you have a complete itinerary in front of you, it’s much easier to narrow in on what you want to bring for the trip. It can help to write out a packing list and even plan out your outfits for each day, to avoid bringing more than you need. Be sure to check with your airline about restricted or prohibited items- and it may even be a good idea to check with the country to which you’re travelling. (Some prescription medications, for example, may be legal in your home country but not in others, and you certainly don’t want to get in trouble there.)

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May we all be elbow-deep in trip planning one day soon! Bon voyage!

How do you approach planning for a holiday? I’d love to hear your tips and hacks in a comment  below!