20 Ways to Plan the Sh*t Out of Your Next Big Trip

As I’ve been working on my blog these past few months, my wanderlust has been reaching some pretty monumental highs, and I’m so excited to finally have a trip in the books! I’ll be heading to Montréal next month with my sister Sarah for a little pre-wedding getaway. (Her wedding, not mine!)

Friends have asked me in the past how I plan my trips, and I figured that as I go about my usual routine prepping for Montreal, it would be a good time to share my go-to tactics. I’m no expert, but as a lover of lists and organizing, I do take great joy in trip planning. At this point, it’s become a pretty cherished activity for me!

Here are 20 ways to plan the sh*t out of your next big trip.

1. So… where to?!

A good place to start is to decide where you’re going! This is easier said than done as there are so many factors to consider, from how much time you have to what your budget is and more.

Luckily, the possibilities are pretty much endless, whether you feel like staying close to home or venturing further out. To get your daydream wheels moving, here’s a round-up of inexpensive destinations recently shared by Refinery 29.

After considering a few different destinations for this trip, from Asheville (hiking) to Mexico (sunning) to New York City (a shared favorite), we landed on Montréal for a few different reasons. In addition to my casual obsession with poutine, we also knew we wanted a drivable destination. Not to mention, this self-described Francophile has never been to Montréal before! I’ve always wanted to visit but just haven’t made it happen, so thank you to my sister for indulging my travel wish list for her bachelorette celebrations! (She’s the best.)

2. Decide when you’re going.

This part is often dictated by factors that may not be within your control, but it never hurts to do a little research into the best time of year to visit your potential destination. Booking tickets for Thailand during monsoon season (v. wet) or the Australian Outback during the dead of summer (v. hot) doesn’t mean you won’t have a great trip, but it might make a lot of things more challenging and get in the way of your main activities.

And don’t forget – seasons reverse when you change hemispheres, so the dead of Australian summer is actually the middle of our New York winter: December, January and February.

That said, there are certainly upsides to traveling outside of peak times. You’ll have far fewer crowds to battle with for those perfect photo vantage points, and accommodation/activity prices are generally cheaper.

3. Determine your trip’s length.

Are you sneaking away for a long weekend? A month? A year?! (Lucky you.) Pinning down the time frame will help you to know how much money you should be setting aside and will allow you to start getting other logistics in place.

As a side note, some of my trip planning steps can automatically be cut out for shorter trips and are more applicable for long-term travel… but it never hurts to have your bases covered, so read on!

4. Book your transportation.

If you’re heading somewhere that involves a flight, I highly recommend using Hopper. Hopper is an app that allows you to search for flights through a straight-forward, user-friendly interface. After putting in your departure and arrival airports, the app generates a 12-month calendar populated with green, orange and red icons to highlight good buys (green), average deals (orange) and higher than usual prices (red). Ever searched for flights before and felt like you’re not sure how much you should be paying or what would be considered a good deal? Well, Hopper does all that work for you! You can also choose to save and watch trips, receiving notifications when prices change and even suggestions for nearby airports if there are better deals to be had.

If I don’t have a specific destination in mind, I also like using Kayak Explore, which will display a variety of good deals across the globe all at once. All you have to do is enter your home airport and when you’re thinking of getting away and they’ll populate a world map with all of the best deals they can currently find.

In the past, I’ve also had a lot of luck with Skyscanner.

5. Find a bed.

These days, Airbnb is my go-to for lodging on the road. I love catching a glimpse of how a local lives, and the personal touches that come along with it are pretty great, too. Whether it’s a handwritten list of brunch recommendations or an assortment of baked goods on the kitchen counter in the morning with a thoughtful note, there’s often a little extra something that takes your stay to the next level.

I’ve stayed in many a hostel, and they can be fun as well. (I guess it’s exciting to reach that ninja-like level of being able to maneuver in the dark as your temporary roommates are snoozing around you on a series of fourteen rickety bunk beds!) Don’t be fooled by the preconception that hostels are automatically the cheapest way to go, though. In expensive cities, you’ll find yourself paying a pretty hefty sum for a bed in a room with a dozen other people. I’ve often found that a private room or even entire apartment through Airbnb can end up being a much better deal, especially if you’re splitting costs with at least one other person.

Interested in trying out Airbnb for the first time? Book through my link and we’ll both save a little on our next trip!

As a third option, I’ve had great experiences with Couchsurfing. No money changes hands with couch surfing, so it’s pretty great budget-wise. But if all you’re looking to do is save money, I wouldn’t recommend it. While that’s obviously a perk, the best upsides are the opportunity to get a local’s perspective and to form meaningful connections with new people you wouldn’t otherwise meet. From making crêpes with a family in Toulouse to barbecuing with Australians in Istanbul to partying with German girls studying in Vienna, each experience I’ve had with it has been entirely unique and memorable.

If you’re thinking of couch surfing but are feeling nervous about it, try it out when you’re traveling with a friend or two and stick to verified members who already have plenty of positive reviews.

6. Stay healthy. 

Needles are no fun, but make sure you’re up-to-date on routine vaccinations as well as any vaccinations recommended for your destination. On the CDC’s website, you can do a search by destination that will list what shots you need (if any) and will outline other advice on staying healthy while you’re on the road.

Some vaccinations may not be available at your primary doctor’s office. In the past I’ve used Passport Health, a travel immunization clinic, to get more rare immunizations and prescriptions for anti-malaria meds.

You’ll also want to make sure you’ve stocked up on any of your day-to-day prescriptions as well (for example, in the past I’ve had to stock up on several months of birth control to avoid running out while I’m abroad). This can be tricky and will vary in process depending on your insurance company, so if this is something you need to address, definitely tackle it sooner rather than later.

7. Stay legal.

Will you need a passport and/or visa where you’re going? If you need to apply for a passport for the first time or renew one that’s about to expire, click here. Most countries require that your passport be valid for three to six months past the date that you’re entering their borders, so if your trip is taking place shortly before your expiration date, renew it beforehand to be on the safe side.

To check whether or not you’ll need a tourist visa along with your passport, enter your destination here at the U.S. Department of State’s website (which also links through to the CDC for vaccination information).

8. Stay safe.

Click here to see if there are any travel alerts or warnings for your potential destination.

And while navigating any type of insurance can be daunting, consider travel insurance in the event that anything unexpected arises, either pre-trip or while you’re away. World Nomads is a great place to start.

9. Save your pennies.

While I’ve never been the best at creating detailed budgets, I try to determine a ballpark figure for what I’ll need (depending largely on where I’m going and for how long) and then I’ll work my way back to see how much I need to save per week to get me to that figure before my trip.

When I went to Australia on a one-year Work and Holiday Visa, it was recommended that I save $5,000 AUD before going. I started setting aside $100 from my weekly paycheck to work toward this goal, and kept going even after I had achieved it. (It helped that I was planning for Australia pretty far in advance.) Once I got there, I was so grateful that I had taken saving seriously, because Australia is expensive and I needed every penny!

Making small changes in your daily routine in the weeks or months leading up to a trip will be hugely helpful once you’re on the road. Whenever I’m actively saving for a trip, I cut down wherever I can, knowing that I’ll appreciate that extra cash while I’m gone. For me, my go-to cost-cutting areas are clothes shopping, eating meals out, and buying expensive coffees (that can cost up to $6 each – aah!).

10. Stock your wallet with the right tools.

Before Australia, I prioritized finding a credit card that doesn’t charge foreign transaction fees. I mainly use Bank of America, so the card I chose was the Bank of America Travel Rewards card. This card has no annual fee and offers 20,000 bonus points if you spend $1,000 within the first three months you have it. There are plenty of other options too if you’d like to find something that better suits your needs: here are two helpful round-ups, one by WalletHub and one by NerdWallet.

If your card does charge foreign transaction fees, 3% of each purchase you make will be added to your credit card bill. While small individually, these add up quickly. Might as well avoid fees wherever possible, right?

Finding the right credit card for travel offers more perks than just waived foreign transaction fees, including cash back, sign-on bonuses and free checked bags. Here’s a helpful article about cards that offer trip cancellation insurance.

The other big thing to consider on the road: ATM fees. I cringe thinking back on all of the money I’ve wasted on ATM fees in the past, which can add up to about $10 per transaction depending on the banks involved. Terrible! Recently, finally, I signed up for a Charles Schwab checking account to use for travel purposes only. They reimburse you for all ATM fees worldwide. That’s the dream, people.

A side note on foreign ATMs: You’ll often be asked when you’re withdrawing money if you’d like to withdraw it in the local currency or have it converted to your home currency and then withdraw it. Always choose to withdraw in local currency and you’ll get a better exchange rate.

Speaking of exchange rates, I use the XE Currency app to keep track of how the USD is measuring up to other currencies. This can have a big effect on how much you’ll be spending on your trip, and it’s good to be prepared either way. (For example, saving $5,000 AUD for Australia meant saving roughly $3,500 USD. Those two figures are pretty different!) This app is especially helpful on a multi-country, multi-currency trip when it can become challenging to keep all of the currencies and rates straight.

My last note on money: remember to let your bank(s) know that you’re traveling, even if it’s a short trip. The last thing you want is to have your account frozen because of suspicious activity.

11. Learn a little.

It’s a good idea to brush up on some background info for your destination, and there are plenty of ways to go about it.

Guidebooks are obviously a go-to in this arena, and I always get excited to pore over them as soon as I’ve booked a trip. While jam-packed with helpful info, they can be pricy, which is a downside when you’re trying to save up for a trip. They can also get pretty heavy, and they will weigh your bags down in a hurry if you’re planning on taking them with you.

As an alternative to buying them and taking up precious weight and space in your luggage, consider checking a few out of your local library. If you have an e-reader, you can also look for e-versions. Same amount of info, waaaay less weight! (As a side note, I only discovered a few months ago that you can check out books from your library onto your e-reader. Exciting, right?! That way, you can save space and money.)

I also find that a quick visit to your destination’s Wikitravel page can be pretty helpful. While a publicly curated site that may contain some outdated or incorrect information, I still find it useful for a basic overview. Montréal’s page outlines the city’s neighborhoods along with information on getting there, getting around, where to eat, what to see, where to sleep, nearby day trips to consider, advice on staying safe and more.

12. Plan the fun stuff.

So now that you’re basically an expert on your destination, it’s time to decide how you’ll be spending your time there! In addition to paging through your newly acquired library guidebooks for suggestions, taking advantage of the vast amount of information online can be helpful, too. For this trip, I Googled some basic topics like “must-see Montréal”, “must-do Montréal”, “top ten Montréal”, “48 hours in Montréal” and “best restaurants Montréal” (you get the idea…) just to give myself an idea of what there is to do (and, most importantly, eat!). I also looked at the website for Montréal’s tourism board.

Over the past couple of years, I’ve also started seeking out travel blog posts about where I’m heading. I find these first-person accounts both helpful and entertaining, not to mention being easier to navigate than some guidebook companies’ online sites. Often times you’ll find recommendations that are a little more unique than what you’ll see on sites like Wikitravel or Lonely Planet, and there are usually some helpful know-before-you-go tips as well.

If you find yourself needing some visual inspiration, head to Instagram. For this trip, I simply searched “Montréal” and the first suggested account that came up was the official tourism board for the city. Once I clicked “follow”, several more Montréal-related accounts came up for me to look through, and voilà! Daily inspiration and ideas are accessible during my already-habitual scrolls through Instagram.

I often find the lead-up to a trip to be almost as exciting as the trip itself, and there’s nothing more fun than scrolling through your feed on a dreary Tuesday and seeing pictures pop up from a place you’re about to visit. Insta pick-me-up!

13. Keep track of the deets.

I usually start a Word or Google doc where I can keep track of ideas and recommendations. I used to be terrible at this, always thinking, “I’ll come across that site again later” or, “I’ll just look up that address when I get there.” But in the end, it’s a big time saver to just keep track of these things as you find them.

Keeping various recommendations in one place with as many details as possible (days and hours of operation, addresses, best times to go, etc.) will save you time once you’re actually on your trip and want to have fun instead of using your precious time to pore over articles on your cell phone.

14. Stay realistic.

As you start to accumulate things you’d like to do, keep in mind that less is more. You won’t be able to fit 45 things into a three-day visit to a new city. Heck, I lived in Australia for an entire year and still left the country not having done everything I was hoping to. (That place is biiiig.) Pick the top things you want to do that are a priority above everything else, and consider the other things you manage to squeeze in a bonus.

Don’t forget, you have to factor in eating meals, getting from one place to the next, and the unexpected things that will inevitably slow you down throughout the day. (Coffee breaks, taking the scenic route through a park instead of sticking to the street, getting lost, getting lost again if your navigational skills are anything like mine, stopping to pet a cute puppy, getting lost while trying to steal said puppy, etc.)

Lastly, there’s nothing wrong with a little spontaneity when you’re in a new place! Filling every last second of your time with various planned activities will quickly take all the fun out of it, so try not to overschedule.

15. Listen to other people’s opinions, but ultimately decide for yourself.

I definitely suggest seeking out recommendations from friends and family, but you know your interests and your travel habits better than anyone else. However much I love sharing stories and giving people ideas (cue this blog!), I like to take people’s must-see declarations with a grain of salt – and I hope anyone reading my recommendations does the same!

Everybody is different, and even your best friend’s favorite activity in a new city might not be something you want to spend time or money on. Ultimately rely on yourself to come up with your “must-do” lists, and don’t let others make you feel like you’re not doing it right or are missing out by not seeing something they loved.

An example of this for me occurred during a visit to Florence, a city full of museums boasting some of the most famous art in the world. Leading up to my trip, most of the guides I read offered advice on how to pack as many museums as possible into my visit. And in the end, the number of museums I went to in Florence was… zero. I was there at Christmastime and the city was decorated so beautifully; wandering the streets, enjoying the architecture, stopping for coffee and gelato, stepping in and out of churches, and climbing everything I could for better views was my preferred way of seeing the city… not standing in line for hours to see the statue of David.

Not that I’d blame someone for wanting to see the statue – but that’s my whole point! There are a lot people who would claim I “missed out” by not seeing David, while in the end I felt like the activities I spent time on were perfect for me. Go with your gut – there’s not simply one “right” way to see a new place.

16. Give yourself a head start with directions.

Once we booked our accommodation for Montréal, I entered the address into Google Maps and started inputting the activities and restaurants I’ve found so far to see where they’re located in relation to our apartment. I highlighted anything close by (a 20-minute walk or less) in yellow. That way, once we arrive, I’ll have a quick reminder of the places that are easiest to get to.

I’ve always found this is especially important for breakfast spots. Is there anything worse than setting off for your first meal of the day in a new city and either getting lost or realizing you’ve chosen a place three subway changes away? I don’t know about you, but I don’t want to go through that while struggling with hanger and lack of caffeine!

17. Rain or shine…

Add your destination to the weather app on your phone so you can plan accordingly. As frustrating as it is to check in a few days before and see that the forecast isn’t great, it’s even more annoying to arrive without the proper gear.

18. Pack (while ideally keeping your sanity intact).

Packing is so challenging but, alas, a huge part of traveling. I had so much to say on this topic that I decided to write a separate post dedicated solely to packing tips: check it out here.

19. Know your arrival plan.

This is especially worthwhile when flying is involved. Navigating new airports can be tricky, and there’s nothing worse than arriving bleary-eyed and jetlagged after a long flight and feeling instantly unsure of what your next step is. While there’s liable to be some confusion either way, it never hurts to do some research beforehand and give yourself a better chance of a smooth exit.

If you’re staying at an Airbnb or are couch surfing, check in with your host for directions on the best way to reach their place, and take screen shots of their tips in case you can’t access the Internet upon arrival. If you’re staying at a hotel or hostel, either check their website for directions from the airport, send an email, or give their front desk a call.

Consider checking the airport’s website as well to familiarize yourself with your transportation options, which could range from a cab to a bus or train or combination thereof.

20. Take the good with the bad and have fun with it.

Honestly, I’m still working on this last one, but it’s an important one. No matter how much you’ve traveled or how much planning you’ve done, the unexpected will likely happen. You might not get to do everything you were hoping to. You might get ripped off. You might miss a tour meet-up time, lose something important, pick a restaurant that ends up being terrible despite great reviews, or experience any number of other potential bummers.

People have super high expectations when they’re traveling because they want to make the most of their time off and their hard-earned money. It’s totally understandable to be frustrated when something goes wrong, but don’t let it define your entire experience; and take it from me that it’s a waste of time beating yourself up about how you should have done things instead. At the end of the day, there’s often nothing you can do to avoid most travel mishaps. Regardless of preparations or precautions, things happen. Take some time to let yourself be disappointed and then try to move on.

After all, it’s not all perfectly-framed Instagram moments. Tough stuff happens, too – especially if you’re traveling for an extended period of time. (A few months into Australia, I, um, got hit by a car. It happened in the midst of dealing with several other challenges and feeling like my dream trip was just not coming to fruition. Read more here if you’re currently traveling long-term and are in need of a little pep talk.)

One of the most valuable lessons I’ve learned through travel – and am still learning – is the importance of facing new challenges with optimism and perspective; how to take the good with the bad and accept that it’s all part of the same amazing, frustrating, eye-opening, demanding, beautiful experience.

Do you have any trip planning rituals or feel like I missed something important here? Have you been to Montréal and have some helpful insight? Let me know in the Comments.

In the meantime, happy planning!

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