Planning a trip

by carrie mah

Planning a trip – how to get the most out of your vacation!

Gum Wall

Growing up, my mom either booked tours or my sister planned our vacation schedule. Last year when I went to Seattle, the only plan I had was attending Penny Arcade Expo and the Pike Place Market. I had a lot of fun exploring the city, but I felt like I could have gotten more out of it and saved a bit more if I planned better.

This year, Mike and I are celebrating his hard-earned Computer Science First Class Honors degree with a trip to Montreal! Technically, he wanted to go because of a computer security conference, but there’s also a Jazz festival and other awesome stuff to see + eat in the city.

 Booking Flights + Hotel

Travel Button

Probably one of the biggest headaches of planning a trip is finding the best deal for a flight and hotel.

Before booking, have an idea of what you want to do: do you want to stay at a hotel in one city, then go on day trips? Do you want to keep moving around and stay at different hotels? Do you want to depart from the city you arrived in, or leave from a different place? Having a clear idea of this will help you with booking things. It might be worth leaving from the city you didn’t arrive in, because ticket prices vary.

 When to Book

There are ton of articles on the web about optimal booking time, but I like to follow this rule of thumb for booking flights (2-5 months depending on your location). The sites I liked to go on is Google’s Matrix Airfare search, but Google also has its own Flight Search which may be of interest to you.

 How to Book

Also, browse for airfare tickets in Incognito mode where cookies aren’t tracked, since ticket prices raise the more times you check. Ticket prices also vary depending on where you’re located. Try changing your IP address or using a VPN to get around this.

 Where to Stay

With living arrangements, you can check out hotels, hostels, motels, or even couch surfing. If you’re planning to stay at the one place for a while, you can even check out house sitting. There’s tons of travel hacks to save money, and it’s worth spending that extra time searching for good deals.

 Planning Activities

Top 253 City SubReddits

Google is your friend! Reddit (or other forums) is also your friend; just go to the city’s subreddit, ask what’s worth checking out, and wait for all the replies to pour in! Getting personal first-hand responses gives you a more accurate idea of what the city is like, rather than relying on travel sites and reviewers.

Some people travel just for a festival or event; but if you’re the type who travels just to see the place, ask around to see if there are any neat events to check out. I find it makes your vacation a bit more exciting when all the locals are celebrating something!

 Day Trips


When traveling, you want to look for the best transportation methods. The most affordable option within a place is public transportation: train/tram/etc., bus, and so on.  Unless you want to walk to every place or rent a bicycle, I suggest looking into renting a pass (depending on how long you’re staying at the place and what places you have access to) or ensure that the hotel you’re staying at is in walking distance of all the cool things you want to check out.

You can take a taxi, but be wary of taxi scams. Sometimes it may be more convenient to hail a cab, but it’s worth checking out a city’s transportation system.

Also check if there are close cities or towns around the place you’re visiting. You can rent a car, take a train, a bus, a plane, or even a boat. I advise against taking a cab, since most drivers won’t go out of city limits and if they do, you’ll be looking at an expensive bill.



It’s important to pack all the medication you think you need: motion sickness, stomach aches, headaches, and so forth. Remember to bring all the bathroom essentials, some clothes plus a few extra (in case of weather change). Avoid bringing expensive items, especially in locations with high theft.

Lifehacker has clever packing tips. You can also roll your clothes to optimize luggage space, organize things into plastic bags, or read some more hacks.


Vacation Meme

I advise against following a schedule to the tee. Vacation is about relaxing, not stressing out about doing things! Sometimes life doesn’t go the way you plan, so you just have to go with the flow. Plan for some extra time before and after an activity in case transportation isn’t on time, or something unforeseen happens (like getting stranded). Sometimes you have to choose one activity over another, but in the end a vacation is about enjoying the culture and the people you’re spending your time with (family, friends, strangers, partner, yourself).


Carrie Mini Bio


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