Step by Step: How I Plan My Trips

There are many steps to planning a new trip. From picking the location to figuring out what to do and where to stay, there is a lot of thought and execution to go into planning. I have always been an organized thinker, which is funny because that is pretty much the only way I am organized (you should see my room); this makes me good at planning trips even ones that are pretty complex (multi-country, multi-week trips). In this post, I will break down how I plan my trips to hopefully make it easier for people who are coming at this for the first time or don’t feel like they are doing it most efficiently.

How I Pick my Location

The location is always the first and most important part of planning a trip as a realtor would say location, location, location. If you don’t feel passionate about where and why you are going somewhere planning, the trip will feel like work. I feel excited throughout the planning process because I always pick places that have been on my travel list for years. Usually, the first thing I consider is what are the top spots on my bucket list that I could visit, within reason. Obviously, if I am traveling for the weekend from London, I will not make plans to go to Thailand. More time I have for the trip, the further I will consider going. For a long weekend, I usually look within a three-hour radius, but I widen the range if I have more time. After I decide on a shortlist of places I want to go, I look at flights. I typically like to travel somewhere; it is easy to fly to, especially if I don’t have much time. I find that it is worth the extra money to not have to travel for a full day with connections and so on. Sometimes it can make planning easy if you just go to explore flights and a flight somewhere you didn’t expect ends up being the most reasonable option. This summer when I was living in London I would use the explore feature on Google to see which options were the cheapest then I would begin to plan my trip there. That is how I ended up going to Edinburgh this summer.

Before I start booking things, I make a Word or Google Document outlining my dates, excursions, flights, transportation, etc. It’s good to have everything all in one place to know where you need to be when and so that you have everything planned out before you begin to book. It is usually just a rough outline to work everything out and make sure each day makes sense. Sometimes I shift my dates if there ends up being an event I am really excited about or an excursion I want to go on that only happens certain days. For example when we were traveling to New Zealand we really wanted to take the Alpine Train so we had to shift our trip in order to make an 8am train ride work for us.

If you are planning a complex trip with multiple stops it is worth it to look into bloggers and/or tour groups to find out what routes they took. This way it cuts out a lot of the planning and figuring out where to stop, when. When we were traveling to New Zealand we followed the route of a hop on/ hop off bus we just did it in a rental car instead.

Plans for my New Zealand Trip

Getting There

Once my destination is decided, the rest of the planning process is pretty straightforward. I look at flights next. Make sure to use an incognito browser so that prices don’t start going up when you start looking. I usually check a handful of websites or airlines to find the flight that best fits my schedule and my budget. As far as websites, I stick to Google Flights to give me an idea of my options and pricing, Skyscanner, to find something cheap and sta travel or Student Universe for student discounted tickets. Usually, with sights like that, however, you don’t get to pick your airlines, or sometimes the time you fly so often I book on discount airlines like Vueling or Ryan Air instead. With discount airlines, you have to be careful about certain things. You can get charged crazy fees for overweight/oversized carry-ons and printing out your boarding pass. When I was flying from Budapest to London, I waited too long to check-in on my phone and had to do it at the airport. We almost missed our flight, and it cost me $50 to get my boarding pass. However, if everything works out in your favor, it is a very cheap and efficient way to fly from country to country.


If I am already on the same continent, especially Europe, I look into trains and other ways to get to my destination. Trains can be an excellent, easy way to get from place to place even if it seems a little bit longer to take the train that usually is the easiest way to travel, in my opinion. You don’t need to worry about getting to the train station hours earlier as you do with the airport and you can bring as much liquid as you want. I find that a 4 hour train hour (like the one from London to Amsterdam) ends up taking less or about as much time as the 1-hour flight, and it is usually less expensive and more scenic. I typically look at Google to find train tickets. There isn’t one specific website that I choose over others since most trains from place to place are usually run by different companies.


The next thing I typically decide is accommodation. The typical three options for accommodation that I consider are Airbnbs, hotels, or hostels. Who I am traveling with and. my budget for the trip usually decide which accommodation I choose. If I am going alone or with one other person my age, I typically look for a hostel. If I am traveling with a group of friends, we usually look for a hotel or Airbnb. If I am going with my mom, we go for hotels. Below I will break down how I choose each:

Hostel in LA

Hostels – Hostels are my favorite types of accommodation. Check out my post on picking the right hostel to get more info about how to pick the right hostel for you. Typically I begin by looking at Hostel World. I find that this has the largest selection of hostels, and I trust the reviews to be accurate and current. I search for my desired location, and then I filter the results in search of my dates and hostels that offer female-only rooms. I look at the areas closest to the city center with the highest reviews, and if I still haven’t found one that looks right, I google the location with the hostel attached. There are fewer hostels in the US, especially if you are looking in a smaller city. Googling might get better results in those cases.

Airbnb in Reykjavik

Airbnb – I typically look for Airbnbs when I am traveling in a location that doesn’t have hotels (some places in Iceland) or traveling with a group of friends where it would be cheaper and easier to stay in an Airbnb than a hotel. Usually, when searching for Airbnb’s, I do a little research to try to figure out the best area to stay in in the city. Then I look at places offering the entire home versus just a room (I usually feel safer that way). I also look by cost and if there is parking provided at the location (I often have a car when staying in an Airbnb, so I want to make sure I don’t have to hunt for parking).

Hotel in Queenstown, NZ

Hotel – Finding a hotel is similar to the others just with another website. I typically look at since that’s a website I trust and look up the location. From there, I look at ratings and locations to pick the right place. If I know I’ll be flying a far distance from that location (ex: from Sydney to Honolulu), I will usually look for a kitchen. That way, I can be sure the last meal I have is safe, and I won’t get sick the day I fly.


Typically if I have already decided on a location, I have excursions in mind. If I don’t have one in mind, I do some research to see if there is anything really fun to do in the area. I usually check TripAdvisor because, like the other websites, I tend to trust them more. I am also a creature of habit, and it’s nice to understand the website backward and forwards so that I know I’m not missing anything. I will look at what is offered in the area, and if anything looks like something I would be upset to miss, I book it. I don’t book excursions in many places. It isn’t unless I feel like I would have major FOMO, aka snorkeling on the Great Barrier Reef, taking a helicopter ride around Hawaii, going to a thermal bath in Budapest, that I book something in a city. I usually enjoy doing less touristy things when traveling. I like to find something off the beaten path that generally makes me feel like I have connected with the location that other people haven’t been able to make. My favorite thing to go anywhere I travel is walking until I get lost and then getting directions back to my accommodation when I feel like I’ve walked enough. This is something you should be very careful within cities that are known to be more dangerous or have more dangerous areas. You don’t want to accidentally walk into an unsafe situation while you are on vacation.

Some excursions, like the Anne Frank House, can be very difficult to book tickets for so consider looking as far in advance as possible to make sure that you get tickets to the excursions you desire. Some museums or popular attractions that are often booked far in advance release a few tickets at night for the following day. This is something worth considering if you weren’t able to get a ticket. I did this when I was in Amsterdam and was able to see the Anne Frank House and the Van Gogh Museum which were both sold out when I originally booked my trip.

Helicopter Tour in Hawaii

Besides excursions, I make a list of things that I want to make sure I see while I am there — the city’s main landmarks that I would be sad to miss. For example, when traveling to London in 2018, I had two days, so I made sure to go to Westminster Abbey, the London Eye, Piccadilly Circus, London Bridge, the Tower of London, Buckingham Palace and I walked along the Thames. I know that sounds like the typical tourist traps, but sometimes when you are in a city for the first time, you want to be a tourist for a while (they’re landmarks for a reason). Some cities are so large that you can’t see everything on one trip, so I usually make a list of things that I want to do when I go back. Something that either I didn’t have time for or didn’t end up being a priority.


Some places don’t have much access to public transportation, so you need to figure out another way to get around. Typically in situations like this, I like to stay within walking distance of landmarks of the city or rent a car. I find that renting a car can be slightly more expensive, but I feel more comfortable doing that overtaking a tour bus. That way, I can stop wherever or whenever I want to see something pretty on the side of the road or get hungry/ need to go to the bathroom.

Franz Josef Glacier, a detour we made in New Zealand

If a city has an excellent public transportation system, I usually take that, whether it is a bus or train. I use Google Maps to map out my route and stick to it. Most metros are pretty easy to figure out once you get the hang of the maps. If you it is too complicated or you don’t feel comfortable, Uber is always an option that can be less expensive if you don’t plan to go very far very often.


If food is something that motivates you to travel something that I recommend you do is plan out your meals or at least your dinners. This enables that you are able to eat everywhere that you want to while you are there. You can look to find the best restaurants in the city and either make a list for when you get there or possibly make reservations before you get there. If you really like to go out to bars you can do this too by looking up the top bars or clubs in the city and creating a plan to go to all of them. Bars can be a really great part of cities and going to the right ones, at least for me, can change my opinion of the trip.


A few days before a trip, I do a little bit of research into the city and country I am going to. I look at things like tipping, gestures that shouldn’t be made, phrases, or words you shouldn’t say or places you shouldn’t go. I also make sure I know what to watch out for in each city, such as dangerous areas or pickpocketing. In cities like Barcelona or Rome where pickpocketing is very common I make sure I know what behaviors to avoid such as people asking for directions or putting a map in front of you or distracting in another way.


Beach in New Zealand

My recommendation is to find somewhere you’re passionate about that way planning the trip is fun. Based on your budget and options you can pick transportation and accommodation and then fill in the rest. Make sure you consider everything before you book so that you know the dates are the ones you want. Sometimes while planning things become clear that they’re not working out the way I wanted them to usually I take this as a sign and look into some of the other places on my list to see if they fit in more. I believe that if a trip is meant to be you will figure it out. From my experience the trips that you aren’t excited about, people you’re going with don’t agree with how you want to travel or you can’t execute the trip the way you want are the trips that don’t turn out well in the end. Those are usually the trips I look back on and regret because I knew that it wasn’t right and I ignored that gut feeling.

I am well aware that my travel opinions especially in this case come from a place of financial privilege. I know that having the ability to pick between flights, accommodations, etc based on want versus something being the least expensive option is a privilege. Same with going on excursions I know that the ability to go on expensive helicopter trips is an extreme privilege. I included some discount flight and travel websites in this post and will continue to include them in my future posts to provide more options for saving money while traveling.


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