Getting Started
The first two things you need to determine go hand in hand: the timing of your trip and the participants.
Are you going in the summer or in the winter?
How long will the trip be?
How many people will you be traveling with?
Will there be any children on the trip?
Researching Potential Destinations
Once you have determined where you are going and who you are going with, it’s time to look at destination options. Some important things to consider are:
Temperature/Climate: Depending on what time of year you have decided to go, be aware that the climate of your destination may be very different than where you live. Make sure to look at what the season brings in that area.
Is it the rainy season? This may not be ideal if you want to do a lot of outdoor activities.
Does it typically snow that time of year? Not necessarily a deterrent, but something you want to make sure you keep in mind as you continue planning.
Tip: Don’t forget that if you are going on the opposite side of the equator that seasons are reversed!
Destination Popularity: Be sure to consider the popularity of the destination in the time frame you plan to go.
Is it typically a time that sees a lot of tourists? Prices for things may be higher during these times.
Is it off-season? Some things may not be available due to there being less tourists.
Tip: It is important to know if there are big events happening in that area, like a music festival, a hot air balloon festival, or other things that may increase tourists and prices during a usual off-season time.
Proximity to Other Destinations:
Are you planning on spending all of your time in one city?
Do you want to hop around to a few different cities? If so, how do you want to get between places?
Choosing Your Destination
Once you have done your research, you’ve probably narrowed the destinations that make the most sense for the time of year and the people you are going with. If you are still going between a few destinations at this point, start looking at the cost of lodging, flights, and other transportation.
If that doesn’t sway you one way or another, talk to the people you are traveling with and figure out which one you all are more excited about!
Going forward, I’m going to refer to the chosen destination as “Destination”.
Compiling Things To Do
This is my favorite part of planning a trip, gathering a list of all of the things I could possibly want to do in that area. This is when I make THE spreadsheet (as it is now referred to by my friends and family).
Tip: Don’t be super selective in this part, jot down anything you think you may be interested in!
I usually start with a broad Google search: “things to do in Destination”. The first things that will come up are things like GetYourGuide, Viator, and Trip Advisor. These are a good place to start – they will give you the most touristy things to do. From there, I briefly look into the list of things and if they’re of interest to me, I just jot them down in a list in my spreadsheet. For me, I’m not much of a museum person. So if it’s not something like the Accademia Gallery with the David statue or the Louvre with the Mona Lisa, it doesn’t typically make my list.
If you keep scrolling down on your Google search, you’ll likely find a U.S. News Travel site as well as a Travel + Leisure site. These will have a lot of the same suggestions, but typically have a few new ones to look into as well.
My next search is “hidden gems in Destination”. This will lead you down more of the travel blog route. This is where I find my true gems. Travel blogs have been extremely helpful for me in planning my trips, especially when I first started. My go-to travel blogs are Earth Trekkers and Condé Nast Traveler.
Earth Trekkers a family who has traveled the world with their kids writing about their experiences. This is a great blog to look at when you are traveling with kids. None of my trips have been with kids, but I still find their blog extremely helpful!
Condé Nast Traveler is a travel magazine and website with articles by several different authors.
These are by no means the only blogs I look at, I have found myself using blogs more and more for specific recommendations. These are just the two I make sure to check for every trip!
I always have to reference my Bucket Lists and add anything I have for those areas to the list.
You can’t forget about food! I usually start with Eater.com to get a sense of the type of food in the area. I then search “best restaurants in Destination”, “best breakfast in Destination”, and “best bakeries in Destination”. If you’re searching for specific types of food, I would search that specifically also. All of these get added to the spreadsheet too! I typically put food in bold face so I remember it’s food.
My last step is to search food, traveling, and hidden gems in Destination in social media (I use Instagram and Pinterest) and let the algorithms work for me!
Narrowing It Down
Once you’ve got a giant list of things to do, it’s time to start turning that into a more realistic list of things you can get done in the amount of time you will be there. When I first started planning trips, I tried to shove wayyyyy too much stuff into each day.
Start with determining the things you want to do the most and figure out how to do them. For example, if you want to see the Trevi Fountain it is flexible, you can show up whenever, but if you want to see the Vatican, I would recommend booking a timed tour which are only offered at certain times and on certain days. Sometimes, it also makes sense to combine a few things into a guided half day or full day tour. It can make your time there more efficient. I don’t do this a lot because I like being on my own time, but sometimes it makes the most sense.
For example, when I was trying to figure out the best way to visit the Cave of Zeus in Crete, I realized I would rather play it safe and book a guided tour from where we were staying in Heraklion. Once I began looking at the guided tours, I found that pretty much all of them included olive oil tastings, wine tastings, Lassithi Plateau, Knossos Palace, or traditional villages. Since Lassithi Plateau was also on my list, I chose a tour that will do that along with the Cave of Zeus.
When you are looking into all of these things, you may realize that there are some things that you don’t really care to do that much and can knock them off the list. It also gives you a chance to notice if there are any redundancies.
For example, while planning one of my trips, I noticed that I had 3 different wine tastings listed for a city I was going to be in for 3 days. This prompted me to look into the different tastings and choose which one I wanted to keep.
I also put everything on a map. I use Google Maps‘ “Saved” feature. This allows you to visualize where everything is in reference to each other. You can also use different colors for food, sites, and whatever other categories you want to make. Most things end up in clumps, but there are occasional things that are significant outliers. Start with those and determine if this is something you really want to do or if it is something easy to knock off the list. If it is something you really want to do, it may be worth looking into a guided tour with pickup from where you are staying – especially if you are not planning on renting a car.
Making Your Itinerary
It is helpful to start by looking at the things that have to be done at a specific time or day – I put those on my itinerary first because everything else needs to work around them.
Tip: Don’t put more than one of these things on the same day if you can help it.
After that, you can see what other things are in the area and put those things on the same day. There are some days that there won’t have anything that has to be done at a certain time. Those days are good for hitting all of the things that aren’t in any of those areas you’ve already hit.
Now that you have a rough idea of the things you want to do each day, it’s time to zoom in on each day. Now I would leave the “Saved” mode on Google Maps and go to the normal Map. Put all of the things you want to do that day on the map and select the type of transportation you will be using – either walking or car.
Tip: If you plan on using public transportation, select car because Google Maps can’t determine public transportation between that many places at once.
Tip: If you plan on using a combination of methods, select walking because Google Maps can’t accommodate multiple methods in one map.
Next, drag and drop the different locations into an order that makes sense. Do this for each day individually.
Going from this…
…to this
I am very Type A when it comes to planning trips and I note the time it will take to get from each place to the next place and the method of transportation. I do this because it is helpful for me to figure out what time I need to start my day to get to my tour that starts at a specific time, or to figure out at what point I will probably be wanting lunch.
Now you need to find a place to stay. I recommend using a site where you can find high end, budget, boutique hotels, and everything in between. I use Priceline because I also use it for flights and car rentals and you can get great deals with bundling them. I like to use the map feature on Priceline in one tab, and my Google Maps “Saved” map in the next tab. Going back and forth between the two, I try to find a hotel that is both in the middle of everything I want to do and in my budget. Priceline also has a lot of options that are refundable which I typically take advantage of.
There are some times that I have a specific hotel I want to stay at, or a specific area I want to stay in, but it’s on the outskirts of the things I wanted to do. At that point you need to make a choice: is it worth the extra walking/driving/transportation every time I go to and from the hotel?
For example, when I went to Rome, I wanted to stay in Trastevere which is on the outskirts of Rome. It added about a 15 minute walk to and from the hotel, but it was worth it to me to be in that neighborhood.
I add food in last. For breakfast, I figure out my first stop of the day and determine if there are any breakfast spots we can hit along the way. For lunch and dinner, I look through my itinerary for each day and figure out where I will probably be around lunchtime and dinnertime. I then look at the map of the restaurants in my “Saved” map and determine which restaurants fit best. There are not always places you have listed that match so you may have to do some more searching into restaurants in the area.
I typically begin loosely looking at flights and other transportation when I am choosing my destination, but I don’t buy them until I have this rough itinerary. I like to wait until this point to make sure I have allotted enough time to each city. Sometimes, when you are putting the itinerary together you realize you need an extra day somewhere or less time somewhere else.
This is also where another round of narrowing down what you want to do. You will realize that not everything fits into your itinerary and those things that are the lowest on the totem pole will get cut.
One of the big things to remember when you are mapping everything out is that there is not a perfect path that you are not going to have to go the same way more than once or go back to somewhere you were prior to get to a restaurant.
It’s also important to know what kind of traveler you are. I have learned that I like planning in some time to go back to the hotel mid-afternoon when I can, just to have some time to relax and decompress. Before I figured this out, my itineraries were just go, go, go all day and I was exhausted every day and that added up throughout the trip.
Fine Tuning Your Trip
The last step is fine tuning your trip. I usually do this closer to the actual trip so I can ensure I’m looking at accurate hours of operation and closures.
At this point you should go through each place you want to visit and each place you want to eat and make sure that it is open on the day you plan on visiting. For restaurants, make sure to look at the hours of operations. Some restaurants close in the middle of the day for a few hours, or are only open for one meal, so it is important to make sure you are not planning on going somewhere when it is not open.
I hope this has been helpful for you in planning your next trip! If there is anything else you want to know about, leave me a message.
Check out Making THE Spreadsheet for more specific information about laying out your itinerary!