Traveling to a new destination is both exciting and a bit overwhelming. Half of the battle is finding the perfect flight and time to travel. See my previous post on finding great flight prices. Once you have booked your flights, you should start planning what you want to do. Depending on your travel philosophy: strict timeline of activities vs. laissez-faire, you may do more or less preparation prior to travel. I am more in the middle when it comes to traveling to new destinations. I love to have flexibility because sometimes things don’t go as planned and you have to be able to go with the flow. Conversely, I fear that without some pre-planning I will miss out on some really amazing site-seeing opportunities.

Given my travel philosophy, I find it helpful to develop a travel itinerary prior to a trip to at least have a blueprint of what you want to do and see. I outline my process below for developing a complete itinerary and offer free printable worksheets to aid you in developing your own itinerary.

Research, Research, Research

There are many ways to find out more about your destination and the notable sites. First, you can visit their tourism board website which generally lists not only some of the best places to visit but usually lets you know about any events that may be happening at the time. This is a great place to start to get an idea of some of the things that are more famous, though they may be more touristy and attract more crowds. My next go-to is blog posts. Not that I am biased, since I am also a blogger, but even prior to starting a blog, I relied heavily on blog posts to plan trips. Travel bloggers are able to give you a sense of what it is like to actually visit a place as a traveler. The best way to find a great blog post about your destination is to search Pinterest which has tons of blog post from travel bloggers. I tend to like the blog posts that are more general and discuss the best things to do and see when visiting a certain destination, but you can also find posts about the best places to stay and eat. While reading through blog posts, make sure to jot down the places you want to go and take note of places that are repeatedly mentioned which may be a good sign that it is worth visiting. Lastly, I also like to look into the available tours that are offered at a destination that may enhance my experience. This really depends on your preference and how long you plan to stay but some companies offer half-day to full day tours that can give you a more in-depth view or offer a chance to go to another city for a day trip. I would advise to also cross check these tours with trip advisor to read reviews when deciding if you want to add a tour to your itinerary.

After all this research, you should have a fairly extensive list of places to see. Depending on how long you plan to stay and how intense you want your visit to be, you may or may not be able to see everything on your list.

See example below for my trip to Cape Town

Map it out

At this point, once I have determined the places I want to see, I determine which things I want to cluster on the same day depending on its location. I use Google Maps which offers you the ability to see where things are in relation to each other and to determine the amount of time it will take to travel between places. If you plan to use the local public transportation, it also offers the option to see how to get from place to place via public transportation. More recently, I have noticed that they also have the option to estimate the cost for a ride sharing fare (ie. Uber or Lyft). I try to cluster activities that are within walking distance or are located on the same line of public transportation to aid in ease of movement between sites.  Also, I try to be cognizant of timing and how long it will take to get to and from places and factor in time to have meals. It is easy to get carried away and plan to do a bunch of things in one day but I suggest only planning to see 3-4 different attractions in one day to prevent burnout and give you time to really enjoy each place.

Once you determine which activities work well together, figure out which days you would like to do these activities. If you are traveling very far and crossing multiple time zones, I suggest taking it pretty easy the day of arrival because jet lag is rough. If you are a more laissez-faire traveler and not really into having a strict day-to-day plan, I would still try to determine what things to cluster and decide the day of what you want to do each day. It is helpful to determine which day during your trip you want to do certain things if you plan to book tours ahead of time as it will decrease your flexibility.


Book Ahead

Once you have determined what days you want to take certain tours, you should try to book them in advance (at least one month prior to departure). Booking far in advance ensures availability during the day you prefer. Additionally, if you plan to check out a show or upscale restaurant, you should look into booking tickets in advance or make reservations. Once you have confirmed your reservations you have set activities that you can plan around.


Once you have confirmed all of your activities that require a reservation, you will be able to create a complete itinerary.


You don’t have to be a travel agent to plan a great itinerary. You just have to do plenty of research and know where to look for the information. I will caution you to be flexible, especially if you are traveling with a group because plans always change and unexpected things can come up. That is why I try to not cram too many activities into one day so there is room to add something on if we are unable to do everything on the pre-planned day. I hope you found this helpful in planning your future trip. Click below to download the free itinerary planner that I used to create my itinerary above. You can duplicate each page to accommodate the length of your trip. You can edit the PDF or print it out and write out your plans by hand. Let me know if you find it helpful!

Download Printable Here!