There is something to be said for aimlessly roaming the streets of an energetic city, not knowing what you will find, popping into quaint cafes and talking to the locals.
Though when there’s a limited amount of time, I also don’t want to leave “seeing something really cool” totally by chance. What if I missed the Skyline Trail hike along the Cabot Trail in Nova Scotia? Or the stunning Piaynemo view in Raja Ampat?
I always create an itinerary.
In order to make sure I don’t miss any amazing bucket list experiences while exploring a new destination, I always create a loose itinerary that leaves room for unexpected opportunity, like exploring the alleyways along the backstreets of Tokyo.
Being tied to a strict itinerary will cause you anxiety, but it also can waste precious time when you don’t have a plan. I never want to be spending hours in my hotel room trying to figure out what to do for the day, when I can actually be out there doing it!
Here’s how I organize an itinerary:
Storing your Itinerary
In the beginning of my travel career, I spent a couple months creating a London itinerary, not wanting to miss a thing. I purchased an expensive map and spent hours putting little numbered stickies on all the places to be visited. These numbers coordinated with an Excel spreadsheet that listed the attractions by name along with other essential information.
It was foolproof, so I thought.
On day one, while walking to Abbey Road, the map fell out of my purse and was gone. Countless hours of planning were down the drain in a matter of minutes. Since then I have never bought a paper map, especially since almost every airport and hotel has a free one you can pick up when you arrive.
Instead, I create and store all my itineraries with the Evernote app. The app can keep maps, photos and links to important websites that can be accessed on any of my devices. You can also set up an offline notebook in order to see your notes without Internet access, but keep in mind that you will need Wi-Fi to access any links.
**Note: You could also use the Notes app on Apple products (though it does not have as many bells & whistles as Evernote) or Microsoft OneNote, which is Evernote’s main competitor.
Do Your Research
If you want to get the most out of your experience, you need to know what you want to do and what will make the ultimate travel venture for you. Are you fascinated by a town’s history, culture or food? Do you want your trip to just be about crazy adventures and a city’s vibrant nightlife? Answering these questions means that you need to do some research for the area you are visiting.
Prior to going anywhere I do an online search of “unique things to do in XYZ”, “traditional foods of XYZ” and “best restaurant in XYZ”. I then scroll through dozens of the result sites quickly, making a list in Evernote of all the things that even slightly interest me. It is important to get past the first few pages of the Google results to find more personal stories and blogs, instead of large generic sites that can give you only a touristy perspective.
If the city or country’s Tourism Board website does not come up within the search results, I always check their site for recommendations. I may also see if Netflix has any documentaries on the destination that can be rented, plus browse a few travel guides at the bookstore.
After there is a rough list, more elaborate research is done on each attraction and restaurant to determine what will be kept of the itinerary versus what will be deleted. Keep in mind that you can’t see and do it all, so put an asterisk by the items that are absolute must-dos.
Divide a City into Sections
Many large cities will be split up in districts, like Paris with its arrondissements or the London boroughs. Look at an online map and determine the sections of a city you are traveling to. Create a header in Evernote for each district; if a town doesn’t have sections, it can be zoned into four quadrants (NE, NW, SE, SW). If your travels will be through several small villages, your headers can just be the name of the village.
Start taking the items from your master list and placing them in the sections that they are located in. This will make planning your day easier when you know what area you will be headed to and all the things you can do there.
***Tip: You can screenshot a Google Map with pins in all the locations you want to visit for the day, then add it to your chosen Evernote file.
Create a Calendar
Make a calendar for each day of your vacation. You can either do this in a simple list format or create a table. Take a look at your “things to do” list, there are bound to be certain attractions/events that have to be done on specific days due to limited open hours or reservation availability, so put those on the calendar first under the appropriate day and time.
If there are free hours on that specific date, then add anything that is in that same district to it, starting with the important items that have an asterisk next to them. Don’t put specific times on these other entries just squeeze as many as you can in before or after you scheduled event. This way you will have plenty of options on what to in the district that you will be in without having to be strict about the time.
Leave Room for Opportunity & Be Realistic
Even when I am in a location trying to make a tick off the bucket list I create loose itineraries, ones that leave room for unexpected opportunities, because a bucket list is just as much about the journey as it is the checkmark.
There are always times while exploring a city that something incredible sidetracks you, and if you are scheduled with events back to back you may have to miss out. Of course you’re going to want to see and do everything on your trip, but also be realistic.
Don’t expect to land in Europe, after twelve hours of travel and hit the ground running jam-packing your itinerary from sun up to down. Leave room for meals, sleep, jetlag and rest. Plus expect a few hiccups along the way; flights can be delayed, restaurants can lose reservations and an attraction may pale in comparison in person to the photographs on the Internet.
In the Bahamas our tour guide forgot to pick us up at the hotel, it rained for 24 hours straight and the buggy we rented got a flat tire in the first half hour. Yes, it changed our itinerary a bit, but instead of the original plan we met a lovely Bahamian couple that graciously drove us to the local fish fry where we ate cracked conch and drank bottles of Kalik beer.
Sometimes the unexpected is the most memorable part of the journey.
Don’t Forget the Extras
Add your flight numbers, hotel addresses, maps, etc. to your itinerary file for easy access. All my itineraries include this information, plus the currency exchange rate (so I know how much 1 US dollar is worth in the country). It is much easier to look at one file then have to scroll through dozens of emails or check different apps to find what I am looking for.
***Note: This should not be a substitute for keeping all that information stored in emails or printed copies of confirmations just in case.
This and a lot more traveling tips can be found in my book Bucket List Adventures.