A New City Solo: The Art of Planning and UnPlanning

You're on your own and traveling to a new city. How to get the best from it is the traveler's challenge.

There's the saying that you don't know what you don't know. This might suggest that research is your first priority.

I would argue that sometimes not knowing is a good thing. Planning is important but a light touch with planning can result in some wonderful surprise experiences. I call this intentional unplanning.

A balance needs to be struck. Planning for your safety, budget and some not-to-be-missed sights is important. Including free time for recommendations from locals, the unexpected discoveries and simply wandering is also important.

Below are suggestions for planning and unplanning.

Planning Solo Travel to a New City

To stay safe and within your budget, a certain amount of planning is absolutely necessary.

1. Study a map. Get to know what's up and what's down. Is the city organized on a grid? Are there landmarks that can be seen from many directions that could be your guide? In New York City you'll notice that streets run east and west while avenues run north and south. In Toronto, the CN Tower is near the lake and therefore south. Glean this kind of information by studying a map and navigating a new city will be easier.
2. Identify your priorities. From guidebooks to blogs, there are so many ways of doing this. Look up city tours and see what's on offer. You don't have to take a tour. Just looking at the itinerary will help you decide what you don't want to miss. Go to the UNESCO site and their World Heritage List to find out whether there is a cultural or natural site of great significance in or near your destination.
3. Find the free stuff. Every city has free stuff. Check out our city-specific 32 Tips posts for free and low-cost options for many destinations around the world. We currently have advice for London, Kauai, Sydney, New York, Chicago, Paris, Dublin, and more.
4. Book accommodation central to your priorities. Make your life easier by booking accommodation relatively close to the area you most want to explore or with convenient public transport connections. One of the reasons we like booking.com is that it shows the location of hotels, hostels, and other types of accommodation in relation to landmarks, neighborhoods, and transit.
5. Understand the transit system. Again, you may want to start by studying the transit map. Is it simple like Toronto's so you can sort out most routes on your own or complicated like London's where you'll definitely want their app to help you get around? Most cities have apps for tourists now. They're worthwhile downloading.
6. Prepare the basics you need for every trip. This is not specific to solo travel to a new city but it needs to be part of all travel plans. Read our planning post and make sure you know what to look for and secure travel insurance. If you won't have a local sim card, get a VPN to protect your privacy on public Wi-Fi.

Unplanning Techniques for Surprise Experiences in a New City

By being open to the unplanned, by reserving time for it, you can enjoy some pretty special experiences.

1. Don't take cabs if you can walk or take transit. There is so much to be seen and learned by walking and taking public transport, not to mention the savings you'll enjoy. Take a cab or Uber at night if safety is an issue but otherwise slow down and enjoy the getting around as much as the getting there.
2. Don't just stay in the city center. Get outta town. Find out what's in the suburbs and even farther afield. A day trip beyond your city destination really rounds out your travel experience. I'm thinking of my trip to the Blue Mountains out of Sydney and Tai O, a fishing village outside of Hong Kong.
3. Don't eat all the same things you eat at home. Branch out and discover some flavors that are new to you. If you’re in a city like New York, try some of the amazing street food. In Toronto, visit Little Portugal, Little India or Little Italy, Chinatown, Greektown or Koreatown for tasty cultural experiences.
4. Don't break any of the fundamental safety rules. Just because you're on vacation, it doesn't mean you can drop all rules. Follow our 5 Fundamental Solo Travel Safety Principles to keep yourself safe. There are 50 safety tips here.
5. Yes, talk to strangers. You'll get a real feel for the place, culture, politics… by simply talking to people. You will also get local recommendations not in guide books. Read Travel Solo and Talk to Strangers for Authentic Connections
6. Talk to the desk clerk or concierge. As a solo traveler you want to leave a crumb trail behind you. Chat with the desk clerk to learn of local things to do and give them an idea of your plan, even if you are not certain of it. Grab the hotel's business card so you’ll have the address handy and have no problem getting back if you get lost.

I always recommend a balance between planning for safety, budget and prime sights and not planning for the serendipitous travel experiences.