How to Plan a City Walking Tour


Touring a new city on foot can be a great way to see the sites, get a feel for the culture and make memories, but planning a city walking tour can prove a little overwhelming if you don’t know where to start.

We have done walking tours in many of the big cities like Philadelphia, New York City and Boston as well as cities like Springfield, Massachusetts. There are some definite things to know that will make your walking tour more efficient and enjoyable.

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How to Plan a City Walking Tour

How to plan a City Walking Tour

Research before you go:

There are some cities that have so many things to see and places to explore that you can miss things if you don’t plan it out. Do some research and make a list of the things you don’t want to miss. Are there places you just have to see? How long will you have to explore the city? Will you tour the landmarks or just see them along the route?

Map it out:

Plot the landmarks on an internet mapping service like Google maps. Once you have the destinations plotted, look to see what the best order is for your path. Make sure you click on the walking icon so you can plan your trip.

Wear Walking Shoes:

Most walking tours will take you all day and cover many miles and thousands of steps. Wear your comfortable walking shoes so you can keep going all day.

Don’t forget to have your Fitbit charged so you can get log your steps!

Pack your BackPack:

We always carry a backpack when we are exploring a new city. You never know how long you will be out or when you will need water or snacks. Here are a few things to pack in a bag for your next walking tour:

  • Sunscreen
  • First Aid Kit – make sure it’s large enough to cover any emergencies but small enough to fit in your backpack;  Think about more than just band-aids and headache medicine, you may want to also include a trauma kit
  • Portable charger
  • Printed map
  • Ponchos or small umbrella
  • Flashlight – important if you find yourself out after dark or in a building in a power failure
  • Small Cash for tips
  • Keys to your hotel and vehicle

Call the Tourism Office:

No one knows the city better than the tourism office. Before we arrive at a new city, we always call the Visitors Center and ask them for tips, coupons, and recommendations of what to see. When we visited Erie, Pennsylvania, we found out that just a few minutes away from downtown Erie was the only statue of George Washington wearing a British uniform. This is a unique statue that we would have overlooked if we hadn’t called ahead.

Take Public Transportation:

Once we arrive at a new city, we typically check into our hotel and either start our walking tour from the hotel or take public transportation to the farthest destination and then walk back. In Boston, we stayed outside the downtown area and rode the T down to Boston Harbor to begin our tour.

Intimidated by the big city public transportation?  Check out these tips for how to navigate the Washington DC METRO.

Many of the big cities have so much traffic that driving from one historical site to the next just doesn’t make sense. You would spend so much time in the car looking for parking and navigating one-way streets that your day would be wasted. Don’t be afraid of public transportation, just do a little research and tackle it!

Self-Guided or Formal Walking Tour?

Should you take a self-guided tour or pay for a guide to lead you on a formal walking tour? We’ve done both and find that there are pros and cons of each. In New York City, we did our own self-guided tour and explored on our own. But in Boston, we did a mix. We had a guide for most of the Freedom Trail and then did the rest of the city on our own.

Professional guided tours give you the opportunity to learn things that don’t show up on the historical markers. They are typically a great way to learn more than you can learn on your own. The down side of the guided tour is that they are sometimes expensive and may take longer than you have to devote to that piece of the trip.

Have you ever taken a walking tour of a city? What are your favorite parts of exploring a new city on foot? I’d love to hear!

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