During the past few years I’ve traveled more than usual, both within the USA and outside it. Along the way, I’ve discovered a few things that can enhance most trips, whether you are traveling with kids, adult friends or as a couple. If you want to get more out of your next city vacation, in addition to visiting the most popular tourist destinations and eating at the best restaurants, this article is for you!


My favorite way to start a trip in a city is to have a tour, and I’m the type that has no problem climbing aboard a double-decker bus and listening to someone point out city landmarks. But, what I really like is a more intimate walking tour. I want to know the history of where I am and have little tidbits of knowledge passed my way, which usually include the skinny on the best restaurants that may not be the media darlings, but are loved by locals. I want to be able to ask questions and get some steps along the way. I’ve had great luck with Context Tours. Their tagline is “Context Tours for the Intellectually Curious” — don’t you just love that? It’s great marketing because who doesn’t want to be intellectually curious?! They only operate out of four U.S. cities: Boston, New York, Washington and Philadelphia. Each one of these cities is dripping with history, culture and unique destinations. Tours can be specifically tailored for families, private tours or joining group tours.

Context Tours also operates out of 40 cities around the world in Europe, Asia, North America, South America and Australia.

I snapped this photo when my family was on a Context Tour of the history of Lower Manhattan.

What types of tours will you find with Context Tours? Food, history, cultural … you want it, they have it! Each city has a variety from which to choose. Several that stand out to me include “Robber Barons and Bluebloods: Philadelphia During the Gilded Age” in Philadelphia, and “Boston Walk with Flytographer Photoshoot” in Boston, which includes both a historic tour and photoshoot so that you can make sure you have stunning photos at Boston’s best places! Love food? How about the “Made in Quebec, A Savory Stroll of the Marché Jean Talon” in Montreal?! Stroll this historic street and taste the flavors of Quebec along the way.

Most tours include a per-person price and a price to book the tour as a private tour. I’ve booked Context Tours several times, and each time I’ve been more than satisfied with the knowledge of our tour guide and the overall experience.


Another fun adventure to have is a scavenger hunt. That sounds odd, huh? With the ability to download scavenger hunts on your smartphone, the world of scavenger hunts has changed. On a recent trip to Charleston, South Carolina, my husband needed to work for a few hours, so I took my kids, ages 13-18, and we spent a couple of hours using Urban Adventure Quest. My kids were not so thrilled to do this, but they did quickly get into it as it’s fun! I think it’s probably good, from our experience, for ages 10 and up. And, if you have a fun adult group, you can split up and make it competitive to see who will finish first.

Your scavenger hunt may have you feeling like you’re part of the National Treasure team breaking code! Here, my daughter is leaning over the fence of a graveyard to use the historical marker to decipher the code our scavenger hunt had given us.

All you need to do is pick your city, pay $49 for the adventure and be entertained for 2-3 hours. If you end up needing to stop, that’s fine, it’s your game!

What I enjoyed is that it brought us to landmarks we would otherwise have missed, so it’s a history tour, puzzle solver and scavenger hunt rolled up into one. Beware that some scavenger hunts need you to get on public transportation (like a city trolley), but each scavenger hunt will note if there are additional transportation costs, and usually there are not.

Through Urban Adventure Quest, there are 43 cities in the United States to consider, so you may even live in a city that has one, making this into a fun summer activity.

SB TIP: Make sure to have a notebook and pen, preferably for each participant, as you will be deciphering clues that are impossible to figure out without writing them down.


When it comes to traveling with friends or your family, have each person/couple pick a restaurant. For us, we have our kids research and pick some restaurants, and it adds an element of buy-in from them. We’ve been doing this since they were about 8 years old and the ownership of helping to choose a restaurant and be part of the planning makes the whole trip better. My only parameters are that it must be local, and I have veto power, which I’ve never had to use. Your kids learn to read reviews, articles, look at food photography, check out the restaurants’ Instagram accounts and more. A whole lot can go into planning meals, and getting everyone involved makes the whole trip more fun.

Sometimes all they really want to plan is to eat Peace Pies (ice cream sandwiches with a layer of pie filling!).

The same philosophy goes for traveling with friends as well. Have each person choose a restaurant, and for those who don’t care, they get a pass. Not everyone cares as much about their meals, and that’s okay. But allowing each person to have the ability to add to the trip by planning where to have lunch or dinner just makes everyone feel that this is their trip as well, and that they are not simply along for the ride.

Above all, try to stop texting and emailing … try to unplug and enjoy your friends, your family and the great place you have paid to escape to!


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