Best of: Boston & Chicago

It’s always a huge compliment to me when someone reaches out to me to tell me they’ve read my blog. When Kendra, a Chicago mom of three, wrote asking me what I love to do in Boston, I couldn’t wait to share with her! Keep reading to find out what we love about our cities…
A Tale of Two City Girls
“A Tale of Two City Girls” (Via


Celebrate Like A Bostonian

First rule of NYE: Decorate with ALL the glitter.
First rule of NYE: Decorate with ALL the glitter.

I can’t help but be inspired by the holiday season so my number one “what to do” would be the annual “First Night” celebration. Every year I have marveled at the ice sculptures, light displays and general revelry that takes place in Boston but I have generally only observed it through a television screen. Last year, one of my best friends threw an unforgettable party at her Back Bay apartment but I opted to stay cozy inside for the entire night. This year I’ll be celebrating on the waterfront at Tia’s, an establishment that is typically not open during the cooler months, and I could not be more excited!

Sip On Something Cozy 

I wish Eggnog Latte season would never end.
I wish Eggnog Latte season would never end.

After being out all night on New Year’s Eve, (or in order to do so,) I imagine that I will be in need of a “pick-me-up” warm beverage. Being the coffee enthusiast that I am, I very much enjoy putting my own spin on “Beantown” (a moniker my city earned for the regional dish known as “Boston Baked Beans”) and by doing so, have visited many different coffee shops in the Greater Boston area. From the “crunchy-granola”-feel at Equal Exchange Café in the North End to the more “indie”-feeling Trident Booksellers & Café in the Back Bay, nothing is more cozy when the wind-chill factor is more than obnoxious.

Go Green

The friends who drink Smithwick's together, stick together.
The friends who drink Smithwick’s together, stick together.

Another festive time of the year in Boston revolves around the heritage of many early residents of the city, St. Patrick’s Day. Even when I was in undergrad, those who were not from the city understood that Bostonians takes celebrations of all kinds quite seriously and St. Patrick’s Day is not exception. While it doesn’t need to be sloppy and grog-filled, there is no better place to don your best Irish-knit sweater and enjoy a fresh Guinness at a “local”…unless you happen to be in Ireland.

Stop & Shop

Fresh produce = delicious & healthy meals!
Fresh produce = delicious & healthy meals!

As it starts to warm up, I find almost any excuse to get into the city on Saturday mornings to shop at open-air farmer’s market known as Haymarket. If you are a city resident (or live within a reasonable distance) and have yet to experience the gloriously low prices of produce, fresh fish and cheese, I’m not sure what you’re waiting for. I took advantage of the excuse to venture deeper into the city (and save an embarrassing amount of money) throughout college and continue to do so simply so I can start my weekends as early and as cosmopolitan as possible.

Be Cool

Lazy summer days by the water in Cambridge are just the best.
Lazy summer days by the water in Cambridge are just the best.

A self-proclaimed summer girl means that when the temperature starts to rise, I like to be as close to a body of water as possible. Whether I’m enjoying a cocktail or lobster roll on a pier or walking along the ocean beyond the Boston Harbor Hotel, the oceanic skyline is one of the best and most romantic sights to be seen.


Chicago is a truly huge city, and it’s full of countless restaurants, museums, events and shopping opportunities. As a long-time resident of Chicago, I can honestly say that there’s always more entertainment around the corner in this city. Here are some awesome Chicago activities that I recommend to travelers.

Experience Chicago’s Artistic Soul

Historic Water Tower Park (Via Pinterest)
Historic Water Tower Park (Via Pinterest)

Chicago’s greatest local artists and photographers exhibit their work at the City Gallery. Located in the Historic Water Tower, this place is essential for anyone who wants to understand Chicago’s art crowd. It’s also easy to find if you visit the Magnificent Mile for a day of shopping. The Historic Water Tower was finished in 1869 and didn’t burn down during the Great Chicago Fire in 1871. Only photographs of Chicago are shown there, and admission is always free.

Find a Thrilling Place to Stay

Vintage shot of the Drake Hotel (Via Pinterest)
Vintage shot of the Drake Hotel (Via Pinterest)

Chicago has so much to offer any tourist with a love of hotels. No matter what type of hotel you’re looking for, you’ll be sure to find it in Chicago if you look hard enough. Older hotels, such as the Drake, appeal to history buffs in particular. At the same time, plenty of low-cost lodgings are available for those who want to save money during their visit. It’s important to note that you don’t necessarily have to go out of your way to find what you want these days.

Eat Real Chicagoan Food

Meet your tasty tour guide, Kelly Purky!
Meet your tasty tour guide, Kelly Purkey!

Visit the South Water Kitchen if you’re eager to try authentic Chicago-style cuisine. This restaurant is in the loop, and a Chicago native heads it. Because it opens at six in the morning and offers breakfast, lunch and dinner, it’s perfect for travelers who are hungry but short on time. The food there is amazing, and the prices are actually reasonable. If you have kids or other family members who are picky eaters, this is the perfect place to go. A huge menu with every variety of vittles provides appealing choices for all.

Educate While You Recreate

Have you ever seen a more regal museum in your entire life?! (Via Pinterest)
Have you ever seen a more regal museum in your entire life?! (Via Pinterest)

Chicago’s Field Museum is easy to find thanks to a location right on South Lake Shore Drive. It’s also an exciting place full of interesting and enjoyable exhibits that both adults and kids will enjoy. In fact, my own children can’t get enough of this place. There is seemingly no end to the range of attractions hosted by the Field Museum, and you can always count on seeing something incredible. On one occasion, my kids and I got to see some gigantic and rare dinosaur fossils that we will never forget.

Chicago has an endless variety of attractions, but the ones I’ve listed here are my personal favorites. With so many things to see, buy and eat, this city won’t leave you searching for something to do. Chicago is truly a world-class city that everybody should visit at least once. If you come here, be sure to follow my recommendations and you’ll have a fantastic time.

Happy travels!

Kendra & Vanessa

Be sure to follow me here, on Facebook and on Foursquare to see where else I’ve been and where I recommend!


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Vanessa M. Gatlin

-Blogger, dancer, fashionista -Self proclaimed "political junkie" with a strong interest in international affairs -2011 graduate of Emmanuel College in Boston

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