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Travel in the Footsteps of a President

Millions traveled to Washington, D.C., for Inauguration Day, to witness the induction of the Obama presidency. There are other destinations, however, that can shed as much light on this historic occasion—the places that shaped Barack Obama’s life, from childhood to today, leading him to the 44th Presidency of the United States.

From the shores of Honolulu to Kenyan plains, tony Harvard Square to the eclectic South Side of Chicago, each featured locale left an indelible impression on Obama. Choose one for your next vacation and you too can walk in his footsteps.


Barack Obama was born in Honolulu, on Hawaii’s island of Oahu, in 1961. In anticipation of visitors wanting to retrace Obama’s roots, there is already a wealth of online resources for self-guided tours. The Hawaii Visitors and Convention Bureau has put together a site just for Barack Obama’s Hawaii, chronicling his upbringings there, family roots, and suggested itineraries; has a detailed self-guided tour including stops at Obama’s first childhood home, his elementary school, and favorite parks, in addition to other must-see attractions. Many stops are clustered in east or west Honolulu, leaving plenty of time for beach lounging, surfing, or snorkeling after your sightseeing.

To start your Hawaii trip planning, check out’s Hawaii Vacation Guide, as well as the latest airfare deals to Honolulu. At press time, airfare started around $300 round-trip. You can also use our price-comparison tool to find the best deals on airfare and hotels.

Jakarta, Indonesia

In early childhood, Barack Obama’s mother married an Indonesian man, and the family moved to Jakarta in 1967. During Obama’s brief time in Indonesia’s capital, he lived on Haji Ramli Tengah Street and Taman Amir Hamza Street (before returning to Hawaii at the age of 10). Beyond visiting his childhood homes, visitors here may find themselves drawn to Jakarta’s popular sites: Fatahillah Square, featuring colonial architecture and an impressive fountain; Jakarta’s National Monument, where tourists can get a bird’s-eye view of the city; and Surabaya Street, home to street vendors, antique sellers, and more unique retailers. Get a full list of possible itineraries on Jakarta’s official tourism website.

Most travel providers offer airfare-and-hotel packages to nearby Bali, skipping over Jakarta entirely. However, you can find trip-planning resources on the official Indonesia Tourism website. Click on the “Traveler’s Tools” link at the top of the screen to find information on travel agents, accommodations, and transportation. You may also want to check out SmarterTravel’s sister site, TripAdvisor, which offers hotel reviews, things to do, forums, and more.


Barack Obama’s father was born in Kenya’s Siaya District and died in Nairobi. The president’s relatives still live in Nyangoma-Kogelo, a sleepy village in western Kenya. If you’re making the journey here, you’re most likely interested in spending time on a safari, to see wildlife and the spectacular vistas unique to the region. The Kenya Tourist Board has compiled a list of the country’s national parks and preserves, including those in Western Kenya (closer to Obama’s ancestral hometown and more off the beaten path), among the more popular destinations. The tourism board also offers a rundown of tour operators, including those based in-country, as well as North American and U.K. companies.

There are countless possibilities for safari vacations. For a benchmark of trips and prices, Friendly Planet’s Kenya Wildlife Safari features 10 days from $3,099 with an optional Tanzania extension, G.A.P Adventures’ Kenya Wildlife Adventure includes nine days from $1,249, and Mountain Travel Sobek’s Kenya & Tanzania Safari includes 14 days from $6,295. Get more trip-planning details by reading SmarterTravel’s Kenya Vacation Guide.

New York City

Obama graduated from Columbia University in 1983. Avoid the usual tourist stomping grounds of Midtown and take a day to explore Morningside Heights, Columbia’s neighborhood, in upper Manhattan. Among the sights: Grant’s Tomb and memorial, Tom’s Restaurant (also known as the Seinfeld diner), and the Cathedral Church of St. John the Divine. And of course, you’ll want to set aside some time to wander Columbia’s spectacular campus, full of neoclassical architecture.

If you’d like to stay in Obama’s old neighborhood, Columbia has assembled a list of hotels convenient to the campus. The Lucerne, a boutique property on West 79th Street, offers doubles from $210 per night, as well as a variety of weekend getaway packages and seasonal promotions. Get more local resources and trip-planning ideas on the NYC & Company website, or read SmarterTravel’s New York City vacation guide.

Cambridge, Massachusetts

One could argue Obama’s political aspirations really got started in Cambridge, Massachusetts, across the river from Boston, where he attended law school at Harvard University. Today, Harvard Square may look different from when Obama graduated in 1991, but there are still plenty of unique sites that can cultivate your own inner academic.

Set aside an hour to browse the stacks at Harvard Book Store, an independent shop that’s been a fixture in the Square since 1932. Taste candies, wines, and other groceries from around the world at Cardullo’s, which claims to have the largest chocolate selection in the Northeast. And, nourish your body and mind with a meal at Grendel’s Den, which caters to students, professors, and locals. Come between 5:30 and 7:30 p.m. daily or between 9 and 11:30 p.m. Thursday through Sunday and your dinner is half price (with a minimum $3 purchase).

Pretend you’re visiting friends with a stay at the Harding House, conveniently located between Harvard and Central squares. Rates start at $85 per person per night and include breakfast, parking, museum passes, afternoon snacks, and wine and cheese. You can also find more trip ideas and information on, the website of the Harvard Square Business Association.


Perhaps no town represents Obama more than Chicago, the place he has chosen to call home since 1985. As a community organizer and resident of the diverse South Side, Obama has certainly spurred renewed interest in Chicago as a city of inspiration, influence, and importance. If you want to experience it like a local, the Chicago Tourism and Convention Bureau has put together a sampling of Obama’s favorite haunts around town. Among the highlights: authentic Mexican cuisine at Topolobampo, great reads at 57th Street Books, and basketball at the courts on Hayes Drive and South Lake Shore Drive.

In addition to self-guided tour recommendations, the visitor’s bureau has partnered with the InterContinental Chicago and Gray Line Chicago tours to create the Presidential Chicago package, including a stay at the InterContinental and a guided tour of Chicago’s South Shore. When I checked prices for January weekends, I was quoted a rate of approximately $92 per person (or $184 double occupancy).

Before arriving, you may also want to check out the Chicago Tribune’s Obama tour, which highlights 21 Presidential destinations across the city. Stops include his former law firm, favorite restaurants, and key locales for his community organizer work.

Washington, D.C.

All roads have led to Washington, D.C., for Obama—first as a senator representing Illinois, now as the 44th President of the United States. Have a visit of historic proportions with a stroll around the National Mall and its museums, memorials, and monuments; call your state representatives to arrange a tour of the White House; or see our government in action with visits to the Capitol Building and the Supreme Court.

Destination DC, the official tourism bureau for the city, has put together a Staying Power package in association with multiple area hotels. Book a three-day getaway (including a Thursday or Sunday) at a participating hotel and get 30 percent off your stay. Prices start at $71 per night, double occupancy, at the Marriott Key Bridge.

For additional trip-planning ideas, visit the Destination DC website. If you’re planning on attending the inaugural festivities, the tourism bureau has a helpful site outlining events, transportation, volunteer opportunities, and free things to do.

Do you have additional recommendations for Obama-themed destinations or activities that we missed? Share your tips by submitting a comment below!

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