Travel Obama's Trail

Posted on: 28 January 2009 by Gareth Hargreaves

To trace Barack Obama's background, get ready for a global game of hopscotch.

From Kenya and Jakarta, to Hawaii and across the United States, many stops on an Obama tour make colourful and intriguing destinations.

If you’re hooked on Obama fever then you’ll want to visit one of the places that influenced the first African-American President. With his inauguration into the White House now over, we’ve put together a guide to help you decide when to visit the places that have shaped his life so far.

Nairobi, Kenya

NairobiBarack Hussein Obama was born in Honolulu, Hawaii to a Kenyan father and American mother from Wichita, Kansas.

The best time for visiting Kenya is between January and March when game viewing is at its best. Stay in the capital Nairobi and explore  from there.

Where To Stay

  • The Sixeighty Hotel is a three-star hotel just five miles from Nairobi National Park with prices starting from £55 per room per night.
  • The Hilton Nairobi is a four-star hotel located in the centre of Nairobi not far from the Bomas of Kenya tourist village. Prices start from £122 per room per night.

Getting There

Kenya has seen an increase in popularity as a holiday destination, and both British Airways and Kenya Airways have increased capacity on their London to Nairobi routes by replacing Boeing 767 aircraft with larger Boeing 777's on many services.

Nairobi Guide

Nairobi is Kenya’s capital and the nation’s biggest city with a population approaching two million. Nairobi is the main gateway to the Masai Mara reserve and the mighty Mount Kilimanjaro - Africa’s highest mountain.

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Wichita, Kansas

WichitaFor a taste of Obama’s American heritage you must make a visit to his maternal homeland of Wichita, Kansas.

In October they hold their annual Tallgrass Film Festival with four days of events and film previews.


Where To Stay

  • The Hyatt Regency is a four-star hotel located in downtown Wichita. Prices start from £98 per room per night.
  • The Broadview Hotel is a three-star hotel just one mile from the Art Museum and Botanical Gardens. Prices start from £76 per room per night.

Getting There

Connecting flights to Wichita are available from hub airports such as Chicago or Atlanta.

Wichita Guide

Situated at the confluence of the Arkansas and Little Arkansas Rivers, Wichita is a major player in the aviation manufacturing industry and the biggest city in Kansas.

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Honolulu, Hawaii

Waikiki BeachObama’s early years were spent on the beautiful island of Hawaii. The busiest time to visit is between December and February mainly because this is when the biggest surf waves appear.

For drier and warmer weather it's best to visit between June and October, especially for diving.

Where To Stay

  • The Ala Moana Hotel is a four-star hotel close to the beach and the main Ala Moana shopping district. Prices start from £97 per room per night.
  • The Waikiki Marina Resort is a three-star hotel with stunning views of the ocean and the Ala Wai Yacht Marina. Prices start from £98 per room per night.

Getting There

Although there are no direct flights to Honolulu from the UK, an extensive range of options to connecting flights via the USA or Canada is available.

Honolulu Guide

Honolulu is the capital of the Hawaiian Islands and the largest city in the Pacific. Honolulu offers a unique mix of modern Americana and ancient tradition, not to mention one of the world’s most famous surfing meccas - Waikiki Beach.

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Jakarta, Indonesia

JakartaWhen Obama’s mother remarried an Indonesian man she moved the family to its capital Jakarta.

The best time to visit this culturally rich city is between June and September when rainfall is at its lowest and there is less risk of flooding.

Where To Stay

  • The ALiLa Jakarta Hotel and Resort is a four-star haven of relaxation in the centre of Jakarta. Prices start from £66 per room per night.
  • The Le Meridien Jakarta is another four-star hotel located within easy reach of all the historical attractions of the capital. Prices start from £84 per room per night.

Getting There

Soekarno airport is the main international hub serving the sprawling Indonesian capital Jakarta. There are currently no flights to Jakarta from the UK, but connections are available through Amsterdam and Frankfurt.

Jakarta Guide

Like many other latter-day cities this is a destination of extremes. Shacks and skyscrapers denote the vast gulf between rich and poor, while the weather goes from a sweltering average humidity of 81%, making air conditioning a must, to all-out flooding during the monsoon season, when the city’s ill-equipped underground canals frequently burst their banks, resulting in flooded streets.

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Los Angeles, California

HollywoodObama spent his school days in Honolulu, living with his maternal grandparents but upon graduating high school he went to study in Los Angeles for two years where he began to shape his political career.

LA is known for its year-round warm weather, so there's never a bad time to visit. Trips to the beach are best saved for late summer and if you’re after some serious celeb-gazing then it’s best to visit during the awards season in February and March.

Where To Stay

  • The Sheraton Los Angeles is a fantastic three–star hotel situated right next to shoppers’ heaven, Macy’s Plaza and the new entertainment destination LA Live. Prices start from £98 per room per night.
  • The Hilton Checkers is a four-star European-style boutique hotel located in downtown Los Angeles. Prices start from £100 per room per night.

Getting There

Direct flights to Los Angeles are available with no less than five airlines based at London Heathrow, but so far attempts to offer regional UK departures have not materialised.

Los Angeles Guide

The city of Los Angeles - also known as the City of Angels or simply LA - is the largest city in California. Located on a broad basin in Southern California. It's surrounded by vast mountain ranges, deep valleys, forests, desert and miles of coastline on the Pacific Ocean.

Los Angeles is an important centre of culture, business, media, and international trade, but is most famous for being the centre of the world's entertainment industry, which forms the base of its global status.

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New York City, New York

New YorkFrom LA, Obama headed straight to the Big Apple, New York, to complete his studies and begin his political career.

New York is great year-round; whether you want to see Central Park in the Spring, go ice skating in Winter, or shop ‘til you drop whatever the weather.

Where To Stay

  • The Radisson Lexington Hotel is a three-star hotel just three blocks from the Rockefeller centre and four from the Broadway theatres. Prices start from £65 per room per night.
  • The Park Central New York Hotel is a three-star hotel located close to Central Park and Fifth Avenue. Prices start from £79 per room per night.

Getting There

Direct flights to New York are available from a wide range of UK regional airports, but the frequencies are much higher from London.

New York Guide

New York is one of the world’s great cities, managing to enthrall everyone from first time visitors to Big Apple veterans.

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Chicago, Illinois

ChicagoAfter four years in New York, Obama moved to Chicago where he met his wife, Michelle. Chicago is a bustling city, popular all year round.

Like most US cities, Chicago is particularly popular in the summer, especially during events such as Taste of Chicago. If you're prepared to brave cold gusts from Lake Michigan, January, February, and March are less busy than the rest of the year and often great hotel deals can be found.

Where To Stay

  • The Marriott Chicago is a three-star hotel close to the University and Little Italy. Prices start from £85 per room per night.
  • The Hyatt Regency McCormick Place is a three-star hotel with incredible views of downtown Chicago. Prices start from £79 per room per night.

Getting There

One of the world's most important aviation hubs, Chicago's two airports offer flights throughout the USA, with feeders inbound from London and some other UK regional airports.

Chicago Guide

Set on the shores of the mighty Lake Michigan and home to the world’s first skyscraper, Chicago is still reaching for the skies and is one of America’s most impressive cities.

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Washington DC, Washington State

WashingtonObama has begun his first term in office at the White House in Washington, the capital of the US.

Washington is a popular place to visit from mid-March through to July, and again from September through early November, if you fancy trying to catch a glimpse of the man himself.

Where To Stay

  • The Grand Hyatt is a three-star hotel right in the cultural heart of downtown Washington DC. Prices start from £79 per room per night.
  • The Madison Hotel is a four-star hotel located just four blocks from the White House. Prices start from £105 per room per night.

Getting There

There are three main airports serving the US capital region - Dulles, Baltimore and Washington Reagan National, which is primarily used for domestic flights.

Washington Guide

Unlike many capital cities, Washington DC does not also serve as a leading business and population centre. Washington DC may be small, but it packs in a huge number of sites nonetheless, including Capitol Hill, the Washington Monument, the Lincoln Memorial, the White House along with some of the best museums in the world.

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Web Links

Hotels - To book any of the hotels featured above, visit

Flights - Find the cheapest flights to your chosen destination by visiting

Have you visited any of Obama's former homes? Do you have any travel tips to pass on to 50connect readers?

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