Context Travel Review - Find new gigs - Make Extra Money On The Side

Context Travel Review

Compensation : -
Category : Travel Services
Skills Needed : Travel and Tours
Gig Type : Work from home gigs

What is Context Travel?

Based in Philadelphia, Pennsylvania, Context Travel offers educational and exploratory experiences in cultural capitals around the world. Its team of experts runs in-depth tours for intellectually curious travelers in more than 45 cities “from Bangkok to Boston.”

Established in 2003, Context Travel was bootstrapped and founder-led until 2017, when it obtained growth funds to expand its offerings, develop an executive team, and expand to more than 100 cities worldwide.

How does Context Travel work?

With the growing popularity of ‘bleisure travel’ (combining business and leisure travel in the same trip), Context Travel, one of the country’s leading travel management companies, offers business travelers unique opportunities to submerge themselves in the history and culture of a city on tours led by local experts

The Docents who lead the tours, made up of no more than six people, hold expertise in areas such as art history, archeology, cuisine or classical studies.

If it’s to gain a better understanding of a city and its people before the business interactions starts or to experience some enrichment and learning for pleasure after the meeting, this new partnership makes it easier for business travelers to maximize their time in a wide variety of destinations around the world.

What are the requirements to work for Context Travel?

  • The Docent must have a people’s skills, enthusiasm and knowledge of the area in which he/she wants to lead the tours.
  • Being bi or multilingual makes you extremely attractive, so if you speak more than one language, your opportunities skyrocket.
  • Pass a criminal background check
  • Civil liability insurance is advisable.
  • A degree, especially in hospitality, certainly helps but is not a requirement.

How do you earn money on Context Travel? aims to deepen travel experiences for backpackers, globetrotters, sightseers, and tourists. The company organizes walking seminars led by archaeologists, chefs, historians, and a variety of local experts.

How much money can you make on Context Travel?

It’s hard to pinpoint precisely how much Docents make for leading a walking seminar. They are likely to make a percentage of the total cost of each walk and Context Travel will take a commission on each walk. You will need to apply to be a Docent with Context Travel to find out.

Pros of working for Context Travel

  • Wake up whenever you want, attend meetings when it’s convenient, go out running errands in the middle of the day. The advantages of working for you are many!
  • It is a great way to learn about new places while making money and it is definitely an exciting job.
  • You meet all kinds of different people, and no two workdays are the same.
  • Now in more than 45 cities worldwide (including 10 in North America), Context Travel is a leading provider of small personalized tours.
  • All Docent live in cities where they guide.

Cons of working for Context Travel

  • Creative exhaustion is always around the corner.
  • Self-motivation can be tricky. With freedom comes a bunch of somewhat difficult responsibilities to navigate.
  • If you will not be productive enough or make the wrong decision, you will see it on your next paycheck.

How do I sign up to work on Context Travel?

Click on “Sign Up” at the top of the website to get started.

What is the Context Travel website?

Does Context Travel have an application?

There are no apps available.


If you love action, history, and working with people, then it might be a good idea to consider becoming a tour guide. If there are specific destinations and activities that you are passionate about and familiar with, then become a Docent.

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Last updated : 2/3/2023

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