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Are companies that manage remote-worker’s travel worth the cost?

travel agencies for remote workers

For many, remote work sounds like a dream job. For others, it’s just the start. The ability to travel the world while working a flexible job has become a popular option for people wanting to maximize their free time. The trend of becoming a digital nomad has become increasingly popular to the point of multiple organizations, like Remote Year and Venture With Impact, helping support and organize these long-term trips.

As long as you have internet access and a safe space to work and manage the time differences, you are all set. By its sounds, you’d be sitting oceanside with a tropical cocktail in one hand and a laptop in the other. But, is it that luxurious? It depends.

Some digital nomads describe their experience as once in a lifetime. Others regret the large tab that goes along with hiring a remote travel company for their services. The cost can total around $2,000 each month. Is it worth it? Let’s compare using a remote travel agency versus booking and managing your own trips.

Why would you hire a remote travel agency?

Girl Traveler Looks At City Map With Suitcase At Town Street In

In many cases, booking travel can be a time-consuming process. Especially a long-term trip that requires knowledge of the area you plan to stay in. From workspace considerations to accessibility within the city, it can be challenging to navigate a foreign country without an expert’s help.

Remote travel agencies take on the responsibility of managing the big-picture details and the realities that most solo-travellers face – such as loneliness and missed opportunities to fully immerse themselves in the city’s culture.

In a Women Digital Nomads review of Remote Year, one remote worker says she was tired of spending multiple hours researching her travels. She didn’t want to worry about internet connectivity and missed flights.

Let’s not forget, though, with any paid service; there are always aspects that don’t fit perfectly with what you need as a client. One of those aspects is the price tag.

What’s the difference in cost between remote travel agencies and DIY travel?

group remote travel

According to a Medium post from Remote Year staff, if you make less than $39,000 annually, you likely cannot afford their services. If you bring in less than $3,250 each month after tax, your budget would be stretched thin.

For international travel using Remote Year, you can expect to pay $2,000 each month directly to the agency, which will cover your travel costs, private accommodation, access to a workspace with the internet, social events, and special discounts in cities you travel. They also suggest you’ll spend an additional $1,000 to $2,000 each month on your expenses outside of the basics. For international month-long trips using Venture With Impact, the price is similar, coming in at around $2,500.

Although the price is somewhat comparable to living in a major city and paying rent or a mortgage, the caveat is that you don’t already have those expenses to upkeep before you leave. For example, the monthly cost of living in Toronto averages $3,541.24.

One of the Venture with Impact trips is a month-long remote work program in Lisbon, Portugal. The cost is $2,600 each month, but if you sign up four months in advance, you can get a $250 discount. Included in the price is your accommodation, workspace, weekly activities, and you’ll be placed into a volunteer program to give time to local organizations. The cost does not include food, drinks or any further adventures you’d like to take during your month-long visit.

To book on your own, the difference in cost is quite vast. With the savings in paying CAD over USD prices, a direct round trip flight from Toronto to Lisbon is around $1,000, and an apartment on Airbnb with WiFi and a kitchen averages $1,500. You’d be saving nearly $1,000 to book on your own. Of course, you don’t get the added benefit of a community, local experts or planned itineraries. Ultimately, it would be best if you considered your needs, lifestyle, and cost.

How to manage travelling on your own as a remote worker

Air Travel In The Coronavirus Pandemic, Safe Travel, Social Dist

A significant difference between using remote travel agencies and booking on your own is the customization of what you desire in travel. For example, the length of time you travel and the type of places you plan to visit.

Alaia Williams, a self-employed Business Systems Strategist, says she chose to book her travel to help her stay on a stricter budget. “Booking things myself gave me the most flexibility,” says Williams. “I could book and pay when I was ready, and find the perfect flight or place to stay.”

Williams says because work is still a priority for digital nomads, there is no option but to over-prepare. She listed many different scenarios that remote workers should consider, from backup batteries and charging cables to jet lag or food poisoning. These typical challenges that anyone may face during a holiday still exist while you travel during work, except you still need to consider deadlines and client meetings that you can’t always reschedule.

Some critical considerations while managing DIY travel are your budget, timeline, work schedule, and the primary way you earn income. You need to be able to dedicate a certain amount of time during your travel to working hours, so knowing exactly how many hours will be crucial.

Williams says that although it may seem as glamorous as some influencers make it seem, working remotely while travelling is not a vacation. “Landing in your destination and seeing what happens is not a great approach,” says Williams. “You need a plan and a backup plan.”

The best way to decide what option is worth the cost is to consider every variable that comes with your day-to-day work, while also reasonably balancing your ideal travel opportunities. If you’re more interested in a laid back approach to travel, it might be best to hire an agency to help sort out the details. If you like control and have specific needs, you’re likely better off to book on your own.

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Alyssa Davies

Alyssa is an award-winning personal finance blogger and founder of She writes about being a mom, overcoming personal debts, and how to get away with affording your ridiculously expensive latte habit. A new homeowner, Alyssa brings her real-life knowledge of the Canadian real estate market and smart money matters to this growing brand.