Resources How to Find the Best Countries to Experience the Winter Holidays for Work and Leisure

How to Find the Best Countries to Experience the Winter Holidays for Work and Leisure

Are you one of many contractors that are looking to work in a new foreign country? 

If so, you might not know where to begin when selecting a work location abroad, or what criteria to use.

Take David as an example.

David is a contractor who is considering the European region, but doesnt know what to expect in terms of climate, culture and holidays.  Without some background information, he could end up in a place they don’t really enjoy.

So we will show you a few ways to narrow down your search.

As you are looking for work abroad, one thing that you may wonder about are the differences between countries during the winter holidays. 

This can be most important for contractors who are considering immigrating to the country, as they will experience the holidays for many years. 

Or you may be looking for locations to easily escape cold weather for a more sunny holiday away from work.  You will have the most variety and options in the European region, with access to both quality work and appealing vacation spots.

Best Countries to Experience the Winter Holidays for International Contractors 

When you are looking for the best countries to experience the winter holidays for work, climate will be a key consideration.  There are also country and cultural factors that might be important to you, depending on  family ties, nationality and simple recreational preference.

Even if you choose to work in a cold climate such as Switzerland or Germany, there are nearby options for sunny winter holidays in Europe.  For example, Portugal and the south of Spain offer beaches and warm weather for winter holidays. 

Those without EU citizenship can avail of short tourist visas for their travel and vacation with no problem.

Then there are those that prefer the cold weather and snow or ice recreation. 

Any European country near the Alps will offer you snow sports, such as France, Austria and Italy. 

If you work in these countries the advantage is that you don’t have to travel for the best European winter holidays, as it’s right at your doorstep.

Contractors that work in Australia or New Zealand will learn that in the southern hemisphere the seasons are reversed, so Christmas holidays are celebrated in ‘summer’. 

This might be hard to get used to for those from the north, but you do have the benefit of warm weather and beaches while much of the world is in cold weather.

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Top Countries Where You Can Mix Remote Work with Vacations

If you are an experienced contractor, you might already know that working in certain countries or regions gives access to vacation spots nearby for sunny winter holidays in Europe. 

This is one great advantage of remote work abroad, as it can give you maximum flexibility.  A remote contractor might select a country sheerly for its vacation-style ambiance, especially if the country offers a digital nomad visa. 

Here are some examples of countries offering remote work visas along with relaxing locations that you might find appealing.

Canary Islands, Spain

The Canary Islands off the coast of Africa are a part of Spain which has a new digital nomad visa (DNV) for remote workers set to begin in 2023. 

One advantage of the Spanish DNV is that a contractor can stay anywhere in the EU short or long term, which opens up travel possibilities. Spain also has a self-employment visa available if you want to work for Spanish clients.

Otherwise, you can only derive 20% of your income from Spanish sources. 

The Canary Islands are affordable, offer white sand beaches and excellent connectivity for online work, a sure attraction for remote workers. 

The digital nomad community is especially vibrant in Tenerife and Gran Canaria, with active Facebook groups offering apartment rentals, social events and even surfing coaches. 

Younger workers will connect easily with like minded expat contractors in the Canary Islands, whether you want to go hiking, rent a scooter or find the best nightlife after a day’s work. 

Algarve, Portugal

Portugal also just introduced a digital nomad visa which allows non-EU remote workers to enjoy living in vacation spots like Algarve.  (Keep in mind that if you are an EU citizen, you don’t need a work permit of any type). 

The primary visa requirement is a monthly income of at least EUR 2800, and there are two visa categories of one or five years. 

Contractors wishing to immigrate to Portugal via permanent residency may do so with the five year DNV.

Algarve is a picturesque beach haven, with traditional architecture alongside rolling golf courses, and an ideal location for remote workers seeking perpetual sunny winter holidays in mainland Europe.

Madeira, Portugal

Another Portugal location that is truly remote are the islands of Madeira near the coast of Africa.  Madeira has a mediterranean climate year-round, whale watching and world-famous vineyards. 

As a part of Portugal, a contractor can avail of all the visa options and benefits.  

Due to the popular new digital nomad visa in Portugal, remote workers have even set up their own expat village in Ponta do Sol. 

In cooperation with the local government, the digital nomad village has a free co-working space, high speed internet, co-living opportunities and networking events for the expat community. 

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There is a dedicated Slack channel for the village, to keep everyone updated and connected.  As the founder of the village stated: “I’ve been in Chiang Mai, I’ve been in Bali — beautiful places.

But in Madeira, there are epic hikes, waterfalls, the green, the ocean all in the same place. And we have the European infrastructure: fast internet, security, few internal borders. When I came to Madeira, it blew my mind,” he says.


Italy has something for everyone, whether it’s skiing in the Alps, exploring ancient Rome, or eating the world famous cuisine oceanside, you can surely find the vacation experience you want. 

Italy has a new DNV along with its self-employment visa for contractors, with a low income requirement of EUR 8500 per year.  There are significant tax breaks for expat workers depending on the region and type of visa, which can increase your net income.

Italy may be one of the best countries for you to experience the winter holidays for work, as you can select a new locale each year for your holiday without leaving the country.

Aside from Portugal and Spain for warm weather European winter locations, other countries in northern Europe are popular for the work opportunities. 

Some of the best places to get work experience abroad are Belgium, France and Germany with their robust and diverse economies.  If you are wondering about immigration requirements.

All these require traditional work visas from your client or through an umbrella company

Also, some of the best European winter holidays can be in colder climes that have a more traditional feel with cultures steeped in history.

Another great option is the country of Netherlands, with an established winter culture offering many recreational opportunities for those who like the snow.  

One American contractor shared how they were able to secure a self employment visa in the Netherlands under the Dutch American Friendship Treaty. 

The visa is available for any type of business and only requires a bank deposit of EUR 4500.  It can be used for both in-country and remote work as long as you can show you have income. 

If a contractor wishes to immigrate to the Netherlands they can apply for permanent residency after five years using this visa.

How Contractor Taxation Works and Can Help You Working Abroad

As you are searching for the best countries to experience winter holidays for work, there are practical issues as well.  If you are new to contracting abroad, calculating taxes and any expat benefits can be overwhelming. 

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Not every country will offer self-employment visas or a DNV, so you will have to find a way to be in compliance. 

This is where contracting through an umbrella company can be of real value: from invoicing, obtaining work permits, receiving payment and paying taxes.

Contractor Taxation has fully vetted umbrella companies across Europe that can assist you with understanding immigration requirements and act as sponsor for your work visa. 

They will also help you know the tax rates and compute your net salary.  This means that you can know your real income pre-hire, and will have an ally throughout your contracting journey.

You can benefit from umbrella companies if you want to avoid:

·  Managing client payments, tax withholding and any social contributions

·  Issuing a payslip each month, to a local or foreign account

·  Sponsoring work permits

·  Setting up the contract with the client

·  Moderating any disputes with your client

·  Advising on access to totalization and double taxation treaties

If you have questions about how an umbrella company can help you as an international contractor in Europe, please contact us at Contractor Taxation.

What You Should know Before Deciding

How do holidays schedules work for companies with workers in multiple countries?

While the client will likely follow their home country holiday schedule, they will still have to accommodate workers located abroad with differing schedules.  This is more than just a good business practice, as some countries will mandate that certain holidays and time periods be observed.

How do international contractors handle the holidays when they have to spend the time in the country of work?

Some contractors may just stay in the work country/location for the holidays due to convenience, cost or need to be available.  In that case, they can participate in local celebrations, try out new recreation or just have some time to relax.  Every country has some type of holiday tradition, and we have described a few of the best countries to experience the winter holidays for work.

What is the advantage of securing a work permit with an umbrella company, even if there is a digital nomad visa available?

DNVs are strictly limited to remote workers who have clients outside the country, and are choosing the host country for its lifestyle or vacation atmosphere.  So any contractor that is hired by a client in-country must have a valid, sponsored work permit.  This can be obtained with the help of the client if they are willing, or through an umbrella company.

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