One of the best ways to travel more without taking a prolonged career break or losing a job you love is to embrace the new trend of working vacations. A 2024 study revealed that almost 40% of US workers take ‘workcations'. Working while you travel enables you to enjoy the best of both worlds. 

If you’re eager to travel more but can’t get that much time away from work, this guide contains top tips to help you embrace work-based opportunities while globetrotting. 

Explore your options

There are multiple ways to take working vacations or work while you travel. It’s beneficial to explore your options before you decide what to do. There are two main routes to consider. The first applies to people who already have a job and want to see more of the world without losing that position. The second applies to individuals who are considering giving up their job or changing careers and those who don’t currently have employment. 

If you have a job and you don’t want to give it up, paths to consider include taking a sabbatical, swapping to an office or branch in a different region, country or continent or working remotely. Remote work has become increasingly common in the last five years. In the US, over a third of workers now operate remotely all the time. Advances in technology and the availability of reliable, fast Internet connections mean that many of us can now work from almost anywhere. Speak to your employer, find out which options are available to you and consider what you want to achieve from your trip. Remote work, for example, will provide you with more freedom and flexibility than relocating to a different office. 

If you don’t have a job, or you’re thinking about giving up your role or changing careers, you could explore routes like getting a casual job while you travel, applying for a position in a different country or becoming a digital nomad. Think about your budget, whether you need a steady and stable income, how long you plan to travel and what you want to see and do on your vacation. If you want to work while you’re traveling, start following relevant social media accounts, look for opportunities and vacancies online and get ideas from travel communities and forums. There are myriad roles that may suit you, ranging from bar work and teaching English to getting an office job or applying for a position similar to your current role and putting down roots in a new city or country. 

Choose a suitable destination

Working remotely is a brilliant way to see the world, but it’s not always plain sailing. If you plan to switch to remote working and keep your current job, or you’re exploring new remote working opportunities overseas, choose a suitable destination. Think about what you need to do your job effectively as well as how you want to spend your leisure time. If you’re on the phone all the time, or your schedule is packed with meetings, you’ll need a reliable WiFi connection and a dedicated workspace that enables you to focus and engage with colleagues or clients. It’s probably best to avoid rural areas or places where there are no modern offices or coworking facilities. If you are an intrepid explorer, you could always schedule some time to explore off-the-beaten-track treasures before you return home rather than trying to combine work and travel. 

If your plan is to work while you travel and pick up an income on the move, you can be more flexible, but you’ll need to make sure that there are jobs available. Casual jobs like working in bars and restaurants and doing deliveries may be easy to find in large towns and cities and established tourist resorts and hotspots, but you might struggle to make money if you opt to stay in more remote locations. Research opportunities before you choose where to travel. 

Find somewhere to stay

Whether you’re going on a 2-week vacation or you plan to be away for months or even years, it’s beneficial to consider where you’re going to stay. Your budget will be influential when it comes to creating a shortlist, but it’s also crucial to think about your plans. Are you going to be in the same place for a while, or will you be moving around every day, week or month? Depending on your budget and travel goals, you could consider everything from luxury real estate and long-term lets to camping, sofa-surfing and booking hotels, motels and guesthouses. 

Research prices, find out more about specific areas, resorts, neighborhoods and communities and draw up a rough plan. If you’re relocating to a different office, or you’re hoping to get a job and stay in the same city or town for a significant period, it’s worth asking locals for advice about where to look for places to stay or live. They will be able to point you in the right direction and they may also have recommendations for real estate and rental agencies, things to see and where to eat and drink. 

The Internet has made it much easier to find accommodation without viewing properties in person or pounding the streets looking for hotels or apartments to rent. Take advantage of virtual tours and viewings, chat with agents online and browse listings to see what’s available. You can sign up for alerts if you have a specific area in mind, or you’re searching for a condo or townhouse in a neighborhood when properties are selling or going off the rental market rapidly. 

Set realistic expectations

The idea of working while you’re on vacation may seem like a dream, but in reality, it can be hard to balance traveling and working. Managing expectations is key when planning any kind of trip that involves work, exploration and relaxation. If you plan to have a full-time job, for example, you’re not going to be able to take full advantage of beach living or enjoy lazy days by the pool. 

If you don’t have a job, you may be able to travel more, but you’ll need to think about how you’re going to fund your trip. Careful planning can help you draw up an itinerary to find the right balance. Many people choose to work for a period and then travel while others have more flexible roles and working schedules that allow them to do both simultaneously. It’s important that you go into the process with realistic expectations. 

Identify potential obstacles and challenges

Most of us are used to working and then taking a vacation. If you’ve never taken a working holiday before, or you’re new to the idea of traveling and working at the same time, it’s crucial to be aware of potential challenges. Examples include differences in time zones, the availability of amenities and facilities and language barriers. 

When you’re researching destinations, consider these obstacles and difficulties and try to find ways to avoid or overcome them before you start your trip. If you’re aware of risks or problems, you can solve them or reduce risks before they cause you issues. If you talk to clients or colleagues regularly, or you have a full schedule of meetings, for example, it’s wise to choose a location that isn’t in a completely different time zone. 

Establish clear boundaries

A working vacation should enable you to work efficiently and effectively and explore your chosen destination. To enjoy the best of both worlds, it’s beneficial to establish clear boundaries. Set out plans outlining what you want to see and do during your time in a specific city, region or country. Create a work schedule or timetable that enables you to complete the necessary work-related tasks and make time for sightseeing, cultural activities and downtime. 

Working remotely provides more flexibility but it can make it more difficult to switch off. Many people find that they work longer hours when they don’t have a set schedule. Using boundaries can help you get the balance right and organize your time. 

Consider your priorities

People travel for different reasons and they have different goals, preferences and ambitions. When you’re planning a work trip, or thinking about where to go to enable you to travel more while earning an income, consider your priorities. What are your goals? What do you want to get from your vacation? How far do you want to go and how long will you be away? Are you focused more on work, or are you looking for flexible, casual opportunities to boost your income so that you can prioritize backpacking, recharging your batteries or living the high life? Tailor your plans to suit your needs and objectives. 

More and more people are choosing to work while they travel or plan working vacations. Whether you have a job, or you’re exploring opportunities to find work while you’re abroad, there are steps you can take to plan a successful trip. Consider destinations and locations carefully, explore different work options and think about your travel and work goals and priorities. Research accommodation options and find out more about vacancies. Identify potential challenges before you jet off and be proactive in finding solutions. Set clear boundaries to enable you to achieve your goals.