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This is a guest post by Rosemary Bointon, a retired digital nomad with decades of experience living on the road.
Travel is probably the number one desire shared by both older people and younger ones alike.
Empty nesters over 50s, seniors, and retirees see all the articles about young things legging it off to Thailand or Bali, and they want to go too.
But then all the doubts creep in. You need to save for your retirement or you want to finance the kids through college. If you’re already retired, maybe you think you can’t afford it. You don’t want to run out of money in case you get ill. And what if you get ill abroad?
The dream starts to look impossible.
But it doesn’t have to be like that. It’s quite possible to take off and exchange your mundane troubles for very different ones. Why not do what the youngsters do and work your way around the globe?
It’s an interesting thought, but it leaves us with one big question…
There are tons of jobs that allow you to travel, but what are the best travel jobs for SENIORS?
Well, it turns out, there’s something for everyone.
In this guide, we’ll explore a bunch of different travel jobs for retirees, seniors, and older people—divided into four main categories:
- Digital nomad jobs for seniors
- Working in the travel industry
- Snowbirding and seasonal work
- Remote work
By the end, you’ll know exactly how to afford to take off into the wide blue yonder.
Let’s dive in.
Table of Contents
- The Digital Nomad Dream
- Working in the Travel Industry
- Going Remote to Do the Same Job Abroad
- Senior Travel Jobs: The Experiences You’ll Never Regret
The Digital Nomad Dream
The seminal work on how to be a digital nomad is probably Tim Ferris’ Four Hour Work Week. He describes how to end up working only a few hours a week and the rest of the time, you live off the passive income. He’s inspired millions to do likewise.
It’s true that some people manage to earn a living by bashing away at their travel laptops from some remote location. We’ve all seen pictures of youngsters lying in hammocks working from tropical islands, carrying their compact digital nomad office setup with them to every new exotic destination…
There’s no reason why we can’t live that dream that too!
In fact, digital nomad trends show that seniors actually make up a big chunk of the demographic.
Before we get into the job ideas, this video covers everything you need to know about the logistics of starting a travel lifestyle.
And with that, let’s jump into our first category: Digital nomad jobs for seniors.
#1.) Blogging and Affiliate Marketing
The Job: If writing your own blog grabs you, then start learning all about it now. When the lockdown is over and travel resumes, you’ll have the ability to take off and still keep earning a few dollars.
The Skills: You need to learn how to write, find your tribe, use blogging platforms, market yourself, master social media, and monetize with ads, affiliate marketing, and other products.
It can be a lot to bite off if you’re tech-challenged, and you can shorten the learning curve (and save yourself some big headaches) by taking a blogging course that guides you through the process systematically.
If you’re specifically interested in travel blogging, this free mini-course will get you off to a good start. Then, check out this Travel Blog Prosperity review for a sneak peek behind an awesome exclusive membership community for travel bloggers.
Long term: It takes a lot of work and a lot of time to build up to earning a decent income from your blog, but it can be a huge amount of fun and you’ll meet a lot of interesting people along the way. Plus, you can do it from anywhere with an internet connection. Check out these travel blogs that make money for inspiration.
Show me the money: Theoretically, you can earn millions, and some people really do (take a look at Pat Flynn’s blog). Some people never earn anything. That doesn’t mean to say that it’s not worthwhile! Most people earn quite modestly and it helps stretch their retirement funds. In fact, even if you don’t earn a cent, it’s still a fun way to entertain yourself while traveling while simultaneously documenting your adventures.
#2.) Write for Other People
The Job: If you’ve got the writing skills, try your hand at writing for others. With so many people creating their own blogs, there is demand for content marketing, copywriting, editing, and proofreading too. Being comfortable with navigating SEO requirements helps a lot. While some jobs are in an office, it’s highly acceptable to work remotely and also freelance.
The Skills: Pretty much the same skills are needed in terms of writing skills as for a blogger. You’ll also need to learn how to land entry-level writing jobs. One way is to learn to navigate the job boards. LinkedIn is also a great place to advertise your wares. You can build up a portfolio of work on Medium.com and if you get into their partnership program, you can start earning a small amount on everything you publish there.
Many new freelance writers find themselves stuck writing for peanuts. Let me assure you, it doesn’t have to be this way. One of the most effective ways to leapfrog into the “big leagues” is to take a content marketing certification course. This free webinar is also a good place to get started.
If you’d rather get paid to proofread other people’s writing, this free workshop teaches how to attract the best proofreading clients.
Medium-term: It takes a while to get jobs and build up a client base. Once you have a good reputation, it’s a lot easier and you can start putting up your rates.
Show me the money: A suggested starting rate is $200 USD for an article of 2000 words (around $0.10 per word). With that rate, you’d be able to make $50 a day online writing just a couple articles per week. And depending on what country you’re traveling in, this is more than enough!
You’ll find a lot of so-called ‘content mills’ offer far less than that. Try them if you want to get some experience but they can be very demanding as to quantity if not for quality. This remote jobs site often has loads of vetted freelance positions. And after you build some experience, this newsletter hand-picks the top 1% of freelance job opportunities and delivers them straight to your inbox each day.
For even more tips, check out this complete guide to the gig economy for boomers.
#3.) Using Your Digital Skills
The Job: If you’re tech-savvy, it’s easy to find gigs you can take on the road. As long as you have a laptop, some sort of mobile hotspot for digital nomads to stay connected (and some quality digital nomad health insurance is a good idea too), you can work somewhere exotic. The kind of digital jobs that travel well are things like building and designing websites and setting up digital marketing systems such as email marketing. Cyber security is currently attracting a lot of interest as well.
The Skills: In this age of lockdown, more people need help with their online presence. They are looking for help with web design, computer programming, cyber security, payment systems, hosting services, agile working, client relationship management systems, software engineering, systems and project management, and many other kinds of information technology systems.
It’s pretty technical. For example, you need to know that Python is not a snake but a coding language (nothing like Parseltongue – it isn’t magic at all) and Java isn’t coffee but another programming language. If you’ve already got some IT or digital technology skills, keep yourself up to date. Team players will have a good chance of finding a great job.
If tech stuff sounds too complicated, check out these easy freelance jobs for beginners.
Medium Term: Try looking for jobs in places like Toptal for higher-end digital jobs. If you want some quick experience, try Fiverr. Their site has a lot of good advice for starting out. As for all consultancy jobs, you need to gain a reputation and build up a client base. Jobs are often full-time, but it is possible just to accept short-term gigs during a specific season as you travel slowly. The Retired Brains website is another good source of senior digital jobs.
Show me the money: Some of these are the best paying travel jobs for retirees. If you’re working for clients on a regular basis, it’s not uncommon to earn USD 80 – 120 per hour for advanced work. If you are doing more routine jobs, it’ll obviously be a bit less. Toptal says its people earn between USD 800 – 3000 per week.
If you’ll be receiving international payments, you’ll also want to open up an account with one of these nomad-friendly banks. It’ll save you both money and headaches.
#4.) Selling products and services online
The Job: Many digital nomads are making a living selling (or rather, re-selling) products and services online.
One example of this is a drop servicing business. This is similar to an agency model, except instead of hiring employees, you outsource work to affordable freelancers. So, say you land a client who pays you $1,500 to create an animated explainer video for their business. You then outsource the job to a freelancer who charges $500, which leaves you a nice $1,000 profit.
Another example is an Amazon FBA business. You source a product to sell on Amazon (usually from China), ship your inventory to Amazon warehouses, and pay them a cut of your profits to handle your orders for you.
The Skills: All of the skills needed for these types of businesses can be pieced together using free information and trial and error. But that’s not always the best way to go. It not only takes a lot longer to get up and running — cutting into your senior travel time — but it also increases your risk.
For drop servicing, this free webinar is a good place to start. I admit that it initially feels a bit “hyped up.” But if you make it to the middle section of the webinar, there are actually some useful gold nuggets in there. If you’re looking to get off the ground as quickly as possible, check out this Drop Servicing Blueprint review.
For an Amazon FBA business, this free masterclass is a good place to start. This is business model requires you to invest in initial inventory, so it’s definitely worth following a proven framework. This Marketplace Superheroes review gives an inside look at one of the most popular training programs.
Long Term: These businesses don’t grow overnight. They require front-loaded effort, but they also can offer the most flexibility and freedom. If set up correctly, they can become almost completely automated.
Show me the money: Since your income is not directly tied to your time, there are really no limits to how much you can earn. It all depends on your margins and sales numbers.
Working in the Travel Industry
#5.) Travel Agent
The Job: It’s always been a classic way to travel. You work for a travel agency and get to try out the holidays they offer so that you can sell them to clients all the better. The easiest way to get started is to get your toes wet working with a local travel agent. Ask if you can be an intern, just for the experience. That way you’ll see if it’s the kind of job for you.
The Skills: You need to have great sales skills, superb organization, a great memory for names and faces, and loads of people skills— including big dollops of patience. You also need to know all about any particular holiday or travel schedule that a client might want. That means an intimate knowledge of all the season alternatives and insider tips that can transform an average holiday into a dream trip (and make your commissions soar).
You need good computer skills to navigate to websites to show to customers. You’ll also have to learn how different booking systems work. To set yourself up for success, it’s a good idea to get certified through companies like The Travel Institute.
Long Term: Working as a travel agent is a long-term job, whether you work for an agency or run your own business. Just be aware that those wonderful-looking familiarization trips are actually rather hard work. You might be required to check out 10 hotels in one day plus get to know all about all the side trips that a client could choose.
Show me the money: Pay rates vary. Some agencies offer commission only, whilst others provide a base salary and pay commission at a lower rate. Expect to earn around USD 18 – 20 per hour.
#6.) Tour Guide
The Job: How about working as a tour guide? There are all different kinds of guides. A guide for a day trip, a museum guide, a guide to monuments, art galleries, and all things historical. If you like to communicate a passion that you have, it’s one of the best jobs for retirees.
I once met a lady who did tours of nature reserves in the Austin area – she was a biologist by training and loved being a tour guide.
An alternative type of tour guide is one who accompanies a group of people on a tour lasting 10 to 14 days. It’s long hours, but you do get to see all the sights and with tips, the pay can be quite good. For example, you might be involved in a tour that takes a group of travelers around Italy. For obvious reasons, it really helps if you speak a foreign language.
Jooble is a great place to look for tour guide jobs.
Snowbirding and Seasonal Working
#7.) Seasonal jobs for seniors
The Jobs: A great way to see different parts of your country (or the world) is to take on seasonal work. There are many opportunities in hospitality, such as working in hotels, bars, and restaurants around the world where older people are welcomed. Another popular option is to work in a ski resort for one season and then leg it down south for some sun.
Alternatively, some companies need their workers to move on a seasonal basis. For example, some pharmacies like people in New Jersey in summer and Florida in the winter.
The Skills: There are so many seasonal jobs on offer, and the skills you need depend on the job you choose. You may need to know how to be a receptionist, a maintenance engineer, a driver, a cleaner, a cook, a bartender, or even a fruit picker (although that might be a bit too physically demanding for some). Fortunately, many of these skills can be picked up fairly quickly through different courses. And once you master one of these in-demand skills, you can offer them all around the world.
To find the best fit for you, you may need to think outside the box. What about working a seasonal retail job selling souvenirs in a seaside resort. Or how about learning some farming skills by working on an organic farm for the summer season? WWOOF is a great place to find this type of volunteer work (with food and accommodation provided).
I knew a couple who taught diving in the summer in the Caribbean and skiing in the winter either in Europe or Canada. What an adventurous retirement!
Short Term: Seasonal work is by its nature transient. You work for a season and move on. The range of jobs and therefore skills required is enormous and you need to spend some time investigating what’s on offer. Try Coolworks for more adventurous senior travel jobs or Retired Brains for seasonal jobs classified as ‘encore careers’.
Hard work? Yes, but think of all the different places you’ll see and the new people you’ll meet!
Show me the money: Most seasonal jobs are not highly paid, although depending on the job, you may have the chance of good tips. Some jobs provide accommodation, although it’s usually pretty basic. Others are couple-friendly, making seasonal work one of the best travel jobs for couples. The cool thing is you’ll get the chance to live and work in all sorts of different places.
#8.) Van Life for Senior Travelers
My friend, Margo, is a brilliant example of a senior nomad who lives and breathes van life and has done for 26 years. Take a look at Margo’s website or find out more from her RV Lifestyle Expert podcast if you think this could be the right kind of travel lifestyle for you. She has loads of practical advice on how to set about your new van life.
The Jobs: Margo is a true digital nomad and earns money from her website and her e-books, but there are lots of other jobs that you can do from an RV. If you love to camp and the outdoors, Margo says that you can work on a campground at a national park that you always wanted to visit while you live in your RV. To find out more, try Margo’s e-book ‘Working on the Road for Professionals and Just Fun-Loving Folks. Margo recommends Workcamper.com as a good place to start to find jobs as an RV-er.
Parks aren’t only about campsites, though. There are jobs going in retail shops, amusement parks, water parks, lodges, farms, and state and county parks as well as in the national parks. You are usually required to live on-site.
The Skills: Like a lot of seasonal jobs, the skills you need will be many and varied, according to the many and varied jobs. But start with a cheerful can-do attitude, a problem-solving mindset, and a love of meeting people. Then add a technical skill, and you’ll be a happy camper!
Short Term: These types of RV and van life jobs are seasonal and so are by definition fairly short term. But if you build up good relationships, you’ll be able to return for another season or you’ll get recommendations to work in other places.
Show me the money: Seasonal jobs tend to be low paid. For RVers working in national parks, expect around USD 8 per hour plus a free RV site and utilities (which boost the effective rate).
#9.) House Sitting and Property Caretaking
The Jobs: House sitting is a fun job for retirees. It means taking care of somebody’s house with everything that comes with it. That means watering the plants, collecting the mail, and oftentimes, looking after a furry friend.
A variant of house sitting is to become a property caretaker. These are a great job even if you’re a senior over 60. They include things like the upkeep of the grounds, buildings, and facilities such as swimming pools. The website CaretakerGazette.com provides lots of information for would-be property caretakers.
The Skills: Your main skill is to be free of crime and to be able to demonstrate your reliability (hopefully that’s not too hard!). This builds up as you get more gigs and more references from happy owners. If it involves pet sitting, then owners want to know if, for example, you know how to look after a horse or goats as well as more usual pets such as dogs, cats, rabbits, or fish. Otherwise, you just need to be sensible and responsible.
Usually landing your first gig is the hardest, but you can better your odds by following the advice in this housesitter jobs guide.
Property caretaker skills include gardening, general DIY skills for maintenance and cleaning plus potentially the ability to look after animals.
Short term – Long Term: House sits vary in length from a few days to several months, depending on what the house owners are wanting to do. If you go for a property caretaker job, it’s more likely to be a longer-term job.
Show me the money: You pay a fee of between $20 – $130 annually to list yourself on a housesitting platform, enabling you to browse destinations and jobs. Some of them are hotly contested. You normally pay for your own travel and generally don’t receive compensation, but you have free accommodation (sometimes in very nice houses) and get to live like a local wherever you get a gig.
Usually, you don’t have to pay for utilities although you do pay for your own food. You also may get the use of a car.
Property caretakers get free accommodation and a salary that can range from minimum wage to generous.
Going Remote to Do the Same Job Abroad
Covid has transformed how people work. It used to be only the privileged few who could work remotely but now everyone is doing it. These are some of the best-paying jobs that allow you to travel the world.
From hospitality jobs to medical jobs, many types of personal service jobs travel well. Here are some regular jobs that you can transform into your very own overseas jobs.
#10.) Bookkeeping and Tax Preparer
The Jobs: When you’re good with numbers and tax rules then bookkeeping or a finance job can be great for you in retirement. You can become a freelance bookkeeper who works online and do the books for different small companies. The IRS in the USA has seasonal jobs from January through May.
Remote work is becoming the norm for bookkeepers. But if you need to be personally present, you can move to where the jobs are and see that part of the world.
The Skills: Obviously it’s best if you have a bookkeeping or tax qualification. You need to be organized and reliable, paying attention to details while sticking to deadlines. Computer literacy and competence in data entry are a must, along with knowledge of a variety of bookkeeping software. This free course teaches how to start your own virtual bookkeeping business.
Medium term – Long term: You can choose to work on a seasonal basis in-person or long-term remotely. You’ll find jobs on websites such as Accounting Department for the US, ClicknWork, or Belay Solutions
Show me the money: A typical salary will be USD 20 – 60 per hour. A great earner for qualified seniors or retirees—especially if you want to boost your travel fund, but don’t want to work all year round.
#11.) Coaches and Counselors
It’s taken you years to create your own career and you’ve gained a lot of wisdom and experience along the way. How about turning your skills into a coaching or counseling career? Rebecca from Retrieving Me has a career in HR and is training to be a counselor. Marc from Career Pivot trained to become a retirement coach and advises over-50s on how to pivot their careers—all from a stunning lake in Mexico!.
The Jobs: These days, working remotely gives you the ability to make a “normal” job into a traveling job. It’s best to specialize. Your niche could be anything from business to weight loss, from self-development to careers with work-life balance. Spirituality, developing your life purpose, and Christian life coaches are becoming more in demand these days too.
The Skills: Above all, you need the ability to listen. Empathy and compassion are great skills for a coach. But a key skill is being able to decipher what your client says and help them identify their stumbling blocks. Then you need problem-solving skills to be able to suggest solutions. On top of that, you need to be able to publicize and market yourself and your business through social media and by speaking at and attending events to attract clients. It’s good to have a website to advertise your business too.
Although you don’t need a qualification as such, it really helps to have a coaching certification. You could try some of the free courses run by MOOCs to test out whether coaching is for you and then move on to gain a recognized certificate from the International Coaching Federation or the European Mentoring and Coaching Council.
Show me the money: Coaches can charge fees anywhere from USD 75 per hour to more than USD 500 per hour for top business executive coaching. Running leadership courses in companies can be even more highly paid. This is a growing field and some of the best-paying jobs for seniors and retirees.
#12.) Hairdressers and Beauticians
The Jobs: If you’re a qualified hairdresser, beautician, or massage therapist, you’ll find lots of travel opportunities. In big cities, it can be very attractive to have foreign hairdressers and beauty therapists, as long as you’re skilled. You’re in demand for cruises, in spas, lodges, and luxury hotels all over the world.
The Skills: You need to have some kind of certificate of qualification and recommendations from past employers. In addition, you’ll need to be creative and artistic with an openness to learning new ideas and techniques. You’ll be friendly with great communication skills paying great attention to cleanliness. Your own appearance will be stylish, with an emphasis on your personal grooming.
Short Term – Long Term: You can end up staying working for a cruise line for a long time. Or you can move on a seasonal basis to tourist resorts to work in hotels or local salons.
Show me the Money: On a cruise ship, beauticians can earn from USD 2000 – 3000 per month (or more). Your pay will depend on the type of cruise, the size of the ship, and the value of any tips you receive. Plus, your accommodation and travel are included!
#13.) Healthcare Travel Jobs for Older Workers
The Jobs: In the hospitality sector, many upmarket facilities require a doctor or nurse on hand (or at least on-call). Cruise ships are required to have medics on board. Pro Sea Staff is the place to look for medical jobs on cruises. There are often locum jobs that take you to exotic locations for short periods.
A doctor friend of mine does locums in the Caribbean which involve island hopping. And his wife and dog get to go with him!
Global Medical Staffing medical is another site that specializes in global locums.
The Skills: You’ll need a medical qualification of some sort, such as a doctor, nurse, dentist, physiotherapist, or other medical specialty.
Short term – Medium Term: Locums tend to cover for doctors wanting to take their own holidays. That said, this may end up being longer-term to cover things like maternity leave. Cruise ship jobs are for up to six months with a couple of months off afterward.
Show me the Money: Doctors on cruises can earn USD 6,000 to 8,000 per month. Locums will be paid commensurately to the period worked. Normally, travel costs are covered, as well as accommodation. Other healthcare staff on cruises or as locums earn quite well according to their qualifications.
Senior Travel Jobs: The Experiences You’ll Never Regret
If wondering what to do in retirement, this is it.
The biggest category of regrets of older people is not having gone traveling, not having done enough with their lives. Don’t let it be you. You are never too old. Well, at least until you tell yourself that you are. So why not tell yourself a different story and work out how you can get traveling, despite your age and circumstances.
Imagine that you worked out how to get a job that lets you afford to travel. It doesn’t have to be on the other side of the world. It might be a job you’ve never done before – imagine what fun that would be. You’d be living a different sort of life, meeting different kinds of people.
Perhaps you’ll get to the other side of the world, but even in your own country, there are so many things you have never seen, so many interesting people you’ve never met. You’ll gain a new perspective on your own life, and it will open your eyes to the perspectives of others.
All you need to do is to find the means to make your move. Long-term or short-term, it could be your experience of a lifetime. You’ll have great stories and few regrets. Because you got up and did it.
So, go find your job. Go traveling, and enjoy the time of your life, whatever your age. You’ll never regret it.
Rosemary Bointon is a certified content writer and SEO strategist. You can find her on Writer.me. She also runs the Long Life, Fun Life blog, where she helps older people work out what to do to live longer, in better health, with more fun and adventures. You can find her on Facebook, Twitter, Instagram and LinkedIn.
Mitch's Travel Recommendations:
Travel Planning Resources - Everything you need to plan your trip on one convenient page.
Safetywing Insurance - This cheap travel insurance has saved me over $15,000 in medical bills.
Booking.com - Book accommodation without adding your credit card (in case you need to cancel).
Skyscanner - Find cheap flights.
Trusted House Sitters - Take care of pets in exchange for free (sometimes luxury) accommodation.
Flexjobs - Find remote jobs without having to sift through crappy ones.
Skillshare - Free trial to take unlimited classes that teach digital nomad skills.
Anytime Mailbox - Virtual mail service that can handle your mail while you’re away.
Wise - Send and receive money abroad cheaply (great for freelancers).