There’s a familiar feeling at the end of most holidays: if only they could be extended for a few days, a few weeks – or, indeed, exponentially. Usually that’s an impossibility, with the demands of work or school-age children defining when and for how long holidaymakers can get away. Returning, or seeing more of the country, is an idea that gets firmly stowed back in the suitcase and forgotten about.
But one of the advantages of getting older is more time. Though there are sabbaticals, gardening leave and unplanned breaks between jobs, retirement – without school-age children and all the monetary and calendar-driven demands they bring – is the perfect time to embark on an extended trip. It’s an increasingly popular choice, and tour operators are cottoning on, offering a variety of holidays, from meeting teenage and post-university children on their gap years to taking a caravan to Spain for a few months.
Though a long holiday may sound like an extravagance, the rising cost of living in the UK means getting away for an extended period could even mean saving money. But there’s plenty to consider, from issues with insurance and visas to pet care. Read on to find out how to plan a long-stay getaway – and meet the people who have done just that.
Choosing a destination
Your choice of long-stay destination, and how long you can be there, will be somewhat governed by visa rules. UK citizens can stay 90 out of every 180 days in Europe, 90 days in the USA and six months in New Zealand (using both country’s travel authorisation schemes), but only up to 30 days in Sri Lanka and Bali. It’s the first thing to check while planning. See gov.uk/foreign-travel-advice for detailed advice.
Once you’ve decided on a country, it pays to think laterally about exactly where to stay. Though that villa hidden in the hills looks enticing, it may feel isolated during off-season. If you’re planning a trip then, look for year-round infrastructure and avoid places where shops and restaurants shut when the holidaymakers leave. You might, for example, swap the little coves of the Costa Brava for the small inland city of Girona 40 minutes’ drive away, or make for lively, working Santa Eulalia in Ibiza instead of a house in the interior.
When heading somewhere more exotic, watch the weather. Seasons change quickly in places such as Thailand, meaning you could arrive to cool breezes but soon be facing extreme heat.
Nevertheless, south-east Asia is hard to beat for a long-haul extended trip. Laos (where, since the beginning of 2025, UK visitors with e-visas have been able to apply for two extensions while in the country, up to a maximum of 90 days) is renowned as a cheap destination thanks to its affordable accommodation, food and transport. And though the region has traditionally been busy with backpackers, many of its towns have now developed a cosmopolitan feel that attracts visitors of all ages.
In Cambodia (where e-visas are valid for 30 days but can be extended from within the country), Siem Reap near the temples of Angkor has become a popular spot for visitors of all ages thanks to its cafés, spas and restaurants, as well as a low crime-rate. It’s so popular with older travellers that it’s now home to a new retirement development for expats, Sullivan Retirement Residence.
In Europe, Portugal consistently tops low cost-of-living surveys, as well as having year-round sunshine (the Algarve gets 300 days per year). If language is a worry, the Algarve is a good choice: English is widely spoken and tourists are generally welcomed. Though it has traditionally been something of an OAP hotspot during the winter months, a rise in digital nomads fleeing pricey Lisbon means more of a mixed demographic these days too.
Long-stay holidays based around parents joining grown-up children for parts of their gap year is also gaining traction, according to tour operator Stubborn Mule.
“Often, parents will travel for a month or so, kicking off with a couple of weeks with the gapper before enjoying at least two weeks holidaying on their own,” says managing director Liddy Pleasants. “Popular destinations include Thailand, where parents can dip in for a relatively short burst of south-east Asia fun; Sri Lanka, which has seen gappers on the increase as they stop over to or from India; and Costa Rica for a splash of central America, with parents generally joining either mid-way through or towards the end of their child’s year out.”
Finding a place to stay
Looking for an extended break from the daily grind? Swapping home for a self-catering apartment might not cut it. Instead, look out for hotel deals: over-50s operator Saga offers four weeks for the price of three at many of its options, including Cyprus’ Alexander the Great Hotel and Madeira’s Monte Mar Palace. The latter costs £2,415pp for 28-day stays in relatively balmy March.
For something a little different, the Caravan and Motorhome Club offers hosted long stays for motorhome and caravan owners during the winter, for up to 15 weeks between December and March at some campsites in Spain. There’s the opportunity to meet fellow long-stayers through walking and cycling trips, quiz nights and group meals, while there are Spanish lessons at some sites too. The nightly pitch rate reduces for longer stays, dropping to as little as £15.
Some Airbnbs also offer discounts for long stays, while social media pages advertise long-term rentals – though it’s well worth checking in with agencies on the ground in your chosen destination before you commit to booking. They often have the pick of holiday rentals out of season, know what is coming onto the market and will be able to advise on proximity to supermarkets, restaurants and attractions – all crucial for an extended break. They may also provide more reassuring contracts.
Pre-departure checklist
Leaving a home for any length of time requires a bit of housekeeping. Turn off all switches, as well as the mains water supply. And, if you’re going in summer, turn the heating off too (in winter, it needs to be kept on at a low temperature to avoid issues such as frozen pipes).
Travel insurance typically covers trips of up to 30 days, so longer breaks will require specialist insurance. The cost of this does, of course, rise with age, especially for those with medical issues, so budget for significant outlay. Make sure you declare all pre-existing conditions too – if you don’t, your policy may be invalidated, meaning the cost of care could fall squarely on your shoulders.
If the break means that your UK house will be empty, check your home insurance policy as well. Many are voided if a home is unoccupied for between 30 and 60 days. Instead, insurers offer (more expensive) insurance for set periods up to 12 months. Find quotes at gocompare.com.
Consider security too. In unoccupied properties, it may be good to have an alarm, timers for lights and perhaps cameras too.
Meeting people
At home, life is punctuated by social events, appointments and time with family. Remove these established networks and loneliness can quickly set in, especially in a place with a different language and customs.
Luckily, social media has made it easier than ever to connect with people in far-flung destinations – and much of the socialising for retirees happens in friendly communities on Facebook. In Siem Reap, for example, there’s a lively Siem Reap 50+ women’s activities group.
To get further acquainted with an area, skip the tourist day trips in favour of local guides and taxi drivers. Around the world, the International Greeter Association runs programmes that connect local people with tourists, in order to show them life away from the main sites during free walks. It operates in 47 countries, with destinations as diverse as Sicily, Ankara and Delhi.
Cultural centres are also fantastic hubs at which to find out more about a place and its customs. They often run language lessons, as well as immersion courses in everything from art to music. On the Algarve, for example, Olhao’s República 14 is popular for its events (everything from samba bands to local produce markets, via language lessons), friendly atmosphere – and excellent cocktails.
FAQs
Will my UK mobile phone work overseas?
Yes, but it might cost you. O2 is currently the only major UK mobile provider with free data roaming in the EU (though smaller budget providers such as Tesco and Lebara also offer it), allowing customers to use their numbers for free for up to 63 days in every four months. Head further afield, and it’s probably better to get an eSim or rent a portable WiFi device.
Do I still have to pay my UK taxes if I’m abroad?
As long as you are in the UK for 183 days per year, you remain a UK taxpayer.
What do I do with my pets?
In Europe, the reintroduction of the pet passport system was announced in May this year, although there is no confirmed start date. The scheme will replace the costly, admin-heavy animal health certificates that came in after Brexit and must be issued afresh for each trip. For animals that need to stay at home, consider a sitter. Sites such as trustedhousesitters.com link people going away with those searching for accommodation.
Can I hire a car long-term?
Car hire firms tout cheaper rates for long-term rentals. Our search for a vehicle from Barcelona Airport in November (for a period of two months) found Hertz to be the most competitive operator, offering a compact car for £1,263 (the next cheapest quote was £1,798). For the best prices, use a consolidator such as auto-europe.co.uk.