Annual leave is one of the year’s more finite pleasures. Used without much thought, it can quickly disappear into the occasional Friday and a handful of Mondays. Place it more strategically, however, and the same allowance can turn four days away from your desk into nine or even ten days elsewhere.
Easter falls early in 2027, May brings two bank holiday weekends, and Christmas Day and Boxing Day fall over the weekend. With a little planning, three days’ leave at Christmas can become ten days off – and 24 days’ annual leave across the year can add up to a generous 57 days out of the office.
Before considering where they might take you, though, here is a quick look at the year ahead.
2027: At a Glance
Annual leave to book
Leave used
Days off
4–8 January
5 days
10 days
22–25 March
4 days
10 days
4–7 May
4 days
9 days
1–4 June
4 days
9 days
31 August–3 September
4 days
9 days
29–31 December
3 days
10 days
Total
24 days
57 days
*These dates are based on the confirmed bank holidays for England and Wales, and while Scotland and Northern Ireland have their own variations, the same principle applies. Look at the days around Easter, May and Christmas, then let the seasons decide where you go.
January: Take five days’ leave for ten days away
With New Year’s Day falling on a Friday, 2027 gets off to a very good start. Book Monday 4–Friday 8 January and you can enjoy ten consecutive days away, from Friday 1–Sunday 10 January, while using only five days of annual leave.
So, where to go? Skiers should look to the French Alps, where the season is properly under way and the villages are still holding onto their festive glow. The first full week of January also follows the Christmas and New Year peak, so resorts are beginning to recover just as the ski season settles into its stride.
One of the Chamonix Valley’s rare ski-in ski-out addresses, Chalet Blitzen is a restored 19th-century farmhouse positioned directly on La Verte, the Kandahar World Cup piste in Les Houches.
If January has already provided quite enough cold, the Canary Islands make a convincing alternative. Winter here means mild days, volcanic landscapes and Atlantic beaches, with blood-red sunsets looking rather more appealing than the grey shores of old Blighty.
For a January escape beneath Fuerteventura’s winter sun,Villa Los Corraletesis a bright three-bedroom retreat in Lajares, with a private pool, sunken lounge and panoramic views across the island’s volcanic landscape.
For full summer sun, head further south to South Africa, where January brings long days around Cape Town, the vineyards in full leaf and the Garden Route at its sunniest. After Christmas at home, ten days beside a pool may be exactly what this new year calls for.
Set within a 275-hectare coastal reserve in South Africa’s Eastern Cape,Paradisepairs four ocean-facing bedrooms with a heated infinity pool, private chef and two kilometres of untouched beach – just right for January’s summer sun.
Easter: Take four days’ leave for ten days away
Good Friday falls on 26 March in 2027, followed by Easter Monday on 29 March. Book Monday 22–Thursday 25 March and four days of annual leave will give you ten consecutive days away.
Easter’s early arrival brings pleasant walking weather to southern cities. Semana Santa takes over Seville’s streets from 21–28 March, with processions moving through the historic centre and crowds gathering around the Cathedral well into the evening. It is a remarkable time to see the city, provided you come for the occasion. Book ahead and allow for procession routes and changes to opening hours when planning your days.
Occupying a beautifully preserved 16th-century palazzo in Seville’s historic centre, Casa del Rosario has three private terraces overlooking the Cathedral and Giralda, with the city’s tiled courtyards, tapas bars and great monuments an easy stroll away.
Across the Strait of Gibraltar, Morocco is entering one of its loveliest seasons, with Marrakech yet to take on the dry intensity of summer and the foothills of the Atlas still green from winter rain. It is a fine time for mornings in the souks, afternoons in the gardens and evenings on the roof terraces, while the countryside beyond the city offers cooler air and views towards the mountains.
After a morning in Marrakech’s souks,Villa Tozeuroffers a serene return, with four en-suite bedrooms, 4,000m² of gardens and an 18-metre heated pool, plus daily housekeeping and a concierge included.
For something quieter, the Algarve is emerging gently from winter, with beaches that still belong to walkers rather than swimmers and reassuringly empty roads between the villages.
Close to the golden cliffs and coves of Benagil,Lux Canagives up to eight guests a bright contemporary base, with wide terraces, garden dining and a private pool for the Algarve’s gentler spring days.
Early May Bank Holiday: Take four days’ leave for nine days away
The Early May Bank Holiday falls on Monday 3 May, so booking Tuesday 4–Friday 7 May turns four days of annual leave into nine consecutive days away, from Saturday 1–Sunday 9 May.
Made for Mallorca’s mild May days,Casa Limonessits a short walk from Pollença’s main square, with a private courtyard, saltwater pool, outdoor kitchen and dedicated bike storage for rides into the Tramuntana.
At this point in the year, southern Europe is enjoying that lovely interval when spring has settled over the landscape, but the summer crowds have yet to arrive. Mallorca’s interior is green, the Tramuntana remains cool enough for walking and the island’s towns have returned to life without filling their streets, leaving plenty of room for market mornings and lunches in the squares.
Once a 14th-century lookout tower,Maison Sebastiennow crowns a Luberon hillside with 360-degree views, ancient terraces and a medieval courtyard – plus the Provençal kitchen where Rick Stein filmed Secret France.
In Provence, wisteria climbs across old stone walls and a morning at the market can be followed by lunch without any need to escape the afternoon sun. Tuscany is similarly unrushed, its hills bright with new life and the roads between villages far calmer than they will be by July.
Four and a half centuries of Chianti history lie behindVilla Sienese Del Tramonto, a restored noble estate and former watchtower surrounded by vineyards, yet within walking distance of Radda’s cafés, trattorias and wine bars.
Late May Bank Holiday: Take four days’ leave for nine days away
The Late May Bank Holiday falls on Monday 31 May, so book Tuesday 1–Friday 4 June and you can enjoy nine consecutive days away, from Saturday 29 May–Sunday 6 June, while using only four days of annual leave.
This is a particularly good time for a Mediterranean villa holiday. Summer has arrived, restaurants are open and the evenings are light well beyond dinner, but the busiest weeks of the season are still ahead.
A private path throughFinca Galdana’s108-hectare estate leads directly to Cala Mitjana, while back at the 18th-century house, a saltwater pool, outdoor bar and private chapel sit among 1,600 olive trees.
Menorca is especially lovely at this time of year, with wildflowers across the countryside, warmer seas and plenty of space around the island’s coves. Spend a morning walking through Ciutadella’s streets, head to Cala Macarella for the afternoon and be back at the villa in time for dinner beside the pool.
Just ten metres separateVilla Mare Sea’sgarden from an almost-private sandy beach, where guests have their own gazebo, while bookable trips aboard the owner’s boat can take you to Paxos, Sivota or a nearby fish taverna.
Corfu is another strong choice, its cypress-covered hills still deep green after spring and the Ionian beginning to warm. Crete is also reliably sunny by early June, giving you warm days beside the water without the more intense heat and crowds of July and August.
Built from local stone and restored by descendants of the original owners,Silver Oliveis divided into two apartments around a pool courtyard shaded by olive trees, with Rethymno’s Venetian harbour just 11 kilometres away.
August Bank Holiday: Take four days’ leave for nine days away
The August Bank Holiday falls on Monday 30 August, so book Tuesday 31 August–Friday 3 September and you can enjoy nine consecutive days away, from Saturday 28 August–Sunday 5 September, while using only four days of annual leave.
Late-summer evenings atVilla Siminiacome with a 90m² roof terrace and hydromassage tub, while downstairs the two-bedroom villa opens onto a private pool, with Spiaggia di Nora’s white sands ten minutes away.
By early September, the sea is at its warmest across much of the Mediterranean, just as the busiest weeks begin to pass. In Sardinia, the water remains startlingly clear, and the island’s white-sand coves regain a little breathing room. San Sebastián pairs beach days around La Concha Bay with evenings among the pintxos bars of the Old Town.
Beach first, pintxos later:Villa Donostiais 300 metres from Ondarreta Beach and a 15-minute walk along La Concha Bay to the Old Town, with four bedrooms and a private roof terrace to return to.
In northern Portugal, the Atlantic keeps the coast around Porto fresh, while the Douro Valley approaches harvest season inland, its steep vineyard terraces heavy with grapes. Divide the nine days between the coast and the river and summer will feel a long way from over.
Where the Douro meets the Atlantic,Casa das Palmeirasoccupies a seafront position in Foz, with a rooftop terrace for sunset and the vintage tram outside carrying you into historic Porto in around ten minutes.
Christmas: Take three days’ leave for ten days away
Christmas 2027 gives you three days of annual leave for ten days off. With Christmas Day and Boxing Day falling over the weekend, their substitute bank holidays move to Monday 27 and Tuesday 28 December. New Year’s Day 2028 also falls on a Saturday, making Monday 3 January another day off. Book Wednesday 29–Friday 31 December and the entire period between Saturday 25 December and Monday 3 January is yours.
Christmas for the whole family looks rather different atAlbury Shores, a waterfront estate of five private villas with nine king bedrooms, a resort-style pool, two secluded beaches and private dockage in Tavernier Key.
Ten days also makes a longer journey feel worthwhile. December is one of the best months to visit Florida, once the heavy humidity of summer has lifted but the days remain warm. Follow the Overseas Highway south to the Florida Keys, where turquoise water, mangrove islands and waterfront restaurants make Christmas at home feel very far away.
If Christmas in the treetops sounds like something from a storybook,Keemala’s Bird’s Nest Pool Villamakes it real: a woven cocoon high in Phuket’s rainforest, with its own pool and the Andaman Sea visible through the trees.
For somewhere further afield, Thailand’s Andaman coast is entering its dry season, bringing calmer seas and plenty of sunshine around Phuket. Southern Vietnam is also enjoying some of its finest weather, particularly around Phú Quốc, where Christmas can be spent between white-sand beaches and the warm waters of the Gulf of Thailand.
The Sirius Villamoves easily between its private pool, tropical garden and the Sailing Club beach club, with three en-suite bedrooms and a sunken lounge providing plenty of space for everyone.
Book a 2027 stay with Oliver’s Travels
However you use your 2027 annual leave, make sure those hard-earned days take you somewhere worth setting your out-of-office for. Find an Oliver’s Travels villa for your chosen dates and put them to good use.
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