Combining dramatic scenery with a rich history, this Balkan city is rapidly becoming a travel
hotspot for those in search of an enlightening city break. Proudly flaunting its status as the
oldest city in Europe, Plovdiv’s convoluted history –
stretching back over 6,000 years – can be seen in disparate
imperial buildings, from ancient Roman and Persian ruins to the
decadent Balkan and Ottoman architecture that lines the city’s
streets. Explore the remnants of past empires as you wander through
Plovdiv’s Old Town. Visit the iconic Roman amphitheatre – only
discovered after a landslide in the 70s – and the 600-year-old
Dzhumaya Mosque next door, then climb the ruined fortress of Nebet
Tepe for sweeping views across the city.

Set on a steep hill, this traditional Campanian town sees
clusters of piazzas, crumbling towers and narrow passageways form a
vibrant patchwork, all overlooking postcard-worthy views of the
glittering Tyrrhenian Sea. Originally a hotspot for trading, thanks
to its wool production, Ravello remains steeped in history.
Exploring on foot will allow you to roam between the sun-scorched
streets, stopping at the cathedral, Duomo di Ravello, Villa Rufolo,
which traces its roots back to the 13th century, and the former
residence of Gore Vidal, La Rondinaia, before rewarding yourself
with an extra-large scoop from Baffone
Gelateria Artigianale. Spend days strolling between independent
boutiques, sailing the vivid turquoise waters and discovering
centuries-old traditions upheld by proud locals.

A waterfront town par excellence, Portland is the place to feast
on lobster and oysters by the bucketful, followed by long walks
along the Eastern Promenade Trail, the sea breeze on your face and
a picturesque lighthouse in the distance. Once you’ve had enough
crisp air, cosy up in a cheap and cheerful waterfront pub with a
pint. Make the most of Portland by spending as much time as
possible drinking in the salty surroundings. Amble between rows of
red-brick houses in the Old Port, pop between old-fashioned shops
and contemporary boutiques and watch wooden sailboats float by the
fishing wharves. Snag a boat of your own and jet over to Peaks
Island for an afternoon.

Planning a holiday abroad right now can be like trying to avoid
the banana skins on a game of Mario Kart… Want to play it safe?
Head to the bonny beaches of the Scottish Highlands. Though it’s known as the
launch point for trips across to the Isle of Skye, the port town of Mallaig
shouldn’t be overlooked as a destination in its own right. Mornings
are best spent watching fishermen haul in their catch, before
taking the easy walk along the Mallaig circuit, from where you’ll
enjoy views over the harbour and Loch Nevis.

Just across the winding Øresund Bridge from Copenhagen, Malmö is the third-largest city in
Sweden after Stockholm and Gothenburg. Rent a bike and spend a long
weekend pedalling along cobbled streets, gliding past multicoloured
cottages fronted by overgrown rose bushes. You needn’t do anything
more than get lost on these charming bungalow-lined roads for a few
days of pure escapism. Make like a local and grab some rye bread
and smoked salmon from a market, then head for a picnic at the
Western Harbour boardwalk. If you’re feeling brave, join the
residents taking an icy dip.

Although its remote location at the very tip of Long Island has
earned it the ominous moniker “The End”, Montauk is far from
sinister. With six sprawling state parks, more than 2,000 hectares
of pristine beaches and some of the best seafood in the US, Montauk
is a must for lovers of the great outdoors. Rise with the sun and
head straight for the beach, surfboard in tow. Ditch Plains has the
best waves, while its white-sands framed by jagged cliffs make a
great spot for sunbathing. Spend afternoons exploring the nearby
hamlet, stopping by farmers’ markets and hiking through Montauk
Point State Park, where you’ll find the Montauk Point Light – the
first lighthouse in New York state. Climb to the top of the 34m
tower and watch the sun go down over the Atlantic.

Slovenia has been riding a popularity wave for a couple of years
now, but this small town on the southeastern coast has only
recently started making waves. Piran’s historical centre is all
peaches and cream, with immaculate apricot- and vanilla-coloured
townhouses stacked around the stunning main square, Tartinijev.
Although it bears many similarities to its Adriatic neighbours
Venice and Dubrovnik, this sienna-roofed town has a calm,
introverted charm all of its own.

Just a two-hour drive from Athens, Nafplio is exactly what you’d picture a
charming Greek getaway to look like: sun-drenched tavernas, leafy squares, steep,
higgledy-piggledy streets and beaches beautiful enough to rival
those of the Caribbean. Which is why it’s a top destination for
those seeking a Greek escape minus the crowds found at better-known
hotspots – Mykonos, Rhodes and Paros, we’re looking at you. The
beauty of Nafplio is that it doesn’t take long to explore the
entire city. Gaze at colourful flowers and overgrown palm trees
hugging Venetian villas, swim between various sandy beaches (Neraki
is the best of the bunch) and feed your inner boffin with a tour
around the many ancient ruins.

Award-winning celebrity chef Hugh Fearnley-Whittingstall is
responsible for putting this quaint market town on the map – his
River Cottage culinary empire is but a short drive from the town
centre. Expect thatched cottages, tea rooms and a high street
packed full of independents. Get stellar recommendations for your
next read at Archway Bookshop or rummage through trinkets and
treasures in The Old Chapel Antiques & Craft Centre. Sunday
mornings call for a cycle to Millers Farm
Shop. The land has been in the family for three generations and
its owners regularly nip across to France to bring back a selection
of edible goodies to accompany local fare. Avignon or Axminster?
Regardless, visitors can expect a cornucopia of fresh produce under
one roof, plus a wine selection that rivals cellars in
Bordeaux.

Not far from Côte d’Azur hotspots St Tropez and Sainte-Maxime,
Ramatuelle is a worthy stopover along the French Riviera. Ensconced
by fields of lavender and sandy beaches, this Provençal village is
the stuff of Tropezian myth. Overlooking purple fields and endless
striped vineyards, the small French village is masked by tall
medieval walls, making it look like something out of a storybook.
Wander through the circular, labyrinthine streets seeking out
historical jewels on every corner. In August, Ramatuelle’s annual
jazz festival fills the place with sounds almost as sweet as the
scent of lavender in the air.

Despite ranking as Croatia’s oldest continuously inhabited city,
Zadar is a place most people would struggle to place on a map.
While jet-setters tend to head for the cliff-clinging paths of Vis
or sun-scorched sands of Split, we suggest swerving the crowds to
discover a destination bursting with history, jaw-dropping beauty
and a surprisingly flourishing creative scene. While life here
dates back to the ninth century, there is absolutely nothing dated
or dull about Zadar, whose beautifully modern streetscape marries
traditional heritage with a free-spirited, urban vibe. Start your
day navigating narrow passageways and wandering alongside the
Unesco-listed fortified walls, before visiting the crumbling ruins
of the famous Roman Forum. Then, while away the afternoon dipping
in and out of charming cafés, independent galleries and
parasol-shaded bars.

Perched on Malta’s southeastern edge, the magical Marsaskala is
home to dusty streets, a harbour lined by a happy mish-mash of
yellow villas and a coastline dotted with deserted caves lapped by piercingly blue waters. No
wonder it’s popular with holidaying Maltese families. Less than a
30-minute drive from the capital, Valletta, the town has long
served as prime territory for long-weekending city types, but its
tranquil trails are fast gaining a following among those looking
for a hit of sun, history and culture – minus the crowds. Beyond
the beautiful beaches, you’ll find a slew of ridiculously cool
beach bars, trendy restaurants and smart hotels to explore.

Set in Essex’s Blackwater Estuary, Osea is just a
90-minute drive from London, but feels far removed. It was the best part of
2,000 years ago that Romans built the causeway connecting this
islet to mainland Heybridge. Today, access is governed by the sea –
the route appears just twice daily, when the tide is low – though
you can take a boat, too. The island is perhaps best known for its
private ownership, celebrity appeal and the rehab retreat that once
stood here, but, in truth, it’s a place where nature takes the
reins: towering oak, sycamore and chestnut trees decorate the
landscape and rare birds flock overhead. Anyone can visit if they
book into one of its houses or cottages, or rent the island in its
entirety.

Backdropped by the Baba Mountain, Bitola is North Macedonia’s
second-largest city. Remaining virtually unknown, this place makes
for a pretty ideal city break – particularly if you’re not one for
crowd surfing to collect your daily paper. Spend mornings rambling
along Širok Sokak (Wide Street) to find your daily espresso fix,
best enjoyed with a side order of people-watching, then explore
some of North Macedonia’s most spectacular nature. Hike in Pelister
National Park or take an hour’s drive to Ohrid. One of Europe’s
oldest towns, it’s flanked by a glassy lake that begs you to grab a
kayak and make some ripples.

With medieval towers, a walled old town and charming trattorias
all surrounded by rolling vineyards, this Etruscan hill town is
ripe for an August getaway. Travel south from Florence through
verdant fields to reach San Gimignano’s crumbling 13th-century
walls, through which you’ll find sand-hued buildings and family-run
cafés, restaurants and shops dating back generations. History buff?
Head to the 12th-century Duomo di San Gimignano, known locally as
the Collegiata, to admire frescoes by Domenico Ghirlandaio, then
pop into the Polo Museale Santa Chiara, where three buildings house
ancient ceramic jars, mosaics and artefacts.

Setenil’s 3,000 residents live under a rock – no disrespect
intended. Burrowed beneath the cliffs of the Río Trejo, the town’s
cave houses provide shade during hot summer days and trap heat in
winter. Originally occupied by 15th-century Moorish residents, many
of these dwellings have now been transformed into some of Cádiz’s
best restaurants and bars, serving up the olive oil, almonds,
chorizo and pastries for which the town is famed. Setenil makes a
perfect day-trip destination from the nearby city of Ronda, a
30-minute drive away.