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.