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Deciding where to stay in Puglia shapes the whole holiday. Puglia runs for around 400km down the heel of Italy, taking in trulli and vineyards in the Valle d'Itria, whitewashed Ostuni above its olive plain, fishing harbours along the Adriatic, baroque Lecce, and the cliffs at the tip of the Salento where two seas meet.

Green, mountainous Lefkada and its smaller sister Meganissi sit in the Ionian Sea roughly halfway between Corfu and Cephalonia, connected to the Greek mainland by a causeway rather than a ferry crossing. Between them, the two islands hold a buzzing town, a mountainous interior built for walking, some of the best water sports conditions in the Mediterranean, and a smaller island reached only by boat. This Lefkada and Meganissi itinerary spends seven days moving through all of it.

Every winter, Italy’s towns and cities take on a different character. Streets fill with colour, music and elaborate costumes as centuries-old customs are celebrated through artistry, community and local pride. From Tuscany’s Tyrrhenian coast to the heart of Puglia and the Baroque streets of eastern Sicily, four destinations offer distinctive ways to experience Carnival: Viareggio, Putignano, Acireale and Sciacca.

Salento occupies the southeasternmost tip of Italy, a stretch of coastline and countryside distinct from the rest of Puglia. Fortified seafront towns, baroque Lecce, and villages tucked away from well-trodden tourist routes sit alongside beaches that range from soft golden sand to rocky inlets carved into limestone cliffs. This Salento itinerary spends seven days moving between the two coasts and the towns that connect them.

Little Paxos and its even smaller sister, Antipaxos, sit south of Corfu, as Italian in feel as they are Greek. Paxos combines a laid-back atmosphere with a gentle cosmopolitan charm, while Antipaxos, with no shops and only a couple of tavernas, is built for switching off entirely. This Paxos and Antipaxos itinerary spends seven days moving between the two, with a detour north to Corfu along the way.

The Mediterranean is wonderfully diverse, offering everything from vibrant coastal hubs to peaceful corners where life moves to a hypnotic tempo. Among its many treasures are a smattering of quiet Mediterranean islands, shaped by small populations, limited ferry links and terrain that never quite suited large-scale development.

Rising serenely above the Tyrrhenian Sea, Villa Talamo is an 18th-century former monastery that has been lovingly restored to create an enchanting, character-filled Tuscan home. Set in a private, 10-acre coastal estate with a 19m-long infinity pool, direct sea access, and extensive, luxuriant gardens, Villa Talamo comes with 10 bedrooms, full service, including a chef, a long-standing reputation for entertaining in style, and a little black book of contacts that means nothing is off the menu when it comes to transforming a great villa holiday into an extraordinary event.

Rising above the cobalt waters of the Ionian Sea, Michaela is a glamorous Lefkada retreat for sophisticated groups of friends and couples looking to celebrate somewhere truly special. Sleeping up to 16 guests across eight bedrooms and 10 bathrooms, the contemporary villa combines crisp architecture with subtle colonial influences, spectacular sea views and a distinctly chic atmosphere. The accommodation is arranged between the main house and two independent guest apartments, giving everyone a degree of privacy while bringing the group together around the villa’s extraordinary outdoor spaces. With a 22m heated infinity pool, private sea access and a highly attentive team, Michaela is particularly well suited to milestone birthdays, anniversaries, reunions and stylish celebrations with friends.

At the top of one of Spetses’ most coveted hills, Cleonice is an impressive private estate made for bringing family and friends together. A long, cypress-lined driveway leads through 5.5 acres of gardens to a collection of beautifully designed buildings, with panoramic views across the island and sea. Sleeping up to 14 guests in seven en-suite bedrooms, it is an especially appealing setting for milestone birthdays, anniversaries and multi-generational celebrations. Just a 20-minute walk from Spetses Town, it offers the rare combination of a secluded estate and easy access to the island’s restaurants, beaches and harbour.

Originally built as a summer pied-à-terre for the socialite Lady Sarah Spencer-Churchill, Villa Aetos was conceived with entertaining, high-society soirées, and festive celebrations in mind. Privacy is guaranteed by the 60 acres of pine woods that seclude the property in a veil of greenery, and with nine fabulously spacious bedrooms, a pool, a virtually private beach at the bottom of the grounds, and a team of staff including cook at the ready, the scene is set perfectly for memory-making moments.

Set among the olive groves of Salento, a few kilometres from Puglia’s Ionian coast, Masseria Palaci is a beautifully restored former agricultural stronghold with the character, space and service to bring a large group together. Sleeping up to 18 guests in nine double bedrooms, all en suite, its accommodation is thoughtfully spread between the main house, an independent guest wing and the original two-storey tower, creating the feel of a private estate rather than a single villa. Original tuff stone, barrel-vaulted ceilings and pale limewashed walls sit alongside refined contemporary interiors, giving the property a distinctly stylish yet welcoming character. There is also a strong connection to the land. Fruit trees, orchards, herbs, vegetables and free-range hens provide produce for the kitchen, while the property's own beehives supply honey. Combined with the exceptional ingredients of Salento, this gives meals at Palaci a wonderfully local, seasonal quality.

Set above Kalo Livadi on the southeastern coast of Mykonos, Villa Theros offers a sophisticated take on the island’s unmistakable style. Sleeping up to 16 guests in eight bedrooms, the villa is arranged across a main house, a separate master suite and three independently accessed guest bedrooms, creating a sense of space and privacy that works particularly well for families and multigenerational groups. There is a distinctly bohemian spirit to Theros, but one that feels considered rather than clichéd. Rich fabrics, natural materials, contemporary art and carefully chosen furnishings give the interiors a warm, highly individual character.