Flowers and houses Italian cliff
Flowers and houses on Italian cliff
  • Greece and Italy

Greece and Italy Vacations

There’s a particular magic to vacations that drift between Greece and Italy, where ancient stories cling to sun-warmed stone and the air carries the scent of citrus, sea salt and something delicious simmering nearby. You might begin in Santorini or Crete, where villages sit high above coves, before crossing to Tuscany’s rolling hills or the Amalfi Coast’s cliff-hung towns. In Athens and Rome, history feels close enough to touch: temples, ruins, Renaissance streets. Arrive curious, and perhaps a little hungry.

Our specialists bring these landscapes to life with carefully chosen stays and experiences that feel personal rather than prescribed. Think family-run villas tucked into olive groves, private boat days that slip past hidden bays, or guided walks through cities layered with centuries of art and ritual. From securing the perfect table at a much-loved trattoria to arranging moments you didn’t know to ask for, they shape each journey with insight, care and a dash of flair.

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Greece and Italy, whilst so culturally distinct, complement each other perfectly. Visit them both on one trip and you’ll delve into histories that span millenia, savor some of the finest cuisine in Europe, and find yourself blown away at the exquisite beauty of their coastlines.

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Shannon

Greece Specialist
Shannon

Suggested Itineraries for Greece and Italy

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Where to go in Greece and Italy

Capri, Italy

Capri is small but striking, with dramatic cliffs, clear water and a long-standing reputation for style. Most visitors arrive via Marina Grande before making their way up to Capri Town or Anacapri, where things feel a little calmer. You can take a boat around the island to see the famous grottoes, or simply enjoy the views from walking paths that trace the coastline. It’s popular for a reason, but with the right timing (early mornings or later afternoons) it still feels surprisingly relaxed.

Mykonos, Greece

Mykonos is best known for its beach clubs and lively nightlife, but there’s more to it than first impressions suggest. Wander through Chora’s maze of whitewashed streets, pause at the harbor in Little Venice, or head out early to quieter beaches on the island’s northern coast. By day, it’s all about sun and sea; by evening, the pace shifts, with restaurants and bars gradually filling. You can dip into the energy or step away from it – either way, Mykonos knows how to compel.

Positano, Italy

Positano is all about the setting: pastel houses stacked into the cliffside, with narrow lanes leading down to the beach. It’s a place best explored on foot, dipping in and out of small shops, cafés and restaurants as you go. The Spiaggia Grande is the main hub, though quieter spots are just a short walk or boat ride away. It can get busy in peak season, but there’s an easy rhythm to it – long lunches, slow evenings and plenty of reasons to pause and take it all in.

Crete, Greece

Crete offers a bit of everything. In Chania and Rethymno, Venetian architecture lines the waterfront, while inland villages feel slower and more traditional. The landscape changes quickly, from mountains to fertile plains to long stretches of coastline, so it’s worth exploring beyond one base. Food is a highlight here, with simple, seasonal dishes that reflect the island’s agricultural roots. Whether you’re visiting historic sites or heading out on a walk, there’s plenty to discover.

Trevi Fountain, Rome, Italy

Rome, Italy

Rome is a city that layers its history in plain sight, where ancient ruins, baroque fountains and everyday life all share the same streets. One moment you’re standing before the Colosseum, the next you’re turning into a quiet piazza where locals linger over coffee. It rewards wandering… across the Tiber into Trastevere, through the Vatican’s galleries, or simply along streets that seem to lead somewhere remarkable without trying too hard. Come with comfortable shoes and an open schedule; Rome has a way of setting its own pace.

Naxos

Naxos, Greece

Naxos has a relaxed, unfussy feel that’s easy to settle into. Its beaches are some of the best in the Cyclades (long, sandy and often less crowded), while inland, small villages and farmland give the island a more grounded character. The main town offers a mix of casual tavernas and low-key bars, and the Portara is a natural gathering point at sunset. It’s a good choice if you’re after variety without the busier atmosphere of some neighboring islands.

 

What to Do in Greece and Italy

Sail Between the Cyclades

Greece

Sailing through the Cyclades gives you access to parts of Greece that are difficult to reach any other way. Set out from Mykonos or Paros and you can drop anchor in smaller islands like Koufonisia or Antiparos, where beaches are quieter and the water is exceptionally clear. Stop for lunch in a seaside taverna (on Schinoussa, for example) where menus are short and based on what’s been caught or grown locally. Distances are manageable, making it easy to combine several islands over a few days without rushing.

Capri Boat Tour

Italy

A boat tour around Capri offers a different perspective on the island, away from the busy piazzas and up-close with its dramatic coastline. Routes typically circle the island, passing landmarks like the Faraglioni rock formations and the Grotta Azzurra (Blue Grotto), known for its luminous water. There are regular opportunities to stop for a swim in quieter coves, particularly along the southern coast. Tours can be private or small-group, and are best taken in the morning when the sea is calmer.

Kolymbithres Beach

Visit Kolymbithres Beach

Greece

Ready to trade typical sandy shores for something a little more otherworldly? Head to Paros and discover the sculpted wonders of Kolymbithres Beach. Here, millennia of wind and sea have carved pale granite into smooth, moon-like rock formations that cradle crystal-clear, shallow pools. It’s the perfect spot to spend your afternoon hopping between these natural sun-loungers, diving into the calm, aquamarine water to cool off under the Mediterranean sun.

Hike the Path of the Gods

Italy

The Path of the Gods (Sentiero degli Dei) is one of the Amalfi Coast’s most well-known walking routes, running roughly 7km between Bomerano (above Amalfi) and Nocelle (just above Positano). The trail follows the contours of the coastline, with captivating views over the sea and surrounding cliffs. A guided hike adds context to the landscape, pointing out local flora, farming terraces and small settlements along the way. It’s considered moderate in difficulty and is best walked in spring or autumn, or early in the day during summer.

What to See in Greece and Italy

The Acropolis and Parthenon

Greece

History buffs won’t want to miss a visit to the Acropolis and Parthenon, Athens’ most impressive sites. The Acropolis sits at the center of Athens’ historical landscape, with the Parthenon dating back to the 5th century BC. It’s worth pairing your visit with the nearby Acropolis Museum, which houses original sculptures and gives useful context before heading up the hill. From the top, you’ll have clear views across the city, including landmarks like Lycabettus Hill and the Temple of Olympian Zeus.

Ravello on Foot

Italy

Set above the Amalfi Coast, Ravello offers a quieter alternative to the busier coastal towns, with a focus on gardens, architecture and open views. A walking tour typically includes Villa Cimbrone and Villa Rufolo, both known for their landscaped terraces overlooking the sea. The town itself is compact, centered around Piazza Duomo, making it easy to explore on foot. Its elevated position means cooler temperatures and a more relaxed pace, particularly in the late afternoon when day visitors begin to leave.

Santorini Sunset

Santorini's Sunsets

Greece

Santorini is home to perhaps the most famous sunsets in the Aegean. You’ll find the very best views in Oia and Fira, where terraced rooftops and hidden balconies offer front-row seats to a nightly spectacle. As the sun dips toward the horizon, the sky ignites in layers of tangerine, blush pink, and molten gold, painting the whitewashed villages in unforgettable light.

Beaches of Capri and Positano

Italy

While much of the Amalfi Coast is rocky, both Capri and Positano offer well-known spots to access the water. In Positano, Spiaggia Grande is the main beach, right at the base of the town, with smaller and quieter Fornillo Beach just a short walk away. In Capri, Marina Piccola is the most popular swimming area, sheltered and with clear views of the Faraglioni. Beach clubs operate in both locations, offering sunbeds, shade and access to the sea, though arriving early in peak season is advisable.

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