Dolomites Mountains, Italy
The best time to visit Italy and Greece is in spring to early summer or in fall, especially from April to June or September to October. When to visit the countries for your perfect trip depends on your travel preferences and the experiences you hope to have along the way.
From skiing in the Dolomites to visiting hanging monasteries in Meteora, lounging on a volcanic island beach to sampling wines during the harvest season, each new destination will give you an opportunity for a new experience, no matter when you travel. There is no better combination than Italy and Greece when uncovering heritage, embracing culture, finding natural splendor, and enjoying the wonders of past civilizations.
Extraordinary travel begins with a human touch and our destination specialists design every journey with care, insight, and personal attention. As you consider a visit to Italy and Greece, use the following information to accentuate your trip before connecting with our travel experts to help you plan your trip.
Meteora, Greece
The ancient stones of the Colosseum warm as morning light filters through cypress groves, while the Aegean breeze carries whispers of mythological tales across marble temples. Spring and early autumn transform Italy and Greece into living museums. Each cobblestone street tells stories of emperors and philosophers, and every sunset paints Renaissance facades and Byzantine domes in golden light.
These shoulder seasons offer the rare privilege of intimate encounters with world-renowned masterpieces, where the rustle of olive leaves provides a soundtrack to your private moments with Michelangelo's David or your pause before the Parthenon. Cool mornings invite leisurely strolls through Vatican corridors and Venetian canals, while warm afternoons beckon you to explore ancient amphitheaters and clifftop monasteries.
Exclusive Cultural ImmersionExperience Italy and Greece through privileged access to their greatest treasures.
Elevate your cultural journey by taking a look at our Best Places to Visit in Italy and Best Places to Visit in Greece.
Italy
The intoxicating aroma of fermenting grapes fills the air as harvest season transforms Italy and Greece. September mornings reveal vineyards heavy with purple clusters, their leaves beginning to blush with autumn's first kiss, while the Mediterranean sun casts golden rays across terraced hillsides that have nurtured vines for millennia. The excitement is palpable as vintners prepare for the year's most crucial weeks, their weathered hands selecting only the finest grapes.
October deepens the sensory experience with the rich, earthy scent of wine cellars and the satisfying crunch of fallen leaves underfoot. Ancient stone farmhouses become havens of warmth and hospitality, where the crackling of wood fires mingles with the gentle bubbling of new wine. The harvest moon illuminates centuries-old traditions, from grape-stomping ceremonies to candlelit tastings in medieval wine caves, creating memories as rich and complex as the wines themselves.
Harvest Season PrivilegesImmerse yourself in the sacred art of winemaking during the most magical time of year.
Reserve your place at Europe's most celebrated harvest tables after taking a look at our Italy Wine Tours and Greece Food and Wine Tours.
Zakyntho, Greece
The Mediterranean awakens in May with crystal-clear waters, while secluded coves and pristine beaches stretch endlessly under brilliant skies. The warmth builds gradually, perfect for leisurely swims in volcanic hot springs and sunset aperitifs on private terraces overlooking the endless blue.
June extends this coastal paradise with warm waters and longer days. Hidden beaches, accessible only by private yacht, reveal their secrets, while luxury beach clubs prepare for the season with chilled champagne. The evening breeze carries the scent of grilled octopus from waterfront tavernas and the setting sun transforms the sky into hues of coral, amber, and deep purple.
Coastal Luxury RedefinedDiscover the Mediterranean's most exclusive shoreline experiences.
Zicasso’s Best Beaches in Italy and Best Beaches in Greece will provide you with a wealth of information for your exclusive Mediterranean vacation.
Rome, Italy
Creating forever family memories becomes effortless when Italy and Greece reveal their most welcoming embrace. May and June offer the perfect balance of adventure and comfort, where your children's wonder echoes through ancient amphitheaters and Renaissance courtyards. The gentle Mediterranean breeze carries the excitement of discovery, from treasure hunts in medieval castles to gelato tastings in sun-drenched piazzas.
October and December transform these lands into fairy-tale settings, where you and your family can explore without summer's intensity as you enjoy harvest festivals and the sweet aroma of chestnuts roasting on cobblestone streets. December brings the cozy embrace of Christmas markets, where twinkling lights reflect off cathedral spires and the warm glow of holiday traditions creates an atmosphere of pure enchantment.
Family Adventures ElevatedCreate unforgettable multi-generational experiences with luxury family travel.
Design your family's luxury Italian and Greek odyssey after looking into what our Italy Family Vacations and Greece Family Vacations have to offer.
Santorini, Greece
Romance blooms eternal in these timeless destinations, where June's gentle warmth creates the perfect backdrop for intimate moments. Enjoy candlelit dinners on private terraces overlooking vineyard valleys, where the evening air carries the scent of Mediterranean herbs and the soft glow of sunset paints everything in shades of gold and rose. The late spring atmosphere encourages long walks through historic gardens and stolen kisses beneath ancient olive trees whose silver leaves shimmer in the moonlight.
September and October wrap couples in autumn's romantic embrace, when the changing leaves create a kaleidoscope of warm colors and cozy moments in firelit wine cellars. Each moment feels designed for romance, from private gondola rides through Venice's secret canals to secluded beach picnics on pristine Greek islands. The harvest season adds an extra layer of intimacy, with wine tastings in candlelit cellars and romantic dinners featuring the season's finest flavors.
Romance PerfectedIndulge in the ultimate romantic escape with experiences designed for two.
Zicasso’s Romantic Italy Tours for Couples and Romantic Greece Tours for Couples will provide you with all the inspiration you need to plan a spectacular romantic getaway.
Tuscany, Italy
Spring awakens the Mediterranean. April's gentle warmth invites exploration of ancient trails that wind through wildflower meadows and alongside crystal-clear streams. The landscape comes alive with new growth, while the air carries the scent of blooming citrus groves and the distant sound of church bells echoing across hillsides. Early summer extends these perfect conditions, creating ideal weather for outdoor adventures that reveal the natural splendor of these timeless countries.
June brings the full glory of Mediterranean spring, with thermal baths steaming invitingly in mountain settings and cycling paths meandering through landscapes that have inspired artists for centuries. The longer days provide endless opportunities for discovery, from sunrise hikes to ancient monasteries to sunset sailing adventures that reveal hidden coves and pristine beaches. Each activity becomes a sensory journey, enhanced by the perfect weather and beauty of the season.
Seasonal Adventures AwaitEmbrace the Mediterranean's most spectacular outdoor experiences.
Embark on your spring and summer Mediterranean adventure. For more information, see our Summer in Italy or Summer in Greece articles.
Sicily, Italy
Autumn transforms Italy and Greece with golden hues and rich aromas October's crisp air carries the scent of woodsmoke and the promise of harvest celebrations. The landscape takes on a magical quality as leaves turn brilliant shades of amber and crimson, while the cool weather creates perfect conditions for truffle hunting and intimate wine cellar visits. The season's authenticity shines through in every experience, from olive harvest participation to cooking classes featuring seasonal ingredients.
Winter brings its own charm, with December's holiday markets sparkling with twinkling lights and the aroma of mulled wine and roasted chestnuts filling the air. January reveals snow-capped mountains perfect for luxury skiing adventures, while coastal regions maintain their mild climate for continued exploration. The winter months offer the most authentic cultural experiences, with fewer crowds and genuine connections to local traditions and seasonal celebrations.
Winter Luxury RedefinedDiscover the Mediterranean's most exclusive cold-weather experiences.
Experience the authentic Mediterranean winter in ultimate luxury. For more information on visiting at this time, take a look at Zicasso’s Italy in Winter and Greece in Winter travel guides.
Tuscany, Italy
Knowing the best time to discover the treasures of the Mediterranean can reveal the wonders of ancient life and the natural beauty that sweeps from the northern mountains to the southern islands as you discover the pleasures of Italy and Greece. From vineyard visits to medieval towns, coastal villages to romantic escapes, the best time for your trip depends on your goals and travel preferences.
Our collection of featured Italy and Greece tours has plenty of inspiration for planning your perfect personalized trip, or you can learn more in our Italy travel guide and Greece travel guide.
Trips curated by the world’s top destination experts
Concierge-level service leading up to and during your trip
Unique, exclusive experiences and insider access