Itinerary #1: Highlights of Italy and Greece: Rome, Florence, Venice, Athens, Mykonos, & Santorini
Consider this trip plan if you want to explore some of the main highlights of the Mediterranean region while still leaving time for a few visits to lesser-known locales. You'll see historical sites in Rome and Athens, visit art museums in Florence, and relax on the beaches of Santorini.
|Day 1||Arrive in Rome & City Walking Tour||Rome|
|Day 2||Colosseum & Ancient Rome Tour||Rome|
|Day 3||Free Morning in Rome & Evening Aperitivo Tour||Rome|
|Day 4||Vatican & Sistine Chapel||Rome|
|Day 5||Rome to Florence, Food & Wine Tour||Florence|
|Day 6||Walking Tour of Florence's Highlights||Florence|
|Day 7||Tuscany Day Trip: Siena, San Gimignano, Monteriggioni, & Chianti||Florence|
|Day 8||Train from Florence to Venice||Venice|
|Day 9||Venice Walking Tour & Afternoon Spritz Veneziano||Venice|
|Day 10||Murano & Burano Excursion||Venice|
|Day 11||Flight from Venice to Athens||Athens|
|Day 12||Guided Acropolis Visit||Athens|
|Day 13||Sunset Tour of Cape Sounion & Temple of Poseidon||Athens|
|Day 14||Athens to Mykonos & Traditional Mykonian Dinner||Mykonos|
|Day 15||Day Trip to Delos||Mykonos|
|Day 16||Mykonos Beach Day||Mykonos|
|Day 17||Mykonos to Santorini||Santorini|
|Day 18||Santorini Tour||Santorini|
|Day 19||Santorini Wineries & Vinsanto||Santorini|
|Day 20||Catamaran Cruise in the Caldera Lagoon||Santorini|
|Day 21||Santorini to Athens - Depart Athens|
Spend time in Italy's top cities — Rome, Florence, and Venice — for an immersive experience into ancient Roman history and Renaissance art. You'll walk down the Via Sacra and see the Roman Forum, admire Michelangelo's ceiling frescoes in the Sistine Chapel, and tour the Uffizi Gallery in Florence to see works by Leonardo da Vinci and more. Sample Chianti wine in Tuscany and visit walled medieval hilltop villages before heading to Venice, where you'll explore ornate palaces and take a day trip to the nearby islands of Burano and Murano.
Catch a flight to Athens for the second half of your trip, which starts with visits to some of the most important archaeological sites in and around the ancient city. Stops include the well-known Acropolis and coastal Temple of Poseidon, as well as a few unexpected gems, like a tour of the historic neighborhood of Plaka. Cross the water to the island of Mykonos, where you'll be welcomed into a local Mykonian household for a traditional dinner and plenty of wine. End your trip in Santorini where you'll visit the medieval villages at Megalochori and Pyrgos, go wine tasting, and spend a full day exploring the caldera and the island's hidden beaches and coves aboard a catamaran cruise. Learn more
Itinerary #2: Off-the-Beaten-Path Greece & Italy Road Trip: Lake Garda, Bologna, Tuscany, Olympia, Nafplio, & More
Take scheduling into your own hands as you explore smaller towns and back roads (as well as a few well-known sites) on this classic road trip across the Greek and Italian countrysides. Check out this trip plan to dive deep into local cultures, making plenty of time for spontaneous stops for coffee and market stands.
|Day 1||Arrive in Milan & Drive to Lake Garda||Lake Garda|
|Day 2||Guided Tour of Lake Garda||Lake Garda|
|Day 3||Lake Garda to Verona & Guided Tour||Verona|
|Day 4||Wine Tour from Verona||Verona|
|Day 5||Drive from Verona to Bologna, Prosciutto & Parmesan Tour||Bologna|
|Day 6||Ferrari Museum & Drive to Florence||Florence|
|Day 7||Florence Highlights and Food Tour||Florence|
|Day 8||Florence to Siena & Chianti Wine Tasting||Siena|
|Day 9||Walking Tour of Siena||Siena|
|Day 10||Day Trip to Volterra & San Gimignano from Siena||Siena|
|Day 11||Siena to Ancona & Overnight Ferry to Patras||Overnight Ferry|
|Day 12||Arrive in Patras & Drive to Olympia||Olympia|
|Day 13||Explore the Olympia Archaeological Site||Olympia|
|Day 14||Olympia to Pylos & Palace of Nestor||Pylos|
|Day 15||Castles of Pylos & Optional Boat Tour in Navarino Bay||Pylos|
|Day 16||Drive to Mystras & Kalamata Olive Tour||Mystras|
|Day 17||Areopoli & Mani Peninsula Driving Tour from Mystras||Mystras|
|Day 18||Citadel of Mystras & Drive to Nafplio||Nafplio|
|Day 19||Mycenae and Epidaurus Day Trip||Nafplio|
|Day 20||Nemea Winery Exploration||Nafplio|
|Day 21||Nafplio to Athens and Depart|
Cruise down windy country lanes in Tuscany and alongside the steep coastal cliffs of the Peloponnese as you explore Italy and Greece from behind the wheel. Start in the north of Italy at Lake Garda, which has been used as a summer getaway since the era when ancient Roman nobles built villas along its shores. You'll explore the area's castles and estates by foot and on water, with plenty of waterfront dinner options to sample the lake's fresh-caught fish. Take a tour of nearby Verona (made more romantic by Shakespeare's "Romeo and Juliet") and go wine-tasting in the Valpolicella region to sample its eponymous wine, as well as Amarone and sweet Recioto varieties.
Continue your drive to Emilia-Romagna — the land of Parma ham and parmesan cheese — before paying homage to the classic Italian sports car at the Ferarri Factory and Museum. Spend a full day in Florence exploring the highlights, like the iconic domed Duomo, the medieval Ponte Vecchio bridge, and the historic Jewish Ghetto neighborhood. Keep heading south for wine tours in Chianti and visits to the walled hilltop villages of Siena, Volterra, and San Gimignano, then cross the Italian peninsula to catch a ferry from Ancona.
You'll begin your drive through Greece in the port town of Patras, then make your way to Olympia — ancient site of the first-ever Olympic Games. You'll have plenty of time to wander through the sprawling archeological site (and through the natural landscape surrounding it with a peaceful hike) before continuing to your next destination: coastal Pylos. Here you'll tour Mycenean ruins and explore Navarino Bay, then drive inland to Mystras, stopping along the way for an olive oil tour of Kalamata. Learn more
Itinerary #3: Best of Mediterranean Food & Wine: Athens, Santorini, Crete, Rome, Tuscany, & More
Neapolitan pizza, Cretan olive oil, and prosciutto di Parma await you on this three-week Mediterranean getaway. Tour Athens' bustling street markets, learn to cook a traditional Italian meal, and go wine tasting in Tuscany's rolling hills with this trip plan.
|Day 1||Arrive in Athens, Welcome Dinner||Athens|
|Day 2||Guided Acropolis Visit & Food Tour||Athens|
|Day 3||Ferry to Naxos||Naxos|
|Day 4||Farm-to-Table Cooking Class on Naxos||Naxos|
|Day 5||Ancient Naxos Guided Hike||Naxos|
|Day 6||Naxos to Santorini & Guided Sunset Tour||Santorini|
|Day 7||Santorini Food & Wine Tour||Santorini|
|Day 8||Free Day in Santorini & Ferry to Crete||Heraklion|
|Day 9||Olive Oil Tour & Drive to Chania||Chania|
|Day 10||Apokoronas Seven Villages Tour||Chania|
|Day 11||Fly to Naples||Naples|
|Day 12||Neapolitan Pizza Cooking Class||Naples|
|Day 13||Naples to Rome & City Walking Tour||Rome|
|Day 14||Guided Food Tour of Testaccio & Trastevere||Rome|
|Day 15||Train to Siena & City Tour||Siena|
|Day 16||Chianti Wine Tasting from Siena||Siena|
|Day 17||Siena to Florence & Afternoon City Tour||Florence|
|Day 18||Florence to Bologna & Walking Tour||Bologna|
|Day 19||Day Trip to Parma: Ham and Parmesan Tasting||Bologna|
|Day 20||Bologna Food Tour||Bologna|
|Day 21||Depart Bologna||Bologna|
They say that food is the Mediterranean's language of love, and you'll get to soak in all the love you can get on this tour of Italy and Greece. Start the trip in Athens, where you'll tour the Acropolis and wander the sprawling Varvakios Market — the city's largest produce and meat market. Sample spicy olive oil, tangy fresh olives, and fresh fruit bursting with sunshine sweetness. Catch a ferry to Naxos, a famed Cyclades island with mountainous terrain and inviting beaches. You'll join a local family in Kaloxylos to prepare a traditional three-course Greek meal, complete with loukoumades (fried donuts), keftedes (meatballs with tzatziki sauce and Naxian cheeses), and of course — kitron, a citron liqueur that's the regional favorite.
Continue island hopping to Santorini, where you'll explore the old-world stone streets of Megalochori and visit a family-owned winery that specializes in growing vines in the island's dry, volcanic soil. Continue to Crete to explore the area's best-known export: fresh-pressed olive oil, which comes from a multitude of small groves that dot the hillsides. You'll visit a few of these olive groves and mills, as well as some of the island's small villages that feature cultural and historic sites, including Ottoman forts and ancient churches.
From here catch a flight north to Naples to learn the secrets of the perfect Neapolitan pizza from the masters themselves before continuing north to Rome, where a guided tour of the city's most important stops includes both the Pantheon and the corner gelateria. Tour the quirky neighborhoods of Testaccio and Trastevere and enjoy lingering over coffee in the late afternoon sunshine, then end your day with prosecco or spumante.
Your next stop is in the heart of Tuscany's wine region: Siena, a walled medieval hilltop city. Visit wine estates to try the famed Chianti wine, then immerse yourself in Renaissance art in the palaces and art museums of Florence.
End your trip in Bologna, home of thinly-sliced prosciutto and salty Parmigiano Reggiano cheese, as well as historical landmarks like the 11th-century University of Bologna. Learn more
More Great 21-Day Italy & Greece Itineraries
Looking for more inspiration for your trip to Italy or Greece? Check out these other 21-day Greece itineraries, or these 21-day Italy itineraries with history-focused experiences, food & wine getaways, and best-of trips to hit the highlights.
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