Three weeks in the Mediterranean gives you enough time to see the main highlights — Rome, Athens, Tuscany, and Santorini — as well as to dive deeper into the regional culture. Plan your trip around food and wine as you eat and drink your way through the best cuisine Italy and Greece have to offer, or opt for a classic road trip to get off the beaten path and explore sleepy coastal towns at your own pace. Read on for unique itineraries spanning some of the top destinations in Europe.

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. 

Canals in Venice
Canals in Venice
Day Highlights Overnight
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. 

O Romeo, Romeo, wherefore art thou Romeo?
"O Romeo, Romeo, wherefore art thou Romeo?"
Day Highlights Overnight
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 KalamataLearn more

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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.

Family-style meal in Greece
Family-style meal in Greece
Day Highlights Overnight
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. 

Or, describe your ideal trip and we will connect you with a local specialist to make it happen.

Map

Map of 21 Days in Italy & Greece - 3 Unique Itineraries
Map of 21 Days in Italy & Greece - 3 Unique Itineraries