Two weeks in Italy and Greece is enough time to get a feel for the Mediterranean culture and experience the best of what interests you, especially if you choose a focus to guide your trip: highlights, family-friendly, beaches, history, or food and wine. Although you can opt to spend more time focused on your favorite activities, each itinerary includes a well-rounded set of experiences: historic sites, bustling city markets, quiet neighborhood cafes, and sunny beaches, perfect for soaking in the sunshine.

Itinerary #1: Highlights of Italy and Greece: Rome, Florence, Venice, Athens, Mykonos, & Santorini

For a chance to explore bustling piazzas and sun-filled beaches, opt for this highlights trip plan that brings you to the best of both worlds. You'll visit major historic landmarks in the capital cities and spend time relaxing on two of Greece's top vacation islands: Mykonos and Santorini

Aerial view of Piazza della Repubblica
Aerial view of Piazza della Repubblica
Day Highlights Overnight
Day 1 Arrive in Rome & City Walking Tour Rome
Day 2 Colosseum & Ancient Rome Tour Rome
Day 3 Vatican & Sistine Chapel Rome
Day 4 Rome to Florence, Food & Wine Tour Florence
Day 5 Walking Tour of Florence's Highlights Florence
Day 6 Train from Florence to Venice Venice
Day 7 Venice Walking Tour & Fly to Athens Athens
Day 8 Guided Acropolis & Plaka Visit Athens
Day 9 Athens to Mykonos & Traditional Mykonian Dinner Mykonos
Day 10 Mykonos Beach Day Mykonos
Day 11 Mykonos to Santorini Santorini
Day 12 Santorini Tour & Sunset in Oia Santorini
Day 13 Catamaran Cruise in the Caldera Lagoon Santorini
Day 14 Santorini to Athens - Depart Athens  

Begin in Rome, the "Eternal City" of the ancient Roman Empire, for three days of big city living and history in abundance. You'll hit all the city's main destinations: the Vatican and Sistine Chapel, Colosseum and Roman Forum, and the historic area surrounding the Pantheon. View pieces by Bernini and Caravaggio at the Galleria Borghese, then transfer to Florence for even more Renaissance art. You'll explore the Uffizi Gallery as well as the city's center, including the Piazza della Signoria — Florence's political heart since the Middle Ages. 

From there, head north to Venice to see the ornate Doge's Palace and Basilica San Marco, well as the Grand Canal — the city's watery main thoroughfare. Catch a flight to Athens, where you'll experience an augmented reality tour of the Acropolis and spend an afternoon exploring the cobbled streets and small cafes that characterize the city's center.  

End your trip with two days each on Mykonos and Santorini, where a traditional family-style dinner, plentiful beaches, sweeping sunset views, and a full-day catamaran cruise await. Learn more

Itinerary #2: Family Adventure in Italy & Greece: Rome, Athens, Naxos, & More

Bring the whole family along on this two-week trip plan of the Mediterranean's top travel spots. You'll explore the capital cities of Rome and Athens, take day trips to see nearby villages and historic sites, and spend several days soaking in the sunshine on the beaches of Naxos — all while enjoying kid-friendly activities.

A coffee shop in Psyrri
A coffee shop in Psyrri
Day Highlights Overnight
Day 1 Arrive in Rome & Citywide Scavenger Hunt Rome
Day 2 Ancient Rome Tour & Pizza-Making Class Rome
Day 3 Family-Friendly Vatican & Art Class Rome
Day 4 Day Trip to Tivoli & Villa d’Este Rome
Day 5 Flight from Rome to Athens Athens
Day 6 Interactive Mythology Experience Athens
Day 7 Athens Food Tour & Olympic Games Experience Athens
Day 8 Sunset Tour of Cape Sounion & Temple of Poseidon Athens
Day 9 Ferry to Naxos Naxos
Day 10 Beach Day on Naxos Naxos
Day 11 Ancient Naxos Guided Hike Naxos
Day 12 Catamaran Cruise on Naxos Naxos
Day 13 Farm-to-Table Cooking Class on Naxos Naxos
Day 14 Naxos to Athens and Depart  

Start this two-week getaway in Rome, the City of the Seven Hills. You'll begin by exploring the city's historic center with a family-friendly scavenger hunt, letting your youngsters lead the way as you look for hidden statues and clues. Follow that up with a trip back to the time of the gladiators with a tour of the Colosseum and Palatine Hill, then round out the day by learning to make pizza as a family. Your next day in Rome includes a trip to the Vatican and Sistine Chapel, designed to engage even the smallest art aficionados, as well as an afternoon art class. End your stay in Rome with a day trip to see Tivoli, an ancient vacation getaway for the Roman elite. 

Fly to Athens, where you'll visit the Parthenon and other historic sites with guides specializing in children's education. Immerse yourself in Greek history as you reenact the battles between the gods and giants, watch professional performers act out stories of adventure, and more. Continue the immersive experience with a day at Zappeion, the first building erected specifically for the modern Olympic games, where you can test your physical prowess in the Panathenaic Stadium. End your time in Athens with an afternoon trip to the 5th-century Temple of Poseidon, which perches on the very end of Cape Sounion. From here you'll have sweeping views of the Saronic Gulf, with one of the best sunset views Greece has to offer.

Bring your trip to a close when you catch a ferry to the sunny island of Naxos where you'll hike to see historic relics, like the kouros — unfinished statues of ancient Greek gods — as well as a 9th-century Catholic church. Explore the island's coast on a full-day cruise, join a local family as you learn to prepare a full three-course meal, and kick back on one of Naxos' many beaches. Learn more

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Itinerary #3: Mediterranean Coast Getaway: Amalfi Coast, Sorrento, Santorini, Crete, & More

The Mediterranean region is renowned for its coasts and beaches, and you'll spend this two-week trip plan making the most of all that sunshine and turquoise water. Spend time on the Amalfi Coast — land of picturesque beaches, old-world villages, and coastal walking paths — as well as cruising through Santorini's caldera and exploring the rocky hillsides of Crete, where ancient ruins and stunning beaches abound.

Main square in Ravello
Main square in Ravello
Day Highlights Overnight
Day 1 Welcome to Naples! Naples
Day 2 Naples to the Amalfi Coast — Pompeii & Mount Vesuvius Amalfi Coast
Day 3 Tour of Amalfi, Positano, & Ravello Amalfi Coast
Day 4 Kayak Tour of the Amalfi Coast Amalfi Coast
Day 5 From the Amalfi Coast to Sorrento, Food Tour Sorrento
Day 6 Capri & Anacapri Day Trip from Sorrento Sorrento
Day 7 Sorrento to Santorini & Sunset Wine Tasting Santorini
Day 8 Santorini Tour & Sunset in Oia Santorini
Day 9 Catamaran Cruise in the Caldera Lagoon Santorini
Day 10 Free Day in Santorini & Ferry to Crete Heraklion
Day 11 Tour of Knossos & Rethymno, Travel to Chania Chania
Day 12 Chania Beach Day & Afternoon Walking Tour Chania
Day 13 Day Trip to Elafonissi Beach Chania
Day 14 Depart Chania  

Start this trip with an arrival in Naples on Italy's southwestern shore. You'll spend the next week exploring the coast, but on the first day, settle in and enjoy the region's famed cuisine: authentic Neapolitan pizza, fresh seafood, and wine. Dive into Roman history on your second day with a visit to the preserved Pompeii ruins, which were buried in ash after the eruption of Mount Vesuvius in 79 CE. 

Spend the next few days visiting the cliffside fishing villages that characterize this part of the country. Go for a hike along the shoreline on a path that connects several towns, enjoy a food tour of Sorrento, and head onto the water for a day trip to see the nearby resort island of Capri, a longtime Italian favorite for vacations.

Catch a flight to Santorini for the second half of your trip, where you'll tour a family-owned winery and visit nearby medieval villages to experience traditional Greek life. Enjoy a leisurely afternoon cruise of the coast to visit hidden beaches and end the day with a jump into the hot springs at Nea Kameni, whose mineral-rich volcanic waters are believed to have therapeutic properties. 

Day ten of your adventure will find you on a ferry to nearby Crete, where you'll visit the 3,500-year-old Minoan palace of Knossos and explore the rich Venetian and Ottoman history of Chania and its charming old town and waterfront. Round out your vacation with a full day on Elafonissi Beach, whose crystal-clear waters and pink sands make it one of the world's most beautiful. Learn more

Itinerary #4: Discover Greek & Italian History: Athens, Crete, Rhodes, Venice, Rome, & More

With an emphasis on ancient empires and a well-rounded itinerary, this two-week trip plan is perfect for hardcore history buffs and casual aficionados alike. Spend time in the big cities of Rome and Athens, then dive deeper into local culture with visits to Rhodes, Crete, and Pompeii

The amphitheater at Delphi
The amphitheater at Delphi
Day Highlights Overnight
Day 1 Arrive in Athens Athens
Day 2 Day Trip to Delphi Athens
Day 3 Mycenae, Nafplio, and Epidaurus Day Trip Athens
Day 4 Guided Acropolis Visit & Flight to Crete Heraklion
Day 5 Explore Knossos and Heraklion Heraklion
Day 6 Heraklion to Rhodes & Medieval Tour Rhodes
Day 7 Ancient Cities of Rhodes Tour Rhodes
Day 8 Flight from Rhodes to Venice & Gondola Tour Venice
Day 9 Historical Venice Walking Tour & Secret Passages Venice
Day 10 Venice to Rome & Guided City Tour Rome
Day 11 Colosseum & Ancient Rome Tour Rome
Day 12 From Rome to Naples Naples
Day 13 Pompeii and Mount Vesuvius Naples
Day 14 Depart Naples  

Kick things off in Athens, where you'll explore the Acropolis' original splendor with a 3D augmented reality tour, which includes the Parthenon, the Temple of Athena Nike, and the temple of Erechtheion. Take two day trips outside of Athens — to Delphi and Nafplio — to visit ancient archaeological sites. In Delphi (once home to priestesses of Apollo), you'll see the main temples, the Treasury of the Athenians, and ancient relics at the on-site museum.

The following day you'll explore Mycenae, Nafplio, and Epidaurus on a full-day history immersion. See the tombs of Aegisthus and Clytaemnestra and the Treasury of Atreus in Mycenae (famous for its role in Homer's Iliad) and view Ottoman and Venetian architecture in Nafplio. End the day among the ruins of Epidaurus, an ancient center for healing and health. 

Catch a flight to the island of Crete and then onward to Rhodes for four days of Minoan architecture, medieval castles, and hilltop villages. You'll tour the 3,500-year-old Palace of Knossos (believed to be Europe's oldest city), visit the Old Town of Rhodes with its complete medieval city and castle, and see the former site of the Colossus of Rhodes. Round out your Rhodes experience with a stop at one the island's major Greek and Phoenician trading centers during the Classical era and the three-level city of Kameiros before catching a flight to Venice.

You'll begin the second half of your trip in the north of Italy in the City of Water. Get to know Venice on the first day with a traditional gondola trip through the city's meandering canals, then head onto dry land for a day two walking tour of the city's historic center. Highlights include the 5th century San Giacomo di Rialto church, the Venetian Gothic Palazzo Ducale which was built in 1340, and a visit inside the palace to see secret rooms and back passages that are typically hidden to the public. 

Continue to Rome for the last leg of your trip. Here, you'll tour the heart of the city and its main landmarks — including the Trevi Fountain and Pantheon — as well as the ancient Colosseum and Roman Forum. End your trip with a visit to Naples and the nearby ruins of Pompeii, which were infamously buried several millennia ago by the explosion of Mt. Vesuvius. Learn more

Itinerary #5: Best of Mediterranean Food & Wine: Athens, Santorini, Crete, Tuscany, Rome, & More

Eat and drink your way through the gastronomic hotspots of both Italy and Greece on this two-week culinary trip plan. With stays in the capital cities, as well as the quiet countrysides of Tuscany and Crete, you'll have ample opportunity to sample the best cuisine that the Mediterranean region has to offer. 

Drinks with a view
Drinks with a view
Day Highlights Overnight
Day 1 Arrive in Athens, Welcome Dinner Athens
Day 2 Guided Acropolis Visit & Food Tour Athens
Day 3 Athens to Santorini & Sunset Tour Santorini
Day 4 Santorini Food & Wine Tour Santorini
Day 5 Free Day in Santorini & Ferry to Crete Heraklion
Day 6 Olive Oil Tour & Farm-to-Table Lunch Heraklion
Day 7 Heraklion Walking Tour & Flight to Bologna Bologna
Day 8 Highlights and Tastes of Bologna Bologna
Day 9 Day Trip to Parma: Ham and Parmesan Tasting Bologna
Day 10 Bologna to Florence & City Walking Tour Florence
Day 11 Full Day Chianti Tour: Winery & Steak Poet of Fiorentina from Florence Florence
Day 12 Florence to Rome & Guided City Tour Rome
Day 13 Guided Food Tour of Testaccio & Trastevere Rome
Day 14 Depart Rome  

Start this two-week stay in Athens, home to several bustling markets that boast fresh-caught seafood, local produce, and street food. You'll visit these and more during your stay here, as well as the must-see Acropolis with its multitude of archaeological sites. Continue to the resort island of Santorini, whose blue-domed buildings are a landmark feature. You'll spend two days here, visiting an anhydrous farm to learn about growing methods in this volcanic landscape and visiting the medieval villages at Megalochori and Pyrgos

From here catch a ferry to Crete, where you can tour a family-owned olive grove and explore Heraklion's Venetian past on a walking tour of the city. From there catch a flight to Bologna in Italy's Emilia-Romagna region, the heart of the country's foodie scene, where you'll continue your culinary exploration with a food tour of the city's Mercato di Mezzo and a day trip to nearby Parma to sample the Parmesan and prosciutto.

Continue your trip with a transfer to Florence in the heart of Tuscany to see to see Michelangelo’s David in the Galleria dell’Accademia and go on a day tour of the nearby Chianti wine region. Round out your trip to the area with a visit to the legendary 8th-generation butcher Dario Cecchini, whose skill with a T-bone has made him world-famous. 

End your vacation in Rome — the Eternal City, where there's as much weight placed on a visit to the Pantheon as there is to the neighborhood gelateria. Sample the many flavors of gelato (each with a regional history), enjoy a pizza accompanied (as always) by a chilled glass of prosecco or spumante, and linger over coffee at one of the many cafes in the peaceful bohemian neighborhood of TrastevereLearn more

More Great 14-Day Italy & Greece Itineraries

Looking for more inspiration for your trip to Greece or Italy? Check out these other 14-day Greece itineraries or these 14-day Italy itineraries, with history-focused trips, 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 of 2 Weeks in Italy & Greece - 5 Unique Itineraries
Map of 2 Weeks in Italy & Greece - 5 Unique Itineraries
Written by Sonya Pevzner, updated Nov 6, 2023