Sample both Grecian and Italian fare on this two-week itinerary as you explore everything from Rome's busy piazzas to Santorini's beaches. You'll start your trip in Greece for equal parts culinary and archaeological education, with stops at the Acropolis and family-owned olive farms. From Crete, catch a flight to Bologna in Italy's Emilia Romagna region for local Parma ham and parmesan, before eating and drinking your way south through Florence to the capital city of Rome.

Highlights

  • Haggle for your lunch at bustling Athens markets
  • Sip wine while you enjoy sunset views in Santorini
  • Visit the 11th-century University of Bologna
  • Try truffle panini, fresh-pressed Tuscan olive oil, & chocolate focaccia
  • Pay a visit to Dario Cecchini, nicknamed the "world's best butcher"

Brief Itinerary

Day Highlights Overnight
Day 1 Arrive in Athens, Welcome Dinner Athens
Day 2 Guided Acropolis Visit & Food Tour Athens
Day 3 Athens to Santorini & Guided 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  

Detailed Itinerary

Day 1: Arrive in Athens, Welcome Dinner

Monastiraki Square and the Acropolis.
Monastiraki Square and the Acropolis.

Welcome to Greece! You'll begin your trip in Athens, home to both the iconic Acropolis and so much more. The mythology of this spectacular city precedes it, with towering temples to Classical deities and the ruins of ancient marketplaces rubbing shoulders with lively nightlife, crowded flea markets, and contemporary cuisine. Make the most of your time in the city at some of these spots:

  • Check out the views of the can't-miss Parthenon. (Pro tip: The Parthenon is the temple, the Acropolis is the hill.) This temple to Athena has enchanted visitors since its construction was completed in 438 BC. It's probably the first thing that comes to your mind when you think of ancient Greece and is visible from many of the city's high points.
  • Stop at the sprawling National Museum for a crash course in ancient iconography. Be sure to seek out the room housing the Antikythera mechanism, essentially an ancient astronomical computer.
  • Visit a smaller archaeological site at the Tower of the Winds, then stroll down neighboring pedestrian Aiolou Street to stop at shops and cafes. 
  • Find your perfect souvenir or sun hat in the busy stalls of the Monastiraki flea market. 

In the evening, you'll sit down to enjoy either a welcome dinner with views of the Acropolis or wine tasting in a bar in downtown Athens.

Day 2: Guided Acropolis Visit & Food Tour

Olives for sale at Athen's markets.
Olives for sale at Athen's markets.

Today you'll get to experience the mighty Acropolis — ruins of the iconic 5th-century BCE complex located on a rocky hilltop overlooking the city. Take a guided tour of the entire area with a professional guide who will share the stories of the country's most famous monument. In addition to the iconic Parthenon, dedicated to the city's patron goddess Athena, you'll view and learn about the Propylaea, the Temple of Athena Nike, and the most sacred temple of Erechtheion.

Your tickets to the Acropolis will be pre-purchased ahead of time, leaving you with more time to explore the ruins. Your guide will also provide you with an iPad, which you can use to view the augmented reality displays of the buildings' original splendor in 3D.

After the morning history lesson, follow your guide to Syntagma Square to start sampling the best of what the city's street food stalls have to offer. You'll learn about the Mediterranean diet and its potential benefits while strolling the city and exploring bustling open-air markets.

Try an afternoon pick-me-up with a Greek coffee at one of the city's landmark coffee houses, then grab some street snacks to sample on the go. Venture into the aromatic Varvakios Market, the largest and most popular fish, meat, and vegetable market in the city, and explore the city's main spice street. Sample olive oils, honey, cheeses from around the country, cured meats, olives, and more. Everything from baklava to souvlaki is available to appeal to even the pickiest eaters.

If you haven't had your fill of adventuring during the afternoon, spend your evening in the Koukaki neighborhood. This area's off-the-beaten-path wine bars will introduce you to a wide selection of Greek wines amid friendly crowds, or if you're with the whole family, a selection of great local restaurants await.

Day 3: Athens to Santorini & Guided Sunset Tour

Santorini's caldera
Santorini's caldera

After breakfast at your hotel, you'll get an early flight or ferry to Santorini. Nothing says "good morning" like watching the sun coming up over the island's iconic cubic architecture. As you arrive, take in views of the island's central caldera—the site of one of the largest volcanic eruptions in history—rising above you.  After you've settled into your hotel, spend some time wandering the streets of Fira, or head to the beach.

In the afternoon, take a guided tour to some spots in Santorini that most travelers don't see. You'll start with a stroll through famous Oia, where your guide will point out hidden treasures, followed by a trip up to the highest peak on the island, with 360-degree views at the top. Then head on to the medieval villages at Megalochori and Pyrgos, which feel a world away from the touristy towns along the caldera rim. Finally, stop for some wine tasting at the caldera's edge to sample varietals dating back centuries, as you watch the sun sink into the Aegean Sea.

In the evening, head back to Oia, passing the Blue Dome of Firostefani on the way. The furthest town along the rim of the caldera, Oia's arty streets are the most famous spot for sunset views, and evenings, after the crowds have left, are one of the best times to wander the alleys and linger in the town's tavernas. When searching for your dinner, seek out tomato keftedes, deep-fried tomato balls, and the Santorini specialty of spelt pie.

Day 4: Santorini Food & Wine Tour

Vineyards on Santorini
Vineyards on Santorini

Go beyond the caldera to see another side of Santorini on today's tour. You'll start by following an expert guide to the stone streets of Megalochori village, where you'll see how the island's full-time residents live. Then head to a small family-owned winery, using centuries of tradition to cultivate vines in the volcanic soil, where you'll taste three different ancient varietals along with local snacks.

The produce grown on Santorini is known for its waterless farming methods that help enhance the flavor of specialties like tomatoes, yellow beans, eggplants, and capers. Your next stop will feature a cooking demonstration using ingredients from an anhydrous farm surrounded by caves and pumice stone canyons.

End your day with a glass of wine and sunset views over the caldera at a winery built into the island cliffs.

Day 5: Free Day in Santorini & Ferry to Crete

Santorini coast
Santorini coast

The day is yours to explore as you wish before your afternoon ferry to Crete. If you're in the mood for archaeology, scope out Santorini's main historical attraction and one of the Aegean's most significant prehistoric settlements. Head to the excavated city at Akrotiri, hidden away at the southern tip of Santorini on the slopes of the caldera. These ruins were once the site of one of the Bronze Age’s most advanced settlements, which prospered for centuries before being buried by a volcanic eruption in the mid-second millennium BCE. Walk through its well-preserved streets and envision the once-bustling city life that filled them.

The Museum of Prehistoric Thera and Archaeological Museum of Thera complement your visit, with findings including murals preserved from Akrotiri and the settlement of ancient Thera once found on the eastern part of the island. If you'd rather see it for yourself, hike up to where ancient Thera once sat to see the ruins and get a sense of why its location was so strategic.

If you would rather spend the day on a beach, you've got plenty to choose from:

  • Kamari Beach: The most upscale and touristy of the beach towns, with plenty of family-friendly options
  • Perissa and Perivolos Beach: Essentially one very long beach that caters to the backpacker crowd and party scene (beach style, not clubs) but still has a wide range of accommodations and restaurants
  • Red Beach: The pebbly sand here is red and the backdrop is stunning
  • Monolithos Beach: The nicest sand and the most family-friendly beach on Santorini. It's quiet, with a small collection of hotels and restaurants.

Another option is to visit some of the other beautiful villages of Santorini, such as Emporio, where locals built their houses extremely close to each other to prevent piracy. 

Once you've wrapped up, catch a ferry over to Crete, the largest and most populous of the 230 inhabited Greek islands.

Plan your trip to Italy
Customize your trip with help from a local travel specialist.

Day 6: Olive Oil Tour & Farm-to-Table Lunch

 Lyrarakis Winery in Heraklion, Crete
Lyrarakis Winery in Heraklion, Crete

Olive oil is one of the keystones of Greek cuisine, and you'll get a hands-on look at its production process with today's tour.

Your first stop of the day is at Takis' olive grove, a local farmer who uses organic methods to cultivate his crop. You'll learn about the many facets of olive harvesting, including the key role of timing and various harvesting methods. Taste the oil while you hear the stories from the owners of this family business and learn about the many uses of this ingredient.

Your next stop is the nearby olive mill that belongs to the Melissakis family, where you'll learn about modern methods of oil extraction, things to keep in mind when purchasing olive oil, and more. 

From here, head to the Monastery of St. George — Crete's largest — before continuing west along the coast to the mountainous village of Vafes

For lunch, enjoy local recipes that use hand-picked ingredients, then return to Heraklion for a free afternoon of sightseeing or relaxing on a nearby beach.

Day 7: Heraklion Walking Tour & Flight to Bologna

Heraklion harbor
Heraklion harbor

Take some time to walk around the old city's medieval streets with architecture representing the island's Venetian past. The neighborhood's surrounding walls were built by the island's Arab population and later reinforced by the Venetians in the fifteenth century. There were originally seven bastions, but only one is left standing today: the Martinengo Bastion. It's now home to the tomb of the renowned writer Nikos Kazantzakis, best known for his works including Zorba the Greek and The Last Temptation of Christ. 

Other highlights include the Venetian gates, elegant arches of the Loggia (now in use as the town hall), and the Koules Venetian fortress along the harbor walls. Look for the winged lion of Saint Mark on the Chanioporta Gate and southern New Gate to see some of the original architecture.

A pleasant pedestrian street in the Old Town connects the port area with the Lions' Square and its Venetian fountain. Don't miss "mama's food" at Anchorage Traditional Mezedopolio nearby.

In the evening, head to the airport for your flight to Bologna.

Day 8: Highlights and Tastes of Bologna

Bologna
Bologna

Enjoy a good breakfast this morning as you will be heading out for the full day on a walking tour of Bologna. You'll be lead through the city center by a guide with expert knowledge of local history, architecture, and food. Experience the sights, smells, and tastes of the capital of the Emilia-Romagna region.

Walk through the downtown area to see many of the city's notable landmarks. The Piazza Maggiore is a sprawling central plaza surrounded by the city's oldest buildings. You will visit the City Hall, the 14th-century Basilica di San Petronio, and the medieval Asinelli and Garisenda Towers, which flank the Piazza. 

Head to the 11th-century University of Bologna to view the Anatomical Theater, formerly used by students dissecting cadavers, and stroll the medieval university grounds. On the way, stop to see the former Jewish Ghetto, then continue to the Pinacoteca Nazionale di Bologna, the National Art Gallery. This building also houses the Academy of Fine Arts.

Next, explore the city via its medieval porticos, a network of covered walkways that connect city landmarks, museums, and neighborhoods while protecting pedestrians from snow, rain, and the hot summer sun. Visitors with an eye for fashion will enjoy browsing the designer boutiques and the medieval Quadrilatero market district for the perfect Italian leather shoes or for gifts to bring home. 

Bologna is famed for its bustling markets and food scene. The Mercato di Mezzo is well worth a visit in the Quadrilatero area. Explore the local markets and shop for regional delicacies, such as artisanal tortellini, mortadella, and a variety of cheeses. Visit traditional food shops like a bakery and pasta maker to see the handcrafting process and to sample the final products. Tip: here you can buy tasty foods for a picnic and find a piazza or park to eat and people watch.

Alternatively, after your tour finishes, pause for a late lunch or early dinner and enjoy some of the city's delicious specialties from a restaurant—tortellini and ragu alla bolognese, a rich tomato and meat sauce.  Ask your guide for a recommendation for lunch or dinner, as they know the city the best. At aperitivo time, around 6 pm, walk to the trendy indoor market Mercato delle Erbe and enjoy a drink with the locals. It was beautifully restored in 2013 and is full of bustling bakeries, restaurants and wine shops. After, head out to dinner and enjoy your evening in Bologna.

Day 9: Day Trip to Parma: Ham and Parmesan Tasting

Browsing the local selections
Browsing the local selections

Head out for a day trip to the capital of Parma ham and Parmesan cheese—the city of Parma, in the Emilia-Romagna region of Northern Italy. The city is famous for its ornate medieval architecture, the beautiful surrounding countryside, and, of course, the food. 

Start the day at the Parmigiano Cheese Factory, where your tour starts with a brief history of Parmigiano Reggiano Cheese. After, proceed inside the factory to see the production of the cheese, which begins with the cheesemakers pulling the cheese from the milk vats. Your next stop is the seasoning and storage rooms to see the final stages of production, before ending the tour with a tasting of various-aged cheeses.

Your next stop is in the idyllic hills of Langhirano, home of Prosciutto di Parma ham. Learn about the historical and cultural aspects of ham production, then head into the cold room to see how the meat is stored. You'll learn about every step of the process: how hams are selected, the salting, and finally dry storage. The final stage is spillatura, a process where the Inspector of the Consortium selects the finest cuts before branding them with the famous Crown of Parma seal. 

After the two stops, enjoy lunch at a local family-owned restaurant, where you'll sample typical Parma fare (including, of course, Parmigiano Reggiano cheeses and Parma ham), as well as other delicacies like torta fritta, tortelli erbetta, zucca, and more. 

Wrap up your day with a visit to a local winery, where you'll tour the vineyard and cellars before ending things off with a glass (or two) or the estate's finest. 

In the evening, return to Bologna.

Day 10: Bologna to Florence & City Walking Tour

Piazza della Signoria, a UNESCO site
Piazza della Signoria, a UNESCO site

Take the train from Bologna to Florence, then spend the day exploring the city's top sites, starting with a guided half-day walking tour. Stroll through the picturesque historic center where you'll find the most important squares and monuments: from the Piazza della Repubblica to the Palazzo Vecchio, you'll explore the beautiful squares and architecture that make Florence so picturesque. Soak in the atmosphere before heading over to the Ponte Vecchio, where you can admire the Arno River.

You'll then make a stop at the iconic Duomo, with its terracotta-tiled dome, where across the way Giotto's Bell Tower and the Baptistery with its bronze doors create an unforgettable scene. Finally, with skip the line entrance tickets in hand, you'll head to the Galleria dell’Accademia to see Michelangelo’s David. Your guide will share stories of Michelangelo and how this masterpiece came to be.

After your tour, continue your exploration of Florence on your own.  Head across the Arno River to visit to Piazzale Michelangelo. It's a bit of an uphill climb or a quick taxi ride away. This spectacular viewpoint offers an incredible view of all of Florence and is the perfect place to watch the sunset before you head over to Piazza Santo Spirito for some pre-dinner aperitivos.

Day 11: Full Day Chianti Tour: Winery & Steak Poet of Fiorentina from Florence

The perfect glass of Chianti
The perfect glass of Chianti

Hit the road today with your private guide to explore the romantic region of Chianti. This large region is located between Florence and Siena and is famous for its unparalleled beauty, peaceful countryside, and namesake wine. Each part of this incredible region is full of vineyards, wineries, medieval towns, and winding rural roads. 

The Chianti region is renowned for producing the delicious red wine of the same name, made primarily of Sangiovese grapes. The region's unique characteristics and local climate have made the region unfavorable to most crops but ideal for growing wine grapes.

Visit the famous Castello di Verrazzano (birthplace of the famous explorer), and spend the morning learning about the winery touring the cellars and vineyards, then enjoy a wine tasting accompanied by a delicious Tuscan lunch of pasta, cured meats, cheeses, and local desserts. 

From here continue to another authentic Tuscan experience: a visit to the legendary butcher Dario Cecchini, nicknamed the "world's best butcher." The 8th-generation butcher of Antica Macelleria Cecchini is known as the "Poet of Fiorentina"—the famous Tuscany T-bone steak—and you'll find him behind the counter of his butcher shop in the heart of Chianti, in Panzano, every day of the week including Sundays.

The walkway behind the counter is raised, so Dario looks much like a large, smiling giant, a benevolent and friendly man who loves entertaining locals and visitors with his recitations of verses of the Divine Comedy. For a real taste of the butchering process, taste his Chianti Butter (lard cream flavored with herbs and spices), and the Sushi of Chianti (thinly sliced raw meat). 

Afterward, return to your hotel in Florence.

Day 12: Florence to Rome & Guided City Tour

Piazza Navona
Piazza Navona

In the morning make your way to the Florence train station, then take the high-speed train to Rome. After settling in, head out for a guided tour of the historical center of the Eternal City. 

According to legend, Rome was founded by brothers Romulus and Remus in 753 BCE atop Palatine Hill. The long-time center of the powerful Roman Empire, Rome boasts nearly 3,000 years of architecture, history, and culture. These days, Italy's capital is considered one of Europe's top cities thanks to its ancient monuments, incredible art masterpieces, and cosmopolitan vibe. It's a center for fashion with a buzzing food culture, and has a growing nightlife scene. 

It may be near impossible to see all of Rome on foot, but to forgo a walking tour of this historic capital is to cheat yourself out of an unforgettable experience. Led by an expert guide, you'll join a late-afternoon/early evening tour that covers Rome's must-visit sights, including the 18th-century Spanish Steps, the iconic Trevi Fountain, and the Pantheon, the only pagan temple in Rome that has been left intact. But this city is as much about taste as it is sights and sounds. To this end, your guide will lead you to local gelateria to sample every Roman's favorite frozen dessert.

Rounding out the tour are stops at some of the city's most famous piazzas to check out the talent and prowess of Rome's foremost street performers and musicians. At the end of the day, your guide will leave you with a recommendation for the perfect nearby restaurant in which to enjoy a traditional Italian dinner.

Day 13: Guided Food Tour of Testaccio & Trastevere

Perfect place for an afternoon coffee
Perfect place for an afternoon coffee

Spend the morning exploring Rome's famous food scene and tasting all the different flavors and ingredients that make Italian cuisines famous around the world.

Start the tour by meeting with your local guide, then enjoy a nice stroll through the quieter neighborhoods of Testaccio and Trastevere. Start in Testaccio to see traditional markets, restaurants, and coffee shops. Sample the local foods from fried artichokes, codfish, and zucchini flowers to delicious porchetta and Supplì rice-balls. 

From here, continue to a very different area, the former working-class neighborhood of Trastevere, whose name literally means "across the river". Nowadays the neighborhood is a quiet bohemian haven with picturesque squares, peaceful narrow alleyways full of potted plants, and small coffee shops with one or two tables to linger at during the afternoon. The area is now a fashionable residential area with a wealth of great restaurants and bars. 

Enjoy a relaxed stroll to see the area's churches and palaces, including the Basilica of Santa Maria, Basilica of Saint Crisogono, and Basilica of Santa Cecilia. 

After some sightseeing, enjoy a light lunch and drinks out on the town. Round things off with an afternoon cappuccino or espresso at a local caffeteria, then head to a gelateria and choose from an incredible variety of flavors, each made with the finest ingredients from all over Italy. Pistachio from Sicily, nuts from Piedmont, and lemons from Sorrento make for a mouth-watering selection. 

If you're still hungry, try a Roman pizza, accompanied (as always) by a chilled glass of prosecco or spumante. In the afternoon, visit some of Rome's iconic museums, such as the Capitolini Museum or the Galleria Borghese, on your own.

Day 14: Depart Rome

Farewell, Rome!
Farewell, Rome!

Time to say goodbye to Italy—for now! After one last Roman breakfast, you'll transfer to the airport for your flight home. Safe travels!