From Crete's rocky hillsides to the rolling farmlands of Tuscany's heartland, this 10-day itinerary delivers top destinations in both Greece and Italy — and leaves you hungry for more. Start the trip in bustling Rome, where archaeological sites and quiet neighborhood gelaterias compete for your attention. Continue north to Florence and Bologna for Chianti and Parma ham, then catch a flight to the Greek islands where wineries and ocean-view sunsets abound.

Highlights

  • Soak in the tradition and culture as you tour Rome's top cultural sites
  • Eat and drink your way through Bologna, Italy’s food capital
  • Pay a visit to Dario Cecchini, nicknamed the "world's best butcher"
  • Learn about the many facets of olive harvesting, from farm to mill
  • Catch sunset views from Oia's arty streets

Brief Itinerary

Day Highlights Overnight
Day 1 Arrive in Rome & City Walking Tour Rome
Day 2 Guided Food Tour of Testaccio & Trastevere Rome
Day 3 Rome to Florence, City Walking Tour Florence
Day 4 Full Day Chianti Tour: Winery & Steak Poet of Fiorentina from Florence Florence
Day 5 Florence to Bologna & Walking Tour Bologna
Day 6 Flight from Bologna to Heraklion Heraklion
Day 7 Olive Oil Tour & Farm-to-Table Lunch Heraklion
Day 8 Ferry from Crete to Santorini Santorini
Day 9 Santorini Food & Wine Tour Santorini
Day 10 Santorini to Athens - Depart Athens  

Detailed Itinerary

Day 1: Arrive in Rome & City Walking Tour

Piazza Navona
Piazza Navona

Welcome to Rome, known as the Eternal City! According to legend, Rome was founded by brothers Romulus and Remus in 753 BCE atop Palatine Hill. As the long-time center of the powerful Roman Empire, you'll find nearly 3,000 years of architecture, history, and culture throughout the city. 

After arriving at one of Rome's airports, you'll transfer to your hotel in the historic center. Settle in and relax, then head out for a small group walking tour and your first look at the city.

The tour will take you to some of Rome's top historical and cultural sites, winding through narrow streets and wide piazzas as you explore the city. You'll learn about Rome's role as Italy's political capital, as well as the city's importance as the cradle of Catholicism. 

Start at the Spanish Steps, then enter the tangle of narrow streets in Centro Storico, one of Rome's most historic districts, to see classical Roman and baroque architecture.  Along the way, your guide will recount stories and historical anecdotes of the many little fountains, important buildings, and hidden piazzas that are tucked away in every corner of this magnificent city. As you weave in and out of the old city's labyrinth, you'll emerge in front of the Pantheon — ancient Rome's only intact Pagan temple.

Your next stop is the Trevi Fountain, where travelers throw coins into the water that according to legend ensure a return to Rome. Take a break at the neighborhood gelateria for the perfect cone of gelato, then conclude your tour at the Piazza Navona, one of Rome's most well-known squares. It sits on top of the former 1st-century Stadium of Domitian which once hosted chariot races and other competitive athletic events (the stadium could even be flooded to recreate naval battles!) The modern-day piazza follows the curve of the stadium's original outline, and traces of the original walls still stand on its outskirts. The 17th-century Chuch of Sant’agnese in Agone, designed by Borromini, marks the spot where the Christian martyr St. Agnes was murdered in 304 CE. 

In the center of the square stands the Fountain of the Four Rivers (Fontana dei Quattro Fiumi), which was designed by Gian Lorenzo Bernini, a leading Italian sculptor. Find a quiet bench in the piazza and enjoy a relaxing evening of people watching and enjoying Rome's many talented sidewalk artists and musicians before making your way to a family-owned pizza shop for dinner.

Day 2: 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 3: Rome to Florence, City Walking Tour

Ponte Vecchio across Arno at night
Ponte Vecchio across Arno at night

Take the morning to say your goodbyes to Rome and head to the city of Florence. 

Florence is home to many masterpieces of Renaissance art and architecture, including the iconic Duomo with its terracotta-tiled dome, and the Galleria dell'Accademia, which displays Michelangelo's 'David' sculpture. 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 Duomo 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 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 4: 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.

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Day 5: Florence to Bologna & Walking Tour

Bologna
Bologna

You'll leave Tuscany today and travel north to Emilia-Romagna, yet another region known for producing excellent food and wine. Arrive in Bologna mid-morning by train (the trip takes about an hour) and check in to your hotel. Once you're ready to start your day, order a cup of Italian espresso from a local café and head out to explore. You'll be led through Bologna by a guide with deep knowledge of the local history, architecture, and food. 

This walking tour will be around 3 hours, discovering 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'll 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.
 
In the afternoon explore the city via the medieval porticos, a network of covered walkways that connect city landmarks, museums, and neighborhoods and protect pedestrians from snow, rain, and the hot summer sun. Visitors with an eye for fashion will enjoy browsing the designer boutiques and medieval Quadrilatero market district for the perfect Italian leather shoes or for gifts to bring home. 

Day 6: Flight from Bologna to Heraklion

Venetian Fortress of Palaiokastro
Venetian Fortress of Palaiokastro

Catch a flight from Bologna to Heraklion, the capital of Crete. It's a bustling, lively city, and with any luck, you'll stumble upon one of its many festivals in its streets as you arrive in Greece.

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.

Day 7: 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 8: Ferry from Crete to Santorini

Fira in the evening
Fira in the evening

After an early breakfast in Crete, catch a morning ferry to Santorini. There's nothing like catching your first glimpse of the island's iconic cliffside architecture. Watch for your first views of Santorini's central caldera—the site of one of the largest volcanic eruptions in history—rising in a crescent. 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 9: 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 10: Santorini to Athens - Depart Athens

Bid Santorini's glorious skies farewell
Bid Santorini's glorious skies farewell

It's time to say farewell to Greece! Savor one more breakfast in Santorini before you transfer to the airport or ferry and begin your journey home.