Best of Mediterranean Food & Wine: Athens, Santorini, Crete, Rome, Tuscany, & More - 21 Days

Day 1: Arrive in Athens, Welcome Dinner

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

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: Ferry to Naxos

Time to ferry over to bustling Naxos after breakfast. With an active main town where you can shop and admire the Venetian architecture, a historic Kastro (castle) area, and expansive beaches, the island offers opportunities for both laidback relaxation, as well as water or land activities. The rest of the day is yours to unwind as you choose. Try out some of these options:

• Hike up to the summit of Mount Zas, the mythological childhood home of Zeus, the ruler of the gods, and the highest point in the Cyclades.
• Head inland to the town of Chalki, home to the island's oldest market and a petite, shady square perfect for whiling away the afternoon. Stop at the kitron distillery to sample the local liqueur and learn about its distillation process over the years.
• Visit the Temple of Demeter at Sangri. Multiple deities of fertility were worshipped here, particularly the goddess Demeter. The temple was constructed in 530 BCE, during the tyranny of Lygdamis, and represents a precursor of classical Athenian architecture. 
• Stroll to the Portara, the entrance to the Temple of Apollo. Construction on the temple began in the sixth century BCE but was never finished, but the still-standing entranceway has become one of the hallmarks of the island. You can find it on the islet of Palatia, just over a causeway from the heart of Naxos Town (Chora).

For dinner, wander up the hill through the streets of the Kastro neighborhood to pick out your favorite of the area's tavernas, where you can sample the island's fresh produce in its best forms.

Day 4: Farm-to-Table Cooking Class on Naxos

Take a leisurely morning after breakfast, adding more shopping or time in the sun to your itinerary. At your choice of time in the afternoon, you'll head to Kaloxylos village to learn how to prepare a typical Greek meal in a local home. Join in the village life, with a 3-course menu that you can help determine based on your personal preferences, season, and what's growing in the village garden. 

Sample (and perhaps even create!) some of the island's better-known dishes, such as loukoumades (fried donuts), keftedes (meatballs with tzatziki sauce and Naxian cheeses), and cheese or olive pie with coffee, juice, bread, fruit, and yogurt.

At sunset, head to the Portara if you haven't yet. The unfinished entrance to the Temple of Apollo on an islet outside of town is one of the island's best views as the sun goes down.

Day 5: Ancient Naxos Guided Hike

After breakfast, head to the village of Myli, where you'll pick up an old footpath that leads to the island's ancient aqueduct. Hike up to the nearby quarry, where you'll find two large kouros, unfinished statues of ancient Greek gods, lying on the ground. Originally intended to hold up a temple roof, these giant statues were abandoned by their ancient sculptors when they discovered faults in the marble, but they're no less impressive for that today.

Pass the statues along with olive groves, orchards, and a shady riverside. You'll visit the Catholic church of Theoskepasti, also known as Agios Mamas, the island's oldest chapel, along with Episkopi, the summer residence of the Catholic archbishop, on this 2.5-hour guided hike.

Stop in Mesi Potamia on your way back to town to take a break at a taverna under the trees on the river bank. Spend your afternoon exploring the town along with its neighboring riverside settlements at Ano Potamia and Kato Potamia, connected by a walking path, or return to town for a well-deserved beach break.

Day 6: Naxos to Santorini & Guided Sunset Tour

After breakfast at your hotel, you'll get an early 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 7: Santorini Food & Wine Tour

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 8: Free Day in Santorini & Ferry to Crete

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.

Day 9: Olive Oil Tour & Drive to Chania

Olive oil is one of the keystones of Greek cuisine, and you'll get a hands-on look at its creation 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. Pause here for lunch, then end your day with a drive to Chania, which sits along the coast on the western end of the island.

Day 10: Apokoronas Seven Villages Tour

Today, you'll have a chance to hear some of the island's history firsthand during a guided tour through nearby Apokoronas. The region's villages — seven of them — are home to a number of sites including an Ottoman fort, historic churches, and a folklore museum. But most interesting will be the conversations you and your guide will have with the local residents of the area.

Some potential highlights include:

• The hillside ruins at ancient Aptera, one of the largest city-states in Crete until it was destroyed by an earthquake in the seventh century, including a Minoan tomb believed to date back to roughly the 13th century BCE
• Two-aisled churches in the village of Stilos from the 13th and 15th centuries, along with a limestone fossil once believed to be a fossilized sea siren and a walk along the Kiliaris river to a Venetian watermill
• A glassblowing factory in Kokkino Chorio
• The old square of  Gavolochori, where you can visit the women's cooperative and see hand-knit lace created using a Byzantine technique or the neighboring Folklore Museum of Gavalochori

In the afternoon, you'll have time to explore Chania and discover streets, buildings, neighborhoods, and monuments that only locals know. Walk the stone paths where the Venetians, the Ottomans, and older generations of Cretans used to live and work, admiring the flower-decorated neighborhoods.

One possibility is to visit the neighborhoods of Topanas, Splantzia, Kolombo, and Kasteli, all high spots with panoramic views of the harbor and traditional Cretan taverns. Also here are the ruins of the great Minoan city of  Kydonia and high walls of former Venetian moats, which are now integrated into the city.

Once you've worked up an appetite, visit the Municipal Market of Chania and the neighboring  Municipal Garden to enjoy a coffee amid the shade of the trees or garden clock tower. 

In the evening, check out Chania's waterfront districts of Halepa and Tabakaria. Wander among former tanneries and factories in these off-the-beaten-track parts of town, just past the end of the main promenade. Or, top it off with a sunset drink on the rooftop at trendy Pallas.

Day 11: Fly to Naples

Welcome to Italy! You'll arrive at Naples Airport and transfer to your accommodation in the city center. Naples sits on a bay near the still-active Mount Vesuvius, which buried nearby Pompeii in 79 CE. There's a lot to see and do here, so make the most of your time in Naples with some sightseeing: 

• Visit the Naples Archaeological Museum to see Roman, Greek, and Renaissance-era ruins, including artifacts from nearby Pompeii
• Tour the Castel dell'Ovo, a seaside castle located on the former island of Megaride
• See the 16th-century Museo Cappella Sansevero, which houses thousands of veiled sculptures
• Go underground to see the network of tunnels and passageways built under the city streets
• Get outside and see the dormant Solfatara volcano, located a half-hour drive west of Naples

In the evening, go for a stroll along the Caracciolo e Lungomare di Napoli, a waterfront promenade, then head to the Quartieri Spagnoli, a lively commercial hub, for dinner at a trattoria. On the way, stop at the Toledo Metro station, the Stazione della Metropolitana dell'Arte, to see beautiful mosaic inlays.

Day 12: Neapolitan Pizza Cooking Class

Today, you're in for a literal treat- you'll participate in a cooking class on how to prepare one of Italy's most famous foods: pizza. Even better, you'll be learning the secrets to great pie production in Naples, the city where pizza was invented. 

This two-hour cooking workshop begins with your arrival in a local restaurant. Here, under the guidance of a professional pizzaiolo, you'll learn a bit about the history of pizza in Italy before beginning to work with the ingredients. You'll learn how to make the ideal dough and sauce from scratch before combining all the ingredients and assembling a traditional pizza Margherita, ready for baking. When it's piping hot out of the oven, you'll sit down and feast on your delectable creation. 

Afterward, you'll return to your hotel and will have the rest of the day free.

Day 13: Naples to Rome & City Walking Tour

In the morning, take the train from Naples to Rome, then 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 B.C.E. atop Rome's 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 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, this late-afternoon/early evening tour 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 a 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 14: Guided Food Tour of Testaccio & Trastevere

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 15: Train to Siena & City Tour

After breakfast, head to the train station for the trip to Siena in the heart of the Tuscany region, then check into your accommodation. The city's historic center is one of Italy's most popular attractions and is a UNESCO World Heritage Site. Siena is famous for its medieval architecture, museums, and for Palio, a popular horse race which takes place twice a year in the Piazza del Campo (the main square). Explore the downtown on your own before lunch, then head out for a guided two-hour tour. 

Start at the 13th-century Palazzo Pubblico which still houses the municipal administration, as well as the Torre del Magnia, a bell tower with fantastic city views. Visit these main highlights, as well as the green and white striped Duomo and its Piccolomini Library, famous for its soaring, vibrant Pinturicchio frescoes. Continue to see the Museo dell'Opera Metropolitana art museum, as well as Siena's many churches, including the Basilica dell'Osservanza, Santo Spirito, and Sanctuary of Santa Caterina. 

Later, tour some of the city's patrician villas, including Villa Chigi, Villa Celsa, and Villa Volta Alte. Head downtown for dinner and wine in a family-run restaurant.

Day 16: Chianti Wine Tasting from Siena

Take the day to continue exploring the Chianti Classico wine region by visiting a typical Tuscan winery. Just a quick drive from Siena in the stunning Tuscan countryside, La Lastra Winery will delight your senses as you learn to savor this region's specialty. The unique characteristics of the local climate have made the region unfavorable to most crops but ideal for growing wine grapes. Soak in the views, as alternating fields of olive orchards and vineyards characterize this idyllic landscape.

The Chianti wine, made primarily of Sangiovese grapes, is the local staple. Learn about the specific grapes and vines cultivated in the region as well as the entire process of wine production. From the vine to the glass, you'll see firsthand all that goes into every bottle and the culture carried with it over time. Tour the cellars and vineyard of this local winery, then enjoy a wine tasting of four regional wines accompanied by local products. End your visit with a light lunch to pair perfectly with your palate. 

Head back to Siena for the afternoon and continue to explore the historic center of this timeless town. 

Day 17: Siena to Florence & Afternoon City Tour

Enjoy your morning with breakfast at your hotel and one final stroll around the neighborhood, then make your way to the train station and catch your train to Florence. From there, head to your hotel to settle in.

Spend the afternoon getting a feel for the city with a guided half-day walking tour. Stroll through the picturesque historic city center where you'll find the most important squares and monuments: from the Piazza della Repubblica to the Palazzo Vecchio, these beautiful squares give Florence its picturesque setting. Stop to enjoy the atmosphere before heading over to the Ponte Vecchio, where you can admire the Arno River. Don't forget to 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.

In the evening, enjoy some gelato and people-watching, followed by dinner and drinks in the hip Sant'Ambrogio neighborhood.

Day 18: Florence to Bologna & Walking Tour

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 19: Day Trip to Parma: Ham and Parmesan Tasting

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 20: Bologna Food Tour

Bologna is famed for its bustling markets and food scene, and today's tour is a snapshot into daily Italian life.

Start your morning with a strong cup of Italian espresso, then visit two local food markets (Erbe and Quadrilatero) and stop in small family shops to learn about Bolognese cuisine and its unique foods. Enjoy a walking food tour with a local guide to explore the local markets and shop for regional delicacies, such as artisanal tortellini, mortadella, and a variety of cheeses. You'll visit traditional food shops, like a bakery and pasta maker, to see the handcrafting process. After picking up items for your lunch from various stalls, feast on your acquired provisions and pasta with bolognese ragù in one of the oldest osterias of Bologna. Finish your day with an artisanal gelato tasting.

After your tour finishes, ask your guide for a recommendation for dinner as they know the city 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. Afterwards, head out to dinner and enjoy your evening in Bologna.

Day 21: Depart Bologna

Transfer to the airport for your connecting flight home. Have a great trip!