Experience the best of Mediterranean food, culture, and history with this two-week grand tour that sweeps you across Rome and Venice before alighting on the islands of Crete and Santorini. Start in Italy to step back in time with visits to the Eternal City's Vatican Museums and Colosseum, and sip fizz underneath the shady vines of the Prosecco Valley. Then, hop over to Greece for laid-back village life, ancient palaces, and a masterclass in Greek cooking.


  • Master the art of pasta and tiramisu in Rome 
  • Sample cicchetti and tour world-leading vineyards in the Veneto
  • Discover Cretan cuisine at the home of a local chef
  • Sip wine and lunch on fresh Santorini produce at an organic farm and winery

Brief Itinerary

Day Highlights Overnight
Day 1 Arrive in Rome (Italy), Explore the Eternal City Rome
Day 2 Colosseum & Roman Forum Tour, Pasta & Tiramisu Cooking Class Rome
Day 3 Vatican Guided Tour, Trastevere Afternoon Food Tour & Wine Experience Rome
Day 4 Train to Venice, Gondola Ride, Explore the City of Canals Venice
Day 5 Tour Le Colline de Prosecco, Sommelier-Led Tasting & Lunch Venice
Day 6 Guided Tour of the Valpolicella Wine Region & Amarone Vineyards Venice
Day 7 Fly to Chania (Greece) via Athens, Guided Tour of Chania Old Town Chania
Day 8 Cretan Villages Food & Culture Tour Chania
Day 9 Transfer to Heraklion, Tour Knossos Palace, Dinner at a Local Restaurant Heraklion
Day 10 Cooking Class & Cheese Tasting in a Local Village  Heraklion
Day 11 Ferry to Santorini, Explore & Relax in Oia Santorini
Day 12 Santorini Farm-to-Table Experience & Wine Tasting, Sunset Walk Santorini
Day 13 Free Morning to Explore, Sunset Cruise Around the Caldera Santorini
Day 14 Depart Santorini  

Detailed Itinerary

Day 1: Arrive in Rome (Italy), Explore the Eternal City

Beautiful Rome at Night
Start your Italy adventure with an evening stroll in the Eternal City

Benvenuti in Roma! Upon arrival at the airport, meet your driver and transfer to your hotel in the historic center. Settle in and relax, then head out to discover Rome's enticing mix of ancient history, laid-back piazza lifestyle, and delicious cuisine that continues to captivate visitors worldwide. Embrace the beloved tradition of passeggiata, where across Italy, locals take to the streets after work to socialize and stroll before enjoying aperitivo as the sun sets.

Start at the historic Piazza del Popolo and head up a steep winding path to the Terazza del Pincio, a gorgeous terrace within the Villa Borghese Park, whose west-facing views capture the highlights of the Rome skyline and the twinkling St. Peter's Dome at sunset. From here, it's a short 10-minute walk south to the Spanish Steps and nearby Trevi Fountain, whose illuminated Baroque carvings are even more spectacular at nightfall. End your evening in the Piazza della Rotonda, admiring the views of the Pantheon while sipping a classic negroni or Aperol spritz. 

Day 2: Colosseum & Roman Forum Tour, Pasta & Tiramisu Cooking Class

Perfect the art of Tiramisu
Perfect the art of tiramisu in today's cooking class

Follow in the footsteps of gladiators this morning with a walking tour of Rome's iconic Colosseum. Built by Flavian emperors in 80 CE as the epicenter of Ancient Rome's public entertainment, you'll slip the queues and discover the amphitheater's highlights and the labyrinthine dungeons. You'll also get special access to the arena itself—it's a moment to remember as the custodian unlocks the gates and you imagine the roar of 80,000 spectators calling your name.

Continue your step back in time with a short walk to Palatine Hill, once an exclusive neighborhood for political leaders and emperors, where you'll see ruins of the sprawling palaces. Admire the umbrella pine-dotted views toward the Vatican, Circus Maximus, and the Roman Forum—the focal point of political life in Ancient Rome and your final stop. Explore the forum's vast 2,000-year-old excavations that reveal the temples, squares, and religious sites used by the empire's noble citizens. 

Later on, you'll continue your immersion into Italian life with an authentic cooking class led by a local, who'll guide you through the different types of pasta used in Roman cuisine and the four classic sauces: carbonara, cacio e pepe, alla gricia, and amatriciana. You'll start by preparing the dolce (dessert). Choose from a classic tiramisu or gelato and leave to set as you work on the pasta. Learn how to mix and knead your flour and eggs, then cut or shape your preferred type of pasta. At the end of the workshop, sit down with your fellow chefs and enjoy your creations.

Day 3: Vatican Guided Tour, Trastevere Afternoon Food Tour & Wine Experience

Santa Maria, Trastevere
Trastevere's wisteria-filled cobbled alleyways are the perfect spot to discover Roman cuisine

Start the day as the locals do with caffé and a cornetto semplice (croissant) at one of the neighborhood bars, then meet your guide for a three-hour tour of the Vatican City, starting with the Vatican Museums. Founded by Pope Julius in the early 16th century, the museums are renowned as some of the world's most splendid, with classical sculptures and Renaissance masterpieces that have fascinated countless generations with the city's art and history. 

You'll pass through 45 galleries and the Raphael Rooms before arriving at the Sistine Chapel, famous for its frescoed ceiling and Michelangelo's "Last Judgement." Take a moment to appreciate the extraordinary setting inside St. Peter's Basilica and see Michelangelo's dramatic "La Pietà," a depiction of the Virgin Mary holding the dead Christ in her arms. Your guide will leave you with some free time to explore the Basilica on your own, where you can view the Papal Tombs, climb to the top of the dome, and, afterward, stroll around Bernini's celebrated Piazza San Pietro

Later on, you'll head to one of Rome's most picturesque neighborhoods, the charming wisteria-filled Trastevere, for a guided food and wine tour. Sink your teeth into Roman street food specialties such as supplì (fried bites) and porchetta (roast pork, stuffed and rolled with herbs) as you wander the quaint streets. Pause for a glass of Prosecco or vino rosso at one of the local bars and learn from your guide how wine and food are paired in Italy. You'll finish with dinner at one of the local trattorias, where you'll feast on Roman classics such as carciofi alla Giudia (Jewish fried artichokes.)

Day 4: Train to Venice, Gondola Ride, Explore the City of Canals

Sunset over the Grand Canal
Discover Venice's waterways with an evocative gondola ride along the Grand Canal

You'll wave goodbye to Rome this morning and make your way to Termini train station for the next leg of your Italy adventure. Venice, located in the country's northeastern Veneto region, has enchanted visitors for centuries with its atmospheric canals and ornate bridges that form the palazzo-lined Venetian lagoon. In just under four hours, you'll arrive at Venezia Santa Lucia station. There's only one main mode of travel here other than foot and that's by vaporetto (water taxi). Hop on to one of the regular services and alight at one of the Grand Canal stops near your hotel. 

Once you've checked in, start your Venice experience with the time-honored tradition of a gondola ride. The primary mode of Venetians for centuries, sit back and relax as you glide through the narrow and intricate networks of waterways to discover parts of the city only accessible by gondola. Afterward, follow the signs to Piazza San Marco (Saint Mark's Square) and stop to admire the splendid Basilica San Marco before soaking up the atmosphere with aperitivo at Caffè Florian, a neo-Baroque 18th-century coffee house that's attracted the city's writers for 300 years. 

In the evening, head to the Cannaregio neighborhood—the city's former Jewish Ghetto retains an authentic charm and is filled with local bacari (bars), which locals flock to in the early evening to enjoy bite-sized cicchetti (Venetian tapas) and excellent local Veneto wine or Prosecco.

Day 5: Tour Le Colline de Prosecco, Sommelier-Led Tasting & Lunch

Prosecco Hills
Tour the beautiful countryside and sip famous Italian bubbles in Veneto's Prosecco Hills

Italy's Prosecco Route runs from Treviso to Valdobbiadene, and since 2019, Le Colline de Prosecco di Conegliano (the Prosecco Hills) and Valdobbiadene have been designated a UNESCO World Heritage Site in recognition of the region's Prosecco production. This morning, you'll meet a local sommelier for a private tour through the renowned hills, where you'll visit two leading Prosecco wineries. Learn about the production process involved in making these effervescent wines and taste different styles and vintages accompanied by a light lunch of regional specialties.

Plan your trip to Italy
Chat with a local specialist who can help organize your trip.

After a day spent exploring the vineyards and cellars, you'll return to Venice, where the evening is yours to spend at leisure. Weave your way through the atmospheric streets and glimmering architecture to the Ponte dell'Accademia, one of the best bridges to grab a picture-perfect view of Venice and the Grand Canal as the sun sets. Then, head to the San Polo district and spend the evening dining on seafood or pasta with fresh truffles at one of the city's renowned restaurants. 

Day 6: Guided Tour of the Valpolicella Wine Region & Amarone Vineyards

Parish Church of Marano di Valpolicella amid the vines
Discover Valpolicella's vineyards, responsible for exceptional reds such as amarone 

Enjoy a relaxed breakfast at your hotel before meeting your private guide for a trip to Veneto's Valpolicella region, a district between the Alps foothills and the surrounding valleys of the Lessini Mountains. Surpassed only by Chianti and Montepulciano d'Abruzzo in Italy's red wine production, the area's renowned vineyards produce four excellent reds: rich amarone, spicy cherry Valpolicella ripasso, sweet recioto, and, of course, Valpolicella.

You'll explore two of the region's favorite wineries, learn about the centuries-old production process, tour the cellars, and see how the barrels are stored for aging. Afterward, in the company of a sommelier, you'll taste various vintages and styles, accompanied by small piatti (plates) to compliment the wines. Once you're done, you can purchase any bottles you particularly enjoyed before your guide drops you back in Venice. Spend your last night in the city in the Dorsoduro district, home to some of Venice's most picturesque canals and palazzi, with plenty of excellent restaurants.

Day 7: Fly to Chania (Greece) via Athens, Guided Tour of Chania Old Town

Chania harbor
Start your Cretan adventure with a stroll around Chania's Venetian harbor

Today, you'll say ciao to Italy and board a 2.5-hour flight to Athens and a short connecting flight to Crete, the largest of Greece's islands. Your onward destination is Chania, a bustling harbor town and former Venetian city that's considered one of the most scenic spots on the island. Settle into your hotel, and when you're ready, head out for a private tour of the Old Town. You'll start at the city's famed 14th-century Venetian harbor and meander the atmospheric alleyways while you learn about the island's rich history and mythology from your local guide. 

Stroll the stone paths in the historic neighborhoods of Topanas, Splantzia, Kolombo, and Kasteli, following in the footsteps of Venetians and Ottomans, before stopping at several viewpoints to take in the sweeping vistas of the Mediterranean. Look out for the remnants of the ancient city of Kydonia, whose many old city walls and gates dot the city. Then, when hunger strikes, wander over to the old Chania Market, where you'll find stalls full of fresh produce and Cretan delights like dakos, twice-baked bread slices topped with tomatoes, feta, olives, and olive oil.

Day 8: Cretan Villages Food & Culture Tour

Kaltsounia, Cretan cheese pies
Discover delicacies such as kaltsounia (Cretan cheese pies) on today's foodie tour

Discover rural village life today as you embark on a guided tour of the Cretan villages that make up the Apokoronas area, a 35-minute drive southeast of Chania. Drive through the olive-clad hills and pass through the picturesque hamlets of Stylos, Tsivaras, and Kalives. Your first stop is Gavalochori, where you'll delve into the area's history with a visit to the Folklore Museum and learn how the lace here is still made according to ancient Byzantine techniques.

Your next stop is Xirosterni, where you'll be greeted with a glass of raki (an aniseed-based spirit) and a tour of the local family-run distillery. Popular throughout Crete, the fiery spirit is considered a sign of friendship and is similar to the Italian grappa. Continue to the village of Emprosneros and visit a local cheese producer, then pause for a tasting of local cheeses, freshly baked bread accompanied by locally harvested olive oil, and Cretan cookies fresh from the bakery. 

You'll end your tour in a traditional kafeneio (café) in the village of Fres, where you'll be warmly welcomed by the locals and enjoy a traditional Greek lunch that showcases the area's fresh produce. Return to Chania in the afternoon and stretch your legs with a stroll around the harbor before dining on local fare such as kleftiko (slow-roasted lamb).

Day 9: Transfer to Heraklion, Tour Knossos Palace, Dinner at a Local Restaurant

Ruins of the Palaces in Heraklion
Step into Ancient Greece with a trip to the Palace of Knossos

You're heading east to Heraklion today, so sit back and enjoy the two-hour journey through the Cretan countryside and the views of the mountains in the distance. Your destination is the Palace of Knossos, an incredible archaeological site excavated and restored over a period of 35 years. On a private guided tour, you'll delve into the legends of Ancient Greece as you explore the 3,500-year-old Minoan palace and maze of frescoed royal chambers, private apartments, and courtyards while your guide shares tales of the rise and fall of Minoan Crete.

Check into your hotel and spend the rest of the day strolling Heraklion's Old Town at leisure. One of Greece's most important cities with a rich cultural and historical heritage, Heraklion is awash with medieval and Venetian architecture. Highlights include the elegant arches of the Venetian Loggia, now in use as the town hall, and the Rocca a Mare Fortress along the harbor walls. Spend the evening on Tsimiski Street, where you'll find plenty of shops and boutiques to browse, then head to dinner at a nearby restaurant for freshly caught fish and authentic Cretan cuisine. 

Day 10: Cooking Class & Cheese Tasting in a Local Village 

Learn How to Make Cretan Delicacies - Photo from MAMAKITA
Learn how to make Crete's classic dishes under the guidance of an expert local

Crete is known for its many cheese varieties, made from either sheep's milk, goat's milk, or both. Today you'll transfer to a small village in the countryside near Heraklion to sample the region's cheeses and learn the traditional techniques behind some of the island's most treasured dishes. After a stroll through the village's cobbled streets (listen for the sound of goat bells), you'll meet your host and enjoy a welcome drink before sitting down to a tasting of some of the island's most popular cheeses, like graviera, mizithra, anthotyro, and xinomizithra.

Hear from your host about the secrets behind the country's healthy Mediterranean diet and how to distinguish the four characteristics of excellent olive oil, then roll up your sleeves and get to work. Depending on your preferences, you'll learn how to cook Cretan classics such as boureki, a dish of thinly sliced potatoes, zucchini, and mizithra cheese, seasoned with garlic, mint, and olive oil, and kalitsounia, small sweet or savory pies filled with cheese and herbs, vegetables and meat, or honey and nuts.

With the dishes out of the oven, you'll enjoy lunch the Cretan way, with new friends, wine, and good conversation, as you swap stories with your host and learn more about daily life on the island. 

Day 11: Ferry to Santorini, Explore & Relax in Oia

Oia, Santorini
Santorini's whitewashed buildings showcase the island's serene elegance

It's an early start this morning as you catch a 1.5-hour ferry to Santorini, the southernmost island in the Cyclades. Famous for its volcanic beaches and cosmopolitan feel, it's a sight to behold as you watch the sunrise over the island's iconic cliffside architecture and see the central caldera, the site of one of the most significant volcanic eruptions in history, rising above you. Settle into your hotel, and when you're ready, head out to explore.

Oia's matte white buildings, stoically perched on the cliffside amid the island's infamous blue domes, are a photographer's dream. Exploring the town only takes a couple of hours, and you'll find plenty of independent boutiques to peruse and dreamy terraces to relax on as you while away in the morning. For incredible views of the Aegean and a stretch of the legs, take a trip up to the highest peak on the island. You'll need your camera for the views at the top and the many stops on your way down. 

Day 12: Santorini Farm-to-Table Experience & Wine Tasting, Sunset Walk

Sit down to a traditional lunch in a small Santorini village

Today you'll discover how islanders have become adept at growing local produce (such as flavorsome cherry tomatoes and fava beans) across Santorini's arid terrain with a technique known as anhydrous farming. You'll explore nearby Megalochori, a hidden gem of a village, where you'll visit an organic farm and winery. Discover how the village's wine production follows centuries-old traditions and witness a cooking demonstration with freshly picked ingredients from the farm. Your tour concludes with a mouthwatering lunch paired with local wines.

Of all the Greek island sunsets, Santorini's always tops the list, and the views from Oia, the island's northernmost tip, are astonishing. Tonight you'll head out to marvel at the views from the caldera with a stroll along the Fira to Oia walking path. The route runs underneath the island's main road, which means you can often beat the crowds and enjoy uninterrupted views. After you've captured a few scenic shots, return to Oia, where the rest of the evening is yours to dine at one of the cliffside restaurants as you watch the sunset over the horizon. 

Day 13: Free Morning to Explore, Sunset Cruise Around the Caldera

Set off in a traditional wooden sailboat to explore the coastline of Santorini

Spend a leisurely morning browsing Oia's shops and boutiques, or head to Fira and immerse yourself in the island's history with a wander around the capital's museums. Highlights include the Archaeological Museum of Santorini and the Museum of Prehistoric Thera. As the afternoon unfolds, head to Athinios Port to board your authentic brigantine, a traditional 100-foot (28 m) wooden boat, for a sailing cruise around Santorini's caldera coastline. Hear fascinating insights from your guide about the island's geology and learn how to identify the visible volcanic layers along the crater walls. 

Your captain will drop anchor near Thirassia, the second-largest island within the caldera, where you can swim in the crystalline sea and bathe in the therapeutic waters of the nearby hot sulfur springs. Refuel after a dip with a traditional Greek barbecue served onboard and sail past the port towns of Ammoudi and Armeni. You'll return to Athinios Port, where the rest of the evening is yours to enjoy your final night on the island. 

Day 14: Depart Santorini

Oia sunset
Oia comes alive at dusk from the island's best sunset viewing spots

It's time to say goodbye to Greece. After one last stroll around the island, you'll transfer to the airport in time for your flight home or onward journey. Safe travels!

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