- Explore the Colosseum and the Vatican
- Take a trip on a gondola through the waterways of Venice
- See the renowned Acropolis in Athens
- Take in sunset views of the Aegean in Mykonos
- Go wine tasting on the volcanic hillsides of Santorini
|Day 1||Arrive in Rome & City Walking Tour||Rome|
|Day 2||Colosseum & Ancient Rome Tour||Rome|
|Day 3||Free Morning in Rome & Evening Aperitivo Tour||Rome|
|Day 4||Vatican & Sistine Chapel||Rome|
|Day 5||Rome to Florence, Food & Wine Tour||Florence|
|Day 6||Walking Tour of Florence's Highlights||Florence|
|Day 7||Tuscany Day Trip: Siena, San Gimignano, Monteriggioni, & Chianti||Florence|
|Day 8||Train from Florence to Venice||Venice|
|Day 9||Venice Walking Tour & Afternoon Spritz Veneziano||Venice|
|Day 10||Murano & Burano Excursion||Venice|
|Day 11||Flight from Venice to Athens||Athens|
|Day 12||Guided Acropolis Visit||Athens|
|Day 13||Sunset Tour of Cape Sounion & Temple of Poseidon||Athens|
|Day 14||Athens to Mykonos & Traditional Mykonian Dinner||Mykonos|
|Day 15||Day Trip to Delos||Mykonos|
|Day 16||Mykonos Beach Day||Mykonos|
|Day 17||Mykonos to Santorini||Santorini|
|Day 18||Santorini Tour & Wine Tasting||Santorini|
|Day 19||Santorini Wineries & Vinsanto||Santorini|
|Day 20||Catamaran Cruise in the Caldera Lagoon||Santorini|
|Day 21||Santorini to Athens - Depart Athens|
Day 1: Arrive in Rome & City Walking Tour
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: Colosseum & Ancient Rome Tour
Dive into the history of the Roman Empire with a walking tour of the Colosseum, the world's largest amphitheater. Learn about the lives of some of ancient Rome's most famous and illustrious citizens, such as Julius Caesar, Emperor Augustus, Nero, and the Flavian Emperors who built the Colosseum.
Continue to the Roman Forum, where you'll see excavations dating back 2,000 years, revealing the ruins of temples, squares, religious sites, and other buildings. These were the venues for public speeches, processions, elections, and, of course, gladiator matches. Historians and archaeologists refer to the Roman Forum as one of the most celebrated places in world history, and you'll see why as you explore the grounds.
Cut through the Roman Forum along Via Sacra, where you'll pass by the Temples of Vesta, Antonino, and Faustina. The Basilica Julia and Aemilia, a public meeting house that was commissioned by Julius Caesar, is also here.
Your tour of ancient Rome ends 131 feet (40 meters) above the city at Palatine Hill. From here you'll have incredible city views, with the Forum on one side, Circus Maximus on the other, and the Vatican in the distance. In between, the River Tiber snakes through Rome's historic neighborhoods.
In the evening, you'll have free time to continue exploring Rome. Grab dinner in one of the city's other neighborhoods, such as bohemian Monti, and enjoy the quiet hum of city life as the day comes to a close.
Day 3: Free Morning in Rome & Evening Aperitivo Tour
Today, you have a free morning to explore Rome on your own.
Some suggested activities include:
- Visit the Museo Nazionale di Castel Sant'Angelo history museum
- Tour the Renaissance-era Villa Farnesina in the Trastevere district
- View art in the Palazzo Colonna - Galleria Colonna and Palazzo Doria Pamphilj
- Go for a stroll in the buzzing Monti neighborhood, an eclectic area in the city center full of hip wine bars and trendy boutiques
- Head out of the city for a day at the Ostia beach for miles of sand and warm sea
- Explore the Musei Capitolini, the oldest and one of the best museums in Italy
Enjoy a light lunch, as you are going to spend your evening eating and drinking your way through Rome's phenomenal food scene. Start with a guided walking tour of the Piazza Campo de' Fiori, known for its bustling open-air markets and striking hooded statue which looms over the market stalls. Shop for local cheeses, cured meats, fresh vegetables, and seafood fresh from the coast.
From here head to Trastevere, a colorful bohemian neighborhood with a working-class history. This area is located on the opposite side of the Tiber River. Head to the Piazza di Santa Maria, a lively meeting area, to order pizza to go. Enjoy your pizza in the sunny piazza while your guide explains the origin of the Margherita Pizza (named after Margaret of Savoy), then continue the walking tour to try some supplì, delicious rice balls with cheese and tomato sauce.
Afterward, head to the most popular ice cream parlor in Trastevere to enjoy gelato for dessert. Wrap up the night with a wine tasting in a traditional trattoria, accompanied by an assortment of cheeses and prosciutto.
Day 4: Vatican & Sistine Chapel
Today, you will visit the Vatican Museums and Sistine Chapel, as well as other top sights, with a 3-hour guided tour. The Vatican is not only rich in history, but also in art, housing some of the most important Renaissance masterpieces in the world. You'll start by visiting the Pio Clementio Museum, the Gallery of the Candelabra, the Gallery of Tapestries, and the Gallery of the Geographical Maps.
Continue to see the magnificent Raphael Rooms, ending in the breathtaking Sistine Chapel to see Michelangelo's Genesis ceiling frescoes and his Last Judgement altar fresco. Continue to St. Peter's Basilica and Square and experience the magic of Renaissance art as you learn about the secret details and untold stories of the masterpieces.
Your afternoon is free to explore the city. If you haven't already, it's worth seeing the world-famous Galleria Borghese, which houses works by Bernini, Caravaggio, Canova, and Rafaello. The gallery's highlights include sculptures and paintings from Cardinal Scipione Borghese’s collection (1579 - 1633). Rafaello's "Entombment of Christ" is also a must-see.
End your afternoon with a peaceful stroll around the Villa Borghese gardens, enjoying the beauty and calm just steps away from the chaos of the city.
Day 5: Rome to Florence, Food & Wine Tour
In the morning, transfer by high-speed train to Florence, an artistic and romantic city in the heart of Italy's Tuscany region.
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. Make the most of your morning with some of the following suggestions:
- Head to Studio Artemisia, located steps away from the Ponte Vecchio, for a class in ancient fresco painting techniques
- Visit the Chiesa e Museo di Orsanmichele, which served as the granary for the Sisters of San Michele in previous years
- Take a walk through the peaceful Boboli Gardens to see the oval-shaped Isolotto, a small island surrounded by various sculptures and lots of greenery.
If you prefer to explore a city's culture through its food, opt for a half-day food tour.
Head to Piazza Mattei where you'll meet your local culinary expert and start things off with a traditional Italian aperitif at a quintessential wine bar. Sample Tuscany's finest red wines and enjoy a plate of charcuterie while your tour guide delves into the history of Italian food and the significance of sharing a meal with family and friends.
From here, continue to the 16th century Jewish Quarter, formerly the Jewish Ghetto, known for its historic importance and tasty eats. Before sitting down to eat, take a quick walk around the area as you learn about the historical and cultural significance of this neighborhood, which was established by the Medici family as a real estate venture. After your tour, enjoy local appetizers like fried artichokes.
Close the food tour with a plate of Italy's famous pasta. Head to a local family-owned restaurant for an in-depth exploration of the different pasta shapes, cooking styles, and sauce pairings. Round out the meal the Italian way — with gelato and a strong coffee.
Day 6: Walking Tour of Florence's Highlights
Spend the day touring the city's highlights with an art historian on a guided walking tour. Long considered a cultural capital and the "Jewel of the Renaissance", Florence is home to many masterpieces of art and architecture from that era which you'll have the opportunity to experience today.
Start in the medieval city center in the Piazza della Repubblica, one of the city's main squares. It has marked the city center since Roman times. See the Colonna della Dovizia, also known as the Column of Abundance, that marks the point where the cardus (north-south oriented road) and decumanus maximi (east-west oriented road) met and also where the Roman forum stood.
Continue to the Piazza della Signoria, the city's political center since the Middle Ages, where ceremonial events, rallies, and festivals are celebrated. Here you'll find several iconic Florentine landmarks—Palazzo Vecchio and the Uffizi Gallery, which houses works by Michelangelo and Leonardo da Vinci. The square's centerpiece is the Neptune Fountain, a popular meeting place. Your tour today includes skip-the-line tickets to the Uffizi Gallery, which houses works by Botticelli & Raffaello.
See the Ponte Vecchio bridge, a symbol of Florence's power for over seven centuries. The bridge houses buildings and shops which have been occupied by merchants and shopkeepers since the Middle Ages. Arrive at the Italian Gothic Cathedral of Florence and climb the 400+ steps to reach Giotto's bell tower. Enjoy a private and exclusive visit to the Cathedral Terraces, which perch high above the city traffic and are generally closed to the public. From here you'll have a birds-eye view of the whole city.
The final stop of the day is the Galleria dell'Accademia, where you'll enjoy priority skip-the-line access to view Michelangelo's "David" and other masterpieces of Renaissance sculpture.
If you've made prior arrangements, head to Enoteca Pinchiorri, Florence's 3-star Michelin restaurant, for a luxurious dinner option, then stroll through the city on your way back to the hotel.
Day 7: Tuscany Day Trip: Siena, San Gimignano, Monteriggioni, & Chianti
In the morning, you'll head to the countryside to explore Tuscany. Your first stop will be the medieval village of San Gimignano, a UNESCO World Heritage Site an hour away from Florence. San Gimignano is known for its unique towers that dominate the village skyline. In the Middle Ages, noble families built these as symbols of their wealth and status. While most of these towers across Tuscany were torn down when the villages came under Florentine control, a number of San Gimignano's were left standing. Explore the beautiful squares, palaces, and churches of the city before taking a break with a coffee in a terraced cafe.
In the afternoon, you'll visit nearby Siena, a medieval city brimming with historic sites. You can't miss the incredible main square, Piazza del Campo, which is surrounded by the Gothic Pubblico Palace, the Tower of Mangia, and the Gaia Fountain. From here, walk over to the 13th-century cathedral, Duomo di Siena, which dominates the skyline of the city. In the summer months, the town comes alive with festivities, as the Palio takes place in July and August. This exciting horse race, held twice a year in the main square of Siena, ignites the town in a fervor.
Finish the day with a visit to the medieval fortress town of Monteriggioni. Intact castle walls still surround this town perched on a hillside, and are a sight to behold. Continue on to the Chianti Classico wine region to visit a typical Tuscan winery before returning to Florence for the evening.
Customize your trip with help from a local travel specialist.
Day 8: Train from Florence to Venice
Time to say goodbye to Florence. Head to the train station and catch your high-speed train en route to Venice, usually about a 2-hour trip. Once in the city, make your way to your hotel and settle in.
Venice in northern Italy is famous for both industry and tourism. With nicknames like "Queen of the Adriatic", "City of Water", and "The Floating City", it's clear that the city's myriad canals are its main draw. Stretching across 117 small islands in the marshy Venetian Lagoon along the Adriatic Sea, the city has long been a commercial and cultural hub thanks to its strategic placement. Silk, grains, spices, and art were traded through the Middle Ages, making Venice very wealthy.
The city is also famous for its many beautiful historic attractions, such as the Piazza San Marco and San Marco Basilica, the Grand Canal, and the ornate Doge's Palace. The Lido de Venezia is a popular luxury destination that attracts actors, critics, and other cinema industry celebrities.
Take the evening to explore the city with a walk through the Cannaregio district. This area of Venice, known for holding the Jewish Quarter, is the perfect place to simply walk and admire the unique, iconic architecture. Cannaregio has plenty of artisanal shops to explore, not to mention a plethora of delicious restaurants and lively bars to stop in for dinner and drinks.
Alternately, take a ride on a historic Venetian gondola, an unmissable experience while visiting the city of water. As unique as Venice itself, the crescent-shaped hulls and traditional forcole of the gondolas allow for a change of perspective as you explore the city from its maze of waterways.
Day 9: Venice Walking Tour & Afternoon Spritz Veneziano
Experience Venice's highlights with a guided walking tour. Start at Piazza San Marco (St. Mark's Square), the heart of the city's cultural and administrative district. Tour Palazzo Ducale (Doge's Palace), a Venetian Gothic palace built as the primary residence for the Doge of Venice in 1340. The palace stands on Piazza San Marco, and its resplendent interior decor and priceless works of art make it a must-see for history and architecture buffs.
The palace is also connected to the next-door prison by the infamous Bridge of Sighs, which has joined the two buildings since the 16th century. The bridge features a small window onto Venice's harbor and earned its grisly name from the prisoners' sighing as they got one last glimpse of the city on their way to execution. While most visitors gather outside the bridge to look in, you'll get the best sense of history from inside the bridge, looking out from the same window as the doomed medieval prisoners.
Adjacent to the palace is the San Marco's Basilica, originally the Doge's personal chapel. The building is one of the best surviving examples of Italo-Byzantine architecture and features a stunning collection of Byzantine art, gold mosaics, and exquisite marble floors. Your tour includes a visit inside, where you'll be able to see for yourself the incredible art and architecture that the basilica holds.
Away from Saint Mark's Square, you'll delve deeper into the heart of Venice and away from the crowds. Grab lunch at one of the city's many cafes before spending the afternoon exploring Venice through its most well-known cocktail: the Aperol Spritz, also known simply as the Spritz. It's a mix of prosecco, Aperol, and soda water that makes for the perfect aperitivo highlight.
As the day winds down and Venetians emerge from their offices for the all-important aperitivo, you'll meet up with your local wine expert to learn about the history and culture of this required afternoon break. Stroll through the colorful piazzas of Venice, pausing at local eateries for a typical post-work Spritz pairing — olives, cheese, polenta, salami, prosciutto, and more.
After the tour, pick one of the many local-recommended restaurants for an evening meal, Venetian-style.
Day 10: Murano & Burano Excursion
When in Venice, a visit to its lagoon and neighboring islands is a must. These picturesque villages offer a getaway from the city of Venice and a unique look into the local life and culture nearby. This morning, head out for a half-day tour of Venice's famous neighbors — the islands of Murano and Burano.
Board your motorboat in the center of Venice and make your way first to Burano, about 45 minutes away. Along the way, your guide will offer insights about the spectacular Venetian lagoon and its various islands. Traditionally a quiet fishing village, Burano is known for its exquisite lacemaking and the colorful houses that adorn its canals.
After exploring the island, head to neighboring Murano, famous for its colorful glass-making. Visit a glassblower to see a demonstration and learn about the history of glass-making on Murano. Marvel at the intricate pieces, and peruse Murano's many local shops to see the numerous forms of this delicate craft for yourself (and bring some home as gifts).
After spending the better part of your morning enjoying the two islands, return to Venice by boat in time for lunch.
In the afternoon, explore Venice on your own with one of these options to make the most of your time:
- Discover art at the Peggy Guggenheim Collection Modern Art Museum and La Biennale di Venezia Art Museum
- See an opera show at the Teatro La Fenice
- Browse textiles, craft shops, unique boutiques, and galleries in the bohemian San Samuele district
Day 11: Flight from Venice to Athens
Welcome to Greece! You'll begin the second half of your trip in Athens, home to the iconic Acropolis and so much more. The mythology of this spectacular city precedes it, with towering temples 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 BCE. It's probably the first thing that comes to 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.
- Spend your evening exploring the up-and-coming Pangrati neighborhood or amid the nightlife and mezze of the Psyrri district.
Day 12: Guided Acropolis Visit
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.
Complement your tour with a trip to the nearby modern Acropolis Museum. Many of the more delicate statues and other artifacts originally found at the Acropolis have been moved here, but you can imagine them in their previous home as you explore the exhibits. Complete your visit with a stop in its cafe for either lunch or a relaxed snack and coffee.
After lunch, head to the historic neighborhood of Plaka to wander down its many cobbled streets and enjoy refreshments at a local cafe.
Day 13: Sunset Tour of Cape Sounion & Temple of Poseidon
Take it easy in the morning, then head down to the Athenian Riviera in the afternoon, an area full of modern luxury, history, and stunning island views. You'll transfer from Athens for a guided tour of roughly 4-5 hours.
Your first stop is at the Flisvos Marina, where you can admire some of the Aegean's most impressive yachts. Then it's on to the seaside suburbs as you head east through the riviera, with a stop at Lake Vouliagmeni. Interestingly, the lake formed inside of a collapsed cave, and its underwater tunnels have never been fully mapped.
From here, head along the coast to visit the 5th-century Temple of Poseidon, which perches on the very top of Cape Sounion. The cliffs overlook the Saronic Gulf, with one of the best sunset views Greece has to offer — it's no wonder that this site was chosen for Ancient Greeks to worship the God of the Sea. Check out the Doric columns, where Lord Byron once carved his name.
Wrap up your day with an early dinner at a traditional taverna on the beach, where the seafood on your plate is hyper-local and the soft sounds of the ocean provide a relaxing soundtrack to your meal.
Day 14: Athens to Mykonos & Traditional Mykonian Dinner
You'll take a ferry in the morning to Mykonos, one of the most famous islands in the Cyclades. Known for its glitzy restaurants and nightlife, art scene, and jet-set crowds (it was recently home to a Gucci pop-up boutique), Mykonos is one of the most quintessential Greek isles.
Your first day's itinerary is up to you. You'll receive a personalized list of tips for exploration, but some highlights include:
- If you need to get your toes in the sand immediately, head to remote Agios Sostis beach to find your own isolated paradise.
- For a more active experience, Ftelia Beach is known for its excellent windsurfing.
- Stroll through Little Venice, an 18th-century neighborhood where colorful former captains' mansions and seaside restaurants seem to sprout straight from the sea. It's also right next to the island's famous hillside windmills for great photo ops.
As the sun begins to set, sit down to a traditional dinner. You'll be welcomed into a local Mykonian household for the meal, where you'll experience the traditional Greek way of life, culture, and cooking. Hear all about their stories of the island's culture and history as well as their own family history, over authentic dishes and free-flowing local wine.
Day 15: Day Trip to Delos
Travel back in time after breakfast with a morning boat ride out to the archaeological site on the nearby island of Delos. You'll board a small boat at the old port to cruise for 45 minutes out to one of ancient Greece's most sacred sites. This small island was the center of the Cyclades during the Classical era and the mythological birthplace of twin deities Apollo and Artemis. Pilgrims from around the region were attracted to the mystical site and helped it evolve into one of the largest trade centers of the Mediterranean.
Your guided tour will wind you through the foundations of former traders' mansions, temples, and landmarks such as the Terrace of the Lions. Don't skip the island museum, where many of the smaller artifacts and frescoes have been moved to protect them from the elements.
You'll return to Mykonos in time to catch up on your shopping in the afternoon as you explore some of the best boutiques in the Aegean, or check out the weathered Faros Armenistis lighthouse perched high above the Aegean on the island's northwestern tip, with views across to the neighboring island of Tinos.
Day 16: Mykonos Beach Day
Today is all about relaxing in the luxury that Mykonos has to offer, which is easy to find considering the island's unparalleled beauty, white-sand beaches, and turquoise waters.
Your driver will pick you up after a leisurely morning, so take your time enjoying breakfast and the pool. You'll be transferred to the beach of your choice, with options ranging from quiet and calm to humming with energy. Your options include:
- Agios Sostis, full of island residents and travelers who prefer tranquility to amenities, with just sand and a nearby taverna.
- Fokos, a quiet beach on the northeastern end of the island, with no distractions and a single taverna serving up local favorites and organic white wine produced on the island.
- Kalafatis, a quiet beach ideal for family relaxation.
- Ftelia on the northern side of the island, known for windsurfing and sailing when the winds are blowing and tavernas along the bay.
- Psarrou, a world-famous beach that attracts all the posh jet setters and features the Nammos cosmopolitan restaurant and club. Arrive early or make a reservation to secure a front-row umbrella and sunbed.
- Panormos, another famous club featured in Vanity Fair, and home to the popular Principote restaurant. It's elegant yet unpretentious, set in a perfect location protected from the wind.
- Elia; this club definitely gets points for its beauty and aesthetic. It also offers excellent sunbeds, umbrellas, services with drinks and foods, and decent prices. Elia has one of the longest seashores, with fine, white sand and amazing sea views.
- Kalo Livadi, a gorgeous little beach is set on the east side of Mykonos. It's much quieter than the party beaches, but keep in mind that the sand is very pebbly. It's a great choice if you hope to swim, as the water is almost always warm and calm.
- Platis Gialos, an area classic offering a great environment, good food, clean water, and some of the best music in the area.
In the late afternoon, head back to your hotel to enjoy more relaxation by the pool or in your room. Then it's time to hit the town! You can't miss the incredible nightlife in Mykonos, as it's some of the best in the world.
Day 17: Mykonos to Santorini
After breakfast at your hotel, you'll get an early ferry to Santorini. Nothing says "good morning" like watching the sun coming up over the island's iconic cubic architecture. Upon arrival, you'll take in the island's central caldera—the site of one of the largest volcanic eruptions in history—rising above you.
The island's volcanic history has led to the formation of some of the more unique beaches in the Greek islands, along with the dramatic cliff views on the island's caldera side. Spend your day relaxing at the beach or catching some exercise—and even more views—from one of Santorini’s more than 12 scenic walking routes, ranging from between two to eight miles each.
As the day comes to a close, make your way to Akrotiri Lighthouse for unparalleled views of the sunset over the water. Enjoy a chilled bottle of wine as you reflect on your day, soaking in the tranquil evening.
For dinner, sample the island's signature cherry tomatoes and white eggplants as guest stars in seafood dishes or the main event.
Day 18: Santorini Tour & Wine Tasting
In the morning, you’ll be picked up from your hotel or from a central point of Fira for a half-day guided tour. After a short excursion of the area, you'll head to the village of Oia, the furthest town along the rim of the caldera. Oia's arty streets, white-washed facades, and pastel-hued homes are the quintessential Santorini scene.
From here, you'll take a trip up to Prophet Elias Monastery, which stands the highest peak on the island. Bring your camera for the 360-degree views at the top, as well as the many stops on your way down. You'll also see medieval villages at Megalochori and Pyrgos and the Blue Dome in Firostefani before ending your tour at Estate Argyros winery to sample varietals dating back centuries.
After the tour, return to Oia to wander the alleys and linger in the town's tavernas into the afternoon. When searching for your meal, seek out tomato keftedes, deep-fried tomato balls that encapsulate the essence of the Mediterranean diet, and the Santorini specialty — spelt pie.
Oia is also the perfect place to catch sunset views. Stake out your viewing platform over the panorama, then stick around to enjoy the town's tavernas into the evening.
Day 19: Santorini Wineries & Vinsanto
Go beyond the caldera to see another side of Santorini on today's tour. Your first stop is to a nearby restaurant, where you'll dine on fresh local ingredients. After brunch, follow an expert guide to a small family-owned winery, which used centuries of tradition to cultivate vines in the poor volcanic soil. Taste three different ancient varietals along with local snacks as you learn about the winery's ancient growing techniques.
Unique to this region, the red-colored Santorinian Vinsanto (holy wine) is Santorini's sun-dried dessert wine made from overripe white grapes.
Spend the rest of the day exploring a few of the island's other wineries as you sample your way through a dozen varietals, each paired expertly with local cheeses and charcuteries. Wrap up the tour at a winery museum to learn more about the wines you sampled earlier.
End the day with dinner and — you guessed it —more wine.
Day 20: Catamaran Cruise in the Caldera Lagoon
Enjoy a leisurely breakfast before taking some time to stroll around and scope out small shops and boutiques. Explore Fira, the capital of the island, with many attractions. History buffs will be delighted by the Archaeological Museum of Santorini, the Museum of Prehistoric Thera, the Folklore Museum of Emmanuel Lignos, and the Church of Hypapante.
In the late afternoon, head to Vlychada Port to board your semi-private catamaran for a cruise around the island. Your first stop will be at Red Beach to swim and enjoy the sun, followed by a second stop at White Beach.
Enjoy a barbecue dinner on board as you sail past landmarks at Aspronisi, the Ancient Lighthouse, Indian Rock, and the ancient city at Akrotiri, hidden away at the southern tip of Santorini. These ruins are the site of some of the Bronze Age’s most advanced settlements, which prospered for centuries before being destroyed by a great volcanic eruption in the mid-second millennium BCE. Top off your day with a jump into the hot springs at Nea Kameni, where the mineral-rich volcanic waters are believed to have therapeutic properties.
Day 21: Santorini to Athens - Depart Athens
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.