Rome, Italy. The Colosseum or Coliseum at sunrise

Highlights of Italy and Greece

12 Days from $7,490 USD / person

Experience the best of Italy and Greece on this superb 12-day tour. Enjoy guided walking tours of Florence, the birthplace of the Renaissance, and Rome, which was the center of the mighty Roman Empire. Visit historic landmarks such as the majestic Duomo and Uffizi Courtyard in Florence, and the Pantheon and Palazzo Madama in Rome. No trip to Italy is complete without a visit to the Vatican City. Learn about Italy’s world-famous wines and olive oil on an excursion to the nearby Chianti region.

Your exploration of the rich history and culture of the region continues in Athens, Greece. Marvel at the Acropolis, visit the bustling Agora central market and watch the world go by at Syntagma Square. Your last stop, Mykonos is best known for its vibrant party scene. You can enjoy the atmosphere of its lively bars, explore the picturesque neighborhoods or go on a cruise in the Aegean Sea.

If you have been dreaming about visiting Italy and Greece, get in touch with our tour experts for a customized itinerary.

Luxury Travel. Your Way.

This itinerary will be customized for you. Please reach out and our experts will work with you to create a journey so unique, it could only be yours.

Ideal For

Adventure & Outdoors

Heritage & Culture

Wine & Food

Sample Itinerary

Day

Place

Hotel Opts

1 – 4

Florence
Highlights: Renaissance History, Ponte Vecchio, Cathedral of Santa Maria del Fiore, Uffizi Gallery & Galleria dell'Accademia

Hotel Gallery Art
Palazzo Castri 1874

4 – 6

Rome
Highlights: St. Peter's Basilica, Colosseum, Trevi Fountain

Hotel Ponte Sisto
Marcella Royal Hotel

6 – 9

Athens
Highlights: Ancient Ruins, Plaka Neighborhood, Monastiraki & Flea Market

Elia Ermou Hotel
Athens Gate Hotel

9 – 12

Mykonos (Mid Apr – Oct)
Highlights: Traditional White Windmills, Culinary Experiences, Visit Island of Delos

Harmony Boutique Hotel
Porto Mykonos

12 – 12

Athens
Highlights: Ancient Ruins, Plaka Neighborhood, Monastiraki & Flea Market

Add to Wishlist

Remove from Wishlist

Plan My Trip

Highlights of Italy and Greece

By submitting this form, you agree to the processing of your personal data as described in our Privacy Policy. You may withdraw your consent at any time.

Your info is secure and never shared with 3rd parties.

Hold tight!

Your request is being submitted…

Thank You for Inquiring

While we review your requirements, why not discover more about your dream destination?

Let our sales team know you’d like more details – just hit the button!

START PLANNING 1 888 263 2574

Sample Itinerary

Day 1 – 4

3 Nights

Florence

Florence, the birthplace of the Renaissance, sits on the banks of the Arno River in Tuscany. The city was once home to the powerful Medici dynasty that transformed it into Europe’s cultural capital. Today, it blends art, architecture and daily life seamlessly. The historic center houses magnificent treasures such as Brunelleschi’s dome that crowns the Cathedral of Santa Maria del Fiore, the sculptures lining Piazza della Signoria and the masterpieces in the Uffizi Gallery. Giotto’s bell tower rises nearby, its striking marble patterns catching the light. Another highlight of Florence is the hearty Tuscan cuisine on offer. Everything from robust meat dishes to delicious pastas, paired with fine Chianti wines. In the Oltrarno district, find leather workers and goldsmiths practising ancient crafts in their workshops. In the evening, join locals on a sunset ‘passeggiata’ across the Ponte Vecchio or climb the hill to Piazzale Michelangelo for stunning views.

Included activities

Florence Highlights Walking Tour

Discover the marvelous city of Florence! Meet your English-speaking guide at your hotel, and kick off your walking tour from the majestic cathedral nearby. Known as ‘Duomo’ for its spectacular dome, find out more about the history behind the structure even as you admire its beauty and form as an architectural feat. From the city’s Roman foundations, move on to its journey leading up to the Renaissance; admire the impressive gate of the baptistery and the famous sculptures. Stop by the leather market and see the city’s revered mascot, before carrying on to the bank of the Arno river from where you can enjoy a sweeping view of Ponte Vecchio, a picturesque old bridge. Once you cross the bridge, continue through the secret corridor built by the legendary Medici family and arrive at the Uffizi Courtyard and the Piazza Signoria, which used to be the city’s political center. Explore its iteration as an open-air gallery today, filled with beautiful sculptures including a copy of Michelangelo’s masterpiece David. Wrap up your tour with a visit to the bustling artisans’ market. (Half Day; Time: 0900 hrs; Private Activity & Guide will meet you at your hotel; Fitness Level: Moderate; Please note that the English-speaking guide is included as a part of the tour, while the entrance fees to the monuments are NOT included. Please remember to wear comfortable shoes, and carry a light raincoat or umbrella.)

Group Chianti Wine and Olive Oil Tour

Explore the Chianti region and taste the fine wines it has to offer on this immersive tour. Make your way to the starting point to meet your guide and travel across the world-famous Tuscan countryside. The region is known for its Chianti Classico, synonymous with the symbol of the black rooster, which is prominently displayed in the villages here. Pass charming country towns, verdant vineyards, and lush olive groves that make for a scenic picture. Along the way, learn about the history of wine and olive oil in the region and the traditions associated with them. Stop at a mill that uses centuries-old techniques together with modern technology to extract delicious gourmet olive oil. Gain insight into the process of harvesting and pressing the olives, before you sample the final product. Later, visit three wineries and their cellars for an in-depth understanding of the process of wine-making and aging techniques used by Tuscan winemakers. Find out from a sommelier how Sangiovese, Canaiolo and different varieties of red grapes are blended to make exquisite wines. Learn about the distinguishing characteristics of each wine such as its acidity, unique taste and flavor pairing with food. Taste some of the wines before you head out to explore a typical Tuscan village. Relish a local lunch and take in the beauty of the landscape before it’s time to drive back. (Duration: full day; Time: 0930 hrs; Shared activity & transfers; Group size: max 16 ppl; Self organized transfers to the meeting point; Meeting point: Florencetown Booking Office, Piazza Mentana, 3, 50123 Firenze FI, Italy; Meals included: tastings & lunch; Please inform us of any food allergies in advance; Fitness level: easy; Please note that children under the age of 18 will be served only non-alcoholic beverages)

Hotel options

Hotel Gallery Art – Opt 1

Style Boutique

Palazzo Castri 1874 – Opt 2

Room Classic Double Room

Meals Breakfast

Style International

Day 4 – 6

2 Nights

Rome

Rome is both a modern city and a living museum. Also known as the ‘Eternal City’, it is home to some of the most famous historical sites in the world. The Colosseum still evokes the violent grandeur of gladiators fighting for their lives, while the Pantheon is a glorious reminder of the architectural genius of the Roman Empire. But even to simply walk through the streets is to walk through history. You might stumble upon the site of Julius Caesar’s assasination or turn a corner and find yourself facing the ruins of Emperor Augustus’ forum. The Vatican City, the smallest country in the world, also lies within Rome’s boundaries, the only example of a country within a city. It contains the majestic St. Peter’s Basilica as well as Michaelangelo’s stunning paintings on the ceiling of the Sistine Chapel. The modern side of Rome offers plenty of good food, with the Testaccio neighborhood a particular highlight. The city is also one of Europe’s fashion capitals, with major luxury fashion and jewelry brands lining its streets.

Included activities

Historic Rome on Foot

Discover the ancient monuments of the city with this interesting walking exploration. Set off with your knowledgeable guide for the open-air market at Piazza Campo de Fiori with its colorful displays of fruits, vegetables, crafts, and other items. Browse through the market as you take a short break before heading on to bustling Navona Square. Stroll around looking at the fountains, churches, and palaces around the square that are the works of famous artists such as Gian Lorenzo Bernini and Francesco Borromini. Walk on till you come upon the magnificent Pantheon, once a temple devoted to pagan deities that now serves as a Christian basilica. Saunter past Palazzo Madama, the seat of the Italian senate, and the Column of Marcus Aurelius constructed in honor of Roman emperor Marcus Aurelius. Leave behind Palazzo Montecitorio, the seat of the Italian Chamber of Deputies, as you make your way to the famous shopping street of Via Condotti with its exclusive boutiques. Amble to the end of the street to the iconic Trevi Fountain made famous by the 1960 movie La Dolce Vita. You could throw a coin into the fountain before heading on to the Spanish Steps with its sloping staircase and the elegant Barcaccia fountain. (Half Day; Private Activity & self organized transfer if required; Fitness Level: Moderate. Please wear comfortable shoes and clothing appropriate for church visits.)

Tiramisu and Gelato Making Group Class

Learn the art of making authentic tiramisu and artisanal gelato from professional chefs in Rome. First you will be introduced to the world of gelato, and how important organic, good quality produce is to the outcome. Taste different flavours and learn about the difference between ice cream and gelato. Then, wear your apron and follow the chef’s instructions to prepare tiramisu, starting with baking biscuits. Follow a step by step process to prepare this delicious dessert, and learn all the secrets to make it in the most authentic way. Sit down for the tasting, and take home the recipes and some wonderful memories of authentic Italian cooking alongside local connoisseurs. (Duration: 2 hrs; Times: 1530 hrs; Shared Activity: Max 6 guests; Fitness level: Easy; Please note that this activity is available on Tuesdays, Thursdays, Fridays, Sundays; Meeting Point: Emporio Sant’Eustachio, Via della Maddalena n° 36, Please arrive at the meeting point 15 minutes prior.)

Majestic Vatican Group Tour

Visit the glorious Vatican Museums, an expansive complex that houses the world’s largest private art collection across 54 galleries and two papal palaces. Admire the stunning architecture and the elegant décor as you enter the premises and walk through the corridors. Accompanying passionate expert guides, absorb centuries of history via anecdotes and hidden details that bring the art to life, showcasing the power and politics of the Vatican City. Amid this treasure trove of priceless art including works by master painters and celebrated artists, see magnificent frescoes, rare sculptures, and prized paintings. Navigate the many rooms including favorites such as the Gallery of the Candelabra, Gallery of Tapestries, and the Gallery of the Maps featuring painted topographical maps of Italy. Take a break at the airy Belvedere Courtyard. Stepping inside the Sistine Chapel, marvel at Michelangelo’s masterpiece paintings that adorn the walls and ceilings. Observe scenes from the Old Testament, with hidden symbols of Judaism. Continue further to the ornate St Peter’s Basilica, considered the world’s largest and the most important church, thanks to the crypt that serves as a site of pilgrimage for Catholics. After browsing Bernini’s Baldachin, climb the dome for a close look at the ceiling mosaics, and enjoy the best view of Rome, concluding an experience of a lifetime! (Half Day; Time: 1430 hrs; Shared Activity with max group size 12 guests; One way shared transfer to the meeting point from centrally located hotel; Fitness level: easy-moderate, Please note that people with physical limitations can participate as long as they have someone to provide assistance; Please wear appropriate clothing – shorts, miniskirts and uncovered shoulders are not allowed in the Basilica – and comfortable walking shoes. If St. Peter’s Basilica is being used for a religious ceremony or function, the tour will continue outside.)

Hotel options

Hotel Ponte Sisto – Opt 1

Room Superior Room

Meals Breakfast

Style International

Marcella Royal Hotel – Opt 2

Room Superior Room

Meals Breakfast

Style Boutique

Day 6 – 9

3 Nights

Athens

Athens sits on the southeast side of the Greek mainland, near the Saronic Gulf and surrounded by the Attica mountains. The ancient city is considered the birthplace of democracy and the cradle of western civilization. The Acropolis is its most iconic landmark. Perched atop a rocky hill, take in panoramic views of the city from here. The historic center is a maze of neoclassical buildings, Byzantine churches and winding cobblestone streets. Plaka, Athens’ oldest and most charming neighborhood, is filled with craft shops, boutiques and tavernas serving authentic Greek food. As you wander, see residents enjoying long coffee breaks at cafes, going on evening strolls and having late dinners that often extend past midnight. Be sure to visit the National Archaeological Museum, which showcases a remarkable collection of artifacts. The changing of the guard ceremony at the Hellenic Parliament in Syntagma Square is quite a sight to behold. For a quick escape, head to Lake Vouliagmeni, a natural thermal lake just outside the city. It is a popular spot for a relaxing swim or lunch by the water.

Hotel options

Elia Ermou Hotel – Opt 1

Room Executive Room with Hammam

Meals Breakfast

Style International

Athens Gate Hotel – Opt 2

Room Standard Room

Meals Breakfast

Style International

Day 9 – 12

3 Nights

Mykonos (Mid Apr – Oct)

Mykonos, also known as ‘The Island of the Winds’, offers a vibrant, sundrenched experience in the summer months. Its numerous sandy beaches attract throngs of visitors and many of the beaches are nudist-friendly too. Enjoy a swim in the crystal-clear waters, try your hand at a range of water sports, or simply lie on the beach and work on your tan. At night, the island hums with the sound of music from its beach bars and clubs. There’s another side to Mykonos too, one that is even more picturesque and charming. Discover whitewashed houses, stone-paved streets, and the signature ‘Kato Milli’ windmills down by the Old Port. The island has a plethora of churches because for many years people had to first build a church before they were allowed to build a house. Nearby Delos Island is famous for its archaeological ruins, while Ano Mera village provides a glimpse into local culture. Mykonos is also home to designer boutiques, art galleries and some of the best restaurants in Greece.

Included activities

Personalized Walking & Tasting Tour of Mykonos

Discover contemporary Mykonos, as you explore the narrow alleyways of Chora, with its lively bars, boutiques, and bougainvillea blooms. Stroll through the neighborhood and coastal streets in the company of your expert local guide. Learn about traditional Cycladic architecture and the white cubist-style buildings with blue accents that are characteristic of Greek islands. See the iconic windmills that highlight Mykonos’ skyline and the colorful fishermen’s houses of Little Venice, among other landmarks. Between breaks at small squares, stop by a local cafe, and the family-run Gioras bakery. Sip on Greek coffee and taste Mykonian specialties including kopanisti cheese, amygdalota sweets and kalathakia (almond tarts). (Duration: 2 hrs; Private Activity & Transfer; Tasting included; Fitness level: Easy; Notes: Wear comfortable walking shoes).

Group Sailing Experience around Mykonos with Lunch

Embark on a day-long sailing cruise in the azure waters of the Aegean Sea, around Mykonos. Explore the beautiful beaches along the southern coast, or visit nearby islands including Delos and Rhenia to see some archaeological treasures. Get a glimpse into the world of sailing while interacting with your skipper and crew. Pick up a few sailing skills, like trimming the sails. Lazing on the bow, enjoy the Mediterranean sun, or stop at secluded bays and hidden coves for a pleasant swim. Drop anchor at select spots to try a snorkeling session. Have a hearty meal with traditional Mykonian favorites matched with Greek wines on board. Take one more dip before you make the journey back! (Full Day; Shared Activity & Transfer; Fitness level: Easy; Notes: Bring swimwear and deck shoes)

Explore Mykonos on your own

Explore Mykonos on your own time, at your own pace. From traditional Cycladic architecture to a vibrant nightlife, the town has plenty to offer. Be sure to check out the iconic windmills. Spot the famed pelicans wandering about the Old Port neighborhood. Visit organic wineries and farms in Ano Mera and sample the local wines. You could take short hikes or bicycle rides to the Armenistis Lighthouse, and secluded beaches on the northern coast, passing through the scenic countryside covered in wildflowers. Drop by the Aegean Maritime Museum and the Folklore Museum of Mykonos, for glimpses into the island’s history. Watch a film at the open-air Cine Manto. Sail around Mykonos in a catamaran, try diving in the Paradise Reef to get a closer look at the fascinating marine life. Try Mykonian favorites such as kopanisti cheeses, kalathaki almond cakes, and louza pork slices, complemented by regional beverages. Enjoy the locally-made craft beer on a tasting tour of Mykonos Brewing Company. (Full Day; Self-explore Activity; Fitness level: Easy)

Hotel options

Harmony Boutique Hotel – Opt 1

Room Seaview Room

Meals Breakfast

Style Beach Resort

Porto Mykonos – Opt 2

Room Greek Double Room

Meals Breakfast

Style Beach Resort

Day 12 – 12

Athens

Athens sits on the southeast side of the Greek mainland, near the Saronic Gulf and surrounded by the Attica mountains. The ancient city is considered the birthplace of democracy and the cradle of western civilization. The Acropolis is its most iconic landmark. Perched atop a rocky hill, take in panoramic views of the city from here. The historic center is a maze of neoclassical buildings, Byzantine churches and winding cobblestone streets. Plaka, Athens’ oldest and most charming neighborhood, is filled with craft shops, boutiques and tavernas serving authentic Greek food. As you wander, see residents enjoying long coffee breaks at cafes, going on evening strolls and having late dinners that often extend past midnight. Be sure to visit the National Archaeological Museum, which showcases a remarkable collection of artifacts. The changing of the guard ceremony at the Hellenic Parliament in Syntagma Square is quite a sight to behold. For a quick escape, head to Lake Vouliagmeni, a natural thermal lake just outside the city. It is a popular spot for a relaxing swim or lunch by the water.

What Our Guests Say

“Lauren Bukowski tailored the Italian trip spot on for our small travel group of 4. She listened well to our goals of the trip and was able to provide excellent accommodations in Rome and Florence, with well curated tours of Rome such as the Roman ruins, Vatican and Panthenon.. Florence was equally done very well with trips to Chianti region, Cinque Terre and the museums in Florence. In addition to the delightful trip the travel connections were seamless. This was certainly appreciated. We would definitely use Lauren and Enchanting Travels again. Thanks for the wonderful trip to Italy 🇮🇹 Sheila, Carol, Carolyn and Brent”

September 2025 Rating 5/5

“Enchanting travel took care of everything for our 2 week Italy trip. The tours, drivers and entire experience was amazing. The team provided great customer service as well.”

October 2025 Rating 5/5

“We had an amazing anniversary trip to Italy planned by enchanting travels. Every aspect of the trip was great! We had a stay in Rome, a Tuscan Villa and then the final leg in Florence. All of the hotels were great and the staffs were very friendly. We had private drivers for all of our transportation needs and private or very small group tours for all of our stops. The driver service and guide service the enchanting travels used were amazing. Cherisse Liptzin was our book agent at enchanting travels and she was amazing in planning the perfect trip for us!!”

May 2025 Rating 5/5

“Trip planners and coordinators are wonderful, knowledgeable, and professional. All local contacts were vetted and fabulous. Our family had a great time in Greece.”

June 2025 Rating 5/5

“Enchanting Travels is such an amazing company to journey with. Their employees were fantastic! The attention to detail was exceptional. They provided 10/10 service! From their recommendations as we started building our trip to Italy. Listening to all our desires. Building our trip with them, to seeing it realized. They made everything so pleasant. Including the travel app that was always so helpful. If you are considering to travel with company, ABSOLUTELY DO SO! I do not give 5 star ratings often, but they earned every star!”

September 2025 Rating 5/5

“Enchanting Travels tailored our Italian trip spot on for our small travel group of four. They listened well to our goals of the trip and were able to provide excellent accommodations and curated tours in Rome and Florence. In addition to the delightful trip, the travel connections were seamless. This was certainly appreciated. We would definitely use Enchanting Travels again.”

November 2025 Rating 5/5

What our Guests Say

Highlights of Italy and Greece

Luxury Travel. Your Way.

Ideal For

Sample Itinerary

Thank You for Inquiring

Sample Itinerary

Day 1 – 4

Day 4 – 6

Day 6 – 9

Day 9 – 12

Day 12 – 12

Florence

Rome

Athens

Mykonos (Mid Apr – Oct)

Athens

Price & Inclusions

Option 1

Option 2

Price Includes

Not Included

What Our Guests Say

Other Itineraries You Might Like

Italy: Southern Culture and Amalfi Coast

Italy: History, Architecture & Cuisine

Fabulous Flavors of Greece