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Italy & Greece Itinerary 14 Days: 2 Weeks of History, Coastlines & Island Life
14 Days
5 Stops
Private transfer
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Trip curated by Roman Karin
ExpertFour nights in Santorini versus the standard two is the call that changes the island from a highlight into an experience. The dawn caldera path walk from Fira, the volcanic hot springs by boat, and an unhurried evening in Oia without the sunset crowd are all things two nights simply can't hold. Vatican Museums before 8am with the Sistine Chapel last; in that first hour the ceiling is close to undisturbed, and what it sets up carries through every Renaissance reference on the rest of the trip. Athens with two nights: the Acropolis Museum on arrival afternoon, always. The frieze panels at eye level make the hill the next morning legible in a way that going up cold never does.
Four nights in Santorini versus the standard two is the call that changes the island from a highlight into an experience. The dawn caldera path walk from Fira, the volcanic hot springs by boat, and an unhurried evening in Oia without the sunset crowd are all things two nights simply can't hold. Vatican Museums before 8am with the Sistine Chapel last; in that first hour the ceiling is close to undisturbed, and what it sets up carries through every Renaissance reference on the rest of the trip. Athens with two nights: the Acropolis Museum on arrival afternoon, always. The frieze panels at eye level make the hill the next morning legible in a way that going up cold never does.
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Rome
Day 1 - 3
Experience Rome, the bustling capital of Italy. This city, rich with exciting history and culture, offers an unparalled mix of ancient explorations and modern living. Immerse yourself in the past and explore the Colosseum, the Roman Forum, and the Vatican. Wander through other must-see destinations like The Spanish Steps, Trevi Fountain, and Pantheon. Experiencing the culinary scene is a delight, from traditional pasta to world-renowned Italian gelati. You can explore daily markets such as Campo de' Fiori for local ingredients and fresh food. A stay in Rome promises great experiences all year round, but it is advisable to take seasonality into account. While spring (April–May) and fall (September–October) offer pleasant weather and less crowds, summer (June–August) has a lively, spirited atmosphere — but can also be hot. No matter when you go, visiting Rome promises an unforgettable journey through the centuries. The unique combination of a rich historical past mixed into a thriving and vibrant modern community makes Italy's Eternal City one of the world's most intriguing and inspiring tourist destinations.
NH Collection Roma Giustiniano
With a stay at NH Collection Roma Giustiniano in Rome (Rome City Centre), you'll be steps from Via Cola di Rienzo and 7 minutes by foot from Chiesa Valdese. This hotel is 0.2 mi (0.3 km) from Castel Sant'Angelo and 0.4 mi (0.6 km) from Statua di Santa Caterina.
Take advantage of recreation opportunities such as a fitness center, or other amenities including complimentary wireless internet access and a banquet hall.
Make yourself at home in one of the 161 air-conditioned rooms featuring minibars. Complimentary wireless internet access keeps you connected, and cable programming is available for your entertainment. Bathrooms with shower/tub combinations are provided. Conveniences include phones, as well as safes and desks.
Your activity
Vatican Museums, Sistine Chapel & more
Not only the complex of the Vatican Museums makes up the largest museum in the world, but it is also one of the world’s most visited, with more than 6 million people accessing it in 2018. After meeting your professional guide at our meeting point, you’ll be given a headset and you’ll reach the Vatican Museum’s entrance, in a group of no more than 20 people. This less stress guided tour will grant you a skip-the-line, saving you the hassle of waiting in line for several hours. You’ll tour the gallery, visiting all those main spots you’ve heard about like the Gallery of Maps, the Gallery of Tapestries, the Borgia Apartments. The guide will tell you everything about the Raphael Rooms and their exceptional frescoes, including The School Of Athens, and will bring you to the Sistine Chapel, whose ceiling is one of the cornerstone works of High Renaissance art. The tour couldn’t be complete without St. Peter’s Square the open space which lies before the basilica, redesigned by Gian Lorenzo Bernini and being itself an architectural masterpiece of the Baroque age. You’ll admire St. Peter’s Basilica (outside) that isn’t only the largest church in the world, but that contains several pieces of fine art: think the canopy designed by Gian Lorenzo Bernini or the Pietà by Michelangelo.
Activity start time: 8:00 am, 9:00 am, 10:30 am -> pick up 45 min before activity starts
Group size: 20 pax
Florence
Day 4 - 5
Florence, the beautiful capital of the Italian region Tuscany, lies in the center of the country. A small city with a big heart, and an even bigger offering of artistic and historical treasures. For centuries, travelers have journeyed to the birthplace of the Renaissance era to marvel at the many masterpieces of architecture and art: Michelangelo's iconic David, the impressive works of Botticelli, the Uffizi Gallery (packed with works by Caravaggio and Da Vinci), and of course, Brunelleschi's remarkable dome — the religious centerpiece of Florence that dominates the skyline. All are absolute must-sees on any itinerary. Once you've ticked off these renowned attractions, you can take a stroll through the vast Boboli Gardens or climb the hill to the church of San Miniato al Monte for a breathtaking view of this beautiful, enchanting city.
Palazzo Castri 1874 Spa & Garden
With a stay at Palazzo Castri 1874 Spa & Garden in Florence (Historic Centre of Florence), you'll be a 3-minute walk from Central Market and 8 minutes by foot from Piazza di Santa Maria Novella. This spa hotel is 0.6 mi (0.9 km) from Cathedral of Santa Maria del Fiore and 0.6 mi (1 km) from Piazza del Duomo.
Relax at the full-service spa, where you can enjoy massages, body treatments, and facials. You're sure to appreciate the recreational amenities, including a hot tub, a sauna, and a fitness center. Additional amenities at this hotel include complimentary wireless internet access, concierge services, and babysitting (surcharge).
Make yourself at home in one of the 59 guestrooms featuring minibars and LCD televisions. Your memory foam bed comes with Egyptian cotton sheets. Complimentary wireless internet access keeps you connected, and satellite programming is available for your entertainment. Bathrooms feature showers with rainfall showerheads and designer toiletries.
Your activity
Highlights of Tuscany: Pisa & more
Depart to Pisa, you will reach the Field of Miracles, a green grass field dominated by the dazzling white buildings of the Cathedral, the Baptistery and the famous Tower, exquisite examples of Pisan Romanesque architecture: the Leaning Tower is almost 56 meters tall (about 183 ft). You are in one of the most world known places: revel in it, take creative photographs or wander off down the local streets.
From Pisa, we drive past hilltop hamlets scattered over some of the most beautiful and enchanting view of the countryside up to arrive at San Gimignano where a traditional Tuscan Lunch with Tasting of 4 different wines, will be served. After lunch, your visit continues to the discovery of a Tuscan medieval pearl, the stunning village of San Gimignano, Unesco world heritage, known for the ancient town planning still intact. Free time to explore the town center, the charming craftsmen’s shops along the cobbled stone streets and small squares.
Our last stop is Siena, which we will reach by driving through the lovely Chianti countryside. Siena is an amazing hilltop town,rich in works of art and traditions, famous monuments and picturesque views with a fascinating pedestrianized historical center and one of the most beautiful Cathedrals in the world. Upon arrival in Siena our local guide will take you on a guided walking tour along the small medieval streets and squares, passing the oldest bank in the world, and the Piazza del Campo - site of the famous 600-year-old Palio horse-race, to the spectacular Cathedral. You will also have free time to walk around the historic center as you like and conclude your memorable experience of Tuscany with the memory of a perfect day.
Meeting point at 7:15 am Piazzale Montelungo at the end of the ramp connecting with the railway station.
Group size - 50/55 pax
Venice
Day 6 - 7
Venice is a small, unique city in Italy’s Veneto region, a historic center made up of 118 small islands in a lagoon of the Adriatic Sea, connected by a complex network of canals and footbridges. The stately palaces and ancient churches remain as fascinating reminders of what was once a major trading hub between Europe and the Orient. From the famous Gothic Doge’s Palace and the breathtaking St. Mark’s Basilica to the awe-inspiring brilliance of Titian’s Assumption altarpiece lighting up an entire cathedral, Venice has remained virtually unchanged for the past 600 years. Other must-see attractions include the Bridge of Sighs, the spectacular Peggy Guggenheim Collection (art gallery), the captivating Gallerie dell’Accademia (museum), and of course, gondola rides along the canals.
Ca' Dei Proverbi Suites - Wenice Deep Culture
With a stay at Ca' Dei Proverbi Suites - Wenice Deep Culture in Venice (Cannaregio), you'll be steps from Grand Canal and 6 minutes by foot from Rialto Bridge. This guesthouse is 0.6 mi (0.9 km) from St. Mark's Square and 0.6 mi (0.9 km) from St. Mark's Basilica.
Make use of convenient amenities, which include complimentary wireless internet access and tour/ticket assistance.
Make yourself at home in one of the 7 individually decorated guestrooms, featuring minibars and Smart televisions. Complimentary wireless internet access is available to keep you connected. Private bathrooms with showers feature rainfall showerheads and bidets. Conveniences include desks and coffee/tea makers, and housekeeping is provided daily.
Your activity
Venice: Gondola Serenade
Enjoy the last rays of sunshine and sit back and relax as your private gondolier serenades you and you glide through the canals, past colorful boats against the backdrop of magnificent Gothic palaces! Soak up the romance of Venice on a 30-minute private gondola ride accompanied by local musicians, and float along the fascinating canals! While your gondolier takes you along Venetian canals, enjoy some evocative Italian songs and look at all the elegant palaces, suggestive buildings, and typical boats around you on the water. Embarking is possible from one of the following gondola stations: Danieli, Dogana, or Vallaresso, Bauer.
MEETING POINT BETWEEN THE TWO COLUMNS IN PIAZZA SAN MARCO For Tours after 6pm (from Nov - Mar) and after 7pm (from Apr - Oct) - For earlier tours please check other tour in system "Venice - Gondola Serenade (Gondola Ride with Music) (Daytime)"
Athens
Day 8 - 9
Dominating the Attica region of Greece, the country’s capital, Athens, is one of the oldest cities in the world. For over two and a half centuries, the astonishing Greek temples and monuments of Athens have continued to intrigue and amaze visitors from around the world. This icon of western civilization seamlessly combines ancient history with modern architecture and a surprisingly lively atmosphere. This is particularly apparent in areas at the foot of the Acropolis, Anafiotika, Plaka, Monastiraki, and Thissio where visitors will find numerous extraordinary Neoclassical buildings, trendy and traditional cafes, and shops, and narrow winding streets with historical treasures at every turn. Once you have enjoyed a history and art fix, try some mouth-watering Greek cuisine at one of the city’s fine local restaurants before indulging in the insatiable nightlife at the chic cocktail bars and waterfront dance clubs.
Fresh Hotel, a Member of Design Hotels
With a stay at Fresh Hotel, a Member of Design Hotels, you'll be centrally located in Athens, within a 10-minute walk of Monastiraki Flea Market and Ancient Agora of Athens. This hotel is 0.7 mi (1.1 km) from Syntagma Square and 1.4 mi (2.2 km) from Temple of Olympian Zeus.
Be sure to enjoy recreational amenities, including a sauna, a fitness center, and a seasonal outdoor pool. Additional amenities at this hotel include complimentary wireless internet access and tour/ticket assistance.
Make yourself at home in one of the 148 guestrooms featuring minibars (stocked with some free items) and plasma televisions. Complimentary wireless internet access keeps you connected, and digital programming is available for your entertainment. Private bathrooms with bathtubs or showers feature complimentary toiletries and hair dryers. Conveniences include phones, as well as safes and desks.
Your activity
The Artist Cooking Class
Perfect on your skills in homemade Greek recipes with interactive, hands-on learning professional local chef, as your guide. You will walk away with lasting memories and a portfolio of tasty recipes to remake them again and again back home. Discover your love and passion for food in The Artist Gastronomy Experience and dive into the world of cooking.
We’ve created magical experiences to entice you and delight you. Look at our cooking class and discover what you can learn with a professional chef in a convivial, fun setting way.
Specifically, The Artist Gastronomy Experience consists of:
· Beverage with food (wine, beer, or soft drinks)
· Tzatziki
· Aegean salad
· Spanakopita (Spinach pie with herbs and feta cheese)
· Greek Authentic Moussaka
· Galatopita
Group size: Min 2 pax
Fira
Day 10 - 14
Perched on a 220-metre-high cliff overlooking the vivid blue waters of the Aegean Sea, Fira is Santorini's cultural and commercial capital that beckons those in search of breathtaking views, stunning sunsets, delectable local cuisine, and unforgettable cultural experiences. Facing the volcano on the island's western edge, Fira is a bustling cosmopolitan town characterised by a mixed sample of Cycladic and Venetian styles woven together by labyrinth streets that cater to daytime adventures and nighttime sprees. Embark on a fascinating exploration of the town's local museums, restaurants, coffee shops, and archaeological sites by hopping on a cable car heading to remarkable churches and iconic landmarks. For a deep dive into local history, visit the Museum of Prehistoric Thira, the Archaeological Museum, and the Santozeum. End the day with a leisurely cruise to the volcano from the Old Port on a luxury yacht or traditional wooden sailing boat.
Porto Fira Suites
When you stay at Porto Fira Suites in Santorini, you'll be in the historical district, a 1-minute drive from Santorini Caldera and 9 minutes from Kamari Beach. This hotel is 5.7 mi (9.2 km) from Athinios Port and 7.6 mi (12.3 km) from Oia Blue Dome Church Viewpoint.
Take in the views from a rooftop terrace and make use of amenities such as complimentary wireless internet access and concierge services. Additional amenities at this hotel include babysitting (surcharge) and wedding services.
Make yourself at home in one of the 12 individually decorated guestrooms, featuring refrigerators and minibars. Rooms have private furnished balconies or patios. Complimentary wireless internet access keeps you connected, and 21-inch LCD televisions are provided for your entertainment. Bathrooms with separate bathtubs and showers feature deep soaking bathtubs and rainfall showerheads.
From$3,850
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Activities
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Why plan with an expert?
200+
Plan with professionals who are explorers themselves.
30+ hours of time saved
Our experts plan and book for you.
12+ Bookings managed
Everything is bundled in one place and perfectly planned.
8+ Transfers coordinated
For optimal transport and comfort.
Excellent
Itinerary inspiration
Connecting Rome, Florence, and Venice by train before flying to Greece gives the Italian section a grounded, sequential feel — you move through the country rather than skip across it. The speedboat transfer from Athens to Santorini, rather than the standard ferry, saves the better part of a day and gets you to Fira with the afternoon still ahead.
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Something worth planning well ahead: the Porto Fira Suites are positioned directly on the caldera rim, and the rooms with private plunge pools fill months in advance. Request one when you confirm the booking — they change the experience of four nights in Fira considerably.
Day 1–3: Rome
Hotel: NH Collection Roma Giustiniano
Three nights is the minimum you need to move through the Vatican Museums, the Sistine Chapel, the Colosseum, and the Roman Forum without feeling rushed. The private transfer from the airport on arrival removes the first logistical decision of the trip and sets a good tone for everything that follows.
Day 4–5: Florence
Hotel: Palazzo Castri 1874
The high-speed train from Rome takes around 90 minutes, arriving with the better part of the afternoon still ahead. The Palazzo Castri 1874 is a well-restored 19th-century property with genuine architectural character — it rewards a slower first afternoon before the gallery visits begin. The Tuscany excursion including Pisa works well on the second day, leaving the historic center for a focused final morning.
Day 6–7: Venice
Hotel: Ca' dei Proverbi Suites
The Ca' dei Proverbi is an apartment-style property in a residential part of Venice, which gives you a different experience of the city than a standard hotel placement would. For the gondola serenade, ask for the quieter back canals rather than the Grand Canal — the atmosphere is more intimate, and the pace feels genuinely unhurried.
Day 8–9: Athens
Hotel: Fresh Hotel
The Fresh Hotel's rooftop pool with its direct Acropolis view is a strong arrival reward after a full travel day. Two nights gives you a proper visit to the Acropolis and surrounding landmarks, with enough time to walk through Monastiraki and Psirri without feeling pressed.
Day 10–13: Santorini (Fira)
Hotel: Porto Fira Suites
Four nights in Fira is genuinely generous for Santorini, and that time opens up a caldera walk, a visit to the wineries around Pyrgos, and a late afternoon in Oia without any of it feeling compressed. The island's volcanic-soil Assyrtiko — grown in low basket vines and producing a mineral character found nowhere else — is reason enough to dedicate at least one afternoon to the wineries before heading north for sunset.
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Tips for your Trip to Italy & Greece
The best time to visit Italy and Greece is from April to October. Both countries enjoy long, sunny days and warm weather during this period, which is ideal for a variety of activities. If you want to avoid the crowds and heat of the peak summer season, consider traveling during the shoulder seasons of spring and fall.
➔ Best time to travel to Italy | Best time to travel to Greece
The cost of your trip will vary based on your budget and travel style. A mid-range, week-long trip to Italy is about $1,700 (excluding flights). A budget-friendly trip to Greece starts at approximately $65 per day.
In Italy, you can visit the ancient Colosseum in Rome, see the famous Leaning Tower of Pisa, and enjoy a romantic gondola ride in Venice. Greece has an incredible history, with must-see sites like the Acropolis in Athens, the ruins of Mycenae, and the stunning Meteora monasteries.
➔ Things to see Italy | Activities Italy | Things to see Greece | Activities Greece
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