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Italy & Greece Highlights: 14 Days of Culture & Coastlines
14 Days
5 Stops
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Trip curated by Roman Karin
ExpertFour nights in Santorini with Fira as the base gives you caldera access and the village-to-village walking paths without the pedestrian congestion of Oia as an overnight, and it's the accommodation call I always make on this circuit. The path north toward Imerovigli and the volcanic ridge to Skaros Rock reads as genuinely wild even in peak season. The gondola serenade in Venice earns most in early evening rather than mid-afternoon: the light in the side canals, the kitchen smells from open windows, and the reduced boat traffic make the experience read completely differently from the sunlit tourist version. For the Vatican, enter before 8am and route your path so the Sistine Chapel comes last: the ceiling is close to undisturbed for the first twenty minutes before the main groups arrive.
Four nights in Santorini with Fira as the base gives you caldera access and the village-to-village walking paths without the pedestrian congestion of Oia as an overnight, and it's the accommodation call I always make on this circuit. The path north toward Imerovigli and the volcanic ridge to Skaros Rock reads as genuinely wild even in peak season. The gondola serenade in Venice earns most in early evening rather than mid-afternoon: the light in the side canals, the kitchen smells from open windows, and the reduced boat traffic make the experience read completely differently from the sunlit tourist version. For the Vatican, enter before 8am and route your path so the Sistine Chapel comes last: the ceiling is close to undisturbed for the first twenty minutes before the main groups arrive.
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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
NH Collection Roma Giustiniano is located in the Prati district, within walking distance of the Vatican and Castel Sant’Angelo. The spacious rooms include minibars, air conditioning, Wi-Fi, and TVs, with some offering views of St. Peter’s Basilica. Guests can start their day with a buffet breakfast featuring fresh fruit and organic yogurt, while the Zenzero & Cannella restaurant serves Roman, Italian, and international cuisine, paired with a curated selection of wines. The hotel is close to Via Cola di Rienzo, a popular shopping destination, and Lepanto Metro Station, making it easy to explore the city. Additional amenities include a fitness center and on-site parking.
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: English: 8:00 am, 9:00 am, 10:30 am
Spanish: 09:00 AM, 02:30 PM
Group size: Min 1 to max 20 pax
Pick up 45 minutes before the departure at centrally located hotel.
- Note: It is mandatory to provide a nominative list of all participants (including children) at the time of booking for the tour.
- Customers have to bring their passport with them during the tour and show it if required.
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
Located in the heart of Florence, Palazzo Castri 1874 is a fully restored boutique hotel dating back to the years of Florentine Impressionism. The hotel's elegant guest rooms feature views of the Cathedral of Santa Maria del Fiore and the luxuriant inner garden, La Limonaia. You can relax in the exclusive on-site spa and immerse in fragrant steam and toning jets of water. The hotel's designer interiors, the fragrance of lemon and magnolia flowers from the hidden inner garden, and the play of light and water in the spa combine to create a fabulous retreat from daily life.
Your activity
Highlights of Tuscany: Pisa & more
Enjoy the rich history and the art of the most spellbinding sights in Tuscany in a single memorable day including lunch in a typical Tuscan restaurant!
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 Toweris 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 withTasting 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
Start time: 07:30 AM
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
Ca’ dei Proverbi Suites offers a charming stay in the Cannaregio district of Venice. All rooms are comfortably designed with air conditioning, tea/coffee-making facilities, private bathrooms, and flat-screen TVs. You can start each morning with a delicious breakfast. Other services and facilities include a 24-hour front desk, Wi-Fi, and a coffee shop.
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
per personAccommodations
Transportation
24/7 support
Activities
Meals
Tourlane App
Travel plan
Flights
Flexible cancellation policies
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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
Rome north to Florence and Venice, then the flight east to Athens before Santorini closes the journey on the Aegean — fourteen days that move from the ancient capital of the Western world to the volcanic caldera above the Mediterranean. Four nights in Fira is genuinely generous for Santorini, and that time opens up the island properly: the caldera walk, a winery visit in the afternoon, and a sunset in Oia without any of it feeling rushed.
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What I always tell people about the Porto Fira Suites: request one of the caldera-facing rooms with a private plunge pool when you confirm the booking. They fill months in advance, and they change the experience of four nights in Fira considerably.
Day 1–3: Rome
Hotel: NH Collection Roma Giustiniano
Three nights with the Vatican Museums and Sistine Chapel on one day, the Colosseum and historic center on another, and the local neighborhoods and piazzas filling the third. Trastevere for a slow dinner on the final Rome evening — the most genuinely lived-in neighborhood in the city — is the right close before heading north.
Day 4–5: Florence
Hotel: Palazzo Castri 1874
Two nights with the Florence walking tour and the Tuscany and Pisa excursion. The Palazzo Castri 1874 is a restored 19th-century property with genuine architectural character — it rewards an unhurried first afternoon before the gallery visits begin.
Day 6–7: Venice
Hotel: Ca' dei Proverbi Suites
Two nights at this apartment-style property in a residential part of Venice. The gondola serenade, the historic districts, and the Venetian culture and cuisine across two days. The gondola on the back canals east of the Rialto rather than the Grand Canal — the pace is genuinely unhurried and the atmosphere more intimate.
Day 8–9: Athens
Hotel: Fresh Hotel
Two nights with the Acropolis and its museum on the first day and the neighborhoods on the second. The Fresh Hotel's rooftop view toward the Parthenon at dusk is worth using for a drink before dinner on the first evening.
Day 10–14: Fira, Santorini
Hotel: Porto Fira Suites
Four nights on the caldera rim with the village exploration, the coastal views, and the local cuisine filling the stay. The island's volcanic-soil Assyrtiko — grown in low basket vines and producing a mineral character found nowhere else — earns a proper tasting rather than just a glass at dinner. For the Oia sunset, position yourself on the path toward the Byzantine castle ruins rather than the main viewpoint.
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Tips for your Highlights 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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