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Italy & Greece Highlights: 14 Days of Culture & Coastlines

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Trip curated by Roman Karin

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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.

Your accommodation

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.

Your accommodation

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.

Your accommodation

Ca' Dei Proverbi Suites - Wenice Deep Culture

Ca' Dei Proverbi Suites - Wenice Deep Culture

Located in Venice (Cannaregio), Ca' Dei Proverbi Suites - Wenice Deep Culture is within a 15-minute walk of Rialto Bridge and St. Mark's Square. This guesthouse is 0.6 mi (0.9 km) from St. Mark's Basilica and 0.7 mi (1.1 km) from Doge's Palace. 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.

Your accommodation

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 0.8 mi (1.3 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

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.