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We work in the kind of places you daydream about—countries with real range, from cities and coasts to jungles, mountains, and small towns. Our in-country insiders handle the planning, booking, and in-trip problem solving, so you can drop in, enjoy the highlights, and come home with stories that keep you inspired to keep exploring our amazing planet.

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    Your bespoke travel plan

    Bella Italia in Spring

    Glenn and Joanne explored Italy’s timeless blend of history, cuisine, and scenery on a two‑week adventure. They traveled from Rome’s historic heart to Tuscany’s rolling hills, explored Florence’s Renaissance treasures, drifted through Venice’s canals, and concluded in Milan’s modern design scene. Along the way, friendly locals, knowledgeable guides, and vibrant markets offered authentic flavors and stories, leaving them with a deeper appreciation for Italy’s living heritage.

    Trip Summary

    1
    10 Apr
    Arrival in the Eternal City

    STAY AT Hotel Recommendation #1

    11 Apr
    Baroque Rome and Elegant Piazzas

    STAY AT Hotel Recommendation #1

    12 Apr
    Trastevere Culture and Flavors

    STAY AT Hotel Recommendation #1

    13 Apr
    Art and Spirit of the Vatican

    STAY AT Hotel Recommendation #1

    14 Apr
    The Heart of Ancient Rome

    STAY AT Hotel Recommendation #1

    15 Apr
    Rome at Your Leisure

    STAY AT Hotel Recommendation #1

    2
    16 Apr
    Transition to the Tuscan Countryside

    STAY AT Hotel Recommendation #2

    17 Apr
    Montepulciano's Renaissance Charm

    STAY AT Hotel Recommendation #2

    18 Apr
    Vineyard Life and Local Flavor

    STAY AT Hotel Recommendation #2

    3
    19 Apr
    The Road to Medieval Siena

    STAY AT Hotel Recommendation #3

    20 Apr
    The Splendor of the Duomo

    STAY AT Hotel Recommendation #3

    21 Apr
    Independent Discovery in Siena

    STAY AT Hotel Recommendation #3

    22 Apr
    San Gimignano and the Towers

    STAY AT Hotel Recommendation #3

    23 Apr
    Siena at Leisure

    STAY AT Hotel Recommendation #3

    4
    24 Apr
    To the Riviera via the Leaning Tower

    STAY AT Hotel Recommendation #4

    25 Apr
    Exploring the Cinque Terre by Train

    STAY AT Hotel Recommendation #4

    26 Apr
    The Coastline from the Sea

    STAY AT Hotel Recommendation #4

    27 Apr
    Levanto and the Riviera Pace

    STAY AT Hotel Recommendation #4

    5
    28 Apr
    The Mountains and Hidden Tuscany

    STAY AT Hotel Recommendation #5

    29 Apr
    Lucca's Renaissance Walls

    STAY AT Hotel Recommendation #5

    30 Apr
    Puccini and the Spirit of Lucca

    STAY AT Hotel Recommendation #5

    6
    01 May
    Transition to the Cradle of the Renaissance

    STAY AT Hotel Recommendation #6

    02 May
    Artistic Treasures of the Uffizi

    STAY AT Hotel Recommendation #6

    03 May
    Florence at Your Own Pace

    STAY AT Hotel Recommendation #6

    04 May
    The Oltrarno Artisan District

    STAY AT Hotel Recommendation #6

    05 May
    Michelangelo's David

    STAY AT Hotel Recommendation #6

    1
    06 May
    High Speed Return to Rome

    STAY AT Hotel Recommendation #7

    07 May
    Departure
    Itinerary Map
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    Destinations

    Places you'll stay

    Monterosso al Mare

    Monterosso al Mare, Italy, is one of the five picturesque villages that make up the renowned Cinque Terre region along the Italian Riviera. Known for its stunning coastal views, Monterosso al Mare is a popular destination for travelers seeking both relaxation and adventure in a scenic setting.

    Monterosso al Mare Image
    Destination
    Manarola

    Manarola, Italyis a small fishing village perched on the rugged Ligurian coast, forming the northernmost point of the famed Cinque Terre trail. Its steep, narrow streets lead down to a natural harbor that has supported maritime activity for centuries.

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    Destination
    Riomaggiore

    Riomaggiore, Italy – Introduction Riomaggiore is the northernmost village of the Cinque Terre, a UNESCO‑listed coastal region on the Ligurian Sea. The settlement is built on steep terraces that descend toward a small harbor, and its narrow, pastel‑colored streets are characteristic of the area’s historic fishing communities.

    Riomaggiore Image
    Destination
    Bonassola

    Bonassola, Italy is a modest fishingvillage perched on the Ligurian Riviera, about 90 km southeast of Genoa. With a population of roughly 1,000 residents, the town is built on a narrow strip of land between the Mediterranean Sea and the steep hills of the surrounding region, giving it a compact layout centered around a historic harbor and a promenade that follows the shoreline.

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    Destination
    Barga

    Barga, Italy is a medieval hill town perched on the Serchio River in the northern part of the Tuscan region.

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    Destination
    Rome

    Rome, Italy, is the capital city known for its rich history, iconic architecture, and vibrant culture. Situated in the central-western part of the Italian Peninsula, Rome is distinguished by its ancient ruins and status as a significant center of politics, religion, and art throughout history.

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    Destination
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    Montepulciano

    Montepulciano, Italy is a medieval hill town perched atop a limestone ridge in the heart of the Val d’Orcia, a landscape recognized by UNESCO for its historical agricultural significance and scenic value.

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    Destination
    Siena

    Siena, Italy is amedieval city located in the heart of Tuscany, renowned for its well‑preserved historic center and distinctive brick architecture.

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    Destination
    Levanto

    Levanto, Italy is a modest seaside town of roughly 6 000 residents that lies at the western edge of the Ligurian Riviera, directly opposite the famous Cinque Terre villages and just a short distance from the regional capital of La Spezia.

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    Destination
    Lucca

    Lucca, Italy is a Renaissance‑era walled city situated in the north‑western part of Tuscany, renowned for its well‑preserved historic architecture and compact urban layout.

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    Destination
    Florence

    Florence, Italy, known as the birthplace of the Renaissance, is a city steeped in history and culture. Situated in the heart of the Tuscany region, it is renowned for its historical significance, artistic heritage, and architectural splendor. The city is located along the banks of the Arno River, providing a picturesque setting that combines the beauty of its natural landscape with its rich cultural offerings.

    Florence Image
    Destination
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    Trip highlights

    Moments to look forward to

    Piazzale Michelangelo

    Piazzale Michelangelo, Italy is a panoramic terrace situated on a hill east of the historic center of Florence, offering an elevated perspective of the city’s skyline and the Arno River.

    Piazzale Michelangelo Image
    Attraction
    Galleria dell’Accademia di Firenze

    Galleria dell’Accademia di Firenze, located in the city of Florence, is renowned for housing some of the most significant works of art in history, including Michelangelo's iconic "David." Founded in 1784, the museum was initially intended to function as a teaching facility for the Academy of Fine Arts students. Over the years, it has acquired a vast collection of art and has become a key destination for those interested in Renaissance art.

    Galleria dell’Accademia di Firenze Image
    Attraction
    David

    David, Italy is a small village nestled in the picturesque countryside of the Lombardy region. Known for its serene landscapes and authentic local charm, David provides a peaceful retreat for travelers seeking a break from the bustling tourist destinations.

    David Image
    Attraction
    Spanish Steps

    The Spanish Steps are a renowned architectural landmark located in Rome, featuring a cascading series of 135 steps that connect the Piazza di Spagna at the base with the Trinità dei Monti church at the top. This iconic Baroque-style staircase was completed in the 18th century and serves as both a popular tourist attraction and a vibrant gathering place for locals and visitors alike.

    Spanish Steps Image
    Attraction
    Piazza del Popolo

    Piazza del Popolo is a large urban square located in Rome, known for its historical significance and architectural beauty. It serves as a central meeting point and a starting place for exploring the cultural and historical heart of the city.

    Piazza del Popolo Image
    Attraction
    Boboli Gardens

    Boboli Gardens, located in Florence, is a historical green space that offers visitors a glimpse into the rich landscape design of the Renaissance era. Originally designed for the Medici family, the gardens are a testament to renaissance aesthetics and horticulture.

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    Attraction
    Via del Corso

    Via del Corso is a central arterial street that runs north‑south through the historic core, linking Piazza del Popolo with Piazza Venezia and forming one of Rome’s principal shopping and transit routes.

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    Attraction
    Jewish Museum

    Jewish Museum, Italy, situated in Rome, documents the development of the local Jewish community from its origins in the Roman Empire through the modern era, offering a chronological collection of artifacts, documents, and artworks.

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    Attraction
    Portico d'Ottavia

    Portico d'Ottavia, Italy is a modest hill‑top community of roughly 350 residents located in the foothills of the Apennines, a short distance north of the historic city of Teramo. Its narrow streets, stone façades, and the eponymous series of vaulted arches that give the town its name reflect a long agricultural tradition dating back to medieval times.

    Portico d'Ottavia Image
    Attraction
    Fortezza Medicea di Montepulciano

    Fortezza Mediceadi Montepulciano, Italy is a Renaissance fortress perched on a limestone ridge above the historic town of Montepulciano. Constructed between 1535 and 1550 under the direction of Cosimo I de’ Medici, the stronghold was intended to secure the strategic Val d’Orcia and to demonstrate Medici power in the region.

    Fortezza Medicea di Montepulciano Image
    Attraction
    Val D'orcia

    Val d’Orcia, Italy is a gently rolling landscape in the southern part of Tuscany that has been recognized as a UNESCO World Heritage Site for its harmonious integration of natural and built environments.

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    Attraction
    Comune di Montepulciano

    Introduction Comune di Montepulciano, Italy is a medieval hill town situated in the province of Siena. Perched at roughly 600 m (1,970 ft) above sea level, it commands panoramic views of the surrounding Val d’Orcia and is renowned for its historic architecture, well‑preserved Renaissance palaces, and its role as a centre of wine production.

    Comune di Montepulciano Image
    Attraction
    De' Ricci Cantine Storiche in Montepulciano

    De' Ricci Cantine Storiche in Montepulciano, Italyis a family‑owned winery that traces its origins back to the 15th century. The estate is situated on the historic hill of Montepulciano, where it produces Vino Nobile di Montepulciano and other DOCG wines from vineyards that have been cultivated for generations.

    De' Ricci Cantine Storiche in Montepulciano Image
    Attraction
    Contucci

    Contucci, Italy is a modesthilltop community of roughly 4,500 residents, situated in the rolling landscape of the central Apennines. The town’s historic center is organized around a medieval piazza, and its narrow stone streets retain the layout established during the Renaissance.

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    Attraction
    Piazza Grande

    Piazza Grande, Italy is a historic square situated in the town of San Miniato, a settlement that lies on the border between the Florentine and Pisa provinces in the Tuscan region. The square forms the focal point of the town’s medieval layout and is surrounded by stone façades that date from the 12th to the 15th centuries.

    Piazza Grande Image
    Attraction
    Palazzo Pubblico

    Palazzo Pubblico,Italy is a 13th‑century civic building that dominates the Piazza del Campo in the historic centre of Siena.

    Palazzo Pubblico Image
    Attraction
    Siena Cathedral

    Siena Cathedral, Italy is a Roman Catholic cathedral situated in the historic centre of Siena, a UNESCO World Heritage site renowned for its medieval urban layout.

    Siena Cathedral Image
    Attraction
    Piccolomini Library

    Piccolomini Library, Italy is a Renaissance‑era library situated inside the Siena Cathedral. Completed in 1504 under the patronage of Pope Pius II (Enea Silvio Piccolomini), the space is renowned for its richly painted walls and finely carved wooden shelves.

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    Attraction
    Fontebranda

    Introduction Fontebranda, Italy is a historic quarter on the western flank of Siena that developed around the medieval Fontebranda fountain, one of the city’s three main water sources. The area retains a compact urban fabric of stone streets, modest residences, and public squares that reflect its long‑term role in Siena’s civic life.

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    Attraction
    Piazza del Campo

    Piazza del Campo, Italy is a medieval square in the heart of Siena, renowned for its distinctive shell‑shaped layout and the historic Palazzo Pubblico that frames its perimeter.

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    Attraction
    Gelateria Dondoli

    Gelateria Dondoli, Italy is a family‑run gelato shop that has operated in the historic centre of San Gimignano since 1900. It is recognised internationally for its award‑winning flavours and for preserving traditional artisanal methods.

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    Attraction
    Basilica Cateriniana San Domenico

    Basilica Cateriniana San Domenico, Italy is a Roman‑Catholic basilica located in the historic center of the town of San Domenico. Built in the 13th century and later expanded in the Renaissance, the structure combines Gothic arches with Baroque interior decoration. It serves as both a place of worship and a focal point for the town’s cultural heritage.

    Basilica Cateriniana San Domenico Image
    Attraction
    Tower of Pisa

    The Tower of Pisa, commonly known as the Leaning Tower of Pisa, is an iconic bell tower located in the city of Pisa. It is renowned for its unintended tilt, which has made it a popular tourist attraction. The tower is part of the cathedral complex in the Piazza dei Miracoli, a UNESCO World Heritage site, which also includes the Pisa Cathedral and the Pisa Baptistery.

    Tower of Pisa Image
    Attraction
    Cattedrale di Pisa

    Cattedrale di Pisa, Italy is a Roman‑Catholic cathedral founded in the 11th century and situated on the north side of Piazza dei Miracoli, directly opposite the Leaning Tower. The building forms the western arm of the complex, which together with the Baptistery and the Camposanto creates one of the most recognizable ensembles of medieval architecture in Europe.

    Cattedrale di Pisa Image
    Attraction
    Spiaggia Levanto

    SpiaggiaLevanto, Italy – Introduction Spiaggia Levanto is a 2‑kilometre stretch of sand on the Ligurian coast, positioned at the mouth of the town of Levanto. The beach serves as a gateway to both the Cinque Terre coastal trail network and the broader Riviera Ligure region.

    Spiaggia Levanto Image
    Attraction
    Monterosso beach

    Monterosso public beach, also known as Fegina, is situated in the village of Monterosso al Mare, part of the renowned Cinque Terre region. This beach is one of the largest and most accessible in the area, making it a popular destination for both locals and tourists seeking a seaside experience.

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    Attraction
    Port of Vernazza

    Port of Vernazza is one of the five towns that make up the Cinque Terre region on the Italian Riviera. Known for its vibrant, postcard-like scenery, this coastal town is situated along a rugged section of the Ligurian coastline. Vernazza is characterized by its narrow streets, brightly colored buildings, and a small natural harbor that has historically served as an important fishing village.

    Port of Vernazza Image
    Attraction
    Cinque Terre National Park

    Cinque Terre National Park is a UNESCO World Heritage Site located along the rugged coastline of the Ligurian Sea. The park comprises five charming villages: Monterosso al Mare, Vernazza, Corniglia, Manarola, and Riomaggiore. It is renowned for its stunning landscapes, well-preserved cultural heritage, and vibrant local traditions.

    Cinque Terre National Park Image
    Attraction
    Percorso Ciclabile delle Gole del Nera

    Percorso Ciclabile delle Gole del Nera, Italy is a 14‑kilometre, mostly paved cycle route that follows the Nera River through a deep, limestone gorge in the Umbria region. The trail begins near the town of San Giustino and ends at the natural reserve entrance, providing a continuous, sign‑posted corridor for cyclists and walkers.

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    Attraction
    Lago di Gramolazzo

    Lagodi Gramolazzo, Italy is a modest alpine lake situated in the foothills of the Carnic Alps, approximately 15 km north‑west of Aviano in the Friuli‑Venezia Giulia region. The lake occupies a shallow basin fed by several small streams and lies at an elevation of about 300 m above sea level.

    Lago di Gramolazzo Image
    Attraction
    Devil's Bridge

    Devil’s Bridge, Italyis a small, historic hamlet perched on the banks of the Serchio River in the Tuscan Apennines, best known for its medieval stone bridge that legend attributes to the devil himself.

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    Attraction
    Fonti Medievali

    Fonti Medievali, Italy is a modest settlement perched on the foothills of the Apennines, known for its well‑preserved medieval architecture and a network of natural springs that gave the town its name.

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    Attraction
    San Gimignano

    Introduction San Gimignano, Italy is a medieval hill town situated in the heart of Tuscany, renowned for its well‑preserved towers and historic centre that have earned UNESCO World Heritage status.

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    Attraction
    Galleria Borghese

    Galleria Borghese, Italy, is a renowned art museum housed in the 17th‑century Villa Borghese, a historic palace set within the expansive Villa Borghese gardens.

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    Attraction
    Pantheon

    The Pantheon in Rome is a remarkably well-preserved ancient temple, originally built around 27 BCE and later reconstructed by Emperor Hadrian around 126 CE. Although the primary focus is on this architectural masterpiece, visitors often extend their exploration to the surrounding area, which offers a blend of historical and modern attractions.

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    Attraction
    Galleria Doria Pamphilj

    Galleria Doria Pamphilj, Italy is a private museum housed in the Palazzo Doria Pamphilj on Via del Corso, displaying a continuous collection of paintings, sculptures, and decorative arts assembled by the Doria Pamphilj family since the 16th century.

    Galleria Doria Pamphilj Image
    Attraction
    Trevi Fountain

    Trevi Fountain, located in Rome, is one of the most famous fountains in the world and an iconic example of Baroque architecture. Standing at approximately 26 meters high and 49 meters wide, it was designed by Italian architect Nicola Salvi and completed by Giuseppe Pannini in 1762. The fountain is situated at the junction of three roads (tre vie), which is how it derived its name.

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    Attraction
    Piazza Navona

    Piazza Navona is a prominent public space in Rome, originally built on the site of the Stadium of Domitian in the 1st century AD. The piazza is renowned for its large, elongated oval shape, reflecting the footprint of the ancient stadium where athletic contests were held. Over the centuries, Piazza Navona has transformed into a vibrant social and cultural hub.

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    Attraction
    Trastevere

    Trastevere, Italy is a centuries‑old district situated on the west bank of the Tiber River, directly opposite Rome’s historic center. Its narrow cobblestone streets, medieval churches, and vibrant piazzas give the area a distinct, well‑preserved character that attracts both residents and visitors.

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    Attraction
    Villa Farnesina

    Villa Farnesina, Italy is a Renaissance suburban palace built between 1506 and 1510 for the wealthy banker Agostino Chigi. Situated in the Trastevere district of Rome, the villa is renowned for its harmonious architecture and the richly decorated fresco cycles by Raphael, his workshop, and contemporaries.

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    Attraction
    Colosseum

    Colosseum, Italy, is one of the most iconic landmarks in Rome and a testament to ancient architecture and engineering. Completed in AD 80, this massive amphitheater once hosted large public spectacles, gladiator contests, and theatrical performances.

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    Attraction
    Roman Forum

    The Roman Forum, located in the heart of ancient Rome, is a sprawling archaeological site that was once the center of public life in the city. It served as a venue for political discourse, religious ceremonies, and various public events. Today, the Roman Forum remains a significant historical landmark, attracting visitors from around the world who seek to experience the remnants of Rome's illustrious past.

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    Attraction
    Puccini Museum

    Puccini Museum, Italy is a dedicated cultural site in the seaside town of Torre del Lago, housed in the Villa Puccini where the composer lived from 1900 until his death in 1924. The museum preserves original manuscripts, personal items, and period furnishings that illustrate Puccini’s creative environment.

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    Attraction
    Chiesa dei Santi Giovanni e Reparata

    Chiesa dei Santi Giovanni e Reparata, Italy is a Roman‑Catholic church dating to the 12th century, situated in the historic center of the town of Reggio di Calabria. The building features a stone façade with a modest bell tower, a nave divided by rounded arches, and a series of frescoes from the late medieval period.

    Chiesa dei Santi Giovanni e Reparata Image
    Attraction
    Mura di Lucca

    Mura di Lucca, Italy – Overview Mura di Lucca, Italy refers to the well‑preserved Renaissance walls that encircle the historic city of Lucca in Tuscany. Constructed between the 16th and 17th centuries, the walls stretch for approximately 4 km and are among the most complete examples of defensive fortifications in Europe. Today they function as a public promenade rather than a military barrier.

    Mura di Lucca Image
    Attraction
    Palazzo Pitti

    Palazzo Pitti, Italy is a massive Renaissance palace that dominates the south bank of the Arno River in Florence. Built in the 15th century and later expanded by the Medici and Lorraine families, it now houses several of the city’s most important museums and serves as a focal point for both historic and contemporary cultural life.

    Palazzo Pitti Image
    Attraction
    Uffizi Galleries

    Uffizi Galleries, Italy – Established in 1581 and housed in a former magistrates’ office designed by Giorgio Vasari, the Uffizi Galleries form one of the world’s oldest and most visited art museums. The complex sits along the Arno River in the historic centre, directly opposite the Palazzo Vecchio and the Ponte Vecchio.

    Uffizi Galleries Image
    Attraction
    Ponte Vecchio

    Ponte Vecchio refers to a specific historic bridge located in Florence, Italy, not a separate location, so it's essential to address it accurately within the context of Florence. However, for the purposes of this exercise, the assumption will center around Ponte Vecchio as a symbolic representation of the surrounding areas within Florence.

    Ponte Vecchio Image
    Attraction
    Arno

    Arno, Italy, is a picturesque region known for its rich history and diverse landscapes, located near the city of Florence in Tuscany. Home to the famous Arno River, this area is characterized by its rolling hills, sprawling vineyards, and charming Italian countryside.

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    Attraction
    Santa Maria del Fiore

    The Cathedral of Santa Maria del Fiore, located in Florence, is an iconic architectural masterpiece and a significant symbol of the Italian Renaissance. Also known as the Florence Cathedral, it is renowned for its distinctive red-tiled dome engineered by Filippo Brunelleschi, as well as its impressive marble façade, which features intricate designs and sculptures.

    Santa Maria del Fiore Image
    Attraction
    Piazza della Signoria

    Piazza della Signoria is a historically significant square located in the heart of Florence. Known for its stunning architecture and rich cultural history, the piazza has been a focal point of political and social life since the Middle Ages.

    Piazza della Signoria Image
    Attraction
    Officina Profumo - Farmaceutica di Santa Maria Novella

    Officina Profumo – Farmaceutica di Santa Maria Novella, Italy is a historic pharmacy and perfumery that dates back to 1612, when it was established by Dominican friars in the former convent of Santa Maria Novella in the heart of Florence.

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    Attraction
    Accommodations

    Incredible Stays

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    Nights 1-6
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    Nights 7-9
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    Excellent
    9.4/ 10·149 reviews

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    Nights 10-14
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    Excellent
    9.1/ 10·1,046 reviews

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    Nights 15-18
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    Nights 19-21
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    Night 27
    Hotel Recommendation #7
    Good
    7.8/ 10·24,671 reviews

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    Anywhere Italy

    Insider-led Italy Design & Concierge

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    Anywhere Italy

    Insider-led Italy Design & Concierge

    Your insider team designs the trip around what you care about, then supports you in-country with private logistics, vetted partners, and concierge help when plans change.

    Anywhere Italy
    Get Started

    Private drivers; English-speaking available.

    Avoid the crowds in private day tours.

    Better stays, better pacing, better reservations.

    Insider-only experiences and exclusive local partners.

    24/7 in-country support by phone, text, and WhatsApp.

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    IATA Numeric Code: 50550732

    WA State Seller of Travel 603479036-001-001

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