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This Itinerary Begins
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ITALY
Itinerary Overview
Days 1 - 3
Milan
Days 4 - 7
BEST TIME
BEST TIME
TAILORED TRIPS
BEST TIME
Days 8 - 12
Puglia
Florence & Tuscany
Highlights of Your Journey
Begin in Milan with a wine tasting of Lombardy’s Nebbiolo, followed by a visit to the Gothic Duomo. Then explore Franciacorta’s sparkling vineyards and Milan’s chic boutiques and dining scene.
In Florence, savor Chianti Classico in the city before touring Chianti’s rolling hills, tasting Brunello in Montalcino, and exploring Montepulciano’s historic wine cellars.
Head to Puglia, starting in Lecce with its Baroque charm and local Negroamaro and Primitivo wines, then enjoy seaside lunches in Polignano a Mare and nature at Torre Guaceto.
Discover Trani’s rose-colored cathedral and marina tastings, ending in Bari’s old town with Susumaniello wine and classic orecchiette alle cime di rapa.
Days 1 - 3
From the sacred Duomo to the sparkling vineyards of Franciacorta and Milan’s boutique alleyways, these days weave together Italy’s reverence for heritage, its passion for craftsmanship, and its gift for la dolce vita.
On the first day, ease into Milan’s elegant rhythm with a tasting of Lombardy’s famed wines, followed by a tour of the Duomo di Milano, the third largest cathedral in the world and where Gothic architecture can be seen at its most prominent. Let the rich flavours of Nebbiolo, (known as Chiavennasca in the Valtellina region of Lombardy) and the cathedral’s 15th century frescoes set the tone for your Italian escape.
On the second day, venture to the Franciacorta wine region, where sun-drenched vineyards slope toward Lake Iseo and some of Italy's finest sparkling wines reside. By the third day, shift gears to Milan’s cosmopolitan centre: designer boutiques in the Quadrilatero della Moda beckon, while the restaurants of Milan promis contemporary Michelin dining or local tavernas brimming with history and personality - whichever takes your fancy more.
Days 4 - 7
In Florence, the artwork of the Renaissance gives way to Chianti's vine-clad valleys, where days unfold between wine tastings and medieval hill towns - each glass of Brunello or Vino Nobile revealing another layer of Tuscany's vinous heritage and breathtaking landscapes.
Your Tuscan odyssey begins in Florence's winding streets, where a glass of Chianti Classico at a candlelit enoteca introduces you to the the bold flavours of Tuscany. As dawn breaks on day five, the countryside calls - escorted through Chianti's postcard-perfect landscapes, you'll become a wine connoisseur for the day, comparing Sangiovese vintages and tasting local dishes laced with Tuscan truffle at family-run estates. The next stop, Montalcino, elevates your wine experience literally and figuratively; perched atop its namesake hills, sipping complex Brunellos while surveying the patchwork of vineyards that stretch into horizon. Your final few days takes you underground in Montepulciano, where time-honoured cellars house barrels of Vino Nobile, their aroma offering notes of cherry and spice, a heady farewell to this central Italian region.
Days 8 - 12
From Lecce's gilded piazzas to the Adriatic Sea's turquoise hues, these final days celebrate Puglia's contrasts - where Baroque grandeur and barefoot luxury go hand-in-hand, and every glass of sun-warmed Primitivo and platter of freshly-caught seafood tells the story of the people and traditions that have cultivated the area.
Your journey through the Italian wine regions unfolds like a well-aged vintage in Puglia - starting in Lecce, the capital famous for its Baroque architecture, and a place where Negroamaro and Primitivo wines dance invite you to a new palate of wine. The beaches of the Adriatic Sea call on day nine; Polignano a Mare's limestone cliffs frame your seaside lunch, each sip of mineral-driven Falanghina echoing the sea spray below. Time dissolves at Torre Guaceto's nature reserve, just north of Brindisa, where protective measures have preserved the last of the Adriatic coastline's famed beauty. The day after, wander through Trani's port towns and become enchanted by its rose-coloured cathedral and marina-side tastings of honeyed Moscato paired with freshly-caught crudi. As your journey starts to wind to a close, visit Bari's complex old town, for one last glass of Susumaniello and a steaming dish of orecchiette alle cime di rapa, cemeting your memories of Puglia in one last captivating dish.
Day 1
From the sacred Duomo to the sparkling vineyards of Franciacorta and Milan’s boutique alleyways, these days weave together Italy’s reverence for heritage, its passion for craftsmanship, and its gift for la dolce vita.
On the first day, ease into Milan’s elegant rhythm with a tasting of Lombardy’s famed wines, followed by a tour of the Duomo di Milano, the third largest cathedral in the world and where Gothic architecture can be seen at its most prominent. Let the rich flavours of Nebbiolo, (known as Chiavennasca in the Valtellina region of Lombardy) and the cathedral’s 15th century frescoes set the tone for your Italian escape.
On the second day, venture to the Franciacorta wine region, where sun-drenched vineyards slope toward Lake Iseo and some of Italy's finest sparkling wines reside. By the third day, shift gears to Milan’s cosmopolitan centre: designer boutiques in the Quadrilatero della Moda beckon, while the restaurants of Milan promis contemporary Michelin dining or local tavernas brimming with history and personality - whichever takes your fancy more.
Days 2 - 4
In Florence, the artwork of the Renaissance gives way to Chianti's vine-clad valleys, where days unfold between wine tastings and medieval hill towns - each glass of Brunello or Vino Nobile revealing another layer of Tuscany's vinous heritage and breathtaking landscapes.
Your Tuscan odyssey begins in Florence's winding streets, where a glass of Chianti Classico at a candlelit enoteca introduces you to the the bold flavours of Tuscany. As dawn breaks on day five, the countryside calls - escorted through Chianti's postcard-perfect landscapes, you'll become a wine connoisseur for the day, comparing Sangiovese vintages and tasting local dishes laced with Tuscan truffle at family-run estates. The next stop, Montalcino, elevates your wine experience literally and figuratively; perched atop its namesake hills, sipping complex Brunellos while surveying the patchwork of vineyards that stretch into horizon. Your final few days takes you underground in Montepulciano, where time-honoured cellars house barrels of Vino Nobile, their aroma offering notes of cherry and spice, a heady farewell to this central Italian region.
Days 5 - 6
From Lecce's gilded piazzas to the Adriatic Sea's turquoise hues, these final days celebrate Puglia's contrasts - where Baroque grandeur and barefoot luxury go hand-in-hand, and every glass of sun-warmed Primitivo and platter of freshly-caught seafood tells the story of the people and traditions that have cultivated the area.
Your journey through the Italian wine regions unfolds like a well-aged vintage in Puglia - starting in Lecce, the capital famous for its Baroque architecture, and a place where Negroamaro and Primitivo wines dance invite you to a new palate of wine. The beaches of the Adriatic Sea call on day nine; Polignano a Mare's limestone cliffs frame your seaside lunch, each sip of mineral-driven Falanghina echoing the sea spray below. Time dissolves at Torre Guaceto's nature reserve, just north of Brindisa, where protective measures have preserved the last of the Adriatic coastline's famed beauty. The day after, wander through Trani's port towns and become enchanted by its rose-coloured cathedral and marina-side tastings of honeyed Moscato paired with freshly-caught crudi. As your journey starts to wind to a close, visit Bari's complex old town, for one last glass of Susumaniello and a steaming dish of orecchiette alle cime di rapa, cemeting your memories of Puglia in one last captivating dish.
Days 4 - 7
In Florence, the artwork of the Renaissance gives way to Chianti's vine-clad valleys, where days unfold between wine tastings and medieval hill towns - each glass of Brunello or Vino Nobile revealing another layer of Tuscany's vinous heritage and breathtaking landscapes.
Your Tuscan odyssey begins in Florence's winding streets, where a glass of Chianti Classico at a candlelit enoteca introduces you to the the bold flavours of Tuscany. As dawn breaks on day five, the countryside calls - escorted through Chianti's postcard-perfect landscapes, you'll become a wine connoisseur for the day, comparing Sangiovese vintages and tasting local dishes laced with Tuscan truffle at family-run estates. The next stop, Montalcino, elevates your wine experience literally and figuratively; perched atop its namesake hills, sipping complex Brunellos while surveying the patchwork of vineyards that stretch into horizon. Your final few days takes you underground in Montepulciano, where time-honoured cellars house barrels of Vino Nobile, their aroma offering notes of cherry and spice, a heady farewell to this central Italian region.
Days 8 - 12
From Lecce's gilded piazzas to the Adriatic Sea's turquoise hues, these final days celebrate Puglia's contrasts - where Baroque grandeur and barefoot luxury go hand-in-hand, and every glass of sun-warmed Primitivo and platter of freshly-caught seafood tells the story of the people and traditions that have cultivated the area.
Your journey through the Italian wine regions unfolds like a well-aged vintage in Puglia - starting in Lecce, the capital famous for its Baroque architecture, and a place where Negroamaro and Primitivo wines dance invite you to a new palate of wine. The beaches of the Adriatic Sea call on day nine; Polignano a Mare's limestone cliffs frame your seaside lunch, each sip of mineral-driven Falanghina echoing the sea spray below. Time dissolves at Torre Guaceto's nature reserve, just north of Brindisa, where protective measures have preserved the last of the Adriatic coastline's famed beauty. The day after, wander through Trani's port towns and become enchanted by its rose-coloured cathedral and marina-side tastings of honeyed Moscato paired with freshly-caught crudi. As your journey starts to wind to a close, visit Bari's complex old town, for one last glass of Susumaniello and a steaming dish of orecchiette alle cime di rapa, cemeting your memories of Puglia in one last captivating dish.
BEST TIME
April - October
TAILORED TRIPS
from £2500 pp, per night
Milan - Florence & Tuscany - Puglia
Days 1 - 3
Milan
Days 4 - 7
Florence & Tuscany
Days 8 - 12
Puglia
Trip Highlights
Begin in Milan with a wine tasting of Lombardy’s Nebbiolo, followed by a visit to the Gothic Duomo. Then explore Franciacorta’s sparkling vineyards and Milan’s chic boutiques and dining scene.
In Florence, savor Chianti Classico in the city before touring Chianti’s rolling hills, tasting Brunello in Montalcino, and exploring Montepulciano’s historic wine cellars.
Head to Puglia, starting in Lecce with its Baroque charm and local Negroamaro and Primitivo wines, then enjoy seaside lunches in Polignano a Mare and nature at Torre Guaceto.
Discover Trani’s rose-colored cathedral and marina tastings, ending in Bari’s old town with Susumaniello wine and classic orecchiette alle cime di rapa.
Days 1 - 3
From the sacred Duomo to the sparkling vineyards of Franciacorta and Milan’s boutique alleyways, these days weave together Italy’s reverence for heritage, its passion for craftsmanship, and its gift for la dolce vita.
On the first day, ease into Milan’s elegant rhythm with a tasting of Lombardy’s famed wines, followed by a tour of the Duomo di Milano, the third largest cathedral in the world and where Gothic architecture can be seen at its most prominent. Let the rich flavours of Nebbiolo, (known as Chiavennasca in the Valtellina region of Lombardy) and the cathedral’s 15th century frescoes set the tone for your Italian escape.
On the second day, venture to the Franciacorta wine region, where sun-drenched vineyards slope toward Lake Iseo and some of Italy's finest sparkling wines reside. By the third day, shift gears to Milan’s cosmopolitan centre: designer boutiques in the Quadrilatero della Moda beckon, while the restaurants of Milan promis contemporary Michelin dining or local tavernas brimming with history and personality - whichever takes your fancy more.
Days 5 - 6
Conclude your time in Florence on the quieter side of the Arno - where Medici gardens, local workshops, and laid-back aperitivo culture come together.
Cross the river into the Oltrarno district to visit the Boboli Gardens, originally designed for the Medici court. Terraced lawns, fountains, and cypress-lined paths offer space to reflect - and provide elevated views back over the city. Just adjacent is the Pitti Palace, a former ducal residence now home to several major galleries and decorative arts collections. This leads into the ideal final day, where we invite you to wander further into the Oltrarno to discover small artisan studios specializing in bookbinding, leatherwork, and traditional marbling. The area rewards a slower pace, ending perhaps with a classic Negroni or local white wine at one of the bars around Piazza Santo Spirito.
Days 2 - 4
From Botticelli to Michelangelo, art and architecture come alive across Florence’s compact historic center - paired with markets and a countryside escape.
The following day, enter the Uffizi Gallery, home to Botticelli’s Birth of Venus, works by Giotto and Caravaggio, and some of the finest examples of Italian Renaissance painting. A morning spent in the gallery is never amiss, and from there, it’s a short walk to the Ponte Vecchio, Florence’s oldest bridge and a hub of goldsmiths’ shops since the 16th century. On the fourth day, visit the Accademia to view Michelangelo’s David, carved from a single block of Carrara marble. Then continue to the bustling San Lorenzo Market - part produce stalls, part artisan food hall - for a casual Florentine lunch. For a change of pace, you then lave the city for its countryside companion. You can either head south to Siena to explore its medieval streets and cathedral, or opt for a day in Chianti to visit small wineries and learn about Tuscan winemaking traditions through tastings and cellar tours.
Days 5 - 6
Conclude your time in Florence on the quieter side of the Arno - where Medici gardens, local workshops, and laid-back aperitivo culture come together.
Cross the river into the Oltrarno district to visit the Boboli Gardens, originally designed for the Medici court. Terraced lawns, fountains, and cypress-lined paths offer space to reflect - and provide elevated views back over the city. Just adjacent is the Pitti Palace, a former ducal residence now home to several major galleries and decorative arts collections. This leads into the ideal final day, where we invite you to wander further into the Oltrarno to discover small artisan studios specializing in bookbinding, leatherwork, and traditional marbling. The area rewards a slower pace, ending perhaps with a classic Negroni or local white wine at one of the bars around Piazza Santo Spirito.
Days 4 - 7
In Florence, the artwork of the Renaissance gives way to Chianti's vine-clad valleys, where days unfold between wine tastings and medieval hill towns - each glass of Brunello or Vino Nobile revealing another layer of Tuscany's vinous heritage and breathtaking landscapes.
Your Tuscan odyssey begins in Florence's winding streets, where a glass of Chianti Classico at a candlelit enoteca introduces you to the the bold flavours of Tuscany. As dawn breaks on day five, the countryside calls - escorted through Chianti's postcard-perfect landscapes, you'll become a wine connoisseur for the day, comparing Sangiovese vintages and tasting local dishes laced with Tuscan truffle at family-run estates. The next stop, Montalcino, elevates your wine experience literally and figuratively; perched atop its namesake hills, sipping complex Brunellos while surveying the patchwork of vineyards that stretch into horizon. Your final few days takes you underground in Montepulciano, where time-honoured cellars house barrels of Vino Nobile, their aroma offering notes of cherry and spice, a heady farewell to this central Italian region.
Days 8 - 12
From Lecce's gilded piazzas to the Adriatic Sea's turquoise hues, these final days celebrate Puglia's contrasts - where Baroque grandeur and barefoot luxury go hand-in-hand, and every glass of sun-warmed Primitivo and platter of freshly-caught seafood tells the story of the people and traditions that have cultivated the area.
Your journey through the Italian wine regions unfolds like a well-aged vintage in Puglia - starting in Lecce, the capital famous for its Baroque architecture, and a place where Negroamaro and Primitivo wines dance invite you to a new palate of wine. The beaches of the Adriatic Sea call on day nine; Polignano a Mare's limestone cliffs frame your seaside lunch, each sip of mineral-driven Falanghina echoing the sea spray below. Time dissolves at Torre Guaceto's nature reserve, just north of Brindisa, where protective measures have preserved the last of the Adriatic coastline's famed beauty. The day after, wander through Trani's port towns and become enchanted by its rose-coloured cathedral and marina-side tastings of honeyed Moscato paired with freshly-caught crudi. As your journey starts to wind to a close, visit Bari's complex old town, for one last glass of Susumaniello and a steaming dish of orecchiette alle cime di rapa, cemeting your memories of Puglia in one last captivating dish.
BEST TIME
April - October
TAILORED TRIPS
from £2500 pp, per night
Milan - Florence & Tuscany - Puglia
Days 1 - 3
Milan
Days 4 - 7
Florence & Tuscany
Days 8 - 12
Puglia
Trip Highlights
Begin in Milan with a wine tasting of Lombardy’s Nebbiolo, followed by a visit to the Gothic Duomo. Then explore Franciacorta’s sparkling vineyards and Milan’s chic boutiques and dining scene.
In Florence, savor Chianti Classico in the city before touring Chianti’s rolling hills, tasting Brunello in Montalcino, and exploring Montepulciano’s historic wine cellars.
Head to Puglia, starting in Lecce with its Baroque charm and local Negroamaro and Primitivo wines, then enjoy seaside lunches in Polignano a Mare and nature at Torre Guaceto.
Discover Trani’s rose-colored cathedral and marina tastings, ending in Bari’s old town with Susumaniello wine and classic orecchiette alle cime di rapa.
Days 1 - 3
From the sacred Duomo to the sparkling vineyards of Franciacorta and Milan’s boutique alleyways, these days weave together Italy’s reverence for heritage, its passion for craftsmanship, and its gift for la dolce vita.
On the first day, ease into Milan’s elegant rhythm with a tasting of Lombardy’s famed wines, followed by a tour of the Duomo di Milano, the third largest cathedral in the world and where Gothic architecture can be seen at its most prominent. Let the rich flavours of Nebbiolo, (known as Chiavennasca in the Valtellina region of Lombardy) and the cathedral’s 15th century frescoes set the tone for your Italian escape.
On the second day, venture to the Franciacorta wine region, where sun-drenched vineyards slope toward Lake Iseo and some of Italy's finest sparkling wines reside. By the third day, shift gears to Milan’s cosmopolitan centre: designer boutiques in the Quadrilatero della Moda beckon, while the restaurants of Milan promis contemporary Michelin dining or local tavernas brimming with history and personality - whichever takes your fancy more.
Days 2 - 4
From Botticelli to Michelangelo, art and architecture come alive across Florence’s compact historic center - paired with markets and a countryside escape.
The following day, enter the Uffizi Gallery, home to Botticelli’s Birth of Venus, works by Giotto and Caravaggio, and some of the finest examples of Italian Renaissance painting. A morning spent in the gallery is never amiss, and from there, it’s a short walk to the Ponte Vecchio, Florence’s oldest bridge and a hub of goldsmiths’ shops since the 16th century. On the fourth day, visit the Accademia to view Michelangelo’s David, carved from a single block of Carrara marble. Then continue to the bustling San Lorenzo Market - part produce stalls, part artisan food hall - for a casual Florentine lunch. For a change of pace, you then lave the city for its countryside companion. You can either head south to Siena to explore its medieval streets and cathedral, or opt for a day in Chianti to visit small wineries and learn about Tuscan winemaking traditions through tastings and cellar tours.
Best Luxury Hotels in Italy: Conte's Seasonal Picks for 2025
Vetera Matera
Matera, Italy
Nestled in the heart of the ancient, UNESCO-listed Sassi di Matera, Vetera Matera reimagines heritage luxury through a collection of 23 exquisitely restored rooms and suites. Carved into tuff-stone caves or housed in early-modern noble floors, each space blends raw local materials, from the vaulted ceilings to the stone arches, with modern amenities.
The hotel’s Elysium Spa is hewn from ancient cisterns and rocks, offering caldarium pools, aromatic steam baths and a serene terrace overlooking Matera’s labyrinth of stone dwellings. Meanwhile, the restaurant elevates regional ingredients such as Materan bread, peperoni cruschi, local cheeses into contemporary Italian cuisine rooted in place.
Forestis Dolomites
Dolomites, Italy
Nestled at 1,800 metres on the southern slope of the Plose mountain above Bressanone, Forestis Dolomites redefines alpine luxury with architectural restraint and natural elegance. The resort’s minimal-design suites, floor-to-ceiling windows and timber-and-stone textures dissolve the boundary between interior and the towering peaks of the UNESCO-listed Dolomites.
Of note is the 2,000 m² spa that draws on the four elements - air, water, sun and climate - and four native trees, offering indoor-outdoor pools, multiple saunas, and treatments inspired by mountain pine and larch. Gourmet dining at the restaurant specialises in ‘forest cuisine’, blending Alpine produce, wild herbs and local foraging under the direction of chef Roland Lamprecht. With ski-in/ski-out access in winter and hiking trails in summer, this adults-only retreat delivers a rare combination of serenity, design and peak-mountain immersion.
Hotel La Palma
Capri, Italy
Once a gathering place for artists and poets, Hotel La Palma is Capri’s oldest hotel and now one of its most dazzling. Reimagined by the Oetker Collection, it retains the island’s effortless charm while introducing a new era of Italian glamour. Fifty rooms and suites designed by Francis Sultana pair cool white tones with splashes of Mediterranean blue, each opening to a private terrace or balcony that frames the island’s vibrant life.
Life here moves to Capri’s timeless rhythm. Days begin with espresso at Gennaro’s, where Michelin-starred chef Gennaro Esposito reinterprets Neapolitan classics, and drift toward sunset cocktails on the Bianca Rooftop, where sea and sky blur into one. The Da Gioia beach club, tucked into Marina Piccola, invites long afternoons by the water, while the pool terrace and spa offer calm after the island’s bustle.
Collegio alla Querce, Auberge Resorts Collection
Florence, Italy
In harmonious design, Collegio alla Querce, Auberge Resorts Collection’s 83 guest rooms and suites marry the old and new worlds, combining high Renaissance art with modern Italian design. Rich colours, locally sourced materials and contemporary furnishings will complement hand-selected antiques and walls of thoughtfully curated, decade-spanning artwork.
Soaring windows look over manicured Baroque gardens, spectacular hilltop views of Tuscany and the historic terracotta tiled city of Firenze. Personal wine cellars, trunk closets for fully unpacking, marble tubs and invisible technology all create a true sense of la bella vita.
The Bvlgari Hotel
Rome, Italy
The Bvlgari Hotel Roma is the ninth jewel in the Bvlgari Hotels & Resorts collection. Occupying an illustrious address at Piazza Augusto Imperatore, in the Campo Marzio area, the Hotel is minutes from Via del Corso, the Piazza di Spagna, and Bvlgari’s historic Via Condotti boutique.
The Hotel celebrates the most refined qualities of the Eternal City and showcases exceptional facets of Italian elegance in every detail of its design, hospitality and experience. Home to 110 Rooms and Suites, five distinctive culinary experiences, and exquisite boutiques and programmes, it is an inimitable expression of the Bvlgari spirit, forged in the history and richness of Rome.
Hotel Grand Tremezzo
Lake Como, Italy
Boasting unparalleled views over Bellagio and the rose-tinted Grigne mountains, the Grand Hotel Tremezzo, a family-run business for over a century of history, is a symbol of the warmest Italian hospitality and the place-to-be on Lake Como to enjoy the flavours of a real vacation. Built in 1910, it combines fabulous period décor characterised by vibrant colours and reflecting the exuberance of times past with contemporary luxuries to make every lakeside vacation truly extraordinary.
The hotel features 80 rooms and suites alongside a number of impressive facilities and amenities; a lakefront sandy lido and three breathtaking pools alongside private Venetian motor launches waiting to show guests the lake and its borgos. To top it all, the hotel boasts a three-level T Spa and five restaurants and snack bars offering the best expressions of the Italian cuisine.
