13 days

Italian Elegance: A 14-Day Cultural & Culinary Escape

An exclusive journey through art-filled cities, rolling Tuscan hills, and the sun-drenched Amalfi Coast.

Discover Italy’s multifaceted history, celebrated cuisine, and timeless style in this 14-day adventure. From the serene canals of Venice to the vineyards of Tuscany, and from Florence’s Renaissance splendors to Positano’s coastal allure, each region showcases its own distinct character.

 

Throughout, enjoy exceptional hospitality at iconic properties—including Aman Venice Piano Nobile Suites, Rosewood Castiglion del Bosco, Le Sirenuse Positano, and Belmond Hotel Cipriani—alongside other handpicked suggestions.

Discover Italy’s multifaceted history, celebrated cuisine, and timeless style in this 14-day adventure. From the serene canals of Venice to the vineyards of Tuscany, and from Florence’s Renaissance splendors to Positano’s coastal allure, each region showcases its own distinct character.

 

Throughout, enjoy exceptional hospitality at iconic properties—including Aman Venice Piano Nobile Suites, Rosewood Castiglion del Bosco, Le Sirenuse Positano, and Belmond Hotel Cipriani—alongside other handpicked suggestions.

Highlights

  • Private Water Transfers and Gondola Rides in Venice
  • Artistic Immersion in Florence and Rome with insider access
  • Exclusive Wine Tastings in the Tuscan countryside
  • Hands-On Culinary Sessions with local chefs
  • Amalfi Coast Boat Excursion to hidden coves
  • Sunset Aperitivos in iconic piazzas

Trip itinerary

3 days

Venice

Begin your journey amid the canals of Venice. Split your stay between two renowned properties for different perspectives of the lagoon: Aman Venice (Piano Nobile Suites) for refined, contemporary style within a 16th-century palazzo, and Belmond Hotel Cipriani for classic lagoon views on Giudecca Island.

Schedule details

Day 1: Arrival in Venice
  • VIP Arrival: Personalized assistance and private water taxi transfer directly to Aman Venice.
  • Check-in: Piano Nobile Suite featuring historic frescoes and Grand Canal views.
  • Exclusive Welcome: Private in-suite aperitivo with Venetian cicchetti and fine Italian wines.
  • Evening: Private, after-hours access to St. Mark’s Basilica for a quiet, awe-inspiring experience.
Day 2: Exclusive Venetian Highlights
  • Morning: Private tour of the Doge’s Palace Secret Itineraries, exploring hidden chambers and secret passages.
  • Midday: A bespoke gondola ride with a personal historian to uncover Venice’s untold stories.
  • Afternoon: Private visit to a master artisan’s atelier in Murano to create your own unique glass piece.
  • Evening: Sunset aperitivo on Aman’s private canal-side terrace, followed by a private chef’s dinner in the palazzo.
Day 3: Refined Relaxation & Farewell
  • Morning: Private visit to a historic Venetian villa or exclusive access to a noble family’s private art collection.
  • Afternoon: Indulge in a personalized Aman spa experience or a private yacht tour of the Venetian Lagoon, including Burano and Torcello.
  • Farewell Evening: Candlelit dinner in Aman’s garden or an exclusive table on a private terrace overlooking the Grand Canal.

Featured hotels

Cipriani Venice

Cipriani Venice

An icon of Venetian luxury, Belmond Hotel Cipriani boasts stunning lagoon views, lush gardens, and world-class dining. This legendary retreat has long attracted celebrities and discerning travelers seeking la dolce vita on the water.

Location
Nestled on Giudecca Island, just a short private boat ride from St. Mark’s Square, the hotel offers both tranquility and easy access to Venice’s top attractions.

Activities

  • Rooftop Pool & Spa: Bask by one of the city’s rare outdoor swimming pools, then indulge in a holistic spa treatment.
  • Private Boat Transfers: Cruise the lagoon in the hotel’s private launch for a stylish arrival at Venice’s landmarks.
  • Cultural Exploration: Visit the Doge’s Palace, Basilica di San Marco, and local art galleries.

Best Time to Travel
Late spring (April–June) or early autumn (September–October) to avoid peak summer heat and high tourist season.

Recommended Dish & Drink

  • Dish: Sarde in Saor, a traditional sweet-and-sour Venetian sardine dish.
  • Drink: The iconic Bellini, famously invented at Harry’s Bar in Venice and celebrated at Cipriani.

Useful Links

Official Website

Aman Venice

Aman Venice

Housed in the regal 16th-century Palazzo Papadopoli, Aman Venice exudes old-world charm blended with contemporary luxury. The Piano Nobile Suites feature lofty ceilings, frescoed walls, and lavish details that transport guests to the grandeur of Venetian aristocracy.

Location
Located on the Grand Canal in the heart of Venice, the hotel is just moments from iconic sites like the Rialto Bridge and Piazza San Marco.

Activities

  • Art & History: Explore the hotel’s private art collection and frescoes by 18th-century master Tiepolo.
  • Gondola Rides: Glide along the city’s waterways for a romantic view of Venice’s ornate palazzi.
  • Culinary Classes: Learn to make authentic Venetian dishes with the hotel’s expert chefs.

Best Time to Travel
Late spring (April–June) or early autumn (September–October) to enjoy pleasant weather and fewer crowds.

Recommended Dish & Drink

  • Dish: Risotto al Nero di Seppia (squid ink risotto), a classic Venetian specialty.
  • Drink: A refreshing Aperol Spritz, the city’s signature aperitivo.

Useful Links

Official Website

2 days

Florence

Depart Venice for the cradle of the Renaissance. Discover Florence’s cultural and artistic wealth, from Renaissance masterworks at the Uffizi to vibrant artisan districts. Stay at a distinguished property like Four Seasons Hotel Firenze for centuries-old charm and expansive private gardens.

Schedule details

Day 4: Arrival in Florence & Historic Center

  • High-Speed Rail Transfer First-class journey from Venice Santa Lucia to Firenze Santa Maria Novella.
  • Check-In at Four Seasons Hotel Firenze Relax in a frescoed suite overlooking the gardens.
  • Private Walking Tour Visit the Duomo, Piazza della Signoria, and Ponte Vecchio.
  • Evening Reserve dinner at a Michelin-starred restaurant showcasing Tuscan cuisine.

Day 5: Masterpieces & Artisan Workshops

  • Guided Uffizi Visit Early entrance to avoid crowds; an art historian provides expert insights.
  • Artisan Craft Visits Meet local goldsmiths, leatherworkers, or perfumers in Oltrarno.
  • Afternoon Leisure Optional private shopping at designer boutiques.
  • Sunset Rooftop Aperitivo Take in stunning city views, then enjoy dinner at your hotel or a nearby trattoria.

Featured hotels

Four Seasons Florence

Four Seasons Florence

Set in a 15th-century palazzo and convent, Four Seasons Florence marries Renaissance grandeur with modern luxury. Its expansive private garden—one of the largest in the city—offers an oasis of tranquility.

Location
Located near the Gherardesca Gardens, just minutes from Florence’s historic center and cultural landmarks.

Activities

  • Garden Strolls: Wander through centuries-old trees and ornate statues in the hotel’s lush park.
  • Art & Culture: Visit the Accademia, the Uffizi, and Florence Cathedral nearby.
  • Wellness: Unwind at the on-site spa, featuring treatments inspired by local Tuscan ingredients.

Best Time to Travel

  • Spring (April–June) or Fall (September–October) for mild temperatures and vibrant city life.

Recommended Dish & Drink

  • Dish: Pappardelle al Cinghiale, a wild boar ragu pasta celebrating Tuscan flavors.
  • Drink: A velvety Chianti Classico from local vineyards.

Useful Links

Official Website

The St. Regis Florence

The St. Regis Florence

Housed in a historic Renaissance palace along the Arno River, the St. Regis Florence exudes timeless elegance and refined hospitality. Its ornate interiors, frescoes, and sumptuous rooms pay homage to the city’s artistic heritage.

Location
Situated in the heart of Florence, a short stroll from the Ponte Vecchio, the Duomo, and the Uffizi Gallery.

Activities

  • Art & History: Explore renowned museums and architectural marvels of the Renaissance.
  • Shopping: Browse luxury boutiques along Via de’ Tornabuoni.
  • Gourmet Experiences: Indulge in fine Tuscan dining at the hotel’s Michelin-starred restaurant.

Best Time to Travel

  • Spring (April–June) or Autumn (September–October) for pleasant weather and fewer crowds.

Recommended Dish & Drink

  • Dish: Bistecca alla Fiorentina, a signature Florentine T-bone steak grilled to perfection.
  • Drink: A classic Negroni, said to have originated in Florence.

Useful Links

Official Website

3 days

Tuscany

Venture into the rolling hills of Tuscany to experience wine estates, medieval villages, and a tranquil landscape. Your base, Rosewood Castiglion del Bosco, offers farm-fresh gastronomy, robust vintages, and an authentic sense of place in the Val d’Orcia region.

Schedule details

Day 6: Transfer to Val d’Orcia

  • Private Chauffeured Drive Picturesque journey through cypress-lined roads and vineyards.
  • Check-In at Rosewood Castiglion del Bosco Enjoy a welcome glass of Brunello di Montalcino.
  • Afternoon Visit the spa or wander through the estate’s historic grounds.
  • Evening Tuscan dinner at the estate’s signature restaurant.

Day 7: Wine Regions & Hilltop Towns

  • Private Wine Tour Exclusive tastings at boutique vineyards around Montalcino or Chianti.
  • Hilltop Villages Optional excursion to Pienza or Montepulciano for local culture.
  • Cooking Class Learn to make homemade pasta and regional specialties with estate chefs.
  • Evening Savor your day’s creations accompanied by Tuscan wines.

Day 8: Tuscan Exploration or Leisure

  • Choice of Activities Sunrise hot air balloon ride, guided truffle hunt, or cycling through vineyard roads.
  • Afternoon & Evening Return for a spa treatment or enjoy a casual wine-pairing dinner on the terrace.

Featured hotels

Castello di Casole, Tuscany

Castello di Casole, Tuscany

Steeped in centuries of history, Castello di Casole (a Timbers Resort) is a restored castle estate featuring elegant suites, a vast winery, and panoramic views of Tuscany’s iconic countryside.

Location
Situated between Siena and Florence, on a sprawling 4,200-acre estate of vineyards, olive groves, and woodlands.

Activities

  • Estate Tours: Discover the castle’s winery, sample olive oils, and stroll through vineyards.
  • Outdoor Pursuits: Hike or bike across rolling hills and cypress-lined lanes.
  • Day Trips: Visit Siena, San Gimignano, or Florence for art, culture, and shopping.

Best Time to Travel

  • May–September for warm days, perfect for exploring Tuscany’s countryside.

Recommended Dish & Drink

  • Dish: Pici al Ragu, a thick hand-rolled pasta with rich meat sauce.
  • Drink: A glass of Castello di Casole’s own red from the estate’s vineyards.

Useful Links

Official Website

Castiglion del bosco

Castiglion del bosco

Set within a 5,000-acre estate in the heart of Tuscany, Rosewood Castiglion del Bosco is a luxury countryside retreat offering rustic elegance, vineyards, and panoramic views. The historic estate dates back 800 years, combining heritage with modern-day comforts.

Location
Situated near Montalcino, known for its famous Brunello wines, the property is surrounded by rolling hills, vineyards, and cypress-lined roads.

Activities

  • Wine Tasting: Tour the estate’s winery and sample the acclaimed Brunello di Montalcino.
  • Cooking Classes: Learn Tuscan culinary traditions, from handmade pasta to artisanal olive oil tastings.
  • Outdoor Exploration: Go hiking or cycling through the scenic Val d’Orcia, a UNESCO World Heritage site.

Best Time to Travel
Spring (April–June) and early autumn (September–October) for mild weather and vibrant landscapes.

Recommended Dish & Drink

  • Dish: Bistecca alla Fiorentina, a hearty Tuscan T-bone steak grilled to perfection.
  • Drink: Brunello di Montalcino, the region’s celebrated red wine.

Useful Links

Official Website

Borgo Santo Pietro

Borgo Santo Pietro

A 13th-century villa turned luxury retreat, Borgo Santo Pietro offers countryside charm, farm-to-table gastronomy, and holistic wellness programs. Expect manicured gardens, a cooking school, and a Michelin-starred restaurant.

Location
Nestled in the Val d’Elsa region near Siena, surrounded by rolling hills, vineyards, and olive groves.

Activities

  • Culinary Classes: Learn Tuscan recipes using fresh ingredients from the property’s organic farm.
  • Wine Tasting: Explore nearby vineyards to sample local Chianti and Vernaccia.
  • Wellness: Enjoy spa treatments, yoga sessions, and leisurely walks in the estate’s gardens.

Best Time to Travel

  • Late Spring (May–June) or Early Autumn (September) for balmy weather and scenic landscapes.

Recommended Dish & Drink

  • Dish: Tagliatelle with Truffle—Tuscan pasta elevated by seasonal truffles.
  • Drink: A robust Super Tuscan wine, pairing beautifully with regional dishes.

Useful Links

Official Website

2 days

Rome

Travel to the Eternal City for an immersion in ancient history and modern flair. Stay at a refined address such as Hotel de Russie, renowned for its secret garden and central location near the Spanish Steps.

Schedule details

Day 9: Transfer to Rome & Ancient Highlights

  • Scenic Drive Private car journey from Tuscany to Rome, arriving around midday.
  • Check-In at Hotel de Russie Relax in a suite overlooking the garden courtyard.
  • Afternoon Tour Colosseum and Roman Forum with a dedicated guide and skip-the-line access.
  • Evening Explore Piazza di Spagna before dinner at a refined local restaurant.

Day 10: Vatican & Artistic Treasures

  • VIP Vatican Tour Early access to the Sistine Chapel and a private tour of St. Peter’s Basilica.
  • Optional Experiences Tailored shopping in upscale Roman boutiques or a gelato-tasting tour.
  • Afternoon at Leisure Stroll through Trastevere or unwind in the hotel’s garden.
  • Michelin-Star Dining Treat yourself to a gourmet meal in a historic palazzo setting.

Featured hotels

Hotel dei Russie, Rome

Hotel dei Russie, Rome

A Rocco Forte hotel, Hotel de Russie is famed for its Secret Garden, sophisticated design, and impeccable service. It’s a tranquil haven amid Rome’s bustling center.

Location
Ideally located between the Spanish Steps and Piazza del Popolo, allowing easy access to Rome’s historic sites and upscale shopping streets.

Activities

  • Cultural Exploration: Walk to the Trevi Fountain, Pantheon, and Villa Borghese.
  • Garden Dining: Enjoy al fresco meals in the hotel’s lush courtyard garden.
  • Spa & Wellness: Relax at the De Russie Spa, offering Roman-inspired treatments.

Best Time to Travel

  • Spring (April–June) and Fall (September–October) for pleasant temperatures and fewer tourists.

Recommended Dish & Drink

  • Dish: Carciofi alla Romana, tender artichokes braised with herbs and olive oil.
  • Drink: A chilled glass of Frascati white wine, a classic Roman pairing.

Useful Links

Official Website

Hotel de la Ville, Rome

Hotel de la Ville, Rome

Another Rocco Forte gem, Hotel de la Ville exudes contemporary elegance, merging 18th-century architecture with modern Italian flair. Its rooftop bar offers sweeping panoramas of the Eternal City.

Location
Set atop the Spanish Steps, within walking distance of iconic landmarks like the Trevi Fountain and Villa Borghese.

Activities

  • Sightseeing: Explore Piazza di Spagna, Piazza Navona, and the Colosseum.
  • Dining & Nightlife: Savor innovative Roman cuisine and enjoy cocktails on the rooftop terrace.
  • Luxury Shopping: Stroll Via Condotti and Via del Corso for designer boutiques.

Best Time to Travel

  • April–June or September–October for mild temperatures and comfortable sightseeing.

Recommended Dish & Drink

  • Dish: Spaghetti alla Carbonara, an authentic Roman specialty.
  • Drink: An Aperol Spritz on the panoramic terrace for a quintessential Italian aperitivo.

Useful Links

Official Website

Palazzo Dama, Rome

Palazzo Dama, Rome

Palazzo Dama is a boutique hotel set in a grand aristocratic villa near the Tiber River. Known for its sleek interiors, private garden, and rare outdoor pool, it provides a serene respite in bustling Rome.

Location
Located just off Piazza del Popolo, a convenient base for exploring Rome’s historic center, shops, and museums.

Activities

  • City Highlights: Walk to the Spanish Steps, Villa Borghese, and the vibrant Trastevere district.
  • Poolside Relaxation: Cool off in the outdoor pool surrounded by lemon trees.
  • Gastronomy: Dine at the on-site restaurant, blending Roman traditions with contemporary flair.

Best Time to Travel

  • Spring and Fall for warm days and fewer crowds; summers can be hot and busy.

Recommended Dish & Drink

  • Dish: Saltimbocca alla Romana, veal cutlets with prosciutto and sage.
  • Drink: A Negroni Sbagliato, a sparkling twist on the classic Negroni, perfect as an aperitivo.

Useful Links

Official Website

3 days

Amalfi Coast – Positano

Depart the bustling city for the sun-drenched Amalfi Coast. Perched above Positano, Le Sirenuse offers dramatic sea views, fresh coastal cuisine, and close proximity to sparkling Mediterranean waters.

Schedule details

Day 11: Arrival in Positano

  • High-Speed Train & Private Transfer Travel from Rome to Naples, then continue by car along the scenic coast.
  • Check-In at Le Sirenuse Experience sea-view accommodations with terraces overlooking Positano’s colorful hills.
  • Afternoon Relax by the pool or head to the beach.
  • Evening Dinner on the terrace, highlighting local seafood.

Day 12: Coastal Exploration by Boat

  • Private Yacht Excursion Cruise along the coast, stopping at small coves and the towns of Amalfi or Ravello.
  • Lunch at Sea Enjoy fresh local dishes prepared on board.
  • Sunset Return Sip Prosecco as you sail back to Positano.
  • Evening Stroll the narrow streets or enjoy live music by the marina.

Day 13: Leisure & Culinary Discoveries

  • Morning at Leisure Optional guided hike along the Path of the Gods or spa time at the hotel.
  • Cooking Class Learn to prepare classic Mediterranean dishes with a local chef.
  • Afternoon Explore boutique shops or lounge at a beachfront café.
  • Farewell Dinner Celebrate your last evening with a chef-curated menu overlooking the Tyrrhenian Sea

Day 14: Farewell to Italy

  • Private Transfer Depart Positano for Naples International Airport or continue onward by private arrangements.
  • VIP Airport Services Fast-track check-in, lounge access, and final assistance with travel details.
  • Arrivederci Italia

Featured hotels

Le Sirenuse Positano

Le Sirenuse Positano

A quintessential Amalfi Coast hideaway, Le Sirenuse combines Mediterranean glamour with warm Italian hospitality. Its whitewashed architecture, bougainvillea-draped terraces, and sweeping sea views encapsulate the magic of Positano.

Location
Perched on the dramatic cliffs of Positano, the hotel is a short stroll from the beach and charming boutiques along the town’s winding, pastel-hued streets.

Activities

  • Boat Excursions: Cruise along the Amalfi Coast, visiting hidden coves and nearby Capri.
  • Gastronomy: Savor local seafood and homemade pasta at the hotel’s Michelin-starred restaurant, La Sponda.
  • Sun & Sea: Relax on the private seaside deck or explore the town’s pebble beach.

Best Time to Travel
Late spring (May–June) and early autumn (September) for mild weather and fewer crowds than high summer.

Recommended Dish & Drink

  • Dish: Spaghetti alle Vongole, a fresh, flavorful pasta dish featuring clams and olive oil.
  • Drink: Limoncello, a zesty lemon liqueur native to the Amalfi Coast.

Useful Links

Official Website

Belmond Hotel Caruso, Amalfi

Belmond Hotel Caruso, Amalfi

An 11th-century palace turned luxury hotel, Belmond Hotel Caruso perches on the cliffs of Ravello, offering infinity pool vistas and lush terraced gardens overlooking the Tyrrhenian Sea.

Location
Situated in Ravello, a serene town known for its romantic villas and breathtaking coastal views, a short drive from Amalfi and Positano.

Activities

  • Coastal Exploration: Take a boat tour along the Amalfi Coast or ferry to Capri.
  • Historical Sites: Visit Villa Rufolo and Villa Cimbrone for gardens and stunning panoramas.
  • Culinary Delights: Enjoy Mediterranean cuisine and fresh seafood at the hotel’s restaurant.

Best Time to Travel

  • May–October for the warm, sunny climate and vibrant coastal atmosphere.

Recommended Dish & Drink

  • Dish: Scialatielli ai Frutti di Mare, fresh pasta with local seafood.
  • Drink: Limoncello, crafted from Amalfi’s famous lemons.

Useful Links

Official Website

Il San Pietro di Positano

Il San Pietro di Positano

Carved into the cliffs of Positano, Il San Pietro is renowned for its panoramic terraces, private beach access by elevator, and signature blend of la dolce vita with refined hospitality.

Location
Perched above the Mediterranean Sea, minutes from Positano’s center, with sweeping views of the coastline and the Li Galli islands.

Activities

  • Beach & Sea: Relax on the secluded beach or explore hidden coves by kayak or boat.
  • Positano Strolls: Wander the town’s narrow lanes, boutique shops, and vibrant cafés.
  • Day Trips: Visit nearby Amalfi, Ravello, or Capri for more coastal charm.

Best Time to Travel

  • May–September for warm, sunny weather; June and September can be less crowded.

Recommended Dish & Drink

  • Dish: Delizia al Limone, a lemon-infused dessert highlighting the region’s citrus heritage.
  • Drink: A chilled glass of Falanghina, a crisp Campanian white wine.

Useful Links

Official Website

Locations

Price
From €15,000 per person
Dates
May - October

Seasonal Considerations

  • Peak Season: May–October (especially along the coast)
  • Shoulder Seasons: April and November for fewer crowds and mild weather
  • Winter: Venice, Florence, and Rome offer year-round cultural charms

Pricing

  • From €15,000 per person (double occupancy)
  • Single Supplement available
  • Group & Family Rates upon request
  • Fully Customizable to accommodate personal preferences

Reservation Process

  1. Initial Consultation
  2. Customization of Itinerary
  3. Deposit & Confirmation
  4. Pre-Journey Briefing
  5. Personal Concierge Contact

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