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Bespoke Luxury Travel Itineraries & Curated Journeys Tuscany: Art, Wine and Tradition
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Tuscany: Art, Wine and Tradition

from $8,600.00

Tuscany: Art, Wine and Tradition

Duration: 7 days
Destinations: Florence · Siena · Val d'Orcia
Style: Heritage · Gastronomy · Craftsmanship | Semi-Guided with OBM Curators

A Journey Through the Soul of Tuscany

In Tuscany, every view is a painting, every dish a story, every encounter a gesture of timeless hospitality. This seven-day journey is designed to uncover not just the beauty of the region, but the wisdom behind its flavors, architecture, and artisan culture.

OBM opens doors to private kitchens, centuries-old wineries, and studios where tradition is not preserved—it’s alive.

Day 1 — Arrival in Florence: The Renaissance City

OBM Description: Welcome to Florence, where every stone breathes art and history. After your private transfer and check-in, enjoy a slow stroll through the heart of the city with OBM's curated walking notes. Dine this evening with a view of the Arno, where the city lights shimmer like a Caravaggio canvas.

Included:

✓ Private transfer from Florence Airport or train station
✓ Check-in at boutique hotel in central Florence
✓ OBM self-guided walk: Duomo, Piazza della Signoria, Ponte Vecchio
✓ Welcome dinner with view, featuring Tuscan specialties and wine pairing

Not included:

✗ Lunch · Monument tickets (optional)

Day 2 — Florence: Hidden Artisans & Atelier Visits

OBM Description: Beyond the galleries, Florence thrives in the hands of artisans. You’ll meet a bookbinder, a goldsmith, and a leather craftsman—all preserving Florence’s soul through their work. In the afternoon, take time for a private viewing of the Uffizi or relax at a secret courtyard café.

Included:

✓ Morning guided visits to 2–3 artisan workshops
✓ Meet-the-maker experience with behind-the-scenes access
✓ Optional private viewing at the Uffizi Gallery (with OBM reservation support)
✓ Dinner reservation at modern trattoria tucked in the Oltrarno

Not included:

✗ Entrance fees (if selected) · Lunch

Day 3 — Chianti by E-Bike: Rolling Vineyards

OBM Description: Today you ride through postcard-perfect Chianti countryside on an e-bike. Hills become gentle slopes, and between villages and vineyards you’ll stop for tastings, a picnic, and endless views.

Included:

✓ E-bike rental with local guide (half-day)
✓ Visit to a winery with tasting of Chianti Classico
✓ Picnic lunch under the olive trees
✓ Return transfer to Florence

Not included:

✗ Dinner (OBM can reserve a wine bar with live music)

Day 4 — Cooking with Nonna in the Hills

OBM Description: In a stone villa outside Siena, you'll join a local “nonna” for a cooking class in her kitchen. With flour on your hands and laughter in the air, you’ll learn to prepare traditional Tuscan dishes passed down through generations.

Included:

✓ Transfer from Florence to villa
✓ Private cooking class and lunch with wine
✓ Afternoon free to relax in the countryside
✓ Check-in at rural luxury hotel in Val d'Orcia

Not included:

✗ Dinner (optional: chef's table at the hotel)

Day 5 — Montalcino: Brunello and Beyond

OBM Description: Brunello is not just wine—it’s time bottled. You’ll explore a family-run winery where grapes grow in harmony with nature. Walk the vineyards, taste aged vintages, and dine beside the barrels.

Included:

✓ Visit to Montalcino winery with owner-led tour
✓ Vertical tasting of Brunello vintages
✓ Light lunch at the estate with local ingredients
✓ Return to Val d’Orcia hotel

Not included:

✗ Dinner

Day 6 — Siena: Medieval Majesty

OBM Description: A private guide will bring Siena’s legends to life as you walk through its Gothic streets, the shell-shaped Piazza del Campo, and the stunning Duomo. Pause for coffee, pause for awe. End the day with aperitivo and views.

Included:

✓ Private transfer to Siena and back
✓ Guided walking tour with art historian
✓ Cathedral access (if open)
✓ Reservation for aperitivo on a rooftop bar

Not included:

✗ Meals

Day 7 — Farewell Tuscany

OBM Description: Wake slowly. Tuscany lingers—in your senses, in your journal, in your heart. Transfer back to Florence or onward to your next journey.

Included:

✓ Breakfast
✓ Private transfer to Florence or other destination

Not included:

✗ Additional meals

Accommodation Options:
Quantity:
Start Planing

Tuscany: Art, Wine and Tradition

Duration: 7 days
Destinations: Florence · Siena · Val d'Orcia
Style: Heritage · Gastronomy · Craftsmanship | Semi-Guided with OBM Curators

A Journey Through the Soul of Tuscany

In Tuscany, every view is a painting, every dish a story, every encounter a gesture of timeless hospitality. This seven-day journey is designed to uncover not just the beauty of the region, but the wisdom behind its flavors, architecture, and artisan culture.

OBM opens doors to private kitchens, centuries-old wineries, and studios where tradition is not preserved—it’s alive.

Day 1 — Arrival in Florence: The Renaissance City

OBM Description: Welcome to Florence, where every stone breathes art and history. After your private transfer and check-in, enjoy a slow stroll through the heart of the city with OBM's curated walking notes. Dine this evening with a view of the Arno, where the city lights shimmer like a Caravaggio canvas.

Included:

✓ Private transfer from Florence Airport or train station
✓ Check-in at boutique hotel in central Florence
✓ OBM self-guided walk: Duomo, Piazza della Signoria, Ponte Vecchio
✓ Welcome dinner with view, featuring Tuscan specialties and wine pairing

Not included:

✗ Lunch · Monument tickets (optional)

Day 2 — Florence: Hidden Artisans & Atelier Visits

OBM Description: Beyond the galleries, Florence thrives in the hands of artisans. You’ll meet a bookbinder, a goldsmith, and a leather craftsman—all preserving Florence’s soul through their work. In the afternoon, take time for a private viewing of the Uffizi or relax at a secret courtyard café.

Included:

✓ Morning guided visits to 2–3 artisan workshops
✓ Meet-the-maker experience with behind-the-scenes access
✓ Optional private viewing at the Uffizi Gallery (with OBM reservation support)
✓ Dinner reservation at modern trattoria tucked in the Oltrarno

Not included:

✗ Entrance fees (if selected) · Lunch

Day 3 — Chianti by E-Bike: Rolling Vineyards

OBM Description: Today you ride through postcard-perfect Chianti countryside on an e-bike. Hills become gentle slopes, and between villages and vineyards you’ll stop for tastings, a picnic, and endless views.

Included:

✓ E-bike rental with local guide (half-day)
✓ Visit to a winery with tasting of Chianti Classico
✓ Picnic lunch under the olive trees
✓ Return transfer to Florence

Not included:

✗ Dinner (OBM can reserve a wine bar with live music)

Day 4 — Cooking with Nonna in the Hills

OBM Description: In a stone villa outside Siena, you'll join a local “nonna” for a cooking class in her kitchen. With flour on your hands and laughter in the air, you’ll learn to prepare traditional Tuscan dishes passed down through generations.

Included:

✓ Transfer from Florence to villa
✓ Private cooking class and lunch with wine
✓ Afternoon free to relax in the countryside
✓ Check-in at rural luxury hotel in Val d'Orcia

Not included:

✗ Dinner (optional: chef's table at the hotel)

Day 5 — Montalcino: Brunello and Beyond

OBM Description: Brunello is not just wine—it’s time bottled. You’ll explore a family-run winery where grapes grow in harmony with nature. Walk the vineyards, taste aged vintages, and dine beside the barrels.

Included:

✓ Visit to Montalcino winery with owner-led tour
✓ Vertical tasting of Brunello vintages
✓ Light lunch at the estate with local ingredients
✓ Return to Val d’Orcia hotel

Not included:

✗ Dinner

Day 6 — Siena: Medieval Majesty

OBM Description: A private guide will bring Siena’s legends to life as you walk through its Gothic streets, the shell-shaped Piazza del Campo, and the stunning Duomo. Pause for coffee, pause for awe. End the day with aperitivo and views.

Included:

✓ Private transfer to Siena and back
✓ Guided walking tour with art historian
✓ Cathedral access (if open)
✓ Reservation for aperitivo on a rooftop bar

Not included:

✗ Meals

Day 7 — Farewell Tuscany

OBM Description: Wake slowly. Tuscany lingers—in your senses, in your journal, in your heart. Transfer back to Florence or onward to your next journey.

Included:

✓ Breakfast
✓ Private transfer to Florence or other destination

Not included:

✗ Additional meals

Tuscany: Art, Wine and Tradition

Duration: 7 days
Destinations: Florence · Siena · Val d'Orcia
Style: Heritage · Gastronomy · Craftsmanship | Semi-Guided with OBM Curators

A Journey Through the Soul of Tuscany

In Tuscany, every view is a painting, every dish a story, every encounter a gesture of timeless hospitality. This seven-day journey is designed to uncover not just the beauty of the region, but the wisdom behind its flavors, architecture, and artisan culture.

OBM opens doors to private kitchens, centuries-old wineries, and studios where tradition is not preserved—it’s alive.

Day 1 — Arrival in Florence: The Renaissance City

OBM Description: Welcome to Florence, where every stone breathes art and history. After your private transfer and check-in, enjoy a slow stroll through the heart of the city with OBM's curated walking notes. Dine this evening with a view of the Arno, where the city lights shimmer like a Caravaggio canvas.

Included:

✓ Private transfer from Florence Airport or train station
✓ Check-in at boutique hotel in central Florence
✓ OBM self-guided walk: Duomo, Piazza della Signoria, Ponte Vecchio
✓ Welcome dinner with view, featuring Tuscan specialties and wine pairing

Not included:

✗ Lunch · Monument tickets (optional)

Day 2 — Florence: Hidden Artisans & Atelier Visits

OBM Description: Beyond the galleries, Florence thrives in the hands of artisans. You’ll meet a bookbinder, a goldsmith, and a leather craftsman—all preserving Florence’s soul through their work. In the afternoon, take time for a private viewing of the Uffizi or relax at a secret courtyard café.

Included:

✓ Morning guided visits to 2–3 artisan workshops
✓ Meet-the-maker experience with behind-the-scenes access
✓ Optional private viewing at the Uffizi Gallery (with OBM reservation support)
✓ Dinner reservation at modern trattoria tucked in the Oltrarno

Not included:

✗ Entrance fees (if selected) · Lunch

Day 3 — Chianti by E-Bike: Rolling Vineyards

OBM Description: Today you ride through postcard-perfect Chianti countryside on an e-bike. Hills become gentle slopes, and between villages and vineyards you’ll stop for tastings, a picnic, and endless views.

Included:

✓ E-bike rental with local guide (half-day)
✓ Visit to a winery with tasting of Chianti Classico
✓ Picnic lunch under the olive trees
✓ Return transfer to Florence

Not included:

✗ Dinner (OBM can reserve a wine bar with live music)

Day 4 — Cooking with Nonna in the Hills

OBM Description: In a stone villa outside Siena, you'll join a local “nonna” for a cooking class in her kitchen. With flour on your hands and laughter in the air, you’ll learn to prepare traditional Tuscan dishes passed down through generations.

Included:

✓ Transfer from Florence to villa
✓ Private cooking class and lunch with wine
✓ Afternoon free to relax in the countryside
✓ Check-in at rural luxury hotel in Val d'Orcia

Not included:

✗ Dinner (optional: chef's table at the hotel)

Day 5 — Montalcino: Brunello and Beyond

OBM Description: Brunello is not just wine—it’s time bottled. You’ll explore a family-run winery where grapes grow in harmony with nature. Walk the vineyards, taste aged vintages, and dine beside the barrels.

Included:

✓ Visit to Montalcino winery with owner-led tour
✓ Vertical tasting of Brunello vintages
✓ Light lunch at the estate with local ingredients
✓ Return to Val d’Orcia hotel

Not included:

✗ Dinner

Day 6 — Siena: Medieval Majesty

OBM Description: A private guide will bring Siena’s legends to life as you walk through its Gothic streets, the shell-shaped Piazza del Campo, and the stunning Duomo. Pause for coffee, pause for awe. End the day with aperitivo and views.

Included:

✓ Private transfer to Siena and back
✓ Guided walking tour with art historian
✓ Cathedral access (if open)
✓ Reservation for aperitivo on a rooftop bar

Not included:

✗ Meals

Day 7 — Farewell Tuscany

OBM Description: Wake slowly. Tuscany lingers—in your senses, in your journal, in your heart. Transfer back to Florence or onward to your next journey.

Included:

✓ Breakfast
✓ Private transfer to Florence or other destination

Not included:

✗ Additional meals

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