Roam Travel Explore
  • Home
  • Tuscan Wanderer
  • Total Tuscany
  • Amalfi Coast
  • Blog
  • Book Your Excursions
  • Contact
  • More
    • Home
    • Tuscan Wanderer
    • Total Tuscany
    • Amalfi Coast
    • Blog
    • Book Your Excursions
    • Contact
Roam Travel Explore
  • Home
  • Tuscan Wanderer
  • Total Tuscany
  • Amalfi Coast
  • Blog
  • Book Your Excursions
  • Contact

Total Tuscany

Sunset over winding road lined with tall cypress trees in rolling countryside.

Day 1 — Benvenuti to Tuscany

Arrive in Montepulciano and settle into your private accommodations, surrounded by vineyards, olive groves, and the quiet rhythm of the countryside.


Take time to unwind after your journey — unpack, explore the property, or simply relax and take in the views.


In the early evening, begin your Tuscan experience with a classic aperitivo — a relaxed introduction to the flavors and lifestyle of the region.


Dinner is thoughtfully arranged, allowing you to enjoy a warm, welcoming first evening with local cuisine, regional wines, and the unmistakable atmosphere of Tuscany at sunset.

As the evening winds down, step outside under the stars — a quiet moment to settle in and savor the beginning of your time here.

Welcome to Tuscany.

Day 2 — Relax, Restore & Unwind Thermal Waters

Begin your day immersed in the healing waters of Tuscany’s ancient thermal baths, where natural mineral springs have soothed body and soul for centuries. Let the warmth slow everything down.


After your soak, enjoy a relazed spa lumch featuring fresh, local ingredients and regional wines. Optional treatments, including massages and facials are available for those who wish to indulge further.


In the afternoon, explore at your own pace. Wander a nearby village, storll quiet cobblestones streets, or simply return to the countryside and unwind.


As evening approaches, settle in for a beautifully prepared dinner featuring seasonal Tuscan flavors, thoughtfully paired with local wines. As day designed for complete relaxation, where time slows down and everything feels effortless.

Day 3 —Truffle Hunting, Cheese & Hilltop Beauty

A day dedicated to Tuscany’s rich food traditions and the people who keep them alive.

A day immersed in Tuscany’s most treasured flavors — guided by the land, the seasons, and the people who know them best. 


Begin the morning in the woods with a private truffle hunt alongside a local expert and trained dogs, uncovering one of Tuscany’s most prized delicacies. Learn how truffles are found, why they grow here, and what makes them so special — a true behind-the-scenes experience few travelers ever have.


Following the hunt, continue to a traditional organic cheese farm where the experience unfolds into a relaxed, truffle-inspired lunch. Enjoy handcrafted local cheeses, seasonal dishes, and fresh truffle prepared simply and beautifully — all paired with regional wines and set against sweeping countryside views. 


In the afternoon, continue to the Renaissance jewel of Pienza. Stroll charming streets lined with specialty food shops, artisan boutiques, and panoramic viewpoints overlooking the Val d’Orcia. A stop for gelato at a favorite local spot is, of course, part of the experience. 

Return to your accommodations later in the day for time to unwind — take a swim, enjoy the gardens, or relax with a glass of wine as the sun begins to set. 

Dinner is thoughtfully arranged, featuring seasonal Tuscan dishes paired with regional wines, followed by dessert. 


A day of flavors, beauty, and simple pleasures — exactly as Tuscany was meant to be experienced.

Day 4 —Brunello & the Heart of Val d’Orcia

Today takes you into the rolling hills of Montalcino, home to one of Italy’s most celebrated and sought-after wines — Brunello di Montalcino.


Begin with a private visit to a highly regarded, small-production estate, where a focus on organic and biodynamic practices reflects a deep respect for the land. Walk through the vineyards, step inside the cantina, and gain insight into what makes Brunello so distinctive — from soil to barrel to bottle.


Depending on the season, the experience may become even more immersive, with opportunities to witness or participate in moments of the harvest and winemaking process (season permitting).

The visit concludes with a beautifully prepared, wine-paired lunch, enjoyed overlooking the surrounding vineyards — a setting that captures the essence of Montalcino.


On the return journey, stop at several of the Val d’Orcia’s most iconic viewpoints, a UNESCO World Heritage landscape. Take in the famous cypress-lined roads near San Quirico, visit the chapel of Vitaleta, and pause to capture the timeless beauty of Tuscany’s most photographed scenery.


Return to your accommodations in the late afternoon with time to unwind — swim, stroll the grounds, or simply relax and take in the countryside.


Dinner is thoughtfully arranged, featuring seasonal Tuscan dishes paired with regional wines, followed by dessert.


A day of exceptional wine, extraordinary landscapes, and the true soul of Tuscany.

Day 5 — Secrets of Montepulciano

Begin the day in Montepulciano, a medieval hill town rich in history, character, and timeless beauty.


A private guided walk through the historic center, led by a trusted local friend, brings the town to life in a way few visitors experience. As you wander through Renaissance palazzi, hidden alleyways, and panoramic viewpoints, you’ll gain a deeper understanding of the region’s food, wine, and cultural traditions. Along the way, meet local artisans, hear stories of noble families, and discover corners of the town that remain quietly off the beaten path.


Continue beneath Piazza Grande into ancient Etruscan wine caves, carved deep into the rock below the city. Here, enjoy a tasting of Vino Nobile di Montepulciano, surrounded by centuries of history and aging barrels — an unforgettable setting to experience the true essence of this historic wine.


In the afternoon, head into the countryside for a visit to a traditional Tuscan farm. Meet local producers, enjoy regional wines and rustic specialties, and take in the peaceful beauty of the surrounding landscape.


Return to your accommodations with time to unwind before the evening.

Dinner is arranged as a wine-focused experience, featuring seasonal dishes paired with carefully selected local wines — a celebration of Montepulciano, its land, and its flavors.


A day that blends history, storytelling, wine, and authentic Tuscan life.

Day 6 — A Culinary Experience in Cortona

Begin the day with a hands-on culinary experience set in the countryside near Cortona, one of Tuscany’s most charming hilltop towns.


Step into a truly unique, old-world kitchen — a stone cantina with rustic walls, a working fireplace, and a traditional gas-fired stove that feels unchanged by time. In this warm and atmospheric setting, you’ll be guided through the preparation of classic Tuscan dishes using fresh, local ingredients.


Learn time-honored techniques, from handmade pasta to perfectly balanced sauces, while gaining a deeper understanding of the region’s culinary traditions. The experience is as much about storytelling and connection as it is about cooking.


The morning flows naturally into a relaxed, wine-paired lunch, where each course reflects the simplicity and richness of Tuscan cuisine — enjoyed around the table in an intimate, welcoming setting.


In the afternoon, take time to explore Cortona at your own pace. Wander its historic streets, browse artisan shops, and take in sweeping views of the surrounding valleys. The town’s timeless beauty and atmosphere make it a favorite for those seeking an authentic Tuscan experience.

Return to your accommodations later in the day with time to unwind.


In the evening, enjoy a relaxed pizza tasting experience featuring a variety of traditional and seasonal flavors, paired with local wines and followed by dessert.


A day centered around food, tradition, and the simple joy of gathering around the table.

Day 7 — A Final Taste of Tuscany

Begin your day with a visit to one of Montepulciano’s most renowned organic and biodynamic estates. Walk the vineyards, explore the historic cellars, and gain insight into the philosophy and craftsmanship behind these exceptional wines.


The experience includes a tasting of their wines, along with a light, beautifully prepared lunch set among the vineyards — a final moment to take in the landscape that defines this region.

In the afternoon, continue to a family-run frantoio, where olive oil has been produced for generations. Here, you’ll be welcomed into the working mill for a guided tasting and behind-the-scenes look at the production process, gaining a deeper understanding of one of Tuscany’s most essential traditions.


Taste freshly pressed extra virgin olive oil, learn how to recognize quality, and experience the remarkable difference of truly artisanal production — a simple yet profound expression of the land.


Return to your accommodations with time to relax and prepare for the evening.

Your final dinner is thoughtfully arranged — a warm and celebratory close to the week, featuring seasonal Tuscan dishes, regional wines, and the kind of atmosphere that reflects everything this journey has been about.


A beautiful ending to a week defined by connection, flavor, and unforgettable moments. an authentic Tuscan experience.


Return to your accommodations later in the day with time to unwind.


In the evening, enjoy a relaxed pizza tasting experience featuring a variety of traditional and seasonal flavors, paired with local wines and followed by dessert.


A day centered around food, tradition, and the simple joy of gathering around the table.

Total Tuscany

Total Tuscany: All Inclusive

This all-inclusive experience includes:

• 7 nights in a luxury suite

• All breakfasts, lunches, and dinners

• Carefully curated food & wine experiences

• Daily guided excursions and cultural experiences

• Private transportation throughout the week

• Wine with lunch and dinner

• Hosting, planning, and on-the-ground support from arrival to departure


Inquire for Pricing:


All-inclusive, double occupancy

or

Single occupancy (private suite)

Total Tuscany Dates

2026


September 2 – September 9, 2026


September 16 – September 23, 2026


October 7 – October 14, 2026


November 4 – November 11, 2026



2027

May 12 – May 19, 2027 


May 26 – June 2, 2027


June 9 – June 16, 2027


June 23 – June 30, 2027


July 14 – July 21, 2027


July 28 – August 4, 2027


September 1 – September 8, 2027


September 22 – September 29, 2027


October 6 – October 13, 2027


October 20 – October 27, 2027


November 3 – November 10, 2027

Total Tuscany

Show More

Copyright © 2026 Roam Travel Explore - All Rights Reserved.

Powered by

  • Blank

All Inclusive Italy

Learn More about our Services

click here

This website uses cookies.

We use cookies to analyze website traffic and optimize your website experience. By accepting our use of cookies, your data will be aggregated with all other user data.

Accept