Country Roads of

Umbria & Tuscany

Presented by K&S Escapes – Your Premier Partner for Luxury Italy Tours

Embark on a 9-day small-group luxury journey through the heart of Italy, exploring the medieval charm of Umbria and Tuscany. From the cobblestone streets of Siena to the Renaissance splendor of Florence, immerse yourself in Italy’s rich culture, cuisine, and history with exclusive experiences like VIP Vatican access, truffle hunting, and world-famous gelato tasting.

Live 'la dolce vita' during this 9-day guided tour of Italy, exploring the medieval hill towns and evocative landscapes of Umbria and Tuscany. Visit Rome, Siena, and Florence, with unique experiences like truffle hunting, pasta-making with a professional, and tasting the world’s best gelato in San Gimignano. Sustainability is core to Insight Vacations’ mission, ensuring authentic and responsible travel.

Why book with K&S Escapes? We offer personalized itineraries, competitive pricing, and dedicated support to make your dream Italian holiday a reality.

Key Highlights

  • Enjoy VIP fast-tracked access to the Vatican Museums and Sistine Chapel.

  • Explore Siena’s Piazza del Campo and see the Torre del Mangia.

  • Learn the art of truffle hunting and enjoy a local lunch.

  • Taste the world’s best gelato in San Gimignano.

  • Marvel at Florence’s Basilica di Santa Maria del Fiore with a Local Expert.

  • Participate in a pasta-making class with a professional chef.

Detailed Itinerary

  • Day 1: Arrive Rome, Italy | Arrive in Rome and transfer to your hotel. Relax and join your Travel Director for a Welcome Dinner at a local restaurant.

  • Day 2: Rome | Vatican & Sistine ChapelEnjoy VIP fast-tracked entry to the Vatican Museums and Sistine Chapel, followed by time to explore Rome’s iconic sites.

  • Day 3: Orvieto & Perugia | Visit Orvieto for a handmade pasta dinner at La Buca di Baco di Ely, then continue to Perugia for its Etruscan heritage.

  • Day 4: Perugia | Artisan Traditions - Explore Perugia’s medieval streets and visit a hand-weaving workshop to see traditional looms in action.

  • Day 5: Assisi & Spello | Visit the Basilica of St. Francis in Assisi and the charming hilltop town of Spello, followed by a truffle-hunting experience.

  • Day 6: Siena | Medieval CharmExplore Siena’s Piazza del Campo and Torre del Mangia, with an optional visit to the medieval cathedral or a panforte tasting.

  • Day 7: San Gimignano & Florence | Taste world-famous gelato in San Gimignano, then travel to Florence to see the Duomo and Piazza della Signoria.

  • Day 8: Florence | Renaissance SplendorEnjoy a full day in Florence with a Local Expert, visiting the Uffizi Gallery and enjoying a farewell dinner.

  • Day 9: Depart Rome | Transfer to Rome’s airport for departure.

What's Included

  • English-Speaking Travel Director and Local Experts

  • Private transfers to and from airports

  • Luxury accommodations

  • Selected meals, including Welcome and Farewell Dinners

  • Entrance fees and gratuities (except Travel Director)

Pricing and Dates

Starting from $3,750 per person (double occupancy). Single supplement available.

2026 Departure Dates: March 29, April 26, May 24, June 21, July 5, August 2, August 30, September 13, September 27

Contact K&S Escapes for exact pricing, availability, and personalized quotes.

Experience the Italian Country Roads

Why K&S Escapes?

  • ✺

    Tailored Just for Two – Every itinerary is designed around your love story—whether it's a honeymoon, anniversary, or just because—crafted to reflect your unique style, pace, and dreams.

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    Exclusive Access & VIP Perks – From candlelit tables at Michelin-starred restaurants to private yacht charters and secluded spa rituals, we secure coveted experiences you won’t find online.

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    Effortless, Seamless Planning – We handle every detail—luxury accommodations, curated dining, private transfers, and hidden gems—so you can focus entirely on each other.

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    Curated Romance in Every Destination – Whether you’re sipping wine in a lemon grove or watching the sun set from your private terrace, every moment is built to inspire connection.

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    Trusted Partnerships with the World’s Best – We collaborate with handpicked hotels, chefs, guides, and local artisans to deliver elevated, heartfelt experiences in every destination.

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    Ongoing Support & Personalized Service – From your first consultation to the final farewell, our team is on hand to ensure your trip is stress-free, magical, and full of unforgettable moments.

Our Signature Travel Design Process

Embark on a bespoke travel journey where every detail is meticulously crafted to your discerning tastes. Schedule a personalized consultation with our expert travel designers and unlock an unrivaled world of luxury exploration. At K&S Escapes, we craft every journey with care, creativity, and a deep understanding of your travel style. Whether you’re dreaming of a romantic escape, a multi-generational adventure, or a food and wine immersion, our process ensures no detail is overlooked.

Book a Consultation

Start by scheduling a one-on-one consultation.

Speak With a Founder

You’ll speak directly with one of our founders who will guide you through inspiration, options, and the vision for your ideal escape.

Receive a Custom Proposal

We’ll craft a beautifully curated proposal. Every element is hand-selected to align with your interests, timeline, and budget.

Refine & Approve

We’ll work together to perfect the details until it feels just right.

Confirm & Book

Once your trip is approved, we handle all the bookings.

Enjoy White-Glove Support

Before, during, and after your travels, we’re here for anything you need—adjustments, recommendations, or just peace of mind. You’ll receive a digital itinerary and access to our destination guides, curated packing lists, and personalized tips.

Submit Your Inquiry for Country Roads of Umbria & Tuscany

Fill out the form below to get started on booking your Italian adventure. Our team will respond promptly with details and options.

Meet Your Designer: Katie

Katie, your expert travel designer, brings her passion for luxury travel and Italian culture to the Country Roads of Umbria & Tuscany tour. With deep knowledge of Italy’s historic landscapes and culinary traditions, she curates unforgettable group experiences tailored for culture enthusiasts, foodies, and discerning travelers.

Extend Your Journey with K&S Escapes

Maximize your AmaWaterways cruise with a seamless extension planned by K&S Escapes. Explore Paris for art and cuisine, or visit Châteauneuf-du-Pape for exclusive wine tastings. Katie will customize your pre/post-cruise itinerary—hotels, transfers, and private tours included. Contact us now to extend your 2026 adventure!

Start Your Wine Journey With Us

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What This Includes:

  • A one-on-one consultation with one of our founders

  • A full discovery of your travel preferences, goals, and priorities

  • Preliminary destination research and inspiration

  • A curated proposal that reflects your unique vision

  • Expert insights on timing, logistics, and luxury touches

This consultation fee secures your spot on our calendar and allows us to devote time, attention, and expertise to the initial design phase of your trip. Should you choose to book your journey with us, this fee is applied toward your total planning package.

Because luxury starts with intention.
Let’s create something unforgettable—just for you.