DATES: September 7-15, 2026

TRIP LENGTH: 9 days / 8 nights

GROUP SIZE: up to 12 people

Spend nine unforgettable days exploring Italy with a small group of travelers. This Tuscan escape blends the energy of Florence with the rolling vineyards, hilltop towns, and peaceful countryside of Tuscany.

We will spend all 7 nights in the stunning Renaissance city of Florence, known for its art, architecture, and history, where every street feels like an open-air museum.

You will visit its most iconic attractions, including the breathtaking Duomo, the world-famous Uffizi Gallery filled with Renaissance masterpieces, the historic Ponte Vecchio bridge, and Michelangelo’s David, one of the most celebrated sculptures in the world.

We’ll also experience the city through its incredible cuisine with a hands-on pasta-making class and a guided food tour through local markets and eateries.

From Florence, we’ll venture into the Tuscan countryside, visiting the medieval towns of Siena and San Gimignano, known for their charm, history, and stunning views. And we’ll visit two beautiful wineries, enjoying tastings, vineyard scenery, and the relaxed pace of the Italian countryside.

*Activities, accommodations, and itinerary subject to change with similar substitutions if necessary

This trip is perfect for couples, solo travelers, and small groups who want to experience some of Italy’s most iconic places and breathtaking views at a relaxed, enjoyable pace. With no hotel changes or rushed early mornings, and plenty of time to soak in the culture, food, and scenery, this journey is designed for those who want an unforgettable trip without feeling constantly on the go.

• 4-star hotel in an elegantly restored 19th-century building in the center of Florence

• Iconic landmarks highlighting art, history, and Renaissance architecture

• Street food tour through the historic Florence city center

• Hands-on pasta-making class in a cooking school in a medieval tower

• Chianti wine tasting experience at two wineries

• Day trip into the countryside with visits to Siena and San Gimignano

• Daily activities with scheduled free time to relax, stroll, or shop

• Optional additional day trips if you choose

A five-minute walk from Santa Maria Novella train station, Hotel Embassy is housed in a beautifully restored 19th-century building that combines the charm of historic architecture with modern comforts. The central location makes it possible to walk to the city's attractions.

There will be up to 12 people in the group. Expect easy-paced days with about 8,000–10,000 steps per day, balanced with free time each afternoon.

• Slow, immersive travel in one of the world’s most picturesque destinations

• A perfect mix of European city charm and the peaceful Tuscan countryside

• A beautiful hotel stay in the heart of one of the world’s greatest cities

• Incredible food, wine, and local experiences

• Thoughtfully planned days with flexibility built in

• Hosted by an experienced couple who visit this region often

• Cost per person:  $3399 (based on double occupancy)

• A $500 non-refundable deposit secures your spot.

• See payment options below.

We require you to have travel insurance that covers:

• Emergency medical treatment

• Evacuation and repatriation

• Personal injury

We also highly recommend coverage for trip cancellation, delays, and lost or stolen belongings.

Note - You will see an option to add travel insurance at checkout with a company I have no affiliation or experience with. I recommend insurance with Faye or SafetyWing, but you are welcome to purchase anywhere you prefer.

Your Tuscan adventure begins! Today is all about making your way to Florence. Get excited, and start dreaming about the incredible experiences ahead.

One more day before you step into the wonder of Tuscany, where cobblestone streets, world-class art, and unforgettable food await. 🤩

Welcome to Tuscany! Today is all about settling in and soaking up your first taste of Florence at your own pace. Arrive throughout the day and take some time to wander - strolling past Renaissance architecture, popping into a café for your first cappuccino, or simply unwinding after your journey.

If you arrive early, I’ll have plenty of suggestions to help you make the most of your time - think hidden gems, scenic viewpoints, and can’t-miss bites.

In the evening, we’ll come together for our first group dinner at a traditional Italian trattoria (one of our personal favorites!). Expect incredible local flavors, a warm atmosphere, and the perfect setting to toast to the unforgettable days ahead. 🍷

Today, we dive into the heart of Florence, where art, history, and everyday beauty collide in the most unforgettable way. We’ll start the morning with a visit to the Accademia Gallery, home to Michelangelo’s iconic David. Seeing it in person is one of those moments that truly stops you in your tracks.

Afterward, the afternoon is yours to explore Florence at your own pace. You might climb to the top of the Florence Cathedral (the Duomo) for sweeping city views, wander through the historic Piazza della Signoria, step inside the impressive Palazzo Vecchio, or track down one of Florence’s charming wine windows for a fun (and very local) experience.

In the evening, we’ll gather for dinner at a hand-selected restaurant (with an unbelievable view!) — another chance to indulge in Tuscan flavors, share stories from the day, and soak in the magic of Florence after dark. 🍝

We’ll start the day immersed in world-class art at the Uffizi Gallery, home to masterpieces by Botticelli, Leonardo da Vinci, and more. It’s the perfect way to experience the brilliance of the Renaissance right where it all began.

In the afternoon, enjoy free time to explore more of Florence’s charm. Stroll across the iconic Ponte Vecchio, wander into the artisan-filled streets of the Oltrarno, relax in the laid-back vibe of Piazza Santo Spirito, or take your time shopping and café-hopping through the city.

Tonight is all about getting hands-on with Italian culture. We’ll come together for a pasta-making class where you’ll learn to craft authentic Tuscan dishes from scratch, then sit down to enjoy the delicious meal you’ve created. A truly memorable (and tasty) evening in Florence! ✨

Today, we escape the city and head into the rolling hills of Tuscany for a dreamy day in the Chianti wine region. Think vineyard-covered landscapes, winding country roads, and postcard-worthy views at every turn.

We’ll enjoy a guided experience visiting two local wineries, where you’ll learn about traditional winemaking and, of course, sample some of the region’s most celebrated wines. It’s the perfect blend of education, indulgence, and unforgettable scenery.

After a relaxing day in the countryside, we’ll return to Florence for dinner — an evening to unwind, reflect on the day, and savor even more incredible Tuscan flavors together. 🍷

This morning, we’ll step into the grandeur of Florence with a visit to the Pitti Palace, once home to powerful Italian families and filled with stunning art and architecture. From there, we’ll wander through the beautifully landscaped Boboli Gardens, a peaceful escape with fountains, sculptures, and sweeping views over the city.

In the afternoon, enjoy more time to explore at your own pace. You might visit the historic Basilica of Santa Croce, or head up to Piazzale Michelangelo for one of the most breathtaking panoramic views of Florence, especially beautiful in the late-afternoon light.

Tonight, we’ll experience Florence through its flavors on a guided food tour. You’ll taste your way through local specialties, discover hidden gems, and enjoy a progressive-style dinner that brings the city’s culinary scene to life. Come hungry — this is always a group favorite!

Today, we journey deeper into Tuscany to explore two of its most enchanting hill towns - Siena and San Gimignano. With their medieval charm, winding streets, and timeless beauty, this day feels like stepping straight into a storybook.

On our guided tour, we’ll wander through Siena’s historic center, including its famous piazza and stunning cathedral, before continuing to San Gimignano, known for its iconic towers and breathtaking countryside views. Along the way, you’ll soak in the rich history, architecture, and slower pace of life that make this region so special.

After a full day of exploring, we’ll return to Florence for dinner - another chance to relax, connect, and enjoy one more beautiful Tuscan evening together.

Today you choose your own adventure, whether that means soaking up more of Florence’s beauty or venturing out for one last Tuscan escape.

If you stay in Florence, there’s still so much to explore. You might visit the stunning Santa Maria Novella Basilica, step inside the impressive Medici Chapel, or wander through Mercato Centrale for a lively mix of local food and culture. Or simply spend your time strolling, shopping, and revisiting your favorite spots around the city.

Prefer one more Tuscan adventure? You’re welcome to take an optional day trip on your own to nearby towns or countryside gems, perfect for those wanting to explore even more of this incredible region at their own pace.

In the evening, we’ll gather for dinner at a hand-selected restaurant, one last chance to savor Tuscany, reflect on the memories made, and celebrate an unforgettable week together.

All good things must come to an end, but not without a heart (and camera roll) full of unforgettable memories. Enjoy a relaxed morning in Florence before heading to the airport or train station for your journey home.

Whether it’s one last cappuccino at your favorite café, a final stroll through the charming streets, or simply soaking in the beauty of Tuscany one more time, this is your moment to savor it all.

Until next time - arrivederci! 🇮🇹