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Experience the magic of Tuscany, Italy's most iconic region.

Florence & the Tuscan Countryside 2025

June 1 – 6, 2025.

Florence & Montepulciano.

All adults welcome; solo travelers, friends, family or couples.

Up to 15 guests.

Artistry, traditions, excellence, Tuscan food & wine.

This 5-night journey is a dreamy Italian vacation in Tuscany.

Discover Florence with a local insider who was born there, then venture into the heart of the Tuscan countryside.

We handle all the details, providing you with the luxury of a bilingual guide and driver.

You have connections the minute you step off the plane.

For people who want fun, easy, insider travel — elevated.

Tuscany with Insider Access Makes Travel More Fun

Travel on a unique itinerary, in a small group with a leader who was born in Florence, knows the culture and language and handles all the details.

We begin our adventure in Florence. Stay in a 16th century palace, in the best area of the city for people in the know. Florence is home for 3 nights and you’ll love how easily walkable everything is — especially when your private guide shows you the ropes.

We depart Florence via private driver to the Tuscan countryside, where we stop for a curated highlights tour of Siena, before continuing on to Montepulciano, where we will stay for 2 nights at our countryside hotel.

Why This Trip is Perfect For You

With Florence’s airport and excellent train connections, this is a conveniently accessible part of Italy, perfect for both arrival and extending your stay. This experience is a “best of” the area in 5 nights, making it the ideal solution for people with limited time, or people new to Italian travel.

Within a couple hours of arriving in Florence you will be unpacked at your hotel, happily strolling through the stunning cityscape.

The rest of your vacation will roll out with expert coordination of activities, plus the uptime and downtime that Italian Fix is known for. This is hassle-free, insider and relaxed-pace travel come together seamlessly for a gorgeous Italian holiday.

WHAT GUESTS SAY

What You’ll Experience Over 6 Beautiful Days of Carefree Living

Travel Florence, Siena & Montepulciano.

The High Notes of Your Brilliant Tuscan Vacation.

Insiders Florence, With Artisan Studios & Excellent Reservations

Oh, what you’ll see in 3 days! Visit our favorite sites and notable monuments, explore Florentine artisan studios, and dine at a selection of the best tables in Florence—from fine dining and hidden gems to rooftop terraces and landmark bars. We provide you with the very best sampling of the city’s highlights, drawing on decades of expertise for you to experience in just a few days.

Tour of the Uffizi, But Different

We skip the line at the Uffizi galleries and we also speed date the paintings and highlights, because dragging-on-for-hours museum tours is not our thing. The Uffizi is one of Italy’s most important museums, housing a priceless collection, especially from the Renaissance. Our private guide has deep subject matter expertise, but we keep the visit fresh, ending the visit with sustenance at a local trattoria.

Private Tour of the Walled City of Siena

Road trip! Enjoy your drive through the lush hills of Tuscany. We have a private tour of Siena, a Unesco World Heritage site, with a local insider who shares the city in the fun and upbeat style Italian Fix is known for. You have free time to shop, wander, or dine in one of Italy’s most famous piazzas, where the Palio di Siena (annual horse race) takes place.

Winery Visit, Tasting & Countryside Lunch

There’s something magical about Montepulciano. Imagine a sun-drenched landscape with medieval roots, historic palaces, incredible panoramic views, and pretty village scenes. Today, we immerse ourselves in the peaceful energy of the Tuscan countryside and enjoy a winery tour. We sample famous wines and savor Tuscan cuisine with a relaxed lunch.

Travel in Comfy Passenger Vans

Our small passenger vans can travel where big buses cannot. We have our own drivers, guides and unique routes to maximize the area without wasting time. Kick back and watch the Tuscan hills roll by.

We’re Different. We’re Not Like The Other Companies Who Have Thousands Of Guests A Season. We Serve Under 150 Guests Per Year.

Florence & the Tuscan Countryside - Daily Itinerary

Arrival Day

Fly into Florence Airport today, and our driver will collect you for your hotel transfer. If you're coming from elsewhere in Italy, we'll assist with logistics and provide a driver upon request. That evening, we meet the group on the hotel’s stunning terrace and head out for our first night in Florence, featuring an iconic view. Images of the hotels are here.

Day 2

A walking tour of Florence gives you the lay of the land. We’ve selected the most notable monuments, as well as some lesser-known “must-sees” that you can't miss, including our favorite artisan studios to which we have exclusive access. It’s so much better to be in Italy with a guide who speaks the language and shows you all the hiddens spots. We’ll spend an evening together at a local favorite spot.

Day 3

We have skip-the-line tickets to the Uffizi (the most famous museum in Florence) with an expert who gives us the “greatest hits” tour so we’re not there all day battling the crowds. Then, it’s time for some drinks and carbs! In the afternoon, you have time to explore (go see David, relax with some retail therapy, or hit our favorite spa in a palace). You’ll have a free night in the city to get your groove on, and we’ll have a long list of hot spots you can spoil yourself at.

Day 4

Road trip! Today we journey from Florence to the Tuscan countryside with our private driver. What’s wonderful about Florence is that within a 10 minutes drive we’re already rolling through the scenic Tuscan countryside. Enjoy a walking tour in the incredible city of Siena with our local expert guide. We’ll complete the short trip to Montepluciano to our noble palace hotel and you can relax by the pool before dinner, which is booked at our favorite spot.

Day 5

The landscape around Montepulciano is so special, it’s protected by Unesco. Today we’ll treat you to the ultimate countryside experience — wine tasting with local producers and meals al fresco. Our final night dinner is a chef's meal at the villa just for us — unwind and soak in your final night in relaxed luxury.

Day 6

Check-out and departure day with transfer back to Florence. You might even be heading to another Italian Fix trip after this. View our calendar to see all of your options. Whatever you need, we’ll help. Buon viaggio!

Arrival/Departure Details

Arrival Details:
Arrival Airport: Florence
First-Day Activity: Drinks at the hotel rooftop at 6pm, followed by dinner.

Departure Details:
Departure Airport: Florence
Last-Day Activity: Breakfast; transfer to Florence airport (or hotel if you’re extending your stay).

Our Incredible Licensed Guides Live in Europe. Unsurpassed Kindness, Expertise & Fun!

Expect Italian Fix signature bilingual guides to provide an authentic European cultural experience and handle all your pre- and post-trip planning expertly.

Tommaso

Karin

Cristina

Book with Confidence

  • 14-day Refund
  • Satisfaction Guarantee
  • 14 Years of Excellence
  • Repeat Guests Every Year

Florence & the Tuscan Countryside

Sunday,
June 1 - 6, 2025

6 Days,
5 Nights

Included

ACCOMMODATION

5 nights in boutique hotels; 3 nights in Florence and 2 nights in Montepulciano.

Our selected properties are former noble palaces. In Florence, stay in our favorite central neighborhood, inside a famous piazza. The noble palace built in 1505 is still owned by the same family.

In Montepulciano, stay in an 18th century country estate, a noble summer residence. The gardens, pool and grounds have lots of space to enjoy the magnificent Tuscan views.

These historical residences-come-hotels embrace the spirit of Tuscany and were carefully selected from hundreds of properties.

Rates are per person (double occupancy).

Traveling solo & prefer your own room? Add $1,100

SEAMLESS PICKUP & DROP OFF

Private transfer from Florence airport on arrival day. Hotel to airport (or hotel or train station) transfer on departure day.

Florence has an international airport. It’s just 90 minutes from Rome via high speed train.

GROUND TRANSPORTATION

All ground transportation, which includes private transfers and taxis.

MEALS & WINE

All breakfasts as well as 3 lunches and 4 dinners, including local wine and alternatives.

Your guide will help you to discover the best of Tuscan flavors with recommendations. Our dining experiences are varied, from plated fine-dining to casual aperitivo in the piazza, just like how an Italian would dine. Dining is at local favorites and places that most travelers wouldn’t find on their own.

ACTIVITIES

6 days traveling with a bilingual guide.

A unique itinerary which brings you from the beauty of Florence, to the walled Unesco world heritage listed center of Siena, to the Tuscan countryside.

Skip-the-line tickets to the Uffizi Gallery and a private guided tour with a resident expert.

Curated walking tour of Florence, with artisan studio visit.

Private tour of Siena with resident expert guide.

Tuscan winery visit with tasting.

Tuscan countryside lunch al fresco.

Taxes and all tips for drivers, included meals and guides.

Not Included

FLIGHTS

Fly into Florence, an international airport.

EXTRA MEALS

When you’re not eating with the group on included meals.

$6,395 USD

Rates are per person (double occupancy)

Interest-Free Payment Plan

Want to defer payments until 2025?
Starting in January, make 4-monthly payments of $1,400 USD.

14 days to refund if you change your mind.

What Guests Say About Italian Fix

HOW IT WORKS

Book This 2025 Trip, Limited to 15 Guests.

A Note From Our Founder, Bianca

One summer, my husband and I spent a week roaming the countryside around Montepulciano on his motorbike. With our daughter at camp in Tuscany (where adults weren’t allowed to hang around), we decided to get lost—literally. And lost we got… in plates of pasta, rolling hills, and winding roads past stunning estates, charming towns, and picturesque wineries.

I have vivid memories of eating these amazing, never-ending meals and sipping on rich reds. The standards are incredibly high in Tuscany, for everything—great hotels, great culture, great service, and, of course, outstanding food. It truly checks all the boxes.

Florence is my favorite city on the planet. In fact, it was a college summer program in Florence that brought me to Italy and that led me to start this company. This experience is perfect for those looking for a short, sweet trip—ideal for a week’s holiday or as a convenient starting point for extending your stay. Tuscany’s “user-friendly” nature also makes it a fantastic choice for those new to Italian travel.

Tuscany remains a timeless favorite for countless reasons—a destination with endless beauty that hooks me every time, no matter how many times I return.

With love + vino rosso,

Bianca

2011

Italian Fix was Founded

150

Maximum Guests We Accept Per Year

96%

Of guests have left us a 10/10 review post-trip (2023)

100% 

Of guests love our customer service

Our guests let their hair down.

“I’m a very organized person, it says a lot when I tell you I had to worry about absolutely nothing for 8 days.”

Our guests come back.

“This was my first Italian Fix tour, and it won’t be my last.”

Our guests love the food.

“The Italian food and wine choices were excellent. I didn’t want to figure this out on my own.”

Our guests appreciate the unique itineraries.

“I wanted a more quaint and local experience and that’s exactly what I got.”

Our guests are there for the friendships and fun.

“What an incredible experience and the group was awesome. I have never laughed so hard in my life.”

Our guests enjoy the flexibility.

“I know what to expect, and if I wanted to opt-out of something it was no big deal.”

Our guests love the variety.

“I loved the flexibility of schedule and the variety of activities planned.”

Our guests rave about the tour leaders.

“The guides are respectful, kind and informative, plus they are a ton of fun.”

Are You a New Guest? Learn From Our Returning Guests ...

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We have so many returning guests because they know they can trust us.

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Return guests sometimes book the exact same trip to repeat the magic.

Our guests protect their investment by purchasing insurance.

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Some of our guests are going through big life transitions; others are celebrating milestones.

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Many guests meet lifelong friends on the trip and they return on future trips, together.

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Make New Friends & Real Connections

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No Expertise of Europe Required

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Research is Done-For-You

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Transparent Trip Costs Upfront

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Unlimited Expert Advice

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Signature Itineraries & Guides

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Frequently Asked Questions

You can buy insurance, or use the insurance they already own (through work coverage etc.) Insurance protects you should you fall ill before you travel, or an immediate family member does and you do not want to leave the country. Policies vary and you can shop around.

Our travelers make connections that are deep and real between each other. With social disconnection on the rise more than ever, infusing your life with good people is a sacred act. (We have a knack for attracting interesting and great people!)

One of the most beautiful things about our trips is that they attract a lot of different kinds of people — and we’re proud of that. Our fun, safe, and let-your-hair-down energy draws the right guests from around the world with different backgrounds — because wanting to live your dolce vita transcends any location or age range.

We have guests who return to Italian Fix year after year. From the person who enjoys traveling solo to the besties who want to take a trip of a lifetime, they all want to have a carefree, fun-filled, and relaxing week. They trust Italian Fix to handle all the details

We’re a boutique travel company focused on unique itineraries that focus on the lifestyle of the areas we visit. We’re intentional about sustainable travel experiences that support local economies. Although we love the finer things in life (we even train our hosts with some of the same service tenets as the Ritz Carlton), we want to do things differently.

We want our trips to be more open to a diverse set of travelers than a typical tour operator that only serves the 1%. We like to think of our experiences as a beautiful balance of activities and cadence that lets you savor your vacation — we do mix things up but we do not run you off your feet.

We might offer a stunning multi-course meal with wine pairings at an award-winning restaurant one evening, and the next day, we’ll eat a panino at the market. Because we know you’re not traveling to Europe for a Disneyland-esque experience. You’re here to experience the lifestyle, which has nothing to do with thread count (although we do love that crisply ironed European bedding).

We offer our guests a beautifully layered and nuanced experience that uplifts and gets you into the heart of the places you’re traveling.

Transformative experiences, connections, belonging, and belly laughter are the ultimate luxuries.

We have a combination of solo travelers, people traveling with friends, and people traveling with partners/spouses on our tours. Choose a “women’s only” or “all adults welcome” experience.

First off, we speak Italian! We also understand the context, the customs, and the community of every location we visit. In Europe, it’s not what you know — it’s who you know. And we know people.

We’re a small company that serves under 150 people per year. You can read more about us here. By comparison, most tour operators are massive — some serve about 30,000 people a year! That’s not who we are — we’re female-owned and getting to know each of our travelers by name is super important! We truly want to get to know you.

Coming with us is like having a backstage pass. If you travel without us, you’re just one in a million foreigners waiting in lines and trying to get service. No connections or language fluency makes you the odd one out.

Our travel style allows you to be among friends and have access to things you couldn’t find on your own. No big-box concept of tourism around here. At Italian Fix, we’re mindful about keeping traditions alive and supporting local economies.

Our carefully crafted itineraries have been perfected over years of hosting successful trips, so they play out like a symphony — with cadence, timing and rhythm. All of our trips have up-time and down-time. The introverts who need quiet to recharge can get it, and the extroverts who derive energy from new connections can thrive too. One of our mottos is “Hey, it’s your holiday — opt out of any days you like.” We have lots to see, eat, do and explore whenever you wish to join in. Just put on your comfy shoes and andiamo!

Many of our guests are in the same boat. We have people who are going through life changes and more traveling is calling them. You’ll fit right in (and life is better with people who get you and you could potentially travel with in the future!).

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Italian Fix Offers 6 Routes in 2025.

Our Community

Our Guests Took These Photos

Our Community

Our Guests Took These Photos

Florence & the Tuscan Countryside

Sunday,
June 1 - 6, 2025

6 Days,
5 Nights

Included

ACCOMMODATION

5 nights in boutique hotels; 3 nights in Florence and 2 nights in Montepulciano.

Our selected properties are former noble palaces. In Florence, stay in our favorite central neighborhood, inside a famous piazza. The noble palace built in 1505 is still owned by the same family.

In Montepulciano, stay in an 18th century country estate, a noble summer residence. The gardens, pool and grounds have lots of space to enjoy the magnificent Tuscan views.

These historical residences-come-hotels embrace the spirit of Tuscany and were carefully selected from hundreds of properties.

Rates are per person (double occupancy).

Traveling solo & prefer your own room? Add $1,100 USD.

SEAMLESS PICKUP & DROP OFF

Private transfer from Florence airport on arrival day. Hotel to airport (or hotel or train station) transfer on departure day.

Florence has an international airport. It’s just 90 minutes from Rome via high speed train.

GROUND TRANSPORTATION

All ground transportation, which includes private transfers and taxis.

MEALS & WINE

All breakfasts as well as 3 lunches and 4 dinners, including local wine and alternatives.

Your guide will help you to discover the best of Tuscan flavors with recommendations. Our dining experiences are varied, from plated fine-dining to casual aperitivo in the piazza, just like how an Italian would dine. Dining is at local favorites and places that most travelers wouldn’t find on their own.

ACTIVITIES

6 days traveling with a bilingual guide.

A unique itinerary which brings you from the beauty of Florence, to the walled Unesco world heritage listed center of Siena, to the Tuscan countryside.

Skip-the-line tickets to the Uffizi Gallery and a private guided tour with a resident expert.

Curated walking tour of Florence, with artisan studio visit.

Private tour of Siena with resident expert guide.

Tuscan winery visit with tasting.

Tuscan countryside lunch al fresco.

Taxes and all tips for drivers, included meals and guides.

Not Included

FLIGHTS

Fly into Florence, an international airport.

EXTRA MEALS

When you’re not eating with the group on included meals.

$6,395 USD

Rates are per person (double occupancy)

Interest-Free Payment Plan

Want to defer payments until 2025?
Starting in January, make 4-monthly payments of $1,400 USD.

14 days to refund if you change your mind.