Florence & the Tuscan Countryside - 2024

Indulge in the art of il dolce far niente — carefree enjoyment — as you travel Tuscany’s idyllic countryside, hilltop towns, and ancient cities. You’ll stay in Florence and Montepulciano. 

5 nights, 6 days
Limited to 15 guests.

Small groups and beautiful itineraries, all handled for you.
Have connections the minute you step off the plane.
For people who want fun, easy, insider travel — elevated.

Tuscany is one of those places — the more you go, the more it works its magic on you. You could return ten times and never lose the burning desire to go back (even if just for the carbs). Tuscany is Italy’s vacation dream epicenter because it’s home to one of the country’s most beloved cities — Florence — not to mention the most photographed countryside in the world. Combining fancy Florence and earthy Montepulciano delivers high returns on your Tuscany portfolio.

Your Italian Fix in Tuscany is designed to be a short, sweet, and delicious stay without the long commitment. Your experience is 5 nights and 6 days divided between Florence and Montepulciano. You’ll also venture to the kinds of places you’ve seen in movies and magazines, like Siena. One evening, you could be eating in the main piazza of a lively local neighborhood in Florence, and the next you could be sitting at a long wooden table in a vineyard. One day, you could be shopping for a new pair of boots in a tiny boutique and the next could be spent in peaceful solitude catching up on a book from the pool in Montepulciano. Italian Fix tours create the perfect balance between staying busy and indulging in the art of il dolce far niente. When you’re in Italy with Italian Fix, you can have it all. This is a tailored tour through Tuscany’s countryside, cities, and towns and its rich local traditions, artisanship, wines and foods. What isn’t traditional? Our never conventional and always inspiring style of high/low boutique travel.

Florence & the Tuscan Countryside - 2024

5 nights, 6 days

Investment is $5,495.00 USD

Rates are per person (double occupancy)

Traveling solo & prefer your own room?

Add $990.00

Book your space with a $795.00 deposit.

What's Included

Included on every Florence and the Tuscan Countryside tour:

A unique itinerary divided between city and country. You’ll experience Florence, Siena, and Montepulciano.

5 nights in boutique hotels. We spend 3 nights in Florence and 2 nights in Montepulciano.

Airport-to-hotel transfer on arrival day. Hotel-to-airport transfer on departure day.

Florence shopping trip including visits to artisan shops.

All ground transportation, which includes private transfers, airport transfers and taxis.

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

Private tour of Siena with resident expert guide. 

Tuscan winery visit with tasting.

Tuscan countryside lunch al fresco.

All breakfasts as well as two (2) lunches and three (3) dinners, including local wine and alternatives.

Entrance fees, taxes, and all tips for drivers and restaurants and guides.

2024 Tour Dates


Florence & the Tuscan Countryside - 2024

5 nights, 6 days

Investment is $5,495.00 USD

Rates are per person (double occupancy)

Traveling solo & prefer your own room?

Add $990.00

Book your space with a $795.00 deposit.

Itinerary Overview

Fly into Florence airport and we’ll send our driver for your hotel transfer. Or, if you’re traveling from anywhere else in Italy, we’ll help you with logistics and a driver upon request. That night, we’ll meet the group for a dining experience with an iconic view in central Florence. 

A walking tour of Florence gives you the lay of the land. We’ve selected the most notable monuments, plus the lesser known “musts” we believe you can’t leave Florence without seeing, including our favorite Florentine artisan studios. We’ll spend an evening together dining at a traditional Tuscan meal.

We have skip-the-line tickets for the Uffizi with your name on them, plus a private tour of the gallery. Our gorgeous lunch is at a classic Florentine trattoria beloved by locals. In the afternoon, you have time to explore more historical sights on your own, or relax with some retail therapy (we can direct you to the best Made in Italy items that are hard to find elsewhere) or 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.

Today we journey from Florence to the Tuscan countryside with our private driver, with a stop along the way in Siena and a private tour of the city. We’ll check into our Montepulciano countryside hotel with dinner at a local trattoria.

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 together in town.

Check-out and departure day with transfer back to Florence, or extend your stay in Montepulciano or elsewhere. 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 Details:

Arrival Airport: Florence

First-Day Activity: Dinner at 7pm

Departure Details:

Departure Airport: Florence (Also Milan or Genoa, ask us for advice.)

Last-Day Activity: Breakfast, then private transfer with airport arrival by noon.

Why Travel with Us?

Our process for curating local experiences, tastes, sights, and sounds is unrivaled. Thanks to our genuine relationships with ethical, family-owned businesses, we expertly arrange a beautifully balanced and magical week of Italian living. Our goal is to create unique moments that set the stage for living your best dolce vita.

When you travel with Italian Fix, you make lasting connections that bridge cultures, continents, and backgrounds, inspiring you to welcome new friends, new ways of thinking, and a renewed sense of being, doing, and exploring. 

Our guests instantly benefit from our exclusive network of travel and logistics experts who use their decades of experience, passion for travel and culture, and love of people and adventure to provide an effortless and elevated travel experience under our care. 

We believe in providing seamless experiences for our guests where everything — and anything — is handled confidently by our compassionate and knowledgeable team who care about the guest experience and their safety and wellbeing. 

So, what are you waiting for? Andiamo!

How We Compare

When booking with any travel company, it’s important to know how long they have been in business, whether their itinerary is proven, whether the meals will be good, whether they offer unlimited pre-travel support, and essentially, what the quality of the experience they provide is. We prioritize quality over quantity, offering only tours in small groups on proven routes in Italy.

Italian Fix
Standard Tours

Access to Italy experts pre-travel and on the ground. Licensed guide travels with you.

Hours of research and comparison shopping done for you.

Transparent and up-front trip costs. No surprise upsells on tour!


Unlimited Italy travel advice as you prepare your trip.

Exceptional-quality meals at restaurants, markets, and private homes included in your trip fee.

Easy-to-book pre-/post-tour extensions and add-ons.


Vetted, proven and refined itineraries.


Small groups under 16 people.

Operating for over a decade.


How It All Works - How to Travel With Us

Find a trip you like

We have six itineraries (view them here). Can’t decide? We’re available to chat and help pinpoint the perfect tour for you.

Book your spot

Confirm with just a deposit.

Start dreaming

Before your trip, get unlimited personalized service from Italy experts, who will help ensure your entire getaway is exceptional.

Travel with confidence

Before your flight, you’ll know exactly what's going to happen and you have friends on the ground on the other side. You’ll get support if there’s a hiccup like a missed transfer or a lost bag.

Get taken care of

We’ll collect you from the airport (or the train station, depending on the tour you choose). While you’re with us — relax — we have everything handled.

Live a richer life

The beauty of travel is also in how it changes you. Our guests leave us having acquired some Italian, learned local etiquette, picked up travel hacks, and created new friendships, among many other life upgrades.

Florence & the Tuscan Countryside - 2024

5 nights, 6 days

Investment is $5,495.00 USD

Rates are per person (double occupancy)

Traveling solo & prefer your own room?

Add $990.00

Book your space with a $795.00 deposit.

A Word From Our Founder

One summer, my husband and I spent a week roaming around the Val d’Orcia countryside on his motorbike. Our daughter was at camp in Tuscany, and they wouldn’t let the adults hang around, so we decided to go get lost. And lost we got… in plates of pasta… rolling hills… and winding roads past gorgeous estates and towns. I have vivid memories of eating these amazing, never-ending meals. The standards are incredibly high in Tuscany, for everything. Great hotels, great culture, great service — it really does check all the boxes. And Florence is my favorite city on the planet. In fact, it was a college summer program in Florence that brought me to Italy the very first time, and that led me to start this company. I hope you love our 5-night trip — consider it as an extension to one of our other tours or just on its own. And I hope you love your stay in this generous region. It’s a timeless favorite for so many reasons you’ll soon discover. 

With love + vino,


What You'll Experience with Us

What They Say...

96% of our 2023 guests have left us a 10/10 review post-trip. 100% of our guests love our customer service.


We’re a boutique travel company, not a luxury travel company. Although we do think of ourselves as fancy (we even train our hosts with some of the same service tenets as the Ritz), we want to do things differently. 

We want our trips to be more inclusive and open to a more diverse set of travelers than a typical luxury tour operator that just serves the 1%. We like to think of our experiences as a beautiful balance of high and low. We might offer a stunning multi-course meal with wine pairings at an award-winning restaurant one evening, and the next day, we’ll be eating a panino at a plastic table at the market. Because, let’s be honest. You didn’t come to Italy to have a Disneyland-esque type of experience. You’re here to experience it all, not just the touristy stuff. We love to offer our guests the kind of beautifully layered and nuanced experience that our Italian friends would plan for themselves. 

Our travel and logistics experts are geniuses at crafting the perfect combination of local experiences, tastes, sights, and sounds. Many of our Italian Fix hosts live in the areas we visit or have lived there before. So, we know people

We’re intentional in our decisions about where we stay, where we eat, and where we visit. It’s important to us that we support the ethical, family-owned businesses we know and love. No chain hotels are on our roster. We purposefully and artfully select the smaller, family-run places that offer next-level experiences and unique boutique-style service. We aim for 10/10 reviews — without the $12K price tag for access.

We have a combination of solo travelers, people traveling with friends, and people traveling with partners/spouses on all of our tours. We also have a mix of “co-ed” and “women only” dates.

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

Coming with us is like having a backstage pass or an insider’s tour, and you need that in Italy because it’s way too busy and too easy to get caught up in the fray. If you travel on your own, you’re just one in a million foreigners waiting in lines and trying to get service. No connections or language fluency makes that so much more frustrating! 

Our travel style allows you to be among friends and have access to things you couldn’t find on your own. We’re into slow — and sustainable — travel. We support family-run businesses and local producers. And we’re picky! No big-box concept of tourism around here. At Italian Fix, we’re mindful about keeping traditions alive and supporting local economies. 

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 kind of guests from around the world with different backgrounds — because wanting to live your dolce vita is something that transcends any zip code 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 one more trip of a lifetime, they all want to live the Italian lifestyle in a carefree, fun-filled, and relaxing week. They trust Italian Fix to confidently handle all the details so the only thing they’re responsible for is embracing the art of living — Italian style.

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!

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

We employ incredibly smart, organized, and hard-working individuals (mostly women) who are passionate about travel, culture, adventure, and people. We also work in our comfy pants and have a sane work schedule where we can pick up our kids from school and enjoy our lives too. We do what we do so that you can live your dolce vita.


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