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A group of travelers in a trip to Tuscany drink wine and eat meats and cheeses.

















A girl on a tour of Tuscany walks through a vineyard.


Our small group trip to Tuscany and Rome caters to travelers in their 20s and 30s looking for Renaissance architecture in Florence, Chianti and traditional cuisine in Siena, and ancient history in Rome.

Kick things off in Tuscany and immerse yourself in the region’s rich, colorful past and well-preserved culture. Mix in the best of small-time charms, old city wonders, and countryside delights, from grand cobbled piazzas to truffle hunts and local wine tastings.

And then, head to Rome to dive head-first into stories of an ancient world, food that just won’t quit, and astounding urban beauty that draws visitors from around the world. This is one eye-opening week of new friends, shared experiences, and lifelong memories.

upcoming dates

Sep 1 - 8, 2024

Labor Day Trip

Sep 29 - 6, 2024

White truffle season

 3 Gal spots + 2 Guy spots + 1 single room left

Oct 6 - 13, 2024

White truffle season

2 Guy spots + 2 Gal spots left

Oct 13 - 20, 2024

White truffle season - likely to sell out

Oct 20 - 27, 2024

White truffle season - likely to sell out

Oct 27 - Nov 3, 2024

White truffle season - likely to sell out

8 days/7 nights

starting at $3,599 USD

Limited single room upgrades starting from $899 are available and can be added during booking, subject to availability.


Payment can be broken down into a $500 deposit + 3 additional installments.


  • All accommodations in a shared room with one other person with the option to upgrade to a private room (limited availability)

  • In-country transportation for included activities

  • 2 nights in San Gimignano, 2 nights in Florence, 3 nights in Rome

  • 7 breakfasts, 1 lunch, 4 dinners

  • Train ticket from Florence to Rome

  • Cooking class

  • Wine-tasting

  • Truffle hunting

  • Day trip to Siena

  • Private walking tour in Siena

  • Private walking tour in Florence

  • Private tour of the Colosseum and Ancient Rome, subject to availability*

  • Private food and history tour in Rome

  • Insider knowledge

  • FTLO Trip Leader


*Please note that all activities are weather-dependent.

not included

  • Flights to and from Italy (see below for more flight information)

  • Airport transfers

  • Mandatory trip insurance

  • Meals not mentioned (budget around $175)

  • Incidental Expenses

The Duomo in Florence towers over the old city.

day by day

*Itinerary is subject to change


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Day by day
Day 1 - Florence
Oh Firenze!

After you get into Florence, make your way to the hotel and drop your bags before you head out to explore the city’s narrow cobblestone streets.

That evening, you’ll meet up with your new travel crew for a cultural walk in the heart of Florence, followed by a family-style Italian meal with enough wine to make you forget your new travel buddies were ever strangers.

You’ve made it to the land of some of the world’s best food and wine. Buon appetito!

A traditional old building near vineyards in Tuscany.


Day 2 - San Gimignano
kiss the cook

Wake up and smell the espresso. 

After breakfast, we'll check out and head into the countryside toward the medieval hillside town of San Gimignano, our home for the next two nights.


Spend some time wandering the tiny streets, climbing stone towers for killer views, or hitting up our favorite local wine bar for crunchy crostones and chianti for a couple euro a glass. 


That afternoon, we’ll all meet up to head to the nearby village of Certaldo for a regional cooking class with a local chef/typical Italian Mamma.

Friends on a group trip drink red wine in Tuscany.


Day 3 - San Gimignano, Siena
day tripping

Today we’re rolling out to explore the cobbled alleys, ancient walls, and iconic architecture of Siena, one of the most well-preserved medieval towns in all of Europe.

After we get into town, roam these famous streets and grab a bite with friends. Then it’s time for a sip or two of the good stuff. We’ll all wind down to an old Etruscan cave for a taste of local vino.

Eventually, we’ll meet up with our local guide, who will walk us through narrow stone alleyways and get us up to speed on Siena’s uniquely fascinating contrade (spoiler alert: these neighborhoods have been competing against one another since the middle ages!).

A group of travelers learn to cook at an Italian cooking class.


Day 4 - San Gimignano, Florence
truffles + wine

After we check out of our hotel, it’s time for one Tuscan good time with a family nearby. We’re heading out into the fields in search of some of the most expensive (and delicious) treats around—that’s right, we’re going truffle hunting.

Our truffle guru will explain the history of the hunt and the tricks of the trade before sending you off to chase after truffle-sniffing dogs. We’ll have lunch prepared with those very truffles you found, and then our favorite local winemaker will introduce you Chianti wines with a tasting of his most recent harvest.  

From there, we’ll hit the road again and cruise back to Florence where you’ve got the rest of the day free to shop, explore, or grab a bite with the crew.

Old buildings and trees in the Tuscan countryside.


Day 5 - Florence, then Rome
On to rome

After breakfast cappuccinos and cornettos, the morning is yours to explore Florence at your own pace. In the afternoon, we’ll grab our bags and roll on south to Rome toward our lovely little boutique hotel in the center of town.


That evening, an excellent local guide will escort us through the capital for a tour of a little bit of everything; we’re talking culture, history, and your first taste of Roman cuisine.

If you're still on your feet, grab your roomie and get to know Rome properly by checking out the popular bar scene in Campo de' Fiori.

A traditional pizza at a restaurant in Rome.


Day 6 - Rome

After breakfast, we'll hop on the bus ride and roll on over to the famous, fabulous, breathtaking, and historic Colosseum and Palatine Hill, subject to availability*.


On our private tour, we’ll discover the relics of 3,000 years of history as our guide narrates the story of this incredible city and the extraordinary figures who helped shaped the world as we know it.

​The afternoon and evening are yours to get lost in the romantic cobblestone streets of Rome. For a bit of extra fun, ask your trip leader where to find the best apperitivo in town.

The skyline of Rome is full of very old buildings.


Day 7 - Rome
Rome Around

Rome is a vast, brilliant city that would take years to fully explore, and while you might not have years, you’ve got today to wander, marvel, and take it all in.

Pick up souvenirs for friends back home, lie down in the Circus Maximus and pretend chariots are speeding by as the crowds go wild, or just ogle these iconic sites and appreciate the fact that they’re still here today.

In the evening, meet up with the group and head to our farewell dinner at one of the city's most beloved local trattorias. Then, wrap things up the right way and dance the night away at one of Rome's outdoor discotecs.

Day 8 - Rome

Sadly, this is your last day in Italy...for now.

After breakfast, the hotel will store your bags so you can explore a bit more. Your trip leader can help you figure out the best way to get to the airport whether it's via taxi or train.


If you’ve got more time in Europe (lucky you!), head out across the sea and check out our Sardinia trip for more Italian magic or pop on over to nearby Slovenia for some off-the-beaten-path country beauty.

The old stone walls of the Colosseum in Rome.



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Fast facts

about italy

Italy is a place like no other.

The country's physical beauty is matched in magnificence by its delectable cuisine, its animated natives, and its fascinating history.  

Come experience the cultural mecca that inspires greatness in literature, art and film. We take you from a hilltop town in the middle of Tuscany, surrounded by rolling hills and famous vineyards, through the elegance and richness of Florence, and finally to the eternal city, Rome (once capital of the world, and now a vibrant modern metro, built up around 2,500+ years of history.) 


  • The national language is Italian

  • The national currency is euros

  • Tap water is ok to drink

  • Tipping is unnecessary but it is common to round up to the nearest euro when settling a bill

  • The closest arrival airport is Florence 

  • The closest departure airport is Rome 

  • Visas are unnecessary for North American travelers

  • Double check your passport is valid for 3-months after your return date


  • While we can’t guarantee private rooms, you should book your trip earlier if you prefer one, as they usually fill up.

  • Tuscany & Rome in the summer can be quite hot, so pack your bags accordingly.

  • On European trips, we stay as close to historic city centers as possible. This means your accommodations will often be on the small side, quirky, and unique (we love this!).

  • We don't spend a ton of time in Florence, so we recommend getting in a day early to explore Florence a bit on your own if you have a lot on your Florence must-see list.

  • More information regarding visa requirements and Covid restrictions can be found here.

  • Ensure your passport is valid for 3-months after your return date

  • If you'd like to visit the Vatican museums, you'll need to book early from the Vatican website. It's best to visit on day 7 of your trip.

flight information

Fly into Florence (FLR)

You'll need to be in Florence by 2pm on Day 1. We do recommend flying in earlier to have some time to explore the city on your own!

Fly out of Rome (FCO)

We recommend flying out of Rome on day 8 or extending your trip and enjoying a few more days in Italy.

While we recommend flying into Florence, it's more budget friendly to book a roundtrip ticket to/from Rome and get a one way flight or train to Florence. You can also fly into Bologna or Pisa.

A group of travelers in Tuscany with vineyards in the background.

Alumni Reviews


We know how much you'll love the Tuscany & Rome trip...
but don't take our word for it! Check out some of our alumni reviews. 

Traditional Tuscan homes and the rolling hills of Tuscany.


Learn More

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