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2023 DATES

April 30 - May 7, 2023

A few Gal spots + 2 Guy spots left

May 21 - 28, 2023

 Gal spots SOLD OUT + a few Guy spots left

MAY 28 - JUNE 4, 2023

Memorial Day trip 

1 Gal spot + 1 Guy spots left


June 11 - 18, 2023

Selling quickly - likely to sell out

Sept 3 - 10, 2023

Labor Day trip - likely to sell out


Sept 17 - 24, 2023

Oct 1 - 8, 2023

White truffle season

3 Gal spots + 2 Guy spots left

Oct 8 - 15, 2023

White truffle season - likely to sell out

Oct 15 - 22, 2023

White truffle season - likely to sell out

Oct 22 - 29, 2023

White truffle season - likely to sell out

8 days/7 nights

from $3,099 USD

P.S. All payments can be broken up into a

$500 deposit + 3 additional installments.

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​We will kick off our 8-day Italian adventure in San Gimignano, a small Italian hill town southwest of Florence. Here we will explore the narrow cobblestone streets, grand piazzas, and try our hand at cooking an authentic Italian meal. Throughout our time in Tuscany you can expect truffle hunting, wine tasting, UNESCO World Heritage site exploring, and of course wandering through Florence. From there we will head to Rome to experience the history, depth, and beauty that this city offers. By the end, you will have connected with new friends and created outstanding new memories to take home and share with everyone. 


















  • Accommodations in a shared room with someone of the same gender (hotels, not hostels)

  • 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

  • Entrance to Siena duomo

  • Private walking tour in Florence

  • Private tour of the Colosseum and Ancient Rome

  • Private food and history tour in Rome

  • Rooftop champagne toast

  • Single trip leader throughout the trip

  • Insider knowledge


*All activities are weather dependent; in the unlikely event that we are unable to run an activity, we will have a suitable alternative in place.

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

more details
Image by Ali Nuredini

day by day

*Itinerary is subject to change


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Day by day
Day 1 - Florence

Arrive in Florence by 3pm and make your way to the first hotel. Drop your bags and explore a bit on your own (aka nap).


At 5pm, 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. Buon appetito!

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Day 2 - San Gimignano
kiss the cook

Wake up and smell the espresso. 

After breakfast, we'll check out and head into the countryside. After an hour's drive, we'll pull up to the castle-like town of San Gimignano, our home for the next two nights.


Spend some time wandering the tiny streets, climbing towers for killer views, or hitting up our favorite local wine bar that serves mouth watering crostone and chianti for 4 euro a glass. 


At 4pm, meet up with the group to head to the nearby village of Certaldo for a regional cooking class with a local chef/typical Italian Mamma.


Day 3 - San Gimignano
day tripping

After breakfast, we'll head to San Galgano Abbey, a stunning roofless structure in the middle of the Tuscan countryside. Take an hour to get your zen on in this peaceful (and amazingly not touristy) place. Don't forget to hike up the hill to see Italy's version of the sword in the stone!


After the abbey, we'll continue onto Siena, one of the best preserved medieval towns in Italy and a UNESCO World Heritage site. A local guide will introduce us to the city with a brief walking tour, including Siena's unique Duomo (note: even if you're not a church person, this one is pretty spectacular).

After the tour, you'll have time for a leisurely lunch and getting lost in Siena's tiny, maze-like streets.

Fun fact: According to UNESCO, "the whole city of Siena was devised as a work of art that blends into the surrounding landscape."




Day 4 - Tuscany
truffles + wine

Leave the hotel at 9am for a unique experience with a local family: truffle hunting! Learn how to find one of the world's most expensive culinary treats in the fields of Tuscany.


Our truffle guru will explain the history of truffle hunting and the tricks of the trade before sending you to chase after truffle-sniffing dogs.


After a lunch prepared with the truffles you find, our favorite local winemaker will introduce you Chianti wines with a tasting of his most recent harvest.


We'll arrive in Florence by 3pm and enjoy some free time to explore, shop, and get dinner on your own. 

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Day 5 - Florence, then Rome
On to rome

After breakfast cappuccinos and "cornettos," today is yours to explore Florence at your own pace. 


At 2:00pm, we will grab our bags and head to Rome to check in to our centrally located boutique hotel.


That evening, a local will escort us through Rome for a tour that has a little bit of everything: culture, history, and typical Roman food.


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. 


Day 6 - Rome

After breakfast, we'll hop on a 10 minute bus ride to the famous Colosseum and Palatine Hill - an absolute must in Rome. 


We'll have a private tour to discover the relics of 3,000 years of history as our guide narrates the story of this incredible city and the extraordinary figures who shaped the world as we know it. 

The afternoon and evening are yours to get lost in the romantic cobblestone streets of Rome. Hint: ask your trip leader where to find the best Aperitivo. 


Day 7 - Rome
Rome Around

Rome is a vast, brilliant city that would take years to fully explore. Today is totally open for you to customize your visit to whatever interests you most.


Meet up with the group in the evening to watch the sunset from one of Rome's best vantage points before heading to our farewell dinner and drinks at one of the city's most beloved local trattorias. End the trip dancing 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. 

"You may have the world, if I may have Italy."

-Giuseppe Verdi (and FTLO's whole team)



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Fast facts

Just for Fun

Italy young adult and young professional group travel tour. Experience Tuscany and Rome's incredible food, art, and people with a group of new friends.

There are over 140 types of pasta in Italy.

Italy young adult and young professional group travel tour. Experience Tuscany and Rome's incredible food, art, and people with a group of new friends.

Everyday, 3,000€ gets tossed into Rome's Trevi Fountain.

Italy young adult and young professional group travel tour. Experience Tuscany and Rome's incredible food, art, and people with a group of new friends.

Carabinieri uniforms are designed by Valentino. Because of course.


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

  • 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.

  • 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.

  • Visas are not required for American travelers

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

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



Fly into Florence (FLR)

You'll need to be in Florence by 2pm on Day 1, however with the recent amount of flight delays we recommend planning to arrive a day early just to be safe.

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.

Want to check out flights for your trip?

Feel free to also set up flight alerts to Italy so you can grab the best deal!

*FTLO is not responsible for any fees or costs related to flights. We strongly suggest that all travelers wait until they receive the official FTLO Greenlight Email to book flights. This will be sent 3-4 months prior to the start date of your trip.

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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. 


"I just returned home from the Tuscany / Rome trip and cannot wait to book my next FTLO experience! I was dreading planning a trip and FTLO took care of everything and connected me with amazing people. The hotels and transportation were top notch, the experiences were perfectly selected and exceptional, and our group leader Nicole was above and beyond supportive. I will be friends with Nicole and the group for the rest of my life."

-Emily, MN

"The trip was incredibly organized and the small group made it easy to get to know everyone. The trip was the perfect balance of planned activities & solo time to explore on your own. Even though there was a good amount of free time, you really don't need to plan anything in advance & the local guide (Nicole!) gave us a ton of food/activity suggestions for free time. The Italy trip was awesome for foodies (my favorite, obviously) and I had my fair share of food and wine... 

FTLO was my first experience traveling solo and I just booked my second trip. I'm so excited to have found FTLO!"

-kelsey, SD

"I just wrapped up a wonderful two weeks with FTLO, going on both the Tuscany & Rome trip and Amalfi & Puglia back-to-back. As someone who doesn't get to travel more than once every 2 to 3 years, I knew that if I wanted to see a country as big and diverse as Italy, I really wanted to experience as much as possible. I feel like I got such a great overview of the country and its history!"

-Virginia, SF


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