Sip, Savor, & Stroll: A Food & Wine Lover’s Italian Escape with Joel

Trevi FountainSienaWine in ItalyFlorenceRome
duration
7 days · 6 nights
travel date
Jul 1 – 7, 2026
activity level
Light/Moderate
group size
12
transportation
Van
Your TourHero
tourhero
Joel Di Ramon
bio

What is good y'all,

I'm Joel, a nomadic creator, avid filmmaker and a lad with a gypsy soul. Currently residing in the city of Angels, working as a freelance videographer and full-time video engineer at Paramount. Through my personal and filmmaking journey, I strive to foster, inspire and encourage others to live their best lives doing whatever it may be. My love for the arts have opened multiple doors to be able to travel, connect and build meaningful friendships along the way. Whether you're a creator yourself or someone who simply loves to travel and meet amazing people, can't wait to meet you all and experience serendipity in its rawest form.

Italy > Sip, Savor, & Stroll: A Food & Wine Lover’s Italian Escape with Joel

From tossing pizza dough in Rome to clinking glasses of wine in an old cellar, every day brings a new way to experience Italy through its flavors, stories, and traditions. Walk through the heart of Ancient Rome with a guided tour of the Colosseum and Roman Forum, then enjoy a hands-on cooking class where a local chef will teach the secrets of perfect homemade pasta and crispy, wood-fired pizza. In Montepulciano, step into the Underground City at Ercolani Winery, where centuries-old wine cellars hold the region’s finest vintages, paired with a Tuscan light lunch of pecorino, truffle crostini, and bruschetta. Wander through the medieval streets of Siena, strike a pose by the Leaning Tower of Pisa, and dive into the artistic grandeur of Florence with a guided city tour before a farewell dinner at a beloved local trattoria. With a perfect mix of guided experiences and free time to explore at your own pace, this trip is all about savoring Italy — one unforgettable meal, a glass of wine, and a breathtaking view at a time.

Itinerary timeline
Day 1 · July 1, 2026 · Rome
Arrive in Rome at FCO Airport
Private group transfer from airport to hotel
Check-in at Napoleon Hotel Roma (or similar according to availability)
Welcome dinner at RomAntica (or similar)
Day 2 · July 2, 2026 · Rome
Breakfast at hotel
Half-day ancient Rome tour (3 hours)
Lunch at local restaurant
Skip-the-line entrance at the Colosseum (no guide)
Return to hotel
Free night
Day 3 · July 3, 2026 · Rome
Breakfast at hotel
Free time
Pizza making class with 3-course dinner
Return to hotel
Free night
Day 4 · July 4, 2026 · Rome, Montepulciano & Siena
Breakfast at hotel and checkout
Transfer to Montepulciano
Guided tour of the Underground City at Ercolani Winery
Wine tasting and vineyard visit (includes light lunch)
Transfer to Siena
Check-in at Executive Hotel Siena (or similar according to availability)
Free night
Day 5 · July 5, 2026 · Pisa
Breakfast at hotel and checkout
Transfer to Pisa
Pisa guided tour (2 hours)
Check-in at Grand Hotel Duomo (or similar according to availability)
Free night
Day 6 · July 6, 2026 · Pisa & Florence
Breakfast at hotel and checkout
Transfer to Florence
Check-in at 4-star hotel (TBD)
Florence guided tour (3 hours)
Return to hotel
Farewell dinner at Osteria dei Baroncelli (or similar)
Day 7 · July 7, 2026 · Departure
Breakfast at hotel and checkout
Private group transfer to FCO Airport
Journey ends
Details
Day 1 · July 1, 2026
Benvenuti a Roma!

-Welcome to the Eternal City! As soon as you step off the plane at FCO Airport, a private transfer will whisk us away to your home for the next few nights.

-After checking in, we’ll kick off this unforgettable journey with a welcome dinner at a charming local restaurant. Think impeccable ambiance, rich Roman flavors, and a toast to the adventure ahead. Salute!

RomeRomAnticaRomAntica
Day 2 · July 2, 2026
See Rome through the ages

-After a leisurely breakfast, we dive straight into history with a guided tour of Ancient Rome.

-Walk in the footsteps of emperors, gladiators, and poets as we explore the city's most legendary sites.

-We’ll refuel with an indulgent Italian lunch before skipping the lines at the mighty Colosseum for a self-guided visit.

-The evening is yours — stroll through the piazzas, sip an aperitivo, or get lost in the magic of Rome at night.

Italian breakfast in RomeRome city tourColosseum Interior
Day 3 · July 3, 2026
Mastering the art of Pizza

-Today, we trade sightseeing for something delicious — an immersive pizza-making class! You’ll learn the secrets of perfect dough, craft your own pizzas, and enjoy a full 3-course meal featuring handmade creations and a decadent dessert.

-Afterward, the night is yours at leisure. Perhaps go on a twilight gelato stroll or duck into a hidden speakeasy?

Pizza making classGelato
Day 4 · July 4, 2026
Tuscany's vineyards and villages await

-We say goodbye to Rome and set off for the rolling hills of Tuscany.

-First stop: Montepulciano, where we’ll explore the Underground City at Ercolani Winery before indulging in a wine tasting paired with a Tuscan light lunch.

-Afterward, it's off to Siena, a medieval masterpiece that feels frozen in time. Check into our cozy hotel, then take the evening to wander through the city's enchanting streets at your own pace.

MontepulcianoErcolani WineryErcolani WinerySiena at night
Day 5 · July 5, 2026
Leaning into Pisa

-Fuel up with a hearty breakfast before heading to Pisa, home to the world-famous Leaning Tower!

-A guided tour will take us through its stunning Piazza dei Miracoli, and of course, there’s time for that iconic photo-op.

-Settle into our cozy accommodation for the night and enjoy the views of Pisa at night.

PisaLeaning Tower of Pisa
Day 6 · July 6, 2026
See the heart of the Renaissance

-Today, we're heading to Florence, the city of art, culture, and delicious food.

-After checking in, we’ll explore the city’s rich history on a guided tour, uncovering masterpieces and hidden gems along the way.

-Tonight, we gather for a farewell dinner at a beloved local trattoria. Enjoy incredible flavors, flowing wine, and one last toast to an unforgettable trip!

FlorenceFlorence walking tourOsteria dei Baroncelli
Day 7 · July 7, 2026
Arrivederci, Italia

-One last cappuccino before we say our goodbyes.

-After breakfast, our private transfer takes us to the airport, but the memories (and all that wine and paste) will linger in our minds for a while. Until next time, Italy!

Tour Price
USD 3,303
per person
Flexible payment plans available
15 people are interested
Looks like this trip is getting views. Secure your spot now!
Your fellow explorers
Age range
18+
Travel interest
City, culture, sightseeing, food
Your local guide
True Italy Experience provide unique tours, experiences, and luxury vacations in Italy. Handpicking the best, most authentic, and most exciting trips for those who want to see, taste, and discover real Italy, True Italy Experience ensure truly satisfactory personal services to their clients. With 22 years in the business, top-class staff to offer advice and suggestions, and local knowledge, their goal is to help you live the Italy of your dreams. For authentic Italian getaways, book with True Italy Experience.
Accommodation
Napoleon Hotel Roma (or similar according to availability)

The Napoleon Hotel Roma is a charming, family-run hotel offering an elegant retreat in the heart of Rome. Located just steps from the iconic Colosseum and a short walk from Termini Station, the hotel is perfectly positioned for exploring the Eternal City’s historic landmarks. The spacious rooms blend classic Italian style with modern comforts, featuring plush bedding, soundproof windows, and thoughtful touches to ensure a restful stay. Guests can unwind at the cozy bar, relax in the inviting lounges, or enjoy a meal at the on-site restaurant serving traditional Roman cuisine. With warm hospitality, a prime location, and a boutique feel, the Napoleon Hotel provides a welcoming and sophisticated base for discovering Rome’s timeless charm. Room type / configuration: Double occupancy.

Executive Hotel Siena (or similar according to availability)

The Hotel Executive in Siena is a 4-star establishment located approximately a 10-minute drive from the city center. Guests have praised the spacious and clean rooms, which feature amenities such as kettles with a wide selection of teas and herbal teas, as well as comprehensive bathroom kits. The hotel offers a breakfast service for €10 per person, which has been described as excellent. Additionally, guests have noted the friendly and attentive staff, contributing to a pleasant stay. Room type / configuration: Double occupancy.

Grand Hotel Duomo (or similar according to availability)

The Grand Hotel Duomo is a 4-star establishment located in the heart of Pisa, just a 2-minute walk from the iconic Leaning Tower and Duomo Square. The hotel offers a variety of room types, including Single Basic, Double Basic, Standard, Superior, Superior Tower, Family Room, and Family Plus, all equipped with amenities such as air conditioning, satellite TV, minibar, and private bathrooms. Guests can enjoy complimentary Wi-Fi throughout the property. The hotel features two on-site restaurants: Sala Ranieri and Tower Sky Lounge, serving Italian cuisine. Additionally, there is a rooftop terrace offering panoramic views of the city. Other facilities include a 24-hour front desk, room service, and pet-friendly accommodations. Room type / configuration: Double occupancy.

4-star hotel in Florence (TBD)

Outside the city center - check back for more info. Room type / configuration: Double occupancy.

Napoleon Hotel RomaNapoleon Hotel RomaExecutive Hotel Siena Executive Hotel Siena Grand Hotel Duomo
Included

  • 3 nights in Napoleon Hotel Roma (or similar)

  • 1 night in Executive Hotel Siena (or similar)

  • 1 night in Grand Hotel Duomo (or similar)

  • 1 night in Florence hotel

  • Shared double occupancy in accommodation

  • All breakfasts

  • Lunch on day 2, 4

  • Dinner on day 1, 3, 6

  • Ancient Rome tour

  • Colosseum skip-the-line entry

  • Pizza-making class

  • Underground City at Ercolani Winery visit

  • Wine tasting at Ercolani Winery

  • Pisa tour

  • Florence tour

  • One group airport arrival transfer

  • One group airport departure transfer

Not included

  • Flights

  • All food and drinks not mentioned in inclusions

  • Optional add-ons

  • Travel insurance

  • Gratuities

FAQ
Cancellation policy

Refunds for deposits
We will hold your spot as soon as you put down your deposit. However, if you decide to cancel your trip, we will be unable to refund your deposit.

Refunds for balance payment
If you cancel your trip on or before Apr 27, 2026 at 11:59 PM local time (GMT +2), you will get a refund of the remaining balance. This may or may not include the deposit amount. See deposit refund section above.

If you cancel your trip from Apr 28, 2026 at 12:00 AM local time (GMT +2) onwards, no refunds will be issued.

You can change or cancel your trip in your TourHero account by clicking on Your Trips.

Trip disclaimer
To offer the best group rates, we need a minimum number of travelers. If that number isn't met—or if unexpected events occur (such as force majeure)—TourHero, the trip host, and the tour operator may need to cancel or reschedule.


If changes happen: You'll be notified by Apr 27, 2026 at 11:59 PM local time (GMT +2), and if the trip is canceled or rescheduled beyond your control, you'll get a full refund. We'll always update you at least 7 days in advance if this date changes.


Book smart: We recommend refundable flights and accommodations to protect your plans from any last-minute changes.

Available add-ons
Single supplement room upgrade for the entire trip

Want a little more privacy during your trip? Select this single supplement add-on and have a room all to yourself.

USD 650
Sold out
Single supplement add-on