Tuscany & Rome with David Cilli

June 12 - 20, 2024 | One Exclusive Departure

Book Now

Italy's Heart & Soul

Immersive culinary & cultural exploration with winemaker David Cilli

June 12 - 20, 2024

One exclusive departure — reserve your spot!

9 Days, 8 Nights

The very best of Florence, Siena, the Tuscan coast & Rome

Price from


per person based on double occupancy; includes internal flight from Florence to Rome

Questions? Text or call us
+1 (855) 219-8018

You’re wandering medieval alleys of Istrian stone. Though you’re technically lost, the hint of bergamot and fresh-baked focaccia convinces you to sit down, have an espresso and soak everything in. Florence is an endless banquet for the senses, from colorful graffiti to stately Renaissance architecture to the finest street food you’ve ever sampled. In the days to come, you’ll sail through shimmering waters, dine at intimate osterias, and revel in the healing hot springs of the Tuscan countryside before heading for the hustle and bustle of Rome. This is Italy like you’ve always dreamed of, an experience made richer by the kindred spirits at the table and the company of a passionate winemaker at the pinnacle of his craft.

With us on this journey is David Cilli, a revered winemaker and a driving force behind Promontory, one of Napa Valley’s most buzzed-about wine estates. Though he’s a leading name in California’s wine scene, David is Tuscan by birth, and he couldn’t be prouder to call the region’s top winemakers and artisans his most cherished friends. To journey with him through his Italian homeland is to experience the very best of Italy’s premier wine destination—an insider-only exploration of Tuscany’s most timeless traditions.

If you like your food and culture layered over thousands of years of history, this trip is for you. From the buzz of Florence’s markets to the Tuscan countryside, from serene gardens to the glamor of Rome by night, we’ll explore the most iconic corners of Italy from every angle, tasting everything as we go.


Tuscany's artisans and producers, winemakers and chefs, at the peak of their craft


Traditional meals, the best street foods, and local flavors paired with top regional wines


Yourself in the beauty of Italy, from medieval hilltop towns to pastoral farms and vineyards


With centuries of tradition, David Cilli, and inspired travelers like you

3 Reasons to Travel with David Cilli

David Cilli has trained among the top winemakers in Italy and worked in the cellars of some of the world’s premier viticultural destinations, from Western Australia and Mendoza to his native Tuscany — where he can’t wait to introduce us to his most profound connections.

Local Flavor

David’s Tuscany is deeply personal. He grew up in Siena, then moved to Florence to study winemaking alongside some of Italy’s top vintners. His knowledge runs deep and he’s full of insider recommendations that drip with character and charm.

Roots to the Land

David grew up with his feet rooted firmly in the earth. He spent his childhood tucked within the leafy tangle of his grandfather’s garden, forging a deep appreciation for the land. Today, he takes hands-on approach in the vineyard to create blends that are a triumph of terroir.

Family Man

David jokes that he knows everyone in Tuscany—and if he doesn’t know them personally, he knows someone who knows them. To travel with David is to travel with family: think home-cooked meals and profound access to the region’s most renowned winemakers.

Your Experience

“In Tuscany, you’re surrounded by beauty and authentic goodness.”
David Cilli

Florence, Siena, Tuscany, Rome

“On the southern Tuscan Coast, the quality of the seafood is unrivaled.”
David Cilli

Day by Day

Day 1: Florence

Benvenuto in Italia! Our adventure through the world’s premier wine destination begins in Florence, the Tuscan capital brimming with art, culture, and positively exquisite cuisine.

We’ll ease into our first day with an unhurried afternoon at the hotel, luxuriating in the opportunity to refresh and get settled after our long transatlantic flights. Nestled at the heart of Florence’s city center, Gallery Hotel Art is an oasis of quiet luxury and stylish, thoughtful touches.

It’s also the perfect backdrop for our first bites of the trip—tonight, we’re paying homage to one of Italy’s long-standing traditions: the aperitivo. Over welcome drinks and plenty of bright, local fare, we’ll learn more about David and his profound connection to the land—as well as its legendary vines.

Day 1: Florence Highlights

  • Arrival transfers
  • Welcome reception
  • Drinks & hors d'oeuvres at hotel
  • Stay at Gallery Art Hotel

Day 2: Florence

As the sun makes its giddy debut over bright-eyed Florence, we can seize the day with an optional running tour and yoga session. Later in the morning, we’ll head together over to Mercato Centrale, one of the oldest and busiest covered markets in Europe, where David will introduce us to some of his favorite ingredients and sources of culinary inspiration. We’ll taste as we go, sampling local delicacies before sitting down for a traditional Tuscan lunch at one of the market’s most storied stands.

Feeling buoyant and inspired from our exquisite market spread, we’ll meander onwards through the historic Santo Spirito district, paying special attention to the city’s 150-odd buchette del vino: small windows attached to the palaces of grand noblemen from which wine was traditionally sold by the fiasco (glass bottle). Our final stop is a visit to the Accademia, one of the oldest drawing schools in Europe and home to the largest number of sculptures by the great Michelangelo of any museum in the world. There’s so much to experience here, and with the help of our expert guide we’ll skip the lines and enjoy a beautifully curated tour.

In the evening we’ll reconvene for dinner at Osteria dell’Enoteca, another Florentine institution. After our meal, David’s inviting those craving an after-dinner nightcap for cocktails and an informal Q&A.

Day 2: Florence Highlights

  • Optional morning yoga & run
  • Guided market tour
  • Accademia Gallery VIP visit
  • Stay at Gallery Art Hotel

Day 3: Siena & Tuscany

We’re bidding adieu to Florence this morning and making the short (and ridiculously scenic) drive to Siena. It’s arguably one of the most beautiful cities in all of Italy, with a car-free central district of ancient alleyways and noble squares. Here, we’ll wind through the same cobbled lanes that locals walked in the middle ages, learning about the city’s rich history of art and cuisine. Along the way, we’ll stop for small bites and pastries at local shops and quaint cafes, testing out the best of Siena’s flavors.

Lunch today is a special treat: an insider’s look at traditional Tuscan cooking. In an old-world osteria at the heart of the city center, a local chef will lead us through an in-depth cooking demonstration. Afterwards, we’ll sample our handicraft over an exquisite lunch of regional specialities.

Glowing with the unique joy of a deeply satisfying meal, we’ll float onwards to a nearby azienda where farmers and artisans work in harmony with the land. Here, we’ll sample a lineup of truly farm-fresh fare: think gem-toned jams, pestos, and Tuscany’s famed Chianina meat (ground zero for Florentine steak!). As the grand finale to a day of impeccable culture and cuisine, we’ll round out our evening at our hotel, joining David and one very special guest for an unforgettable masterclass in Italian wines.

Day 3: Siena & Tuscany Highlights

  • Siena city tour
  • Cooking demo & lunch
  • Wine tasting with David
  • Stay at Le Fontanelle

Day 4: Marina di Grossetto

This morning, we’ll head to Marina di Grossetto for a day of aquatic adventure. With white sand beaches that stretch for miles, the region is a stunning exemplar of Tuscany’s natural beauty—which, of course, we’ll be exploring in style. From breezy sailboats, we’ll bask in the magnificence of our surroundings, cooling off with a swim or snorkel before a hyperfresh lunch onboard.

For dinner, we’re taking advantage of our coastal location and indulging in a Tuscan seafood feast. As we breathe in the salty sea air at a nearby restaurant (a favorite among locals), we’ll share our favorite memories from the day and savor the impeccable flavor of just-caught frutti di mare.

Day 4: Marina di Grossetto Highlights

  • Morning bicycle excursion
  • Marina di Grossetto by boat
  • Seafood dinner
  • Stay at Le Fontanelle

Day 5: Tuscany

We’re starting the day off in elevated luxury—literally. As the sun rises over the countryside, we’re floating high above Tuscany’s patchwork quilt of rolling vineyards, medieval towns, and ancient forests in vibrant hot air balloons. It’s a pinch-yourself moment, but the vineyard brunch that follows is an equally extravagant affair, dominated by local wine and a symphony of fresh, seasonal offerings.

After our jaunt in the sky, we’re heading back to our hotel, the afternoon ours to reflect on the magic of our morning. Drink in the warm afternoon sun from the terraced garden, or hit the reset button with a nourishing massage at the in-house spa. We won’t meet up again until later in the evening for dinner, and trust us on this one—it’s a truly remarkable experience. While we don’t want to give any spoilers, we’ll leave it as this: we’re in for an intimate evening of celebration, heartfelt flavors, and friends we’ll cherish for the years to come.

Day 5: Tuscany Highlights

  • Sunrise balloon ride
  • Picnic brunch
  • Special dinner
  • Stay at Le Fontanelle

Day 6: Tuscany

This morning, we’re rounding out our adventures through Tuscany with a horseback ride—it’s an unforgettable immersion into the region’s fabled countryside. Atop our steeds, we’ll wind through peaceful valleys and timeless vineyards, reveling in views so beautiful they beg to be made into a postcard.

Of course, riding horses is no small feat, so after a morning in the saddle we’ll head onwards to Terme di Saturnia for an afternoon of sumptuous relaxation. Tucked away within 120 hectares of secluded Tuscan countryside, these ancient hot springs are rich in minerals and healing bioplankton—they’re also outrageously beautiful: we’re talking otherworldly blues and glimmering turquoise as far as the eye can see. Surrounded by natural beauty, it’s the perfect conclusion to our time in Tuscany. Next stop: Rome!

Day 6: Tuscany Highlights

  • Horseback ride
  • Hot springs visit
  • Stay at Le Fontanelle

Day 7: Tuscany to Rome

It’s time to swap Tuscany’s tranquil delights for the hustle and bustle of Rome. We’ll commence our adventures through Italy’s capital city with an exclusive tour of the Villa Borghese, the country’s largest and most famous art museum that’s set in a verdant park in the heart of the city. Afterwards, the afternoon is ours to relax back at the hotel or wander through Rome’s endless offering of breathtaking plazas and ancient streets.

Dinner tonight is at an all-time Roman favorite: Rimessa Roscioli. This traditional trattoria is run by one of Rome’s famous baking families and it’s the perfect celebration of the city’s classic dishes. As a special treat, David’s hand-picked the wines for tonight and we can’t wait to sit back and savor his thoughtful choices.

We’ll end the day with the ultimate when-in-Rome adventure: zipping around the city in classic, candy-colored Fiat 500s. Some three million of these iconic little beauties were produced between 1957 and 1975, and nothing could be more quintessentially la dolce vita than this very special nighttime excursion.

Day 7: Tuscany to Rome Highlights

  • Transfer to Rome
  • Villa Borghese tour
  • Rome by Fiat
  • Stay at Anantara Rome

Day 8: Rome

We’ll slip right into the teeming street life of Italy’s capital this morning as we enjoy a curated walking tour, visiting and tasting our way through bakeries, covered markets and gelaterias in the storied Trastevere neighborhood. A morning of grazing will segue into lunch on our own, with the balance of the afternoon for further exploration of Rome’s backstreets and cafe-lined squares, a chance to saunter slowly amid the bustle.

We’ll reconvene late in the afternoon for a deep dive into two of Italy’s greatest culinary gifts to the world: pizza and gelato. First, we’ll try our hand at gelato, learning how to source the very best ingredients and proper mixing techniques. While our gelato sets in the freezer, we’ll turn to pizza, crafting and rolling out our own dough and selecting just the right toppings. Later, we’ll tuck into the fruits of our labour for dinner, but not before we raise a glass to toast David, our new friends, and la bella Italia—we know our lives have been forever enriched by this time together.

Day 8: Rome Highlights

  • Trastevere food tour
  • Gelato masterclass
  • Farewell pizza dinner
  • Stay at Anantara Rome

Day 9: Departures

Arrivederci Italia! After eight full days of immersion in the best Italy has to offer, it’s time to say ciao to David and to each other, knowing the memories we’ve made will stay with us for a lifetime. Until we meet again!

Day 9: Departures Highlights

  • Breakfast
  • Transfer to Rome's FCO airport

Where We Sleep

Beautifully curated accommodations—we’ll immerse ourselves in contemporary art in Florence, enjoy the quiet beauty of the Tuscan countryside, and feel like we’re part of the vibrant story of Rome

Gallery Art Hotel


Set in a quiet courtyard just steps from the Ponte Vecchio, this intimate boutique hotel was dreamed up by a Florentine architect as a home away from home for art lovers, and its pleasingly minimalist interior doubles as a contemporary art space featuring rotating exhibits by the likes of Andy Warhol, Dave Lachappelle and Roberto Koch. Make like a local and head to the buzzy, indoor-outdoor terrace bar for exceptional cocktails.

Le Fontanelle


Nestled in serene Sienese countryside, this 5-star hotel embodies discreet elegance—beside the panoramic pool and Turkish bath sit medieval walls and stonework that dates back centuries. It's a true sanctuary that honors the traditions of Tuscany, both past and present.

Anantara Palazzo Naiadi Hotel


More than 2,000 years of Roman history are here in one gorgeous space. Ancient ruins of the baths of Diocletian are visible beneath the property's glass floors, and there’s no more quintessentially Roman setting than the hushed, soaring lobby. The hotel has every comfort you'd expect, and some that are wonderfully unexpected (like sunset cocktails at the poolside rooftop bar).

Each hotel became more beautiful, each quaint and modern and staffed by the greatest humans ever.
Sarah L.
Every day we had a new surprise that blew my mind!
Sharzad K.
I loved the efficiency, service, quality and personal touch... an amazing time!
Cristina L.

Book Tuscany & Rome with David Cilli

Number of Travelers


Reserve your spot today with a $1,500 per-person deposit plus room supplements (if relevant). Full payment is due 180 days prior to your trip departure date. We’ll email you a reminder. If your trip departs in less than 180 days, we’ll collect full payment either 30 days from when we receive your deposit, or 60 days prior to your trip departure date, whichever is sooner. For details read our Deposit FAQs


per person based on double occupancy; includes internal flight from Florence to Rome

Can't travel on these dates?
Call us at

+1 (855) 219-8018


That’s OK, we have answers. Read our FAQs below. Or text or call us at +1 (855) 219-8018 to speak with a Modern Adventure Trip Specialist.

  1. What does the price include?

    Eight nights at unique four- and five-star accommodations; internal flight from Florence to Rome; private travel for all day trips and excursions; arrival and departure airport transfers; private tours with local guides and cultural experts; exclusive VIP access and tastings; guided activities, adventures and expeditions; entrance fees; daily breakfasts, most lunches and dinners; local beverages with meals.

  2. What does the price not include?

    International roundtrip airfare; travel insurance; activities not included in the trip itinerary; hotel incidentals including room service, laundry service and hotel bar tabs; food and beverages not included in itinerary; gratuity for tour leader.

  3. Where does this trip start and end?

    Our adventure begins at Florence’s Airport (FLR), where we’ll transfer to Gallery Hotel Art. Our last day is in Rome. The closest airport is Rome’s Leonardo da Vinci International Airport (FCO). Your flight should be scheduled to depart at 12pm or later from FCO airport.

  4. What travel documents are needed?

    US citizens are not required to have a visa for stays in Italy of under 90 days. Just bring a valid US passport. For citizens of other countries, please check with the Italian embassy or consulate for information and requirements.

  5. Do I need to pay a solo traveler supplement?

    For solo travelers, there is a $2,000 single-supplement fee paid at the time of booking to secure a private room. These spots are extremely limited and available on a first-come, first-served basis.

  6. Who is going on this trip?

    Our adventures typically have between 10 and 20 guests, and our Modern Adventure Team. Our experiences are fun and inclusive and you can expect to be joined by a diverse group in terms of age, background and interests—including solo travelers, couples and friends traveling together. This adventure is for travelers age 18 and above.

  7. Who is leading this trip?

    This trip is led by an expert Modern Adventure trip leader. They’re an experienced travel guide, a representative of Modern Adventure and your go-to person for questions or concerns on the trip. We’ll be joined throughout our adventure by local, expert guides who are deeply knowledgeable with respect to local cultures, customs and history and are passionate about sharing that with us.

  8. Do I need travel insurance?

    We highly recommend purchasing travel insurance. Travel insurance allows you to seek reimbursement for your trip costs; if your trip plans change for unforeseeable reasons, or if you need to get medical help, emergency transport, and for theft, loss or damage of items while traveling. For best coverage, always insure the full trip cost within two weeks of your initial trip deposit and note that most ‘Cancel For Any Reason’ policies must be purchased on the date of your initial deposit.

  9. What is the cancellation policy?

    You may cancel on or before February 13, 2024 and receive a full refund minus a $500 per-person service fee. If you cancel on or after February 14, 2024 there is a 50% cancellation fee. On or after April 13, 2024 there is a 100% cancellation fee. We highly recommend purchasing travel insurance as we are not able to make exceptions to this policy in cases of family/medical emergency or cases of the trip being canceled (see our Terms and Conditions for full details).

MO/AD News

Modern Adventure makes the Fast Company list of Brands that Matter in 2022. Next-level creativity and sustainable business practices build a brand with impact.

For the second year running, Modern Adventure is recognized as one of the top travel operators in the world by ​Condé Nast Traveller’s​ annual Readers’ Choice Awards, the most prestigious in the travel industry.

“I’d had Oaxacan food before, but few restaurants served meals like this—'celebration food' worth the effort only for births and weddings. And, apparently, for Modern Adventure.”

“Modern Adventure is curating a slew of foodie getaways, each spearheaded by the world’s most prolific culinary influencers. Who wouldn’t want to venture to faraway lands... eating really, really good food?”