Rome & Tuscany


The best of Tuscany—its iconic cities and medieval villages, its hillside vineyards and farms, its art and ancient monuments


La dolce vita with rooftop cocktails, fresh farm-to-table feasts, meet-ups with local artists and winemakers, food tours on the back of a Vespa


The world’s most exquisite pastas and seafood, Roman pizza, elegant five-course meals, the finest ingredients at markets and local farms

Why Rome & Tuscany

Tuscany is a timeless treasure where medieval villages cling to hilltops, and vineyards and olive trees bathe in golden sun. Each region has its own tradition, each village makes pasta with their own succulent twist . The world’s greatest art springs from here, too, along with iconic sites such as Florence’s Duomo or the Vatican galleries in Rome. Experiencing the region is best when taken slowly, and deeply. We’ll show you.

Moments That Matter

Meet an eighth-generation butcher and some of the region's top vintners. Dive into art and sculpture at Florence's Uffizi and Galleria dell'Accademia museums. Soak up the bustle and vibrancy of Rome's Trastevere district, explore the Pantheon and Colosseum with a local historian, walk with chefs tasting your way through Rome's glorious markets. Art, architecture, food, wine, medieval markets—it's the Tuscany you've always dreamed of.

Your Private Experience

Who It’s For

From a couple’s romantic jaunt through the Tuscan countryside to a group of wine enthusiasts, our trip is made to be savored by all.

When to Travel

May, June and September are ideal times to visit for the weather. April, July, August and October still have pleasant temperatures and opportunities to avoid summertime crowds.

Make It Yours

Stop at Tuscany's best wineries, or take extra time admiring the history and artistry of Florence and Rome, we’ll help craft your ideal Tuscan experience.

Day by Day

It’s easy to spend more time in Rome or Florence, or dive deeper into Tuscany. Here’s our recommendation to use as a starting point:

Day 1

Start in Rome, in the heart of the vibrant Trastevere district, and prepare for a food-lover’s introduction led by an expert on Italy’s highly evolved food culture: from Rome’s humble street stalls and centuries-old bakeries to its traditional bars and grand trattorias. In the evening, head to dinner at a traditional Roman pizzeria, tucked away in cobbled back alley and serving up slow-rise dough that crisps up beautifully in the wood-fire oven. With no disrespect to Neopolitan-style pizza, Roman pizza is where it’s at.

  • Rome market tour with local food expert
  • Roman pizzeria visit and dinner

Day 2

Get acquainted with Campo de’Fiori, Piazza Navona, the Arno River via Ponte Sisto—and stop for an espresso and walk-through of the mighty Pantheon, all led by a local historian. After lunch, you can choose either a ride-along Vespa tour of the city, motoring through Rome’s iconic neighborhoods; or a walking tour of ancient Rome and a deep dive into archaeology and architecture, including a private VIP visit to the Colosseum.

  • Tour Rome’s iconic sites
  • Afternoon Vespa or walking tour
  • Private VIP Colosseum tour

Day 3

Stay an extra day or two in Rome—or head to the idyllic Tuscan countryside. Lunch, in a glorious medieval setting, is in the hilltop village of Civita di Bagnoregio, home to fewer than 50 people. Then it’s off to a tasting at Oliviera Sant’Angelo, a family-owned olive grove and mill that produces some of Tuscany’s finest varietals (Frantoio, Coorreggiolo, Moraiolo, Pendolino). Dinner is an elegant, open-air affair in an ancient courtyard surrounded by vineyards.

  • Private transfer to Tuscany
  • Lunch in Civita di Bagnoregio
  • VIP tour and tasting at family-owned olive grove
  • Open-air Tuscan dinner

Day 4

After a leisurely morning breakfast, it’s time to explore one of Tuscany’s near postcard-perfect villages: Pienza. It’s a UNESCO World Heritage Site and a pearl of Renaissance Italian architecture. Then it’s off to an organic cheese and dairy farm to taste their divine yogurts and to see how the unique Pecorino Toscano, a firm ewe’s milk cheese, is made. After lunch explore the winding streets of Montepulciano, a medieval hilltop town surrounded by ancient vineyards. An expert sommelier will lead us trough a tasting of Montepulciano’s most memorable Chianti Classicos and Brunellos. Magnifico!

  • Explore Pienza
  • Private organic cheese and dairy farm visit
  • Wine tasting in Montepulciano

Day 5

Start off with a VIP tour and tasting at medieval Castello di Volpaia, with a VIP tasting of their very best Chianti Classicos (DOCG, Riserva, Coltassala) overlooking the vines. Lunch is at Dario Cecchini’s legendary butcher shop, Macelleria Cecchini. Dario, whose family has been in the business for eight generations, is a master of nose-to-tail butchery. Your five-course lunch around Dario’s open grill is about celebrating the craft and culinary traditions of Tuscany.

  • VIP tasting at Castello di Volpaia
  • Five-course lunch at Macelleria Cecchini
  • Private transfer to Florence

Days 6 - 7

Florencethe cradle of the Renaissance, and arguably Italy’s most important art city. Start at Florence’s iconic cathedral, the Duomo, with its magnificent Renaissance dome designed by Filippo Brunelleschi. Then walk the streets of Florence with a focus Renaissance art and architecture, finishing at the Mercato Centrale to sample the fresh local produce on offer. Depending on your interest in art and sculpture, we’ll organize private VIP tours of either (or both!) of Florence’s most notable museums, the Uffizi and the Galleria dell’Accademia. Or simply get lost and wander the endlessly fascinating streets of Florence shopping for leather,  stopping at cafés and gelaterias.

  • Walking tour of Florence’s iconic sites
  • Explore Mercato Centrale
  • VIP tours of Uffizi and Galleria dell'Accademia

Where We Sleep

Boutique design hotels in Rome and Florence, a luxurious medieval villa overlooking the vineyards of Tuscany - our accommodations reflect the beauty and grace of Italy.


In the capital, we set up in hip Trastevere in a boutique hotel made from a converted 17th-century monastery. It’s footsteps from the neighborhood's excellent trattorias and bars, with a rooftop terrace ideal for a glass of wine and big Roman views.


The full Tuscan experience means luxuriating in the countryside, in an unforgettable hilltop hotel housed in a former medieval convent. Spacious rooms overlook an ancient village and fields of vineyards, while you can order cocktails while lounging at the dreamy pool.


Our art-filled hotel is perfectly situated between Michelangelo’s iconic statue of David and the majestic Duomo cathedral. The rooftop garden views look over terra cotta tiles and cathedral spires and distant mountains, the perfect spot to sip a glass of wine and look over the majesty of Florence.

People Love MO/AD's Rome & Tuscany

Everything was done superbly.
Kelly S.
I was blown away by how flawlessly Modern Adventure fulfilled and exceeded my expectations.
Josh S.
I loved the warmth, sincerity and caring of the Modern Adventure team.
Bob Z.


  1. How many people is this itinerary suitable for?

    We can plan a custom, private departure for any group size. Our custom trips are perfect for a couple wishing to travel on their own, a family, or a multi-generational group. If you’re looking to travel on one of our group departures on a private basis, a minimum number of travelers may apply.

  2. Can you curate an itinerary for a larger group?

    Yes, we can craft an unforgettable milestone celebration or company retreat for groups as large as 40 or more.

  3. What makes a MO/AD experience different?

    Our level of curation, care, and in-country connections. We handle everything, overseeing your experience from beginning to end with the highest levels of ownership and responsibility. We support you every step of the way with comprehensive itineraries, detailed day-by-day descriptions, insider destination info, and 24/7 dedicated support.

  4. How far in advance should I plan my trip?

    Preferably six to nine months in advance and earlier for holiday travel. We stay in unique, in-demand boutique and luxury hotels where advance reservations are important to secure the best accommodations possible. We can help with last-minute travel planning, however availability may be limited.

  5. What is typically included?

    We curate your MO/AD Private Departure to ensure the experiences are authentic, immersive, and included in your trip price. Your itinerary typically includes accommodations, airport transfers, private transportation for all day trips and excursions, privately guided tours with local guides, exclusive VIP access and activities, and meals as detailed in your itinerary.

  6. How much will it cost?

    MO/AD Private Departures typically cost $750 to $1,500 per person, per day, and vary by destination, time of year, number of people in your group, and types of activities you prefer.

  7. What's not included?

    MO/AD Private Departures do not include roundtrip airfare to/from your destination, travel insurance, gratuities for local guides, hotel incidentals, and any activities and meals not included in your itinerary.

  8. What deposits are required?

    After learning more about you, your interests, preferred style of travel, dates, and budget, we will present you with initial ideas and examples of what we can plan for you. In order to design a detailed itinerary and check availability, there is a $500 non-refundable planning deposit due. This will be applied to your final trip cost. Once your itinerary is perfect, we require a 25% non-refundable confirmation deposit to start confirming all of your arrangements. Many of our local partners and hotels require additional advance deposits to secure the best accommodations. The balance of your trip cost is due 90 days prior to travel.

  9. What travel documents are needed?

    US citizens do not require a visa to enter Italy as tourists for stays up to 90 days. The only requirement is a valid US passport. We recommend that your passport is valid for six calendar months beyond your planned departure date from Italy.

  10. Where can I find the complete terms of my booking?

    See our Terms & Conditions for complete details about our policies regarding your MO/AD Private Departure booking.