Overseas Adventure Travel Announcing 2026 Adventures by Land & Small Ship | Tuscany & Umbria: Rustic Beauty in the Italian Heartland

EUROPE

Vineyard, Umbria
Vineyard, Umbria
Siena, Tuscany
Siena, Tuscany


Italy: Lucca, Chianti region, Pienza, Spoleto, Rome
Small groups of no more than 16 travelers, guaranteed

From the grape-laden vines of Chianti to the olive groves blanketing the hills of Trevi, Italy's Tuscany and Umbria regions are ripe for discovery. Travel along the narrow lanes of small towns, marvel at medieval fortresses, and stroll between elegant cypress trees. Immerse yourself in this rustic, romantic part of Italy, and enjoy a way of life as timeless as the rolling vineyards warming under the Tuscan sun.

15 days starting from $4,595
including international airfare from New York
Single Supplement: FREE
Departure Dates: Mar-Dec
Activity Level: 1 2 3 4 5 Moderate

IT'S INCLUDED

Florence
Florence
Montepulciano
Montepulciano
Chianti Valley
Chianti Valley

ITINERARY

DAY 1 • Depart U.S.

Fly overnight to Florence, Italy.

DAY 2 • Arrive in Lucca, Italy

Transfer to Lucca, check into our hotel and meet those who traveled on our optional History and Culinary Delights of Bologna & Parma, Italy pre-trip extension.
Hotel San Luca Palace or similar

DAY 3 • Lucca

Set off on a walking tour to explore Lucca, a UNESCO World Heritage Site. As we explore, we'll find quiet, tree-lined squares and ancient churches with ornate facades of green, gray, and white marble. Our stroll also takes us by the Duomo di San Martino, or St. Martin's Cathedral, which was originally built in 1063. After a free afternoon to explore on your own, we'll gather for a Welcome Dinner at a local restaurant.
Meals: B,D Hotel San Luca Palace or similar

DAY 4 • Lucca Carrara Marble Quarries • Conversation about marble production • Home-Hosted Lunch

Depart for Carrara and visit the ancient marble quarries. Afterward, meet a former quarry worker to discuss the impacts of marble quarrying in the area. Later this afternoon, enjoy a Home-Hosted Lunch with a local family in Marina di Carrara before returning to Lucca.
Meals: B,L Hotel San Luca Palace or similar

DAY 5 • Lucca • Florence • Chianti region

Board a bus to Florence, birthplace of the Renaissance and a UNESCO World Heritage Site. In the company of a local guide, set off on a walking tour of the historic city center. Highlights include the Ponte Vecchio, the Church of San Miniato, the Oltrarno neighborhood, and the Piazza Santo Spirito. After some free time to explore the city on your own, depart for the Chianti countryside.
Meals: B,D Villa II Leccio or similar

DAY 6 • A Day in the Life in the Chianti Valley

Enjoy A Day in the Life in the Chianti Valley, first stopping at a local goat farm to learn about sustainable agricultural methods and then enjoying lunch with our hosts. Later, join your Trip Experience Leader on an optional hike through the Chianti Valley.
Meals: B,L,D Villa Il Leccio or similar

 

ADVENTURE HIGHLIGHT

On Day 6, spend A Day in the Life of the Chianti Valley, a region rich in gastronomic heritage.

DAY 7 • Chianti countryside • Olive oil mill • Cooking class & farmhouse lunch

Drive through the Chianti countryside, traveling through Tuscany's rolling, vineyard-carpeted hills. Stop at an olive oil mill and enjoy a tasting of this staple of Tuscan cooking. Then, continue to a nearby town for a cooking lesson and lunch at an agriturismo farmhouse.
Meals: B,L,D Villa Il Leccio or similar

DAY 8 • Transfer to Pienza • Siena

Transfer to Pienza, beginning with a short ride into Siena. Discover Siena's Old Town, a UNESCO World Heritage Site, and stroll from Piazza del Campo to Porta Romana. Departing Siena, a scenic drive brings us through the hills of Tuscany before arriving in Pienza.
Meals: B,D Piccolo Hotel La Valle or similar

DAY 9 • Etruscan Museum Montepulciano

Visit the Etruscan Museum for a talk on the history of the Etruscans in the Chianciano community. After, we'll explore the medieval hilltop town of Montepulciano.
Meals: B,L Piccolo Hotel La Valle or similar

DAY 10 • Pienza • Optional Pitigliano & Sovana tour

Today is yours to make your own discoveries in Pienza. Or, join our full-day optional tour to discover the rich Jewish heritage of Pitigliano and the ancient Etruscan necropolis of Sovana.
Meals: B Piccolo Hotel La Valle or similar

DAY 11 • Pienza • Perugia • Chocolate-making experience • Spoleto

We'll depart Tuscany and set off for Umbria, known as "the green heart of Italy." We'll first stop in Perugia, a hilltop town of medieval walls and elegant piazzas. Our walking tour through the city center concludes at a former goldsmith workshop turned chocolaterie. Try your hand at chocolate-making, then transfer to Spoleto.
Meals: B,L,D Hotel Clitunno or similar

DAY 12 • Spoleto • Optional Umbrian Folk Music tour

Explore Spoleto, a walled hill town framed by the towering Apennine Mountains, featuring the Duomo di Spoleto, an eleventh-century cathedral, and a 774-foot-long medieval bridge. Later, join the optional tour to Spello for a concert in a local Umbrian musician's home before dinner in a local restaurant.
Meals: B,L Hotel Clitunno or similar

DAY 13 • Spoleto • Truffle hunting • Conversation about truffle exclusivity

Visit a small mountain village nestled in the Apennines and meet up with local truffle hunters and their dogs to seek out the precious mushrooms. Later, return to the village for lunch and conversation with a local shepherd about truffle hunting.
Meals: B,L,D Hotel Clitunno or similar

ADVENTURE HIGHLIGHT

On Day 13, take part in the cherished tradition of truffle hunting in an Umbrian mountain village.

DAY 14 • Umbria • Rome

Bid farewell to Umbria and begin the overland transfer to Rome. In Rome, enjoy a walking tour of the Trastevere district, a young and bohemian area of the city. Tonight, we'll toast our memories of our Italy and Tuscany travel experiences during a Farewell Dinner at a local restaurant.
Meals: B,L,D River Palace Hotel or similar

DAY 15 • Return to U.S.

Transfer to the airport for your return flight home. Or, begin your Rome: Ancient Sites & Hidden City Gems post-trip extension.
Meals: B

Trastevere district, Rome
Trastevere district, Rome
Tuscany
Tuscany

Want to know more? Find the full itinerary and dates & pricing at www.oattravel.com/bta

PERSONALIZE YOUR EXPERIENCE on your Italy adventure

OPTIONAL EXTENSIONS

Choose to maximize your discoveries and value when you add a pre- or post-trip extension—or both to your adventure.

History and Culinary Delights of Bologna & Parma, Italy

PRE-TRIP: 6 nights from $2,395

Parma, Italy
Parma, Italy

Witness the red-brick palazzi and culinary treasures of Bologna, and stroll along the cobbled lanes of historic Parma.

IT'S INCLUDED

Learn more at www.oattravel.com/bta-bologna-2026

Rome: Ancient Sites & Hidden City Gems

POST-TRIP: 4 nights from$1,795

Rome, Italy
Rome, Italy

Explore Rome's ancient, bubbling fountains, cobbled plazas lined with espresso cafés, and awe-inspiring monuments dating back to the Roman Empire.

IT'S INCLUDED

Learn more at www.oattravel.com/bta-rome-2026

ARRIVE EARLY

We recommend that you relax after a long flight or explore more in depth before your trip. Price shown includes accommodations and private airport transfer.