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Tuscan Escape | Summer | 2027 route map

Meet the group in Rome and take a coach orientation of the city with the Trip Manager. Join locals for an evening passeggiata.

Leave Rome and ride a funicular to the hilltop centre of Orvieto for views of the city and countryside. At Casale Polegri near Baschi, meet the Polegri family, tour their vineyard and olive grove, learn about their farming, and have lunch with their wine. Continue to Siena to explore its medieval streets and Piazza del Campo at your own pace, then travel to the hotel in Tuscany.

Meals: Breakfast,Lunch

Walk from Radda to a local vineyard for a wine tasting with a light snack of cured meats and cheese. Then visit the hilltop town of San Gimignano, known for its medieval towers and views across the Chianti valley.

Meals: Breakfast,Dinner

Take a locally guided walking tour of Florence, seeing the Duomo, Basilica Santa Croce, Giotto’s Bell Tower, the Baptistery, Piazza della Signoria and Ponte Vecchio, with a photo stop at David. Enjoy free time to shop, sightsee or try Bistecca Fiorentina, and visit Il Porcellino before leaving.

Meals: Breakfast

Tour Pisa with a Local Guide and see the Leaning Tower. Stop in Lucca to explore its piazzas, Renaissance architecture, historic cafés, cobbled streets and 16th-century walls. Visit Fattoria Al Dotto winery outside Lucca to taste local wines with a platter of snacks.

Meals: Breakfast

Spend the morning relaxing at the hotel or join an optional Tuscan cooking class. Travel to Montalcino, where you can choose to have dinner and try the town’s Brunello di Montalcino wine. Return to the hotel for the final night in Tuscany.

Meals: Breakfast

Travel from Tuscany to Rome, arriving in the afternoon, and say goodbye to the group.

Meals: Breakfast

What’s included

Rome orientation walk with your Trip Manager on arrival.
6 breakfasts, 1 lunch at Casale Polegri with house wine and dessert, and 1 dinner included.
6 nights in hotels: 1 night in Rome at a conveniently located hotel and 5 nights at Park Hotel Chianti (or similar) in Tuscany.
MAKE TRAVEL MATTER Experience at Casale Polegri: guided walk through the family vineyard and olive grove with a traditional lunch and wine tasting.
Locally guided walking tour of Florence covering the Duomo, Basilica Santa Croce, Giotto’s Bell Tower, the Baptistery, and Piazza della Signoria.
Guided tour of Pisa with a Local Guide.
Wine tastings with light snacks in Chianti and at a local winery near Lucca.
Coach travel throughout the trip, including Rome–Tuscany–Rome and day trips to Siena, Florence, Pisa, Lucca, Radda, San Gimignano, and Montalcino, plus the Orvieto funicular ride to the hilltop center.

What’s not included

Travel insurance is not included and should be arranged by the traveller.
Flights to and from Rome are not included.
Visas for Italy (if required) are not included and must be arranged independently.
All other meals not listed in the Dining Summary (6 breakfasts, 1 lunch, 1 dinner) are at your own expense.
Optional experiences, such as the Tuscan cooking class in Tuscany, are not included.
Personal expenses such as additional drinks, snacks, souvenirs, and other incidentals are not included.

Additional information

  • 6 Breakfast (B)
  • 1 Lunch (L)
  • 1 Dinner (D)
  • Baschi: We’ll head to the rocky (but so picturesque) village of Baschi to visit Casale Polegri. Stroll around the vineyards and olive orchards on a short tour of the azienda agricola. We’ll learn about the farming techniques used by the Polegri Family to harvest their fresh plants and fruit. We’ll end the afternoon with a crunchy bruschetta topped with homemade extra virgin olive oil, focaccia bread with homegrown rosemary and vegetables. And of course, some risotto or pasta. All of this with a glass of their homemade wine and dessert. Happy tummy, happy life!
  • Florence: See the Duomo, Basilica Santa Croce, Giotto’s Bell Tower, the Baptistery & Piazza della Signoria on a locally guided walking tour of Florence.
  • Pisa: Get a Pisa the action! Your expert guide will enlighten you, and you’ll finally get the ‘propping up the tower’ pic you’ve longed for. 
  • Lucca: Visit the Fattoria Al Dotto winery outside Lucca and taste local wines accompanied with a delicious platter of snacks

Hop on the funicular to crest Orvieto’s dramatic tufa plateau, where breezy belvederes reveal quilted Umbrian hills and vineyards. Step out to admire quiet lanes and sunlit squares perched high above the valley floor.

From the ridge, take in the striped facade of Orvieto Cathedral and the clifftop maze that once thwarted invaders. This swift ascent doubles as a scenic lift and a primer on how geology shaped a medieval stronghold.

Begin your Italian journey by meeting your Trip Manager and joining a guided orientation through the storied streets of Rome. Pick up practical tips on local etiquette, dining, and navigating neighborhoods, while tuning into the rhythm and personality of the city’s piazzas and boulevards.

As twilight approaches, slip into Italy’s social ritual and enjoy a relaxed passeggiata. Savor the warm glow on stone facades and the conversational hum that gives the Eternal City its timeless allure.

Stroll the vineyards and olive orchards at Casale Polegri, a family-run azienda agricola in the Umbrian countryside. Meet your hosts and learn how tradition pairs with biodiversity and water-wise practices during this MAKE TRAVEL MATTER Experience.

Settle beneath a veranda for bruschetta drizzled with homemade extra virgin olive oil, rosemary-scented focaccia, seasonal vegetables, a risotto or pasta course, dessert, and estate wines. Each bite and sip reflects the Polegri family’s land and hands.

Explore Siena’s brick-hued heart, arriving at the scallop-shaped Piazza del Campo, home to the thundering Palio di Siena. Trace narrow Contrade lanes strung with flags and browse artisan workshops tucked beneath Gothic facades.

Lift your gaze to the striped marble of the Gothic Duomo and the Torre del Mangia spiking the skyline. Civic pride and medieval wealth are written into every stone, fresco, and bell chime.

Walk from Radda to a local vineyard along rosemary-scented lanes and terrace rows framing Chianti’s rolling hills. Arrive among cypress and vines to sample Chianti Classico paired with a light spread of cured meats and pecorino.

Hear how Sangiovese grapes, the Gallo Nero emblem, and careful oak aging shape ruby hues and violet notes. The landscape, labor, and heritage are poured straight into your glass.

Explore San Gimignano, the Town of Fine Towers, where a turreted skyline crowns vine-clad slopes. Wander stone alleys to sunlit squares lined with artisan stalls and inviting gelaterie.

A UNESCO World Heritage site, the town preserves merchant-built tower houses that signaled status in the Middle Ages. Pause for photos and sweeping views over the Val d’Elsa from its ramparts.

Join a locally guided walking tour to the Duomo and Giotto’s Bell Tower, cross the Ponte Vecchio, and thread among statues in Piazza della Signoria. Hear how banking, trade, and craft guilds powered the city’s Renaissance bloom.

Stand before the replica of Michelangelo’s David and uncover stories of Brunelleschi’s engineering and Medici patronage. Florence unfolds as a living gallery where ideas sculpted stone and civic life.

Follow your Local Guide into Pisa’s monumental heart, the Piazza dei Miracoli. Frame that essential shot with the Leaning Tower of Pisa while learning how soft subsoils tilted its elegant arcades.

Trace the artistry of the Cathedral and Baptistery, where Romanesque proportions and haunting acoustics elevate marble into music. Pisa’s maritime past and scholarly present meet on these luminous lawns.

Wander Lucca’s Renaissance walls and tree-lined ramparts for an elevated look at church spires and terracotta roofs. Drop into the old town to browse artisan boutiques and linger at historic cafés on shaded squares.

The city’s Roman roots still echo in the oval outline of Piazza dell’Anfiteatro, while graceful palazzi and simple trattorie keep daily life humming within the fortifications.

Visit Fattoria Al Dotto outside Lucca for a guided cellar conversation and tasting flight. Sample regional expressions while hearing how vineyard aspects, harvest timing, and fermentation choices shape each vintage.

Pair your pours with a platter of Tuscan salumi and cheeses as your host shares stories of small-scale winemaking in the Lucca hills. A relaxed, flavor-first window into local terroir.

Visit Montalcino, a stone-clad hilltown crowned by a 14th-century fortress and circled by sunlit vineyards. Stroll lanes lined with enoteche, craft shops, and quiet churches set against countryside panoramas.

Learn how exacting rules and extended aging forged the reputation of Brunello di Montalcino. Elevation, exposure, and Sangiovese’s character converge here to create a wine of structure and depth.

Roll up your sleeves for a hands-on cooking class with a local chef, shaping fresh pasta and sauces from seasonal ingredients. Learn knife skills, dough techniques, and the kitchen wisdom that turns simple produce into abiding flavors.

This culinary session is at additional cost and bookable on tour, often available during your Chianti stay on day 6. Sit down together to enjoy the dishes you’ve prepared.

Craft your own leather keepsake in an artisan bottega, selecting hides and learning traditional tooling and stitching from skilled makers. Watch edge-burnishing and pattern cutting before assembling a small accessory to take home.

This hands-on session is at additional cost and bookable on tour, typically scheduled during your time in Florence on day 4. Support local craftsmanship and carry a piece of the city’s heritage.

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