Two Countries
Unforgettable
Wine & Culture
Join us for two extraordinary journeys — through sun-drenched southern Portugal and the rolling hills of Tuscany & Umbria. Insider access, world-class wine, medieval towns, and exceptional food.
PORTUGAL - MAY 2027| ALENTEJO, BASED IN USESCO EVORA
ITALY - OCTOBER 2027 | SOUTHERN TUSCANY & UMBRIA, BASED IN MONTEPULCIANO
HOSTED BY THE DISTRICT PIT & TINTO TRAVELS
2027 Tour Destinations
Southern Portugal, the Alentejo
An Insider's View of Alentejo
May 17–23, 2027 · 6 Nights · Based in UNESCO Évora
Six nights in one of Europe's most unspoiled regions — ancient whitewashed villages, native Portuguese grape varieties, prehistoric megaliths, and a living cork forest. Hosted by District Pit, The Wine Concierge & Vino 301.
Tour Highlights
UNESCO Évora — Chapel of Bones, 800-year-old cathedral & a 1,800-year-old Roman temple
Portugal's Native Grapes — taste Antão Vaz, Arinto, Aragonez & Alicante Bouschet across the week
A Living Cork Forest — walk a working montado with a local expert guide
Fairytale Monsaraz — one of Portugal's best-preserved hilltop villages
Portugal's Stonehenge — Cromeleque dos Almendres, 2,000 years older than the English original
Estremoz Saturday Market — one of the oldest outdoor markets in all of Europe
Day-by-Day at a Glance
Day 1 The UNESCO World Heritage City of Évora
Day 2 Cork, the Montado & Portugal's Stonehenge
Day 3 Alentejo Wineries & Local Gastronomy
Day 4 Monsaraz & São Pedro do Corval (Pottery Town)
Day 5 Estremoz Saturday Market & Free Afternoon
Day 6 Farewell Dinner & Return to Lisbon
$4,300
per person (shared)
$1,000
Deposit to reserve
Southern Tuscany & Umbria,Italy
An Insider's View of
Southern Tuscany & Umbria
Oct 4-10, 2027 · 6 Nights · Based Hilltop Montepulciano
Six nights based in one of Tuscany's most stunning hilltop towns, exploring four world-renowned wine regions across medieval Umbria and Tuscany. Days built around wine, food, and culture — evenings free to wander.
Tour Highlights
Chianti Classico with I Sodi — visit Andrea's family vineyard, often the favorite stop of the tour
Medieval Siena — guided walking tour through one of Tuscany's most storied cities
Brunello di Montalcino — a world-famous tasting at Santa Giulia with a home-cooked family lunch
Vino Nobile di Montepulciano — the picture-perfect winery Le Bertille, just below your home base
Orvieto — an outdoor lunch in Umbria with Giovanni on Day 1
Cooking Class & Farewell — hands-on class at a spectacular location overlooking Tuscany
Day-by-Day at a Glance
Day 1 Pick-up in Rome & Lunch in Orvieto
Day 2 Settling into Montepulciano + Vino Nobile at Le Bertille
Day 3 Brunello di Montalcino & Gardens of La Foce
Day 4 Medieval Siena & Chianti Classico with I Sodi
Day 5 Pienza & Group Dinner in Montepulciano
Day 6 Cooking Class & Farewell Tasting
Day 7 Drop-off in Florence
$4,300
per person (shared)
$1,000
Deposit to reserve
