October 16-23, 2027 (likely to sell out!)

Puglia's Autumn Bounty

HIGHLIGHTS

Bari Vecchia

A welcome dinner and guided walk through Bari’s old town

Matera, Basilicata

A day trip to Matera, with a guided tour of the Sassi caves

Olive harvest

A visit to an olive farm during the harvest, with a hearty lunch

Alberobello

Tour the Valle d’Itria’s hilltop towns and magical trulli dwellings

Baroque Lecce

Sightsee and taste your way through Baroque Lecce, Puglia’s golden city

PRICED FROM

$5,899

per person

$750 deposit

Payment plans available


CHECK
AVAILABILITY

📅 DATES

October 16-23, 2027

🗓 DURATION

8 Days/7 Nights

👤 GROUP SIZE

Max 12

🏅 ACTIVITY LEVEL

Daily walking, stairs, uneven pavement

📍 LOCATION

Begins in: Bari

Ends in: Bari

Food market in Puglia

About This Trip

October in Puglia brings the start of the olive harvest and a bountiful season for food and wine, which is the focus of this tour. On this immersive tour, two of the region’s most distinctive landscapes unfold before you: the trulli-dotted Valle d’Itria, where whitewashed hill towns preside over ancient olive groves, and the golden Baroque city of Lecce, gateway to the wild Salento coast.

Food and culture are intrinsically linked across Italy, and Puglia epitomizes this connection. Our days are built around hands-on cooking with Pugliese women, private olive oil and wine tastings, and street-food walks through ancient lanes. Mornings include guided tours, experiences and tastings that may last through lunch, while evenings may offer group dinners or free time to explore on your own. At each stop on our tour, we’ll immerse ourselves in the history, heritage and traditions of this ancient land, and learn about Puglia’s rich culinary culture.

The tour begins with a night in Bari, then three nights either in the Valle d’Itria or coastal Ostuni, and finally, three nights Lecce.

What's Included?

Experiences & Activities

Private guided tours, a hands-on cooking class & plenty of tastings of local products

4-Star Hotels

Characteristic hotels, hand-picked for their charm and comfort

Most meals & wine

Sample the delicious, seasonal & farm-to-table bounty of Puglia. Wine is always included with our meals!

Expert Guides

Expert local guides for every activity — people who know the towns, landscapes and people of Puglia

Special Moments

New friends, long, festive meals and lots of unscripted fun!

Transportation

From airport pick-up to transfers to drop-offs, we'll travel in luxury vans or minibuses

Itinerary at a Glance

Day 1: Welcome to Puglia!
  • Arrive Bari, Puglia’s capital, and settle into the hotel before we gather for a welcome dinner in the city.

    Accommodations: Four-star hotel in Bari

Meals: Welcome dinner

Day 2: Bari Vecchia, then on to the Valle d'Itria
  • After breakfast, a local guide will walk us through Bari Vecchia, the old town, including the Basilica di San Nicola (home to the relics of St. Nicholas, yes, that one) and the lanes where women make orecchiette by hand outside their front doors.
  • After a group lunch in Bari, we’ll transfer to the Valle d’Itria, about an hour away, our base for the next three nights.
  • Dinner is on your own tonight, either at the hotel or in a nearby town (transportation provided)

Accommodations: Four-star hotel in the Valle d’Itria or Ostuni
Meals: Breakfast, lunch

Day 3: Matera and Alberobello
  • Today is our day trip to atmospheric Matera, just over the border in Basilicata.
  • A local guide will take us through the Sassi, the ancient cave dwellings and rock-cut churches that were lived in until the 1950s and are now a UNESCO World Heritage Site. (Fair warning: there are a lot of steps!)
  • After lunch in Matera, we’ll stop in Alberobello on the way back to see its famous trulli.
  • Evening free.

Accommodations: Four-star hotel in the Valle d’Itria or Ostuni

Meals: Breakfast, lunch

Day 4: Olive harvest and a Valle d'Itria winery
  • October is the start of olive harvest season in Puglia, and this morning we’ll head to a masseria (a traditional fortified farm estate) where, depending on the weather and the year, you might find the harvest in full swing.
  • We’ll visit the mill, taste the new oil and sit down to lunch.
  • In the afternoon, we’ll visit a winery in the valley for our first tasting.
  • Evening free.

Accommodations: Four-star hotel in the Valle d’Itria or Ostuni

Meals: Breakfast, lunch

Day 5: Cooking class, then on to Lecce
  • This morning it’s a hands-on cooking class, where we’ll learn to make orecchiette and other Pugliese dishes, and then eat everything we’ve made for lunch.
  • Afterward, we’ll transfer to the Baroque city of Lecce, about 90 minutes south, for the last three nights of the tour.
  • Evening free.

Accommodations: Four-star hotel in Lecce

Meals: Breakfast, lunch

Day 6: Baroque Lecce and street food
  • Our local guide will join us for a morning walk through Lecce’s historic center, with its honey-colored stone churches and palazzi, the Basilica di Santa Croce and a Roman amphitheater right in the middle of town.
  • Lunch is on your own, and the afternoon is free for strolling and shopping.
  • Early evening, we’ll convene for a street food tour featuring Leccese delicacies such as pasticciotto, rustico leccese and caffè leccese,

Accommodations: Four-star hotel in Lecce

Meals: Breakfast, dinner (street food tour)

Day 7: Salento wine country and Otranto
  • This morning, we’ll head into Negroamaro country for our second wine tasting, with lunch at the winery.
  • In the afternoon, we’ll visit Otranto, a walled town on the Adriatic whose cathedral has a 12th-century mosaic floor covering almost the entire nave.
  • Back in Lecce, we’ll gather for our farewell dinner.

Accommodations: Four-star hotel in Lecce

Meals: Breakfast, lunch, farewell dinner

Day 8: Arrivederci, Puglia!
  • After breakfast, we’ll say our goodbyes and get you transferred to Bari or Brindisi airport or the Lecce train station.

    Meals: Breakfast

Tour Gallery

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5 Roadblocks to an “Authentic” Italy Trip

(…plus how to avoid them, from someone who’s lived here for 17 years).