A Journey to Beautiful Puglia October 12 – 24, 2026
Feel the warm, resounding beat of southern Italy’s heart on the October 2026 Friends of Montauk trip.
Italy’s lesser-known locales leave a major impression—and nowhere more so than Puglia and Basilicata, the sun-drenched heel of the boot and one of Italy‘s most charming regions. Known for its never-ending coastline, whitewashed hill towns, and sublime food, the feeling here is quite different from the more familiar Mediterranean side of the country.
With the Adriatic Sea to the east and the Ionian Sea to the south, the region’s pretty coastal towns are perched high atop the rocks looking out over the turquoise waters. The towns themselves are clusters of low laying white houses punctuated by the occasional church spire. Its coastal position meant that Puglia was invaded and colonized many times, and each dynasty, from the Greeks, Romans and Byzantines, to the Normans and Spanish, left their historic mark.
And if that was not enough, the food in Puglia is some of the best in the country. Expect fresh burrata, incredible seafood and wonderfully rich and heart-warming peasant dishes.
We will be touring the region known for its food, wine and olive tastings … plus learn how to make burrata, bake bread and more unique tour inclusions on this most memorable holiday.
TOUR INCLUDES
Round trip transportation from Montauk to JFK
Round trip air to Italy
11 night’s outstanding hotel accommodations
Hotel service charges and taxes
Breakfast every day
5 lunches
8 dinners
Transportation throughout by coach
Sightseeing as per itinerary
Sightseeing entrance fees
SPECIAL FEATURES
Pasta cooking class
Cheese making (Mozzarella AND Burrata) & tasting class
Street Tasting Lunch in Bari
Bread workshop and tasting in Matera
Visit to the cave dwellings in Matera
Lunch at a local Puglia seafood restaurant
Cooking class and lunch at Orto Terra Madre
Special dinner at Braceria with local grilling
Olive Oil tasting and lunch
Visit to local farmhouse vineyard along with wine tasting and farewell dinner
ITALY TOUR ITINERARY
1st day: Monday, October 12 – To Bari, Italy
Depart the East End for JFK to board our connecting flights for Bari, Italy.
2nd day- Tuesday, October 13: Arrival Bari. Onto Santo Stefano di Cassano (D) Arrive in Rome to connect to our flight to Bari. After arrival, we will be escorted to our hotel where we will have some time to relax before our welcome dinner at our hotel.
3rd day- Wednesday, October 14: In Santo Stefano di Cassano (B) This morning, we will have a SPECIAL scenic walk on an easy loop trail with some panoramic stops. Return to our hotel for lunch on our own. This evening, why not dine at a family-run trattoria specializing in fresh pasta tossed with basil-laced pesto alla genovese. Toast the start of your journey with a glass of Vermentino while lanterns glow overhead. Drift back to your accommodation lulled by the distant hum of cicadas and river currents.
4th day- Thursday, October 15: In Santo Stefano di Cassano (B/D)
A Free day in this the amazing 16th century village of Santo Stefano di Cessanio on the edge of the Campo Imperatore plain in the Gran Sasso National Park. Walking in town is an architectural delight with its archways, cobbled streets, Head to the town’s central piazza to sip an espresso at a sun-drenched café, listening to locals chat animatedly. Browse tiny artisan shops brimming with handmade ceramics and regional delicacies like squacquerone cheese. Lose track of time as you meander along the riverbank path, spotting swans gliding just offshore. This evening, we have dinner at our hotel.
5th day- Friday, October 16: To Trani and Bari (B/L/D) After enjoying breakfast, we will check out of our hotel for a full day of touring as we make our way to Bari. The first stop is in Trani where we will have lunch served at a typical local restaurant by the port. It will be a chance to savor fresh regional specialties and local flavors. Following lunch, a guide of the town where we will explore the charming historic center, with its medieval streets and picturesque harbor and visit the iconic Trani Cathedral, a remarkable example of Apulian Romanesque architecture. The tour is expected to last around one to one and a half hours, providing insights into the city’s history, culture, and architectural highlights before we continue to Bari, where we will check in at our hotel and have time to relax before the evening. Dinner at our hotel.
6th day- Saturday, October 17: Discovering Bari (B/L) This morning it’s a walking tour of Bari Vecchia, the atmospheric old town characterized by narrow streets, lively squares and everyday local life. Highlights include the Basilica of Saint Nicholas, one of the most important pilgrimage churches in Europe and a symbol of unity between Eastern and Western Christianity, as well as the Castello Svevo, originally built by the Norman king Roger II and later fortified by Emperor Frederick II. The walk continues along the elegant Lungomare, one of the most scenic seaside promenades in southern Italy. Our lunch features a street food tasting, allowing us to experience Bari’s culinary traditions with specialties such as focaccia barese, panzerotti, and sgagliozze. The afternoon are evening are free to independently walk along the waterfront and also dine at a typical local restaurants.
7th day- Sunday, October 18: In Bari. Touring to Matera, the City of Stone (B) After breakfast, we depart for Matera, one of the oldest continuously inhabited cities in the world. Famous for its Sassi, ancient cave dwellings carved into limestone, Matera offers a unique landscape shaped by thousands of years of human history. Once a symbol of poverty, the city has undergone a remarkable transformation and is now a UNESCO World Heritage Site and former European Capital of Culture. Our guided tour explores the Sassi districts, ancient churches, and panoramic viewpoints. The experience continues with a traditional “Matera Bread” workshop, where we learn about the centuries-old baking tradition that earned Matera’s bread a protected status. Return to our hotel for the balance of the day and evening free.
8th day- Monday, October 19: To Polignano a Mare and to Monopoli (B/D After breakfast we depart for Polignano a Mare, dramatically perched on limestone cliffs above turquoise waters. Famous as the birthplace of singer Domenico Modugno, the town offers spectacular viewpoints, intimate streets, time for photos and a stroll through the historic center and having lunch on our own at one of the seaside restaurants. Then continue to Monopoli, a charming coastal town with whitewashed houses, a historic port, and traces of Greek, Roman, and medieval influence. Its old town preserves ancient walls, noble palaces and picturesque squares overlooking the sea. We end the day with arrival at our hotel accommodations, followed by dinner at our hotel.
9th day- Tuesday, October 20: In Monopoli. Excursion to Lecce, the Florence of the South (B/L/D) A full-day excursion takes us to Lecce, often referred to as the “Florence of Southern Italy,” for its exuberant Baroque architecture. Built almost entirely from local golden limestone, the city flourished between the 16th and 18th centuries. A guided tour explores the historic center, including the richly decorated Duomo, Piazza Sant’Oronzo, and the remarkably preserved Roman Amphitheater, a reminder of Lecce’s ancient Roman origins. During the visit, we will enjoy a street food tasting of local specialties such as Pasticciotto, Puccio, Rustico, and the traditional caffè Leccese, blending espresso with almond syrup and ice. Return to our hotel in the late afternoon. Tonight, we will enjoy a Braceria BBQ dinner, showcasing grilled local meats and regional flavors.
10th day- Wednesday, October 21: In Monopoli: Tour to Alberobello and Puglian Cooking Traditions (B/L/D) After breakfast we have a guided visit to Alberobello that introduces the iconic Trulli, unique dry-stone dwellings with conical roofs, recognized as a UNESCO World Heritage Site. These structures date back to the 14th century and reflect ingenious construction techniques using local limestone.Lunch is included in a hands-on Puglian cooking class, held in an orchard setting. Here we will learn to prepare traditional pasta and fresh cheeses, gaining insight into the region’s agricultural and culinary heritage. In the afternoon, arrival at the selected Masseria, a traditional farmhouse that reflects Puglia’s local cultural heritage. Dinner and overnight at our hotel.
11th day- Thursday, October 22: In Monopoli. Excursion to Ostuni and Olive Oil Tasting (B/L) After breakfast and a short ride, we reach Ostuni, known as the “White City” for it limewashed houses that gleam under the southern sun. A guided tour of the historic center reveals layers of history from Messapian, Roman, medieval, and Renaissance periods. Our Ostuni experience continues with a stop at a local Masseria for some olive oil tasting, highlighting one of Puglia’s most important agricultural traditions. Lunch follows, featuring seasonal products and authentic rural cuisine. The afternoon is free for exploration before returning to our hotel and dinner on our own at one of the local restaurants.
12th day- Friday, October 23– In Monopoli: (B/D) Most of the day is at leisure, offering time to relax at our hotel. In the later afternoon we visit a local winery, strolling among the vineyards and learning about Salento’s winemaking traditions. The day concludes with a wine tasting and farewell dinner at the vineyard, celebrating the flavors, landscapes, and cultural heritage of Puglia. Return to the hotel in the evening.
13th day- Saturday, October 24: To JFK (B) After breakfast we will transfer to the airport in Bari for connecting flights back to New York via Rome. Same day arrival at JFK and then back to the East End.
Hotels or similar
Santo Stefano di Cassano (3 nights) Sextantio Albergo Diffuso hotel. Set amidst a former medieval agricultural village, with views across the surrounding mountain range, this property oozes historic charm. Enter your room with the clink of a huge iron key and you will be pleasantly surprised by the ‘rustic-chic’ decor. Although there is nothing primitive about the handwoven rugs and throws, not to mention immersive baths and remote-controlled underfloor heating, this property will be a unique experience.
Bari (3 nights) Nicolaus Hotel. In the heart of Poggiofranco, a lively neighborhood few steps away from Bari city center, The Nicolaus Hotel rises grand and elegant. Enjoy the best of our luxury and exclusive services, get started in efficient and functional spaces with the latest technologies. Live a contemporary and timeless experience. Mixing style and comfort, the Nicolaus rooms are an expression of the sophisticated refinement of the spaces.
Monopoli (5 nights) Il Melogtano is an authentic enclave of the magnificent Apulian landscape, enveloped by the verdant embrace of ancient olive trees that amplify its beauty and character. It is renowned for being the first Masseria in Italy to host guests, unveiling the secrets of 400 years of history. Nestled in the countryside of Monopoli among centuries-old olive trees, this 17th-century farm is now a delightful resort. The slow rhythms draw a resort framed with the vibrant colors of the bougainvillea. A swimming pool and Spa among the olive trees, are a perfect venue where you can laze and relax.
** Bonus! SAVE! You will receive a 5% discount if ALL payments are made by check or money order. This discounted price is noted below in red. Special No Interest + No Payments for 6 Months Plan Now Available! RMC Travel now offers the “PayPal Credit” Plan (Click here for details)
PRICING
Per Person in Double Occupancy Room: $5,899 payments via check
$6,199 payments via credit card
Per Person in Single Occupancy Room: $7,098 payments via check
$7,469 payments via credit card
Upgrade to Premium Economy Class on Transatlantic Flights (8 seats available) – All 8 seats are now booked. Additional seats “On Request” Extra legroom and ergonomic, extensively reclining seats. Dedicated cabin. Priority check-in, boarding and baggage claim. Baggage allowance: 2 x 23 kg checked bags $1,119 supplement ($1,179 via credit card) PLUS tax
Upgrade to Business Class on Transatlantic Flights (10 seats available) – Only 2 seats left $3,650 supplement ($3,839 via credit card) PLUS tax
Add to above costs:
U.S. airline facility security and tax charges to both Economy or Business Class $599 ($629 via credit card)
Prepaid Gratuities $175 ($185 via credit card)
Payments: Initial Non-Refundable Deposit of $1,000 per person ($1,050 via credit card) is required to secure your space on the tour.
Note: $2,000 ($2,100 for credit cards) for Business Class travelers.
Final Payment is due on or before August 1, 2026.
If you have already registered and are looking for payment details, please click here.
Travel Insurance As travel professionals, RMC Travel highly recommends travel insurance. Sometimes unexpected circumstances can arise. A sudden emergency just before or during your trip could spoil your vacation and deplete your resources.
We have recently seen some of our valued travelers lose not only their non-refundable deposits, but also their entire tour payments because they hoped they would not need trip cancellation insurance.
You should protect your trip investment and yourself in regards to health, property and trip payments. That is why we provide you with an easy way to contact BMSJ’s preferred insurance provider, Allianz Global Assistance. If you need additional information or have questions, please call Allianz directly at 1-800-284-8300, and refer to code F025323.
RMC Travel will be sending you additional details and a brochure with your confirmation on trip cancellation/interruption travel insurance
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