Puglia and Southern Italy

August 28 - September 7, 2027

This intimate small group journey of just 30 travelers offers an unforgettable exploration of Southern Italy's UNESCO destinations including Alberobello, Matera, Ostuni, Rome, Capri, and Naples. This tour has been thoughtfully designed with highlights including a guided tour of Pompeii, an Italian cooking class, skip-the-line access to the Vatican, and an olive oil tasting in a historic grove. You’ll also enjoy lunch at a local Italian winery, savor time on the beautiful island of Capri, and tour of the iconic Colosseum. With a blend of Italian highlights and authentic local experiences, this journey offers a truly immersive way to experience Italy.

Price

Double: $6,599 pp | Single: $7,599 pp

*Join our roundtrip group flight (JFK to Naples, Rome to JFK). Call for pricing.

Inclusions

Full itinerary as listed
17 meals (B=breakfast, L=lunch, D=dinner)
Local Italian Tour Director
Highest Travel Tour Director

Spend Three Nights in a Trullo

This is the most unique Italy tour available ANYWHERE. One of the defining highlights is a three-night stay in an authentic trullo, the iconic white limestone cone dwellings of Puglia. Nestled in the heart of southern Italy, this experience offers a rare opportunity to sleep within a UNESCO-recognized architectural tradition, surrounded by olive groves, quiet countryside, and timeless charm.

Call 262-207-4668 to book

Day 1/2 - August 28/29

Welcome to Italy!

After your overnight flight, step into the vibrant city of Naples as we start this small-group trip. Take in the sights with a driving tour that will showcase iconic highlights of this UNESCO-listed historic center. Then enjoy special admission to Cathedral of Santa Maria Assunta before checking-in to The Royal Continental along the water with impeccable views of Castel dell'Ovo and the Mediterranean Sea. This evening our group will venture to an authentic Neapolitan restaurant for a welcome dinner as we celebrate this first evening in Italy. D

Day 3 - August 30

Pompeii Archaeological Park / Wine Tasting Lunch / Naples

Rise this morning at our hotel on the coastline of the Mediterranean and travel to Pompeii Archaeological Park for an informative guided tour. Our small-group will see the remarkably preserved ruins of this Roman city buried by the eruption of Mount Vesuvius in A.D. 79, including streets, houses, shops, temples, baths, theaters, and public squares. The site is one of the best places to get a vivid picture of everyday Roman life. Our afternoon then takes us to an exquisite Italian winery for a multi-course tasting followed by lunch. Then, travel back to nearby Naples to enjoy this coastal city at leisure this evening. B, L

Day 4 - August 31

The Island of Capri

After breakfast, our small-group will cruise from Naples to the beautiful island of Capri where dramatic scenery, crystal-blue water, and a relaxing pace will showcase why it has been a resort destination since Roman times. Known worldwide for its refined elegance, Capri invites you to spend the day at leisure savoring a glass of Italian wine, enjoying handmade pasta, admiring sweeping sea views, and browsing the island’s famous shops. There’s no better place to slow down and enjoy the natural beauty, style, and charm that make Italy unforgettable. B

Day 5 - September 1

Matera / Alberobello / Trullo Stay

Today our small-group will depart Naples for the region of Puglia where our first stop will be the old town of Matera (known as Sassi), a UNESCO World Heritage Site. Together we'll take in its dramatic ancient cave dwellings, stone houses, and winding paths carved into the rock as we enjoy a group lunch. After this special meal, continue on to Alberobello which is world-famous for its whitewashed limestone trullo houses with conical stone roofs. Our group will check-in to a unique, immersive, and relaxing stay at Trulli Holiday Albergo Diffuso. This property is a one-of-a-kind accommodation with vaulted stone ceilings, original limestone features, and traditional Puglia character. B, L

Day 6 - September 2

Alberobello / Trullo Lunch / Historic Olive Oil Tour

This morning, discover the fairytale town of Alberobello with a local as they lead us on a guided walking tour of the town's Rione Monti and Aia Piccola districts. Our tour will conclude with an unforgettable and iconic lunch inside a trullo offering Puglia flavors and local specialties. Following this lovely meal, we'll have a unique visit to a Puglian historic olive oil producer and learn more about this important industry to the country of Italy. Our time here will include meeting the staff, seeing the olive groves, and tasting their local oil creations. B, L

Day 7 - September 3

Ostuni / Cathedral of Santa Maria Assunta / Mozzarella Farm

The day begins with travel to Ostuni, one of Puglia’s prettiest hill towns known as La Città Bianca (“the White City”) because of its whitewashed homes and bright character. Explore this distinctly Mediterranean town and photograph its bougainvillea flowers spilling over the white buildings before our visit to the 15th century Cathedral of Santa Maria Assunta. This afternoon, take in more Italian countryside sights as we visit a local mozzarella farm for a guided tour of the property with a tasting of their fresh cheeses and antipasto for lunch. Then travel back to Alberobello for free time to immerse yourself into the town and enjoy dinner on own. B, L

Day 8 - September 4

Polignano a Mare / Bari / High-Speed Train / Rome

This morning our group will visit Polignano a Mare, a spectacular cliffside town on Puglia’s Adriatic coast where dramatic sea views create one of southern Italy’s most memorable settings. After time to explore and take in the town’s beauty, we continue on to Bari where our small-group will board a high-speed train for Rome, the Eternal City. Upon arrival, we will check in to the centrally located River Palace Hotel, a boutique hotel ideally positioned for our time discovering the city’s famous sights. This property is only three blocks from the River Tiber and across from the Villa Borghese. Our celebratory group dinner this evening will be a proper Italian welcome to Rome. B, D

Day 9 - September 5

Colosseum / Roman Forum / Italian Cooking Class

Today begins with an unforgettable step back into ancient Rome as we visit the iconic Colosseum, one of the world’s most famous landmarks. With an expert local guide, we’ll discover the fascinating history of this extraordinary amphitheater and learn about its lasting importance in Roman culture and daily life. We then continue on to the Roman Forum where the ruins of temples, basilicas, and civic buildings once formed the beating heart of the Empire. This evening, our small-group will enjoy an elegant cooking class in the heart of Rome where local chefs will guide us in preparing a delicious three-course dinner together. B, D

Day 10 - September 6

The Vatican / Sistine Chapel / Farewell Dinner

After breakfast, our small-group will head to the Vatican, the world’s smallest country by both area and population. With skip-the-line access to the Vatican Museums, our group will enjoy ample time to explore its extraordinary collection of historic art and prestigious history, including the breathtaking Sistine Chapel. This afternoon, enjoy lunch on own and soak up time in Rome at leisure before our very special farewell dinner. B, D

Day 11 - September 7

Travel Home

Today we travel back to home to the USA from Rome, taking with us memories of Italy and new friendships from this small-group tour. B

August 28 - September 7, 2027

Arrive

Depart

Naples, Italy

Rome, Italy

Accommodations

Nights 2-4: The Royal Continental

Nestled along Naples’ scenic seafront promenade, The Royal Continental offers a luxurious stay with sweeping views of the Bay of Naples and the Castel dell’Ovo. This 4-star hotel combines modern comfort with classic Italian hospitality and features amenities such as a restaurant, bar, rooftop pool, gym, concierge service, and more.

Nights 5-7: Trulli Holiday Albergo Diffuso

Trulli Holiday Albergo Diffuso is located in the heart of Alberobello and is a highlight of this tour. The unique property offers a one-of-a-kind stay in traditional trullo, the iconic cone-roofed stone homes that define Puglia. This authentic and distinctive hotel combines historic character with modern comfort with thoughtfully appointed accommodations featuring vaulted ceilings and original stone details.

Night 8-10: River Palace

River Palace Hotel is a stylish 4-star boutique hotel in central Rome with easy access to many of the city’s major sights including the Villa Borghese. It offers elegant interiors and antique furnishings with an onsite restaurant and Italian bar. Just three blocks away from the River Tiber, this property is the perfect base for our time exploring the Eternal City.

Call 262-207-4668 to book