Highlights of Italy - August 26 - September 10, 2026 $5665.00 per person

Highlights of Italy Tour

14 Nights

Come along with Your Man in Europe for a delightful tour of some of Italy’s most stunning iconic locations, as well as hidden gems. We’ll see much of the most beautiful scenery in the entire country while visiting fantastic destinations, many of which are overlooked by most organized tours, and never seen by Big Bus tours or cruise ship side trips. Stay in boutique hotels featuring truly amazing views and unique settings with rooms specially-selected just for our tour guests. Our group will enjoy traveling on high-speed trains between destinations, in private vans for more local connections, and on air flights for longer distances. From Tuscany to Sicily, this trip is a feast for the senses! You’ll savor this truly unique travel opportunity.

ITINERARY

August 26, Wednesday - TransAtlantic overnight flights. Plan to be in Florence, Italy for the beginning of the tour on August 27th. (Early arrivals will be checking into the same hotel before the tour starts.) No activities are planned for this afternoon or evening.

August 27, Thursday – For the early arrivals, we’ll begin our official tour itinerary right after breakfast this morning. First, we’ll have a casual walking tour that will give everyone an overview of the incomparable city of Florence. There is simply no other place on earth like Firenze (the Italian name for Florence), the “Cradle of the Renaissance”! Few cities are so compact in size or so packed with extraordinary art and architectural masterpieces at every turn. Much of the old town has hardly changed since the Renaissance, so its narrow, cobbled streets are a showcase for elegant 15th- and 16th-century palaces, medieval candle-lit chapels, fresco-decorated churches, marble basilicas, and world-class art museums brimming with paintings and sculptures by Botticcelli, Michelangelo, and many others. It’s no surprise that the entire city center is a UNESCO World Heritage Site. Locals declare that their city is so incredibly beautiful that many guests actually swoon and feel overwhelmed – suffering from “The Florence Disease”!

Our walking tour ends near the world-famous Uffizi Museum. Together we’ll head for a charming restaurant right around the corner for a light – what else? – pizza lunch together. After lunch our party will split up to go to various attractions. Some will be going to the Uffizi Museum for an afternoon “skip the line” tour (Tickets must be purchased in advance, so if you want to go, let us know well before the trip date). Others will continue the guided tour to visit the wonderful Bargello Museum, a world class art museum featuring sculptures by renowned artists. It’s a small museum, so the visit there will take only about 1 ½ hours. Still others will head for the Academia Museum to visit perhaps the most famous statue in the world: Michelangelo’s David. (Again, tickets must be acquired well before the trip – so let your preferences be known.)

In the evening, we’ll all rendezvous back at our hotel to go for a very special “Welcome to Florence” dinner together at a fabulous historic restaurant specializing in Florentine cuisine.

August 28, Friday – After breakfast we will have a “choose your own adventure” day. Here are just a few of the possibilities:

A visit to the spectacular Pitti Palace and Boboli Gardens – a 15-minute walk from our hotel - a massive Renaissance complex serving as a former Medici, Lorraine, and Savoy residence. The palace houses five museums, including the Palatine Gallery and Costume Gallery, while the adjacent 45,000 sqm gardens are an open-air museum with sculptures, grottoes, and fountains. Tickets can be purchased after arrival in Florence.

Visit the interior of the Duomo and the Baptistry (not included in our walking tour) OR Climb the dome of the Duomo or the magnificent bell tower (advance tickets required)

Enjoy a day just relaxing, or exploring the narrow streets and alleyways of the old city. Florence is also a wonderful shopping destination – renowned for its leather goods, gold jewelry, and fashion shops for men and women.

Lunch and dinner will be on your own today.

August 29, Saturday – After another nice breakfast, we will be transported by private van deeper into Tuscany. On the way we’ll have a stop at the gorgeous Piazzale Michelangelo with its magnificent panoramic views of Florence.

Enroute we’ll also visit the impressive Antinori Winery for a wine tasting and lunch together overlooking the vineyards. Antinori’s story began in 1385 in the heart of the Chianti Classico region. Today it’s a place where tradition and innovation coexist harmoniously. The incredible ecologically innovative facility incorporates natural materials such as terracotta, wood, Corten steel, and glass. It centers on a deep connection with the land, respecting the beauty of the place that made possible the Antinori family's vineyards.

Our journey continues to San Gimignano. This stunning little village is the very image of idyllic Tuscany, with its picturesque location right atop a commanding hill, and it’s absolutely breath-taking vistas of the surrounding countryside. Our enchanting hotel is in the old town center, and features incomparable vistas of the Tuscan landscape. This is quintessential Tuscany, surrounded by beautiful vineyards and rolling hills. Not only is San Gimignano an idyllic place to see, but it’s also a wonderful place just to be. Have plenty of storage on your phone or camera because virtually everywhere you look will be a “Kodak Moment”! The beauty of this dream-like place will be something you’ll never forget.

After checking into our rooms, we’ll have a brief orientation tour of the quaint village. Enjoy the rest of the afternoon with free time to have a glass or two of the delicious local wine, or indulge in a world- famous gelato. Make the trek to the small square at the top of the village if you feel energetic. In the evening we’ve included a fabulous dinner of northern Italian cuisine and wine in the hotel’s atmospheric dining room before turning in (night life in San Gimignano is pretty slow.)

August 30, Sunday - We’ll take our time enjoying breakfast at the hotel (with some of the most spectacular views you’ve ever seen - maybe, except from own room’s window), before taking a very short ride to a nearby villa, where we will all dive into a real Tuscan Cooking Lesson! A delightful local family will teach us how to prepare and properly taste the fabulous local cuisine. And afterward we will sit down to savor the meal we have prepared, along with a few glasses of Tuscan wine.

After our luncheon, woozy but still on our feet, we’ll spend some time in San Gimignano itself. It is probably the most picturesque hill village in all of Tuscany. And don’t pass up the shop voted “The Best Gelato in Italy” for dessert located right across the piazza from our hotel. When you’ve worked up an appetite, enjoy a dinner on your own at just the right spot in San Gimignano tonight. Or opt to do some hunting and gathering, and have a potluck picnic together on our spectacular private terrace.

August 31, Monday - After a lovely buffet breakfast at the hotel, our private van will pick us up to continue our exploration of Tuscany. We’ll set off on a morning drive to visit Volterra. This most remarkable town traces its history back 500 years before the Romans to the Etruscans, for whom “Tuscany” is named. The town, once one of the most important cities in Tuscany, boasts both Etruscan and Roman structures, including a massive amphitheater and historic Etruscan city gate. The beauty of this enchanting, and somewhat mysterious place will be something you’ll never forget. Experience an excellent walking tour and enjoy shopping in some of the town’s excellent alabaster shops and Pecorino cheese outlets. Lunch will be on your own, so be looking for just the right spot as you roam around the enchanting streets.

After our visit to Volterra we’ll return to our very special hotel in San Gimignano. There will be a bit of free time, and dinner will be on your own this evening.

September 1, Tuesday - After our last “breakfast with a view” we’ll start on our next adventure. Our private driver will return us to Florence to catch our high-speed train to Rome. Everyone should plan to pick up a lunch to take on the train at the station in Florence on your own – there are many good offerings there. Beverages will be available on the train, but the snack car food is not recommended.

We will meet our new driver to drive through the gorgeous Italian countryside to the ancient and enchanting city of Tivoli. This small city is so close to Rome that the vast majority of its visitors are day-trippers focused on its two UNESCO World Heritage sites, and don’t actually spend much time or stay overnight in the town itself. The result is that Tivoli remains a quintessential Italian town, and not a touristy place. We’ll actually be staying in a fantastic skillfully-restored, 500-year-old Palazzo right in the heart of the oldest part of town. Our group will have exclusive use of the entire place, including its amazing Roman bath!

After getting settled in, we’ll take a stroll through the village square to orient everyone. For the rest of the afternoon, we’ll take it easy. There’ll be time to rest or spend more time exploring our neighborhood. Or take a swim in the incredible Roman bath inside our palazzo. You’ll feel like a member of Roman aristocracy of old.

We’ll gather for a nice Welcome to Tivoli dinner at a wonderful restaurant – a favorite of the locals - before heading back to our palazzo rooms and turning in for a good night’s sleep.

September 2, Wednesday – After a wonderful breakfast in our exclusive palazzo, we’ll make our way to the incredible Villa d’Este, dating back to the 1500s, one of Tivoli’s two World Heritage sites. What stands out most at the Villa are the marvelous gardens defined by terraces, grottos, staircases, grand slopes, pools, and promenades. It all evokes the legendary Hanging Gardens of Babylon, now long lost in antiquity. The intricate water system, with an aqueduct and a tunnel under the city, was inspired by the highly-advanced engineering of the Romans. The 100 Fountains lining the longest promenade make a breathtaking impression. This stunning display has been a popular background for several films – such as in the banquet scene in William Wyler’s "Ben Hur". In addition to the gardens, we can explore the magnificent villa itself, with its small, but impressive art collection.

All that splendor will have made us hungry, so we’ll break for lunch together. After lunch, for those feeling hale and hearty, feel free to venture to Villa Gregoriana, also quite near our palazzo rooms. This huge park is not actually a villa, nor is it a lavish garden, but rather a natural park with hiking trails set among Roman ruins and fabled, legendary sites. Located at the feet of the city's ancient acropolis, the massive project was commissioned by Pope Gregory XVI in 1835 to rebuild the bed of the Aniene River, which had been damaged by a catastrophic flood in1826. The undertaking served to protect Tivoli from future such floods. The site consists mainly of thick woodlands with paths that lead to the caves of Neptune and the Sirens, as well as a series of gorges, cascades, and the Great Waterfall. Dress cool, and plan to get plenty of exercise at Villa Gregoriana!

For those who prefer more level ground, take the afternoon to explore old Tivoli, shop, or just relax at a sidewalk café with a glass or two of the delicious local wine, and just think about your fellow travelers trooping up and down the trails at Villa Gregoriana.

For dinner enjoy one of the town’s many terrific restaurants on your own before returning to your palazzo rooms to luxuriate, or perhaps take a dip in the Roman bath.

September 3, Thursday - After our fabulous breakfast we’ll try to get an early start - our driver will take us to the outskirts of town to visit the magnificent Hadrian’s Villa, where we will meet our expert tour guide. The Roman Emperor Hadrian was a consummate builder who chose the hills of Tivoli for his own residence. Designed in about 117 AD, the vast complex is a monumental living edifice that even today continues to display the lavishness and enormous power of Ancient Rome. Not only is it a testimony to the power and wealth of the Roman Empire, but it’s a prime example of architectural genius. The symmetries and the interdependence of the structures – connecting one to another via guarded access points created for both the privacy and security of the Emperor – make it clear that, together, they composed a monumental compound that mirrored Hadrian's image as a great and sophisticated man. To show off his tastes and inclinations, he reproduced inside this residence many of the buildings and monuments that had fascinated him during his innumerable travels around the known world. Hadrian’s Villa is one of the finest Roman constructions to be found anywhere.

After our guided tour, we’ll have a bit of time to further explore on your own. Afterward we’ll return to Tivoli to enjoy lunch on your own, and a little free time before gathering for a wonderful dinner together in a most remarkable and memorable restaurant before spending one last night in our unique palazzo.

September 4, Friday – We’ll have to get an extra-early start, but there will be time to enjoy one more delightful breakfast at our private palazzo before our departure to Rome’s Termini station to catch our high-speed train to Bari in southern Italy. Onboard, we’ll enjoy a Train Picnic featuring local specialties as we roll along through the magnificent scenery. On arrival in Bari we’ll meet our driver to continue the journey to Matera.

We are in for a fairytale-like experience in one of the world's oldest continuously inhabited cities – dating back over 9000 years! Matera is famous for its ancient cave dwellings known as sassi, stunning rock churches, dramatic landscapes, and delicious food, making it an unforgettable destination that feels like stepping back in time. For the complete Matera experience, our hotel there is situated in one of the cave complexes. Our unique rooms have been literally carved out of the mountainside.

Matera is also known as a filming location for major motion pictures. Mel Gibson’s Passion of the Christ,

No Time to Die (James Bond), and The Young Messiah, among many others. This hilltop city is sometimes known as “Little Jerusalem.”

After we’re settled into our hotel, we’ll have a little walk around our new neighborhood and a bit

of free time before dinner together at an intriguing nearby restaurant. Afterward, we’ll retreat into our caves for a good night’s sleep.

September 5, Saturday – After a very scenic breakfast, we’ll embark on a remarkable open mini-bus tour of this ancient city. Our expert tour guide will fill us in on the amazing history of this unique place,

which includes a visit to Casa Grotta di Vico Solitario, a glimpse of what cave dwelling was like - with period furniture and artisan tools.

After the tour we’ll have lunch together in the old town. Then the rest of the afternoon and evening will offer free time to further explore the fascinating ancient city. Consider checking out nearby rock churches including the stunning Santa Maria di Idris, and St. Lucia alle Malve, with 13th-century frescoes. A stout walk can take you to into the ravine below the town. The trail is rocky and quite steep, so decent shoes are a must. At the bottom of the ravine, you reach the suspension bridge, Ponte Tibetano della Gravina, about 15 minutes from the start.

Matera’s network of underground cisterns is one of the reasons it gained UNESCO World Heritage status. Palombaro Lungo is the largest of the cisterns, a below-ground “Cathedral of Water” carved out of the rock. It was used for collecting and storing rainwater up until the early 20th century.

Dinner tonight will be on your own – find a cozy cave cafe or splurge on a gourmet meal at our hotel’s atmospheric restaurant.

September 6, Sunday – This morning we’ll have a leisurely breakfast and an open morning. You may want to attend worship services at one of the several unique churches near our hotel. There is also a spa-in-a-cave at our hotel, so it’s also possible to spend some time in the hot tub. We’ll check out, and leave our luggage at the hotel while we go out for one last memorable lunch together in Matera.

After lunch our driver will take us to the Bari airport, where we’ll board a flight for the one-hour trip directly to Palermo in Sicily. We’ll be able to get settled into our unique boutique hotel right in the heart of the oldest part of the city. By then we’ll be ready for a nice dinner together a short walk from our hotel.

September 7, Monday – After a delicious breakfast at our hotel – perched on a glass floor over ancient ruins – We’ll have a wonderful guided tour of the old city, including some great “foodie” experiences. Palermo was founded in 734 BC by the Phoenicians as Ziz. Later it became a possession of Carthage, then Greece, and was later part of the Roman Republic and Empire for over a thousand years. From 831 to 1072 the city was under Arab rule until the Norman conquest, Palermo became the capital of a new kingdom (from 1130 to 1816), the Kingdom of Sicily, and the capital of the Holy Roman Empire under Emperor Frederick II and King Conrad IV.

Today Palermo is Sicily’s cultural, economic, and tourism capital. It is a city rich in history, culture, art, music, and food. Tourists from the world over are drawn to the city for its famed Mediterranean weather, delicious cuisine, and wealth of architectural masterpieces – as well as its night life and vibrant music scene.

During the tour, we’ll head for an area where vendors will provide samplings of Sicilian cuisine for a “lunch on the go.” Afterward there’ll be free time to further explore the exotic market, or return to our hotel for an afternoon swim in a truly unique pool. Dinner this evening will be on your own. Seek out an atmospheric restaurant, or think about having a picnic by the pool, consisting of goodies obtained at the market earlier in the day – and, of course, some of the excellent local wine.

September 8, Tuesday – After an early breakfast we’re off on a full day private tour to The Valley of Temples in Agrigento. This UNESCO World Heritage site boasts many of the best-preserved temples of the Hellenistic period. We’ll visit the Temple of Demeter, the Temple of Juno, the Temple of Concordia, the Temple of Zeus, and more. If time permits, we can stop in to see the National Archaeological Museum.

At mid-day we’ll move on to the gorgeous beaches at San Leone, with their intense blue water, and golden sand. Along the promenade there we’ll have time to shop and have a lunch on your own

Afterward we’ll make our way to the famous “Stair of the Turks” to enjoy panoramic views of one of the world’s most beautiful coastlines. After a full day of sight-seeing, we’ll return to Palermo for a free evening and dinner on your own.

September 9, Wednesday - After another nice breakfast at our hotel we will have a fabulous escorted tour to visit Monreale, a historic hill-town just outside Palermo. It's a picturesque place most famous for the exquisite mosaics in the town's great Norman cathedral. The cathedral and cloisters at Monreale, dating to the twelfth century, are frequently cited as the island's greatest Norman buildings. The upper part of the cathedral's interior is completely covered in gleaming gold mosaics; more than 6,000 square meters of mosaic. They were almost certainly created by Byzantine craftsmen, and the combination of Norman, Byzantine and Islamic art and architecture here is a spectacular example of the influences which created Sicily's Medieval era.

After a half day of excellent sightseeing, we’ll return to our charming hotel for some free time to enjoy a relaxing swim, or a venture out for more exploration. Lunch will be on your own. In the evening we’ll have one last dinner together in Palermo.

September 10, Thursday – After an early breakfast, we’ll check out of our hotel to head for the airport for our flight to London’s Gatwick Airport. The tour ends on arrival in London, as our tour members have various extension plans departing from Gatwick.

Special Note: This itinerary includes 2 (two) short-hop flights on local European airlines. Baggage and carry-on requirements tend to be strict. One checked bag per person is included + one small carry-on item – not two. The checked bag allows 33 pounds (which is heavier than most single suitcases.) The carry-on, however, is not so generous. It can be a purse, man purse, or small backpack that can fit under the seat. Be prepared to temporarily transfer items to the checked bag before arriving at the gate in order to comply. Please follow the packing guidelines that will be in your tour information packet. Please contact Larry if you are unsure about luggage requirements.

What’s in store for us?

This tour is custom-planned for a small group of no more than 9 guests. Even if you are a seasoned traveler, you have never experienced Italy like this. We’re sure the journey will captivate you. You’ll be part of a magical adventure - complete with music, and surprises that will delight you at every turn. There are no exhausting bus rides or inconveniently-located hotels.

We do our best to set the mood, to weave a spell, and to make yours a total experience. Hotels and most restaurants on the entire tour have been selected for their very specific location or high level of “atmosphere”. The small group size allows us to personalize the experience in a way large groups simply cannot do. We make it easy, comfortable and stress-free. No guest has to worry about the details of where we are going next. You will feel as if you are not a tourist, but a guest of your Italian friends.

Your Tour Guide: Larry Ivy is the Tour Coordinator and guide for Your Man in Europe, and a long-time veteran of European travel and unique private tour-leading. Larry wants just one thing: for you to have “the best time of your life”!

Complete Prices for the August 26 – September 10, 2026 Tour:

$ 5665.00 Per Person

*All prices are based on Double Occupancy. Single supplement is an additional $595.

A $700 deposit has held your place on the tour. Because of more than normal advance booking deposit requirements, a first payment of 25% of the balance due ($1250.00) is requested by April 15, 2026. The remaining balance may be paid in increments on your own schedule, but the final payment is due by July 30, 2026. Make checks payable to “Your Man in Europe” - 2608 S University Drive - Fort Worth TX 76109 USA - Please inquire about other means of payment or visit our website "Tour Details" page for information about PayPal and credit card payments.

Tour Includes: Fourteen (14) nights of overnight accommodation (based on double occupancy) in exceptional, very specially selected hotels, all fourteen (14) breakfasts, eight (8) lunches, and eight (8) dinners; all ground transportation; 1st class rail travel (where available), two (2) air flights; admissions to all attractions included in the tour itinerary, knowledgeable guide services, and standard gratuities. Guests are encouraged to offer gratuities for outstanding service. There will be no additional charges for the tours and events specifically included by Your Man in Europe. There may be extra charges for optional tours not included in the detailed itinerary.

Not Included: Airfare to Italy, and returning from London; strongly recommended travel insurance; extra beverages (meals will include one beverage (wine, beer, coffee, soft drinks, bottled water) -cocktails or mixed alcoholic drinks ARE NOT included as a beverage, and will be charged separately); a la cart or premium menu selections beyond the established meal allowances; between meal snacks; gratuities for extra services such as baggage porters, or for superior service (normal gratuities are included in the trip cost); souvenirs; and privately arranged activities. The flight from Palermo to London on September 10th is included.

All overnight accommodations, as well as railroad and minibus travel will be NO-SMOKING.

This tour is strictly limited to a maximum of 9 guests travelling together