Italy Adventure: Rome, Tuscany, and Venice – October 9-22, 2025
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Duration
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Overview
An incredible Italian Adventure awaits featuring a six night stay in a private Tuscan Villa bookended by stays in Rome and Venice. Explore the rich history of Rome (Vatican City, Colosseum, Forum, Palatine Hill, Catacombs, Sistine Chapel, and more!) while staying four nights in the Centro Storico and enjoying fabulous Italian cuisine. In Tuscany, the Villa will serve as home base for day trips into hilltop villages (Siena, Montepulciano, San Gimignano, Montalcino, Florence, Perugia, Rasiglia, and Umbertide) and allow guests to relax and feel at home while still being pampered by the luxurious surroundings and food prepared by a private chef. Cap off the adventure in Venice with its narrow streets, ubiquitous canals, historic buildings, and romantic charm. Do not miss this excursion.
Day 1 – October 9, 2025: Travel Day
Get ready for pickups at our usual spots in Salem, Woodburn and Tualatin. Since this is an extended trip, we do not recommend that anyone leave their cars in Woodburn or Tualatin. Parking at the Holiday Inn in Salem will be fine. The group will leave on an early afternoon flight on United 776 bound for Rome, Italy! Today is a travel day; sit back, relax with a book, or watch a movie or two.
Day 2 – October 10, 2025: Arrive in Rome
The group will arrive in Rome early afternoon. After clearing customs and immigration, a motor coach will take the group to the Hotel St. Martin, a 4 Star hotel where it will stay for the next four nights. After settling in, the group will have diner and then have free time to explore or rest until the next day. (D)
Day 3 – October 11, 2025: Vatican City and Sistine Chapel Tour
After breakfast at the hotel, the group will travel by motor coach to the Vatican City for a guided tour with a local Step-on Guide to explore St. Peter’s Square, the Vatican Museum, stunning architecture and art, and the most famous ceiling in the world, Michelangelo’s masterpiece in the Sistine Chapel. In the late afternoon, the motor coach will return the group to the hotel for free time. Dinner will be as a group in a local restaurant. (B, D)
Day 4 – October 12, 2025: Colosseum, Forum, Palatine Hill
After breakfast at the hotel, the group will again set out with the Step-on Guide to explore Rome. Today, more world-famous locations are on the agenda: Colosseum, Roman Forum, and Palatine Hill. These three locations, monuments, and archeological sites will give insight into the lives of people from the most ancient parts of the city and the nucleus of the Roman Empire. In the afternoon, the group will have free time to explore before dinner at a local restaurant. (B, D)
Day 5 – October 13, 2025: Roman Catacombs and Capuchin Crypts
After breakfast, the group will spend its final full day in Rome first exploring the Roman Catacombs and the Capuchin Crypts. The group will join their Step-on Guide for a tour of these underground burial locations, the oldest of which date back almost 2000 years. The Capuchin Crypt is a slightly more modern burial site for friars beneath the church of Santa Maria. This afternoon, the group will have more free time to explore the city center and culinary delights. Guests will have their farewell to Rome dinner tonight in a local restaurant. (B, D)
Day 6 – October 14, 2025: Ancient Ostia, Bomarzo, Tuscany and the Villa
After breakfast as the hotel, the group will check out and say ‘Arrivederci’ to Rome and take a circuitous route to Tuscany by way of Ancient Ostia, an archeological site at the ancient port town which Rick Steves calls “the most underappreciated sight in all of Italy”. From here, the group will travel toward Tuscany with a stop to see the ancient stone monsters in Bomarzo. The group will arrive at the Villa, home for the next six nights, greeted by fantastic views and dinner prepared by a private chef. This evening, settle in and relax, maybe with a glass of wine from the region. (B, D)
Day 7 – October 15, 2025: Villages of Siena and San Gimignano
Breakfast today will be provided at the Villa for all guests to enjoy and soak up the surrounding landscape before heading out to visit two amazing hilltop villages in Tuscany, Siena and San Gimignano, to absorb the beauty of their cathedrals and piazzas. The two villages will be introduced by a Step-on Guide from the Tuscany so that both the beauty and the history of the region can be truly appreciated. Dinner will be enjoyed in a local countryside restaurant near the Villa with plenty of time to savor the food, drink, and the surroundings. Return to the Villa and relax in style. (B, L, D)
Day 8 – October 16, 2025: Florence Art and Architecture of Renaissance Masters
This morning guests will have breakfast before departing for Florence for the day. Guests will be dropped off just outside Florence’s city center and then make their way on foot toward the terracotta-tilled roof of the Duomo and amazing Renaissance art and architecture. A local Step-on Guide will lead the group through the streets to the Uffizi Gallery to see artwork by Renaissance masters including Botticelli’s The Birth of Venus and da Vinci’s Annunciation. The Accademia Gallery will also astound with more masterpieces including Michelangelo’s David. After a full day in Florence, the group will return to a meal at the Villa prepared by our private chef and a wonderful evening. (B, L, D)
Day 9 – October 17, 2025: Montalcino and Montepulciano History and Culinary Delights
After breakfast at the Villa, the group will prepare for their day exploring the historical villages along pilgrimage routes to Rome…. and most importantly, exploring their food and drink. The group will again be led by a Tuscan Step-on Guide for the exploration of the wineries, for which the region is famous, and even a tour of a local Pecorino cheese producer and their lovely sheep. The villages of Montalcino and Montepulciano will reinforce the depth of history and culture that pervades the region – something that will be remembered long after this adventure is over. This evening, dinner will be in a local restaurant close to the Villa. (B, L, D)
Day 10 – October 18, 2025: Perugia and Rasiglia
After breakfast, depart for the capital of the Umbria region, Perugia, which is known for its medieval buildings and stone defensive walls around the city center from the 13th and 14th centuries. Explore the streets, fountains, and art that was produced when the buildings were newly built. From Perugia, a short trip will bring the group to the small medieval village of Rasiglia, known as the Little Venice of Umbria, with its streams and brick homes. The group will return to the Villa and then head out to a local restaurant for dinner. (B, L, D)
Day 11 – October 19, 2025: Villa Time and Cooking Class
This morning, the group will have the morning to enjoy the Villa and countryside, with both breakfast and lunch prepared by the private chef. In the early afternoon, head out to nearby Umbertide for a bit of shopping and exploration followed by food. The group will try their hands at making some authentic Italian food and then eating their efforts. This evening will be the last night in the Villa, perfect for sitting on the patio with a glass of local wine. (B, L, D)
Day 12 – October 20, 2025: Travel to Venice & Orientation Tour
Arrivederci Villa! After breakfast, say goodbye to the Tuscan Region and the Villa and head to Venice. With a stop along the way, the group should arrive early afternoon and then will get acquainted with the canal riddled city. A Step-on Guide will orient the group to the layout, major sites, and history of Venice. With so much to see and do around each corner, this will allow guests to explore at their leisure the next day. Guests will check in to our hotel a very short distance to the Piazza San Marco and then go out together for dinner. The evening will be perfect for a stroll along quiet canals. (B, D)
Day 13 – October 21, 2025: Venice Choose-Your-Own-Adventure Day
Today is your day. Ride a gondola. Catch a water taxi to Murano Island. Sit in a café and people watch in St. Mark’s Square. Find a quiet trattoria down an alley for some of the best pasta around. Guests can do one or all of these with a free day and a centrally located hotel in one of the most beautiful cities on earth. In the evening, the group will come back together for a farewell dinner and be amazed at just how much they have experienced. (B, D)
Day 14 – October 22, 2025: Return Home
This morning the group will check out and depart after breakfast to make their way to the Venice Airport for a late morning departure on United 169 to make their way back to PDX, landing that evening in Oregon. What a trip. (B)