Italy 2026 Sept 5-15 | Kindred Women

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10 glorious days in Italy - September 5-15, 2026
Lake Como - switzerland - Tuscany

our trip - This journey features stays in two stunning regions of Italy: Lake Como in Lombardy and San Casciano In Val di Pesa in Tuscany. In Lake Como, we'll hop on a ferry to discover picturesque villages and savor their local dishes. Additionally, we’ll embark on a full-day tour which includes St. Moritz in Switzerland and the captivating Swiss Alps. As for Tuscany, its rich history and breathtaking landscapes speak for themselves. We'll immerse ourselves in the natural beauty of the area and indulge in a wine tasting or two, all while enjoying the people we meet along the way. This promises to be an unforgettable adventure!

Sustainable Tourism in Italy

Italy it one of the environmental sustainability leaders in Europe. Many businesses in Italy are at the European forefront of improving the environment, as well as promoting respect for all people, inclusion and social solidarity. They are leading other European nations in lowering greenhouse gas emissions, consuming fewer raw materials, consuming less energy, and recycling.

What Makes our Trips So Special

Limited to just 7 women! The beauty of small-group travel is that our itinerary is somewhat flexible. It also gives us time to really get to know each other and develop friendships. Many of our travelers keep in touch with each other long after the trip ends, some even traveling again with the same group of women.

Getting Around - We will travel through Italy in a variety of ways...by boat, bus, van and train. Just like the locals!

Lodging - By renting local homes, we are better able to get to know each other and really relax when we get home from a day of touring.

Meals - In each house, the kitchen will be stocked with breakfast foods catered to your preferences. Lunches will be simple to allow us to keep exploring. Most dinners will be at local restaurants so you can order from the menu. In addition to dining out, we will have a private chef come to the house to prepare dinner for us on our day of arrival.

Activity level for this trip: Moderate - Italy is VERY hilly, so travelers need to be prepared to climb hills and LOTS of stairs. (Women with mobility issues should consult their physicians.)

activity level

initial itinerary

(Kindred Women Travelers reserves the right to make changes to the itinerary as needed.)

SATURDAY, SEPT. 5th

Start your trip by flying to Maplensa Airport in Milan, arriving by mid-day of the 6th.

SUNDAY, SEPT. 6th

Upon arrival, we will meet at the airport where our private driver waits to transport us to our first home in Moltrasio, a village on the western shore of Lake Como in Lombardy, close to the Swiss border. The house features 7 bedrooms and 8 bathrooms. Click HERE for more pictures. We'll spend a few hours unwinding at "home" while our private chef crafts a delightful dinner for us.
(Meals: D only)

MONDAY, SEPT. 7th

We'll begin our day slowly as we acclimate to the time difference. Around mid-morning, we'll depart for the ferry to Nesso, a charming village that boasts a genuine Italian vibe and breathtaking lakeside scenery. We'll savor a delightful fish lunch at a cozy lake-side restaurant. Afterward, we'll take a bus to Bellagio, famous for its cobblestone streets, beautiful architecture, and Villa Serbelloni Park, an 18th-century terraced garden offering stunning lake views.
(Meals: B, L, D)

TUESDAY, SEPT 8th

Today is a full-day adventure to the highest reachable point by train in all of Europe. We'll start off with our driver bringing us to the luxurious resort town of Saint Moritz, nestled in Switzerland’s Engadin Valley. We'll enjoy some leisure time for exploring, shopping or indulging in delicious pastries. We then ride the Bernina Red Train for a 2.5 hour jaw-dropping journey to the Swiss Alps along a UNESCO World Heritage route.

(Meals: B,L,D)

WEDNESDAY, SEPT. 9th

We'll start our day with a ferry ride up to Tremezzina, located on the western shore of the lake opposite Bellagio. We'll visit the magnificent Ville Carlotta and stroll through their amazing gardens. After grabbing a bite to eat, we'll jump back on the ferry to Bellano, a historic, scenic town on the east side of the lake. Here we'll have the opportunity to explore the Orrido di Bellano gorge, a dramatic natural gorge/ravine with walkways, waterfalls, and the mysterious "Cà del Diavol" (House of the Devil) tower.
(Meals: B,L,D)

THURSDAY, SEPT. 10th

ROAD TRIP! After breakfast, our driver will take us back to Milan where we'll board the train to Florence and check into our Tuscan villa! The villa is in the town of San Casciano in Val di Peso, 10 miles south of Florence. It is considered the gateway to the Chianti wine region. Our home for the next 6 nights has 7 bedrooms and 7.5 baths. Click HERE for more pictures of the house.
(Meals: (B, L, D)

FRIDAY, SEPT. 11th

FREE DAY! By now, we've certainly been on the move and may want to take it easy. There are no specific plans for today. Slow down, relax, sit by the pool. Explore the local town which has a tight ring of 14th-century walls enclosing its small historic center. Go on another tour not included in the itinerary. Go into Florence (even though we will be going into the city later in the week.) The choice is yours! Expenses for the day are not included in the cost of the trip.
(Meals: B only)

SATURDAY, SEPT. 12th

Today we will explore the medievil towns of San Gimignano and Volterra. San Gimignano is a small hill-top town encircled by a 13th century wall, with a skyline of medieval towers. Volterra is also walled with history that dates back to before the 8th century. We'll explore each town on foot, soaking up the culture and dining on authentic Tuscan cuisine.
(Meals: B,L,D)

SUNDAY, SEPT. 13th

We'll head into Florence for the day starting with a-2 hour private walking tour to get an overview of the city. We'll also have timed-entry to Galleria dell'Accademia where we'll see Michelangelo’s original David. After stopping for lunch, we will explore on our own and have dinner together in the city.
(Meals: B,L,D)

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Siena stock-photo-piazza-del-campo-in-siena-italy-at-twilight-767524354.jpg

MONDAY, SEPT. 14th

Today we head down to Siena, distinguished by its medieval brick buildings. The fan-shaped central square, Piazza del Campo, is the site of the Palazzo Pubblico, the Gothic town hall, and Torre del Mangia, a slender 14th-century tower with sweeping views from its distinctive white crown. On the way back, we'll stop in Chianti for a wine tasting at a beautiful vineyard.
(Meals: B,L,D)

TUESDAY, SEPT. 15th