About this trip
Women Only Tuscany Small Group Tour
Dates: April 11 - April 20, 2027
Destinations: Rome, Cortona, San Gimignano
Trip length: 10 days / 9 nights
Overview
Spend 10 unforgettable days exploring Italy with a small group of like-minded women. This Tuscan escape blends the energy of Rome with the rolling vineyards, hilltop towns, and peaceful countryside of Tuscany.
We begin with two nights in Rome, where ancient history meets vibrant street life. Highlights include a guided street food tour and a sunset golf cart ride through some of the city’s most iconic landmarks.
From there, we travel north to the charming hilltop town of Cortona where we settle into a beautiful countryside villa for a full week in Tuscany. From this relaxing home base, we’ll explore some of the region’s most scenic towns and landscapes, including San Gimignano and the stunning Val d’Orcia.
Expect incredible food, local wine, breathtaking views, and meaningful connections with a group of women traveling together.
Who this trip is for
Women who want connection, culture, and comfort — without early mornings or constant hotel changes.
Perfect for solo travelers who want companionship and independence.
Trip highlights
🤍 Welcome dinner in Rome
🤍 Street food tour through historic Roman neighborhoods
🤍 Sunset golf cart tour through Rome’s iconic landmarks
🤍 Villa stay in the Tuscan countryside near Cortona
🤍 Chianti wine tasting experience
🤍 Val d’Orcia day trip with visits to Pienza and Montepulciano
🤍 Cooking class with local ingredients
🤍 Thermal spa day at Terme di Saturnia
🤍 Day trip to the medieval town of San Gimignano
🤍 Farewell dinner at a private countryside villa
Where we stay
🏨 Rome: Boutique hotel in the historic center
🏨 Cortona: Beautiful Tuscan countryside villa for a relaxed week exploring the region
What’s included
✔️ 9 nights boutique accommodation (single or double occupancy*)
✔️ Daily breakfast after Day 1
✔️ Select group lunches and dinners
✔️ All listed tours, tastings, and entry fees
✔️ Ground transportation throughout the trip
✔️ Local expert guides for select experiences
✔️ Airport transfers on arrival and departure days
What’s not included
International airfare, required travel and medical insurance, tips for guides, alcohol unless noted, and meals not listed.
Group size and pace
Maximum 12 women for intimacy and flexibility. Expect easy-paced days with about 8,000–10,000 steps per day, balanced with free time each afternoon.
A €500 deposit non-refundable deposit secures your spot.
Payment plans available on request.
Balance due 45 days before departure.
Comprehensive travel insurance required.
Why travelers love this tour
🍷 Slow travel in the Tuscan countryside
🍷 A beautiful villa stay surrounded by vineyards and rolling hills
🍷 Incredible food, wine, and local experiences
🍷 Thoughtfully planned days with flexibility built in
🍷 Hosted by an experienced solo female traveler who knows Europe
Ready to join us? Reserve your spot and receive the full itinerary, hotel details, packing list, and access to our private group chat after booking.
9 nights in hand-selected properties in Rome and Cortona
Our hotels include Breakfast
Traditional Roman dinner with drinks included
See iconic landmarks and hidden gems comfortably with a local guide via a golf cart
Guided evening food experience with dinner and wine
Comfortable transportation from Rome to Cortona
Private introduction to this charming Tuscan hill town
Cheese tasting + winery lunch
Two tastings with vineyard lunch
Hands-on pasta + dinner
Thermal park entrance
Guided medieval town visit
Winery dinner with wine
Included from arrival in Rome and Departure from Florence. *Addition fee to return to Rome
Mandatory local hotel taxes (paid locally)
Airfare to and from Italy
Required
Optional add-on experience
Treatments or rentals at Saturnia
Meals not listed in itinerary
Tips for guides and drivers
Shopping, minibar, personal items
Benvenuto in Italia. After arriving at Rome FCO, we’ll transfer to our boutique hotel, Donna Camilla Savelli, and settle in. I like to keep this first day gentle so you can breathe and adjust. In the evening, we’ll gather for a warm welcome dinner at a traditional Roman trattoria. This is where strangers start becoming friends.
Meals Included: Dinner
This morning we explore Rome by private golf cart, because I believe in seeing everything without exhausting ourselves. You’ll experience the icons and hidden corners while hearing the stories that bring the city to life.
In the evening, we head into Trastevere for one of my favorite experiences, a guided food tour through one of Rome’s most charming neighborhoods. Think pasta, wine, gelato, and that magical Roman energy after dark.
Meals Included: Breakfast, Dinner
We leave the city behind and head into the Tuscan countryside. Rolling hills, cypress trees, the whole dreamy landscape.
We’ll settle into Cortona for seven nights at Hotel Villa Marsili. I chose this intentionally so we can unpack once and truly relax. That afternoon, we’ll take a guided stroll through town to get our bearings and soak in the views.
Meals Included: Breakfast
Today is Tuscany postcard day. We visit Pienza for pecorino tastings and wander Montepulciano before sitting down for a vineyard lunch with Vino Nobile. This is slow travel done right. Good wine. Good views. No rushing.
Meals Included: Breakfast, Lunch
A full day in Chianti visiting two wineries and enjoying a relaxed vineyard lunch. You’ll learn about the wines, but more importantly, you’ll experience what makes this region so special. Expect long tables, olive oil, and stories.
Meals Included: Breakfast, Lunch
Slow morning in Cortona. Sleep in. Journal. Espresso in the piazza.
In the afternoon, we roll up our sleeves for a hands-on pasta cooking class. You’ll learn traditional techniques, then sit down together for dinner with the dishes we prepared. This is always one of the most bonding nights of the trip.
Meals Included: Breakfast, Dinner
A full day at leisure. Wander Cortona, shop, relax, or simply enjoy being in Italy.
Optional guided excursion to Siena available for those who want to explore more.
Meals Included: Breakfast
We spend the day at the famous thermal springs of Saturnia. Warm mineral waters, natural rock pools, and that relaxed Tuscan countryside energy. It’s a reset day for the body and soul.
Meals Included: Breakfast
We visit medieval San Gimignano, often called the “Manhattan of the Middle Ages,” before heading to a Tuscan estate for our farewell wine tasting and dinner. This final evening is always special. Reflecting, laughing, and realizing how quickly the days flew by.
Meals Included: Breakfast, Dinner
Group transfer to Florence Airport. Hugs, promises to stay in touch, and one last “arrivederci.”
Meals Included: Breakfast