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Women-Only Tuscany Small Group Tour

Cortona-San Gimignano-Siena-Rome

Join a women-only small group tour of Tuscany designed for travelers who value slow travel. With fewer hotel changes, daily free time, and intimate groups, you’ll experience Italy at a pace that lets you truly connect with both the destination and the women beside you.

March 31st to April 9th 2027
WHAT TO EXPECT • WHAT TO EXPECT • 

The Group Tours You’ve Been Searching For…

  • Small groups of never more than 12 women, creating a more personal and relaxed travel experience.
  • Fewer hotel changes and thoughtfully paced itineraries, so you can settle in and truly experience each destination.
  • Handpicked boutique hotels that combine charm, comfort, and excellent locations.
  • Daily free time to explore at your own pace, with no giant tour buses or 6 a.m. departures.
group of women in Naxos at the table cheers

The Tuscany Tour Departing in

  
Save me a spot!

How It Works

Reserve a Spot

To join the tour, a non-refundable deposit of €500 is required at the time of booking. 

Make Payments

Set up your payment installments or pay in full. The trip must be paid in full 45 days prior to departure.

Bon voyage!

Prepare for your trip! We will send you travel details and add you to our group chat and private group webpage.

Our Itinerary

What We’re Doing

Day One

Arrival in Cortona

Fly into the Florence airport and board the group transfer to our centrally located hotel in beautiful Cortona. Get refreshed and ready to meet our group for a welcome cocktail and dinner!

  • Group airport transfer to our hotel
  • Welcome drink & welcome dinner at a traditional Italian restaurant

Day Two

Guided Tour of Cortona & Cooking Class

We start the day today around 9:30 AM, heading straight to the city center for our guided tour.

After learning all about the town and its historical significance, you will have free time to roam around, shop, or go back to the hotel to relax.

Later, we will come together for a hands-on Italian cooking experience.

With the guidance of a local chef, we’ll learn to make fresh pasta from scratch, seasonal sauces, a traditional main course, and an Italian dessert.

Afterward, we’ll sit down together to enjoy everything we’ve prepared, paired with local wines.

  • Breakfast & dinner
  • Private guided tour of Cortona
  • Cooking experience

Day Three

Wine Tasting in the Hills of Chianti

After breakfast, we’ll set off for the beautiful Chianti wine region for a day among Tuscany’s rolling hills, vineyards, and olive groves.

We’ll visit two wineries for guided tastings of local Chianti wines, learning about the region’s grapes and winemaking traditions.

At our second winery, we’ll enjoy a traditional Tuscan lunch paired with wine and locally produced olive oil before continuing to our accommodation in the afternoon!

  • Breakfast & lunch
  • Transport to wine region
  • Winery visits

Day Four

A Taste of Val d’Orcia

Today we’ll explore the beautiful Val d’Orcia, traveling through Tuscany’s rolling hills and cypress-lined countryside.

We’ll visit Pienza for a stroll through its charming streets and a tasting of its famous Pecorino cheese, before continuing to Montepulciano for a guided Vino Nobile wine tasting and vineyard lunch.

Afterward, enjoy some free time to explore Montepulciano before returning to Cortona.

  • Breakfast & lunch
  • Day trip to Pienza

Day five

Free Day in Cortona + Optional Siena Day Trip

Today is yours to enjoy! Relax at the hotel, explore Cortona, shop, or simply enjoy some free time at your own pace.

Those who choose our optional day trip to Siena will travel by private transfer to this beautiful UNESCO-listed city for a guided walking tour, including Piazza del Campo and Siena’s magnificent Gothic Cathedral.

Afterward, you’ll have free time to explore, shop, or grab a bite before returning to Cortona.

  • Breakfast
  • Optional day trip to Siena at additional expense

Day six

A Day at the Terme di Saturnia

Today we’ll escape to the beautiful Terme di Saturnia for a relaxing day surrounded by the Tuscan countryside.

We’ll have time to soak in the naturally warm thermal waters, enjoy the pools and Thermal Park, and experience the famous Cascate del Mulino.

You’ll also have free time for lunch before we return to Cortona in the afternoon.

  • Breakfast
  • Transport and entrance to Terme di Saturnia

Day seven

San Gimignano & Tuscan Winery

Enjoy a leisurely morning before we depart for San Gimignano, one of Tuscany’s most beautiful medieval hill towns.

We’ll explore this UNESCO World Heritage Site on a guided walking tour, discovering its cobblestone streets, historic architecture, and famous medieval towers.

Afterward, we’ll head into the countryside to visit a Tuscan winery, where we’ll enjoy a guided wine experience with a sommelier.

  • Breakfast
  • Transport to San Gimignano
  • Guided tour of San Gimignano
  • Wine Tasting

day eight

Transfer to Rome & Food Tour

This morning we’ll leave Cortona and get into our transfer to Rome!

We will check into our hotel and relax for a bit.

Later we’ll explore Trastevere on a guided food tour, tasting our way through one of Rome’s most charming neighborhoods.

We’ll sample Roman street food, pizza, pasta, local meats and cheeses, gelato, and wine while discovering some of the neighborhood’s hidden gems.

  • Breakfast & dinner
  • Transport to Rome
  • Food tour

Day Nine

Rome City Tour & Farewell Dinner

This morning we will explore the Eternal City by private golf cart, an easy and fun way to see more of Rome without all the walking!


Over approximately three hours, our private guide will take us past iconic landmarks, beautiful piazzas, fountains, and hidden gems, sharing stories about Rome’s fascinating history along the way.

After the tour, we’ll be dropped back at our hotel with the rest of the day to enjoy at our leisure.

Tonight, we’ll come together one last time for our farewell dinner, celebrating an incredible trip through Italy!

  • Breakfast and dinner
  • Rome city tour

Day Ten

Departure Day

Today is the day we all head our separate ways. Breakfast will be available at the hotel.

  • Breakfast at the hotel
  • Group airport transfer

the Hotels

Where We’re Staying
Canopy bed with crisp white pillows and floral-patterned bedding and wallpaper at Hotel Eldorado Paris.

01.

Hotel Villa Marsili
Naxos boutique hotel

02.

Aria Palace by OMINA

Past Trips Photo Diary

  • Assorted Italian appetizers in a deli showcase in Rome, enhancing authentic culinary experience.
  • A mouth-watering array of Italian tapas served in Brescia restaurant. Perfect for aperitif or snack time.
  • A picturesque street view highlighting the historic architecture in Rome, Italy.
  • Explore a picturesque medieval street with iconic tower in an old European town.
  • Stunning aerial photo of Saturnia Hot Springs with turquoise waters and natural limestone terraces.
  • A woman enjoys a peaceful moment in Saturnia's stunning thermal baths, Tuscany, Italy.
  • Stunning aerial view of Siena Cathedral, showcasing medieval architecture in Tuscany's historic cityscape.
  • Delicious spaghetti with rich tomato sauce topped with grated Parmesan cheese on a wooden table.
  • Charming street scene in Montalcino with a historic clock tower during evening light.
  • Scenic view of a vineyard during sunset in Novigrad, Croatia, capturing the serene countryside.
  • From above picturesque view of ancient town with brick buildings and green trees located on hill in sunny day in countryside
  • Breathtaking view of rolling hills and cypress trees in Tuscany, Italy, under a clear blue sky.

What’s Included

Pricing

Inclusions

  • Arrival & Departure Day Group Airport Transfers
  • 9 Nights Accommodation
  • Select Lunches & Dinners
  • Daily Breakfasts
  • Local Guides
  • Ground Transportation
  • Entry Fees & Tickets
  • Tours & Tastings

Exclusions

  • International Airfare
  • Travel & Medical Insurance (Required)
  • Tips for Guides
  • Alcohol
  • Meals Unless Mentioned
  • Gifts

Pricing

  • €5,599 for Single Occupancy
  • €4,699 for Double Occupancy
  • Includes €500 Non-Refundable Fee
  • Payment Plans Available

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ITINERARY DISCLOSURE

*THE PUBLISHED ITINERARY FOR THE TUSCANY TRIP IS A SAMPLE ITINERARY. ACCOMMODATION, ACTIVITIES, AND EXPERIENCES MAY BE MODIFIED BASED ON WEATHER, AVAILABILITY, OR OTHER UNFORESEEN CIRCUMSTANCES.

TRAVEL INSURANCE DISCLOSURE

A TRAVEL INSURANCE POLICY THAT COVERS MEDICAL EXPENSES, AND OTHER TRAVEL-RELATED ISSUES IS REQUIRED FOR ALL TOURS. POLICIES OFFERED BY TRAVEL CREDIT CARDS DO NOT MEET THIS REQUIREMENT FOR COVERAGE.

Travel medical insurance is mandatory for all participants. To join us, your insurance policy must include at least $100,000 USD coverage for medical emergency evacuation and repatriation.

Credit Card insurance will not be accepted as valid travel insurance for our tours. Therefore, we strongly advise securing a travel insurance policy BEFORE you make any payments towards the trip.

While many of our guests prefer Faye, it’s important to find a policy that aligns with your specific needs. Other reputable providers include Allianz Travel Insurance, Nationwide Travel Insurance, and John Hancock Travel, among others.

Keep in mind, all payments made towards the tour are non-refundable. Travel insurance typically covers cancellations only for covered reasons, which may include unexpected illness (yours or a family member’s), severe weather conditions, or job loss.

For those interested in “cancel for any reason” coverage—which is pricier but can reimburse you for 50-75% of the trip’s total cost—consider options like John Hancock’s “Gold” Travel Insurance or Nationwide’s “Prime” Travel Insurance, Faye Insurance. Note that these policies often need to be purchased within 14 days following your initial trip deposit.

IMPORTANT: When arranging your travel insurance, please account for any extra days you might be traveling outside our official tour dates, such as arriving a day early or staying an additional night at our suggestion. For instance, if you plan to fly out on October 2nd to ensure your timely arrival for the tour’s start, make sure your insurance coverage begins from October 2nd.

NON-REFUNDABLE PAYMENT DISCLOSURE

ALL PAYMENTS MADE TOWARD THE TUSCANY TRIP ARE NON-REFUNDABLE. WE STRONGLY RECOMMEND PURCHASING COMPREHENSIVE TRAVEL INSURANCE TO PROTECT YOUR INVESTMENT AGAINST ANY UNEXPECTED EVENTS OR CIRCUMSTANCES.

COVID-19 VACCINATION DISCLOSURE

FOR OUR 2027 TUSCANY TOURS, PARTICIPANTS WILL NOT BE REQUIRED TO BE FULLY VACCINATED AGAINST COVID-19. OUR PRIMARY GOAL IS TO SAFEGUARD THE HEALTH AND WELL-BEING OF OUR TOUR PARTICIPANTS WHILE ALSO PROTECTING THE COMMUNITIES WE VISIT. ALTHOUGH MANY DESTINATIONS HAVE RELAXED THEIR VACCINATION REQUIREMENTS, WE ADVISE ALL TRAVELERS TO STAY INFORMED OF AND COMPLY WITH LOCAL HEALTH GUIDELINES AND REQUIREMENTS. PARTICIPANTS MUST UNDERSTAND AND AGREE TO FOLLOW ANY DESTINATION-SPECIFIC COVID-19 REQUIREMENTS, WHICH MAY VARY FROM OUR GENERAL POLICY.

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What They’re Saying
  • Woman standing on the ledge of a bench under the Greek Flag.
    The trip was perfect. All the excursions were well planned and appealed to all the different individuals in our group. Our travel guide, Melissa, even added a personal touch by planning the naming ceremony/activity.
    The day on a private boat was magical. I never imagined myself swimming in caves and exploring quaint seaside villages. The trip exceeded my expectations.

    Pat K.
    Greece 2024
  • A woman in a bright blue dress smiling in front of a classic blue door on the island of Milos.
    Melissa did a great job on planning a wonderful trip for us. She had all our accommodations made, which were prefect. Day trips were planned and were all amazing. Melissa was very easy to communicate with and responded quickly to any questions I had. The trip was seamless. Meet some wonderful women that I now can say are friends. Would absolutely book another trip with Melissa in a minute, actually planning one for next year. Best decision I could have made.
    Birgit G.
    Greece 2025
  • Girl in the blue water
    This is my THIRD trip with Melissa…I think that says it all!!!
    This was my second time in Greece with Melissa, only one year later. I definitely fell in love with this country the first time, and I plan to go back and visit another part. The water, the food, the weather, the charm, and history.
    It’s all mesmerizing. And I’m certainly happy for all the new and continued friendships. Booking my first trip to Greece in 2025 has been one of the best decisions of my life!
    Daniela S.
    Crete 2026
  • Women in a restaurant
    Great balance of activities around food, history, exploring the islands and cities, as well as downtime to relax and refresh. Melissa did a great job of making everyone feel comfortable and a part of the group. And I love how she communicated so much before the trip so we all knew what to pack and what to expect each day. I’d totally Recommend her trips!


    Zeta K.
    Greece 2026
  • Woman in Greece behind the wheel of the boat
    I’ve always wanted to go to Greece and this was the perfect opportunity as a single woman.

    Melissa is a gem. She plans every aspect of the trip with care, has a lovely spirit, and truly enjoys the trip and experience with the group. I’m so glad I found her group trips on Tiktok.
    Memories that last, new friends, and a wonderful experience.

    Brooke H.
    Greece 2026
  • A swimmer floats peacefully in the unbelievably clear turquoise waters of Milos, surrounded by rocky coastal cliffs.
    I would give this trip ten stars if I could. Everything was so well organized. It was the perfect balance of planned activities and free time. We stayed at boutique hotels that had personality. We dined at a number of great restaurants. We were spoiled with boat trips, wine tastings and jeep tours.
    I can’t say enough wonderful things about how Melissa conducted this trip. It was the vacation of my dreams.

    Lisa b.
    Greece 2025
Read More Reviews!
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Questions about travel planning? We have answers.

Our tour begins at 4pm on the first day, so it would be nice to arrive a day before the trip starts. I can help you coordinate accommodations.

While the tour isn’t considered adventurous, our destinations do have their fair share of hills and inclines. I do my best to arrange transportation that minimizes stairs. On average, you can expect to do at least 10,000 steps a day.

While many travelers can enter on a tourist visa with no extra steps it is important to confirm on the government website.

Yes. While a lot of travelers come alone, many decide to travel with a friend.

Breakfast is included each day of the tour except the start day. Additional meals are included, which are specified on the itinerary above.

The tour starts in Tuscany; fly into Florence (FLR) and ends in Rome; fly out of Rome Fiumicino Airport (FCO).

Meet Your Host!

I’m Melissa

Your go-to girl for all things travel

I’ve traveled solo to over 40 countries! And I’m passionate about helping you explore the world.

My favorite part about traveling is trying the local food, taking photographs, and making new friends!

I’m a big believer that anyone can achieve their goals if they are willing to work at it!

More Questions?
Book a call Contact us
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