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Tuscany Tour For Women

Indulge in La Dolce Vita with a Chic Italian Escape

Ready for a taste of Tuscany that’s as delicious as it is unforgettable? Get ready to fall head over heels for Italy’s heartland as we embark on an enchanting journey through some of Tuscany’s most charming villages and the fabulously historic Florence!

For six blissful nights, we’ll call the very center of Siena our home base, a stunning open-air museum where history and vibrancy come alive. Siena’s colourful Contrade (districts) are brimming with life, inviting you to explore delightful artisan boutiques, decadent pastry shops and charming coffee bars. With this chic hub as our base, we’ll set off each day to uncover the hidden gems of Tuscany. Picture yourself wandering through Cortona’s picturesque streets, soaking up the ancient allure of Arezzo, and marvelling at the medieval splendour of San Gimignano.

But hold on, there’s more! We’ll indulge in wine tastings amidst Chianti’s celebrated vineyards, roll up our sleeves for a hands-on farmhouse cooking class to master those irresistible Tuscan recipes and capture breathtaking photos of landscapes that seem straight out of a dream.

Florence will be our grand finale, offering two days of art, culture and fabulous shopping. Immerse yourself in the city’s artistic treasures, enjoy the vibrant market scene and hunt for those must-have finds.

Join WTN host Jeanette Dame for an unforgettable Tuscany tour for women where every moment is a blend of stunning sights, divine food, and the true essence of dolce vita. This is your chance to savour Tuscany in all its glory!

Our team is currently putting the finishing touches on this itinerary, and once it’s ready, we’ll release it first to the women on our pre‑registration list. To join our pre‑registration list for this tour, simply email Natalie at natalie@worldwidequest.com. You’ll have two full weeks to review the details, ask questions, and decide if it’s the right fit, before it’s shared with the general public. There’s no cost or obligation to joining the list, just the privilege of being first in line.

Click Here to explore our photo gallery, which includes photo from our previous Tuscany Tours in 2025 and 2023.

⭐ Extend Your Adventure

This tour will have an optional post-trip extension to Rome. If you are interested in this please contact natalie@worldwidequest.com for more details.

Trip Details

  • September 2027 - Approximately 9 days
  • 13 – 16
  • Estimated Cost: Approximately CAD $9,500
Preregister for this tour

Signature Moments

  • Learning all about winemaking in Chianti
  • Learning Italian recipes at our farmhouse cooking class
  • Searching for leather goods at the famous Florence market
  • Tasting gelato, cappuccino, wine and pasta…everywhere!

Trip Hightlights

  • Guided walking tour in Arrezzo, visiting the Church of San Francisco
  • Guided walking tour in Cortona, made famous by the book and movie “Under the Tuscan Sun”
  • Explore the Chianti Region including wine tasting and visiting an olive oil mill in Volpaia and stopping in Radda, Gaiole, Greve and Panzano
  • Explore southern Tuscany, visiting the serene Abbey of Sant’Antimo and the hilltop town of Montalcino
  • Stroll through the charming town of Pienza and sample the regions famous Pecorino cheese at a local artisan shop
  • Enjoy dinner at a countryside trattoria
  • Guided walking tour in Siena, visiting the imposing green and white marble Cathedral
  • Explore market day in Siena’s town square
    Enjoy a hands of cooking class at Querceto Wine Estate
  • Guided walking tour in San Gimignano, encircled by 13th century walls and a square lined with medieval houses
  • Guided walking tour of Florence to discover the Ponte Vecchio, the Piazza della Signoria, the Duomo and Santa Croce Church
  • Enjoy a free day exploring Florence, shop for finds at the leather market, take in fine Italian art at the Uffizi Gallery or visit the Accademia Gallery to see Michelango’s David
  • Airport transfers on tour start and end dates
  • Accommodations, based on double occupancy in beautiful, well-appointed hotels, 4-star or better.
  • Meals: 7 breakfasts, 2 lunches and 6 dinners
  • Wine with dinners
  • Cooking class
  • Wine tastings
  • Transportation by private air conditioned coach
  • Bottled water supplied daily
  • Expert English-speaking guide throughout
  • All activities as indicated in the itinerary
  • All entrance fees
  • Gratuities for local guides, drivers, hotel and group meals
  • Porterage of one standard piece of luggage per person
  • All taxes
  • Fully escorted by your Womens Travel Network tour host
  • Roundtrip airfare from your home city
  • Airport transfers, if not travelling with the group
  • Items of a personal nature
  • Meals other than those mentioned in the detailed itinerary
  • Travel insurance
  • Items of a personal nature
  • Additional transportation required due to any emergency or other situation
  • Any item not mentioned in “What’s Included”

Moderate
A good level of fitness is important for this trip. You must be comfortable walking on uneven terrain and irregular paving and climbing stairs. You should be able to walk unassisted for up to three hours at a time in warm temperatures. We usually walk more than 10,000 steps per day, so good walking shoes are necessary.

We are staying in well located four-star or higher level hotels throughout our trip. All rooms have private facilities.

During this tour
We will be travelling by comfortable, air-conditioned coach and using regional ferries as required.

Joining Instructions
The tour commences with a group transfer from the Airport to the hotel (based on group flight schedule). The tour concludes with a group transfer from the hotel to the Airport (based on group flight schedule). Please contact us to verify the timing of this transfer prior to making any flight arrangements.

International Flights
*Roundtrip international flights are not included in the cost of your tour and must be arranged separately. Our team are happy to assist you in booking your flights, this way we can do our best to keep the group together. If you’d prefer to book your own flights, please check with us first to ensure the trip has been confirmed before booking and to verify the timing of these group transfers to ensure your flight schedule fits our program. When you book a pre or post trip night with Worldwide Quest, your airport transfer will be included. If you are making your own pre or post trip arrangements, these transfers can be provided at an additional cost.

We expect clear sunny skies with average daytime temperatures between 25 and 30°C and overnight lows of about 18°C.

You will require a passport for this trip.  Please ensure it is valid for at least 6 months beyond your scheduled return home.

Their are no health alerts for this trip, but if you would prefer, you can see your travel doctor to prepare for this trip.

If you are travelling on your own and would like to share accommodation, we would be happy to try to match you with a suitable roommate. We do our best to ask each woman some questions to help our matchmaking process 🙂
If we are unable to find you the right match, the single cost applies.

We’d like to make sure that you know about our Worldwide Explorers Club. Travel twice with us and we’ll say a special thank you by taking 5% off all your subsequent trips. The bonus applies to our brochure trips only, is non-transferrable, and cannot be used in conjunction with any other discount or credit.  Note that some exceptions may apply as indicated on the tour’s Detailed Itinerary.

For Reservations, to Request a Detailed Itinerary or to Discuss the Trip details use the “Add Yourself To The Preregistration List For This Tour” or the “Get More Information About This Tour” contact form on this page

Or contact our reservations team directly:

Email:  natalie@worldwidequest.com

Phone: (416) 633-5666 ext 114 or toll free at 1-800-387-1483

Or contact Womens Travel Network directly:
Email:  melissa@womenstravelnetwork.ca
Website: www.womenstravelnetwork.ca

If our Tour Ready criteria are not met, your tour will not operate and we will transfer your payments to your choice of tour within 2 years of your initial travel date.

Our tours will proceed when all the following Four-point Tour Ready criteria are met:

  • The Canadian government does not have an ‘avoid all travel’ to the country or region within a country for any part of the tour.
  • No region of the tour has any significant COVID-19 related restrictions.
  • There is reliable airline access for arrival and departure.
  • Worldwide Quest and our in-country partners are confident that your trip can operate safely and enjoyably.

Payment Details:
A non-refundable deposit of CAD$750 per person is required to reserve a space on this tour. A second non-refundable deposit of CAS$2000 is required six months prior to departure. Final payment is due 90 days prior to departure.

CANCELLATION TERMS AND CONDITIONS CLICK HERE

Add Yourself To The Preregistration List For This Tour

Tour Host:  Jeanette Dame
Womens Travel Network Tour Host Jeanette Dame