Together in Tuscany
- Email address verified
11 reviews
Apr 25 - May 2, 2026
Group size: 8 - 14
The Heart of Chianti Small Group Tour
50026 San Casciano In Val di Pesa, Metropolitan City of Florence, Italy
Together in Tuscany
- Email address verified
11 reviews
Apr 25 - May 2, 2026
Group size: 8 - 14
About this trip
Here's Where You'll Stay: San Casciano
Terms and conditions
What’s included
- Villa accommodations7 nights in the villa
- Personal chef dinners4 dinners in the villa
- Breakfasts6 breakfasts in the villa
- Restaurant dinners2 restaurant dinners
- Pre-arranged activitiesprivate group activities
- Transportationto and from the activities and the designated train/airport
- Cooking class
- Wine at the villa1/2 bottle of wine pp per day included
- Local tourist tax1-4 euros pp per day
- Tips and gratuitiesfor the tour guides, chef, housekeeping, drivers, etc.
- On-site group leader
What’s not included
- Airfare
- Travel Insurance
- Personal expensesAnything not specified in the travel package
- Wine and alcoholwine and alcohol outside of what's included in the itinerary
Available Packages
Shared Twin Room/Private Bath
Deposit: $500
4 left
$5,714
Deposit: $500
Shared Standard King Room/Private Bath
Deposit: $500
Only 2 left
$5,714
Deposit: $500
Shared Deluxe Double Room/Private Bath
Deposit: $500
Only 2 left
$5,830
Deposit: $500
Shared King Suite/Private Bath
Deposit: $500
Only 2 left
$5,830
Deposit: $500
Shared King Superior Suite/Private Bath
Deposit: $500
Only 2 left
$5,830
Deposit: $500
Shared King Suite Exterior Entrance
Deposit: $0
Only 2 left
$5,830
Deposit: $0
Available Add-Ons
Upgrade private king room
$600
4 left
Deposit: $500
Itinerary
Saturday
Welcome to Tuscany!
Your Organizer
Together in Tuscany
11 reviews
Ciao! I’m Janine! It’s my mission to curate unforgettable villa vacations for travelers seeking la dolce vita. I do this by finding the best villas, cooks, drivers, wineries and tour guides. My tours and retreats are all-inclusive packages, limited to 8-14 guests, and provide you with hands-on, immersive and off-the-beaten path experiences. I remove the stress of planning a vacation by taking care of all the details so you can relax and enjoy the journey. You can feel comfortable knowing I am with you every step of the way.
Reviews
JC
As a solo traveler, I was so impressed with Janine O'Rourke's passion of creating a safe, enjoyable wellness and travel experiences for silver aged travelers. Our excursions were well organized and informative. My favorite part was hiking the high stone steps in Cinque Tera. It was a personal fitness victory for me that I never would have experienced without this trip.
Janine has the unique ability to lead while also enjoying herself. She loved being with all of us and it showed. There was never a time where I didn't feel included and valued as a participant even though most of the other women knew each other.
The villa in Tuscany, Laura, our host and her staff were OUTSTANDING. The food was so delightful and all fresh, of course, my room was perfect. The cab drivers, the cooks, the massage therapists were all top notch. I highly recommend Travel in Tuscany.
By Janine C for Women's Wine and Wellness Retreat on Sep 12, 2025
Thank you Janine for sharing your experience! I enjoyed meeting you and getting to know you during the retreat. You were meant to be on this retreat and we were meant to connect - Janines spelled the same way! Thank you also for providing a great workshop to the group on bravery. You were courageous yourself for coming on this retreat as a solo traveler. I look forward to seeing you on future trips!
By Together in Tuscany on Sep 12, 2025
I would recommend this trip to anyone looking to spend a week together with like minded women. The experience included a balance between visits to local wineries, touring a few lovely villages, walking, biking, hiking, yoga, cooking class, swimming, boat rides, shopping and an optional opera! There was also time available to relax at the villa and have a massage. This review would not be complete without a shout out to the chef. The vegetarian food was amazing.
By Barb M for Women's Wine and Wellness Retreat on Sep 03, 2025
Thank you Barb for this lovely review! I enjoyed getting to know you on the retreat and am happy to hear you had a great time!
By Together in Tuscany on Sep 03, 2025
The trip to Portugal was beyond amazing! I have always planned my own trips but this time Janine took care of everything and did an exceptional job. Janine is extremely organized and does everything with a smile. She arranged lovely hotel accommodations, amazing excursions, all our transportation around Portugal and it was all done seamlessly. We had so much fun at the wineries, open air jeeps thru the countryside, a tuk tuk tour, boat rides, a cooking class at an intimate restaurant and so much more. The hotels we stayed in were very nice with comfortable beds, pretty gardens and one even had a pool! Janine's thoughtful planning made this trip a very memorable one.
By Karen R for Portugal Girls Trip on Jul 13, 2025
This trip to Portugal was an amazing cultural experience! Our trip was full of fun, informative activities while we visited several different towns and cities. Walking tours, food tours, winery tours, boat rides, tuk tuk rides, and open air jeep rides, this guided vacation with Janine did not disappoint! I was so very impressed with the accommodations and the activities… I had a worry free travel excursion!
By Kim W for Portugal Girls Trip on Jun 30, 2025
A year ago, Janine and I sat down to discuss planning a Portugal Trip. To celebrate my 60th birthday. On June 14, 2025 we arrived in Porto and had 8 fun filled days with daily excursions, wine and food tours, beautiful hotel accommodation, three boat tours and so much more. Eight fun filled days with eight wonderful ladies. Best trip ever. Thanks Janine. The ultimate trip planner!!
By Holly B for Portugal Girls Trip on Jun 29, 2025