Assisi Fall Tour

October 10-17, 2026

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Explore the Hidden Gems of Umbria

Date: October 10-17, 2026

Duration: 8 nights, 7 days

Location: Santa Maria degli Ancilotti Relais, Assisi

Group size: 8-14

Who is this for: Women craving connection, culture & self-discovery

Fitness Level: Ability to walk up hills and uneven surfaces

Pricing: $5,399 per person shared room; only $500 due now

Join This Exclusive Retreat – Secure Your Place Today!

Here’s Where You’ll Stay: Santa Maria degli Ancillotti

Santa Maria degli Ancillotti is a luxurious villa with buildings dating back to 1100. It dominates the valley of Santa Maria degli Angeli and is just a 16-minute drive to the main square of Assisi.  It offers its guests seven elegant suites and a restaurant exclusively dedicated to estate’s guests.  The 16-meter outdoor swimming pool immersed in the heart of the estate is perfect for cooling off on hot summer days.

When you stay here you will experience outstanding hospitality and care directly from the family owners and a breathtaking view. The customer service is top notch and the estate is very well maintained. The on-site restaurant chefs prepare Michelin-star worthy cuisine.  Breakfast and dinner are served in style and every guest is made to feel special.  

A historic stone building with outdoor lighting, surrounded by a landscaped circular garden with a fountain, trees, and a well-maintained lawn, at dusk.
A stone house with a front garden featuring pink and orange roses, a stone fountain, and garden decorations. Two black vans are parked in front of the house, and there are trees and a clear blue sky in the background.
An outdoor patio with multiple empty metal chairs and tables next to a stone building, with a sunset sky, trees, and a large pot in the background.
Photo of a swimming pool with clear blue water, surrounded by a brick deck, white lounge chairs with umbrellas, lush green trees, and a stone building under a clear blue sky.
A cozy restaurant dining room with rounded tables covered in white tablecloths, set with plates, glasses, and silverware, surrounded by wooden chairs, accented with vintage cookware on a stone wall, and decorated with a chandelier.
Outdoor restaurant patio with round tables covered in yellow tablecloths, set with glassware and cutlery, surrounded by metal chairs, under a wooden roof with hanging plants and trees in the background.
A garden with green grass, trees, and bushes, featuring a vintage metal wagon sculpture, and a stone house in the background.
A lush green orchard with trees and grass, surrounded by rolling hills and a clear blue sky.
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Restaurant meal.jpg
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Suite living room.jpg

Room Accommodations

Suite Standard

Suite Superior

Join This Exclusive Retreat – Secure Your Place Today!
Hotel room with a double bed, wooden furniture, a stone accent wall, and a wall-mounted TV.

Master Suite

What’s Included

  • 7 nights in a luxury villa (all rooms feature en-suite bathrooms)

  • 5 in-villa, regionally inspired, chef-prepared dinners

  • Daily traditional Tuscan breakfast

  • Wine with dinner

  • Daily housekeeping

  • All activities and associated fees

  • Private drivers to and from activities

  • Private transportation to and from the airport/train station

  • Planned itinerary

  • Private tours for just your group

  • Gratuities for villa staff and drivers

What’s Not Included

  • Airfare or booking flights

  • Trip insurance

  • Local tourist tax

  • Meals outside the villa

  • Alcohol and wine outside of what is specified in the trip package

  • Travel plans outside of the villa stay

  • Personal expenses

  • Anything not specified in the trip package

Payments

  • $500 non-refundable deposit due within three days of booking

  • Balances due 150 days and 120 days before villa start date

  • Accepted payments: Zelle, Venmo, credit card, bank transfer

  • Interest-free payments customized to your needs

Here’s What Our Guests and Partners Are Saying…

  • “I experienced the magic of Tuscany with a group of wonderful women. Janine curated a luxurious vacation for us, inclusive of unique experiences that were personalized to our group, and she made sure we had whatever we needed while on the trip. What’s more is that everything was taken care of - I didn’t have to do any of the planning which saved a lot of time and heartache! This was a one-of-a-kind experience that I’m grateful to have had!"

    Christine D.

    Virginia

  • "Janine organized a great trip that brought us all together. We strengthened old friendships and formed new ones."

    Tammy K.

    Virginia

  • "My trip in May 2024 was truly fabulous! Janine handled everything seamlessly and ensured our comfort throughout our time together. Our villa was nestled amidst the estate's vineyard and olive groves and was simply beautiful. Unlike my typical travel planning, all I had to do was show up, explore charming towns, markets, and museums, and savor relaxing dinners at the villa. It was an unforgettable experience!"

    Cindy S.

    Virginia

  • “I miss all the wonderful women, the wine, the laughter and the great friendships that were formed. I want to go back! I will never forget this trip!"

    Benette P.

    Colorado

  • "What a special trip! Thanks Janine for your hard work to make it happen and to all the women brightening the journey. I love the encouragement of women friendships."

    Kathy S.

    Virginia

  • "What a beautiful experience! It was a true pleasure for Antonella and me to cook for your lovely group. We worked hard, yes, but always with joy, thanks to the warm and cheerful atmosphere you created. Your group is full of heart, humor and kindness. And you, Janine, were the soul of it all: attentive, well-organized, precise, and always with a smile. Thank you for your trust, your energy and all the good vibes."

    Anna and Antonella

    Tuscany villa cooks

  • "I had such amazing experiences on this retreat! A great opportunity to connect with old and new friends. As a previous B&B/retreat owner and many years spent in the industry, I can say that this retreat was well beyond my expectations and I sincerely wish for folks to just jump in and follow your heartstrings. The food, the ambiance and all the memories with our hosts, facilitators and new comrades (including tour guides) equates to a 10+++. As much as I loved my own retreat chalet, this was on a whole different, unique and fabulous level! Janine, Monica and Laura blended their incredible talents to create magic with this “Yoga on Italy” retreat! Ciao ❤️

    Susan W

    Maryland

  • "As a solo traveler, I was so impressed with Janine'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 Together in Tuscany."

    Janine C

    Colorado

  • "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."

    Barb M

    Virginia

Cancellation Policy

A non-refundable deposit of $500 is required to secure your booking. Half of your trip balance is due 150 days prior to the trip start date and the remaining balance is due 120 days prior to the trip start date.  All bookings made within 120 days of the trip start date require full payment. 

We understand that plans can change and emergencies come up. However, due to the nature of our business, deposits and payments are applied to third party vendors very shortly after payments are received. As such, we have a strict no-refund policy with the following exception: if the trip is cancelled by Together in Tuscany, the guest will receive a full refund for all payments made.

Travel Insurance

We HIGHLY recommend that you obtain travel insurance. If you must cancel your participation in a Together in Tuscany trip for any reason whatsoever, including health conditions, death of a family member, travel difficulties, personal reasons, or any other reason whatsoever, the travel insurance can cover some or all of these expenses. 

Service Agreement

All guests are required to review and accept the Terms and Conditions outlined in the Service Agreement which will be provided upon booking your room. The Service Agreement addresses risks and liabilities for the Provider (Together in Tuscany) and the Purchaser (Guest).