mapping your path



June 27 - July 2, 2022

Mapping Your Path is a week long retreat where exploration, creativity, community, and connection collide, and where you get to show up unabashedly as yourself.




Filmmaker, Activist & Social Entreprenur



Designer, Creative Coach & Workshop Facilitator

Are you ready for the next chapter? Do you ever feel like you’re stuck on auto-pilot? Encountering the same roadblocks/excuses over and over? Running in circles? Uphill? Doing all the things the gurus told you, and it doesn’t feel true to you? Playing by a set of rules that leave you exhausted and depleted?

WHAT IF there was another way from what society told us, from what school taught us, from what family modeled, and what we’ve told ourselves? WHAT IF we could do the things we really want deep down?

What if the journey didn’t have to be hard and heavy? WHAT IF it could feel fun, energizing, engaging, and inspiring? WHAT IF you could step away from what you know and do it in Tuscany?


Welcome to Mapping Your Path, a devoted time to focus on YOU for a whole week. It’s time to be intentional, take (aligned) action, and do things differently. Show up for yourself, with the support, encouragement, and company of an incredible community of humans. You don’t have to do this alone, you’ll be guided every step of the way.


All levels and places in life are welcome. 

Each morning the creator of Mapping Your Path, Anne Ditmeyer, will lead us in a  session where we’ll be exploring creative mapping exercises as part of our journey to map our paths forward. We’ll explore mindset, our strengths, what brings us joy and energy, and more to focus on our paths  forward that light us up—all through the help of pen, paper, and mapping!

Along the way, it will be a lot of FUN and you’ll uncover your superpowers and learn to embrace the secret sauce within you. No artistic skills are required. This is about learning to see the world through a different lens. No two paths are the same. There’s no one-map-fits-all. Maps help show us where we are, and where we want to go. You get to be the one who maps your path forward.


Afternoons are loosely structured sessions both at the villa and in the surrounding villages, allowing us to dig deeper into the work we did in the morning and use Tuscany as a lens for exploration.  There will be also plenty of time to spend at the villa relaxing, wandering through the vineyards and reading or journaling by the pool. 


Each evening we will come together again and check in either through an informal group session or yoga - or maybe both! Dinner reservations will be made for the group in  neighboring towns, you can choose to eat with the group or set out on your own - dinners (except for the first and last night) are at your discretion and not covered by the cost of the retreat, allowing you flexibility. There is a full kitchen at the Villa you can also choose to prepare meals in!


Anne Ditmeyer is a creative coach and workshop facilitator. A native Virginian, American by birth and French by hard work, she believes "travel is not about where you go, but how you see the world." Her blog, Prêt à Voyager (translation: ready to travel), explores the intersection of travel and design. Her year studying abroad had a huge influence in how she sees the world and approaches her work, driven by experience and viewing the city as her classroom.

Anne as never been one to do things the traditional way, pulling from her various studies and continued curiosity to design a life she loves. She’s pivoted her career multiple times from a career in graphic design and global communications, into education (traditional and online), creative coaching, and she now combines all the skills and tools and hosts creative workshops. She’s called Paris home since 2009, and started her own business in 2011 mastering French bureaucracy to earn French (dual) citizenship in 2016.

Her greatest joy comes from working with clients in collaborative settings and watching them light up as they unlock the magic within themselves. She supports them as they write their own rules and map their paths forward, and is known to have participants map on bananas. She’s on a mission to make the world more human.

She’s run workshops for CreativeMornings, Adobe, LouisVuitton, Parsons Paris, and more, in addition to regularly running her 3-month Mapping Your Path cohorts. Her work has been featured in Psychologies Magazine UK and Forbes.

The journey is the destination. (Even if it’s messy and not always straight forward.)

meet Anne


meet Ashley

Ashley Bearden is a filmmaker, activist and social entrepreneur based in New York City. Originally from Arkansas, she grew up inspired by her mother’s childhood spent abroad as the daughter of an Air Force pilot. She always knew she was meant to see the world too. After a short stint on Capitol Hill post college she landed in New York working on film and television sets for projects as varied as Lost in Translation, The Sopranos and Reading Rainbow. For the past 10 years she has focused on documentary film work and has had the opportunity to travel the world as a documentary filmmaker through her production company Do Good Films


Ashley has found that seeing the humanity of people and places through the lens of a camera gives you a relentlessly truthful perspective on injustices around the world. These perspectives led her to activism along the way. In 2020 she founded The Activist Collab - a virtual community of young changemakers supporting each other around the world.

From road trips in Spain working with Anthony Bourdain, to filming female empowerment programs in South Africa, to covering social justice protests in Los Angeles, she has followed her heart and taken her career along with it. 

Ashley’s love for travel, her unique way of seeing the world as a filmmaker, and her passion for social justice led her to create Travel Parallel - a community for those who love to travel and want to follow that love towards careers where they can use their unique gifts and truly feel alive. 



monday - 

June 27

As everyone will arrive at different times this afternoon is for exploring the Villa, hanging by the pool and jetlag recovery. We ask that everyone join the group for dinner so rest up as you need to. 

*if you are self driving , we ask that you arrive by 4PM.

A cocktail hour followed by dinner will begin at 5:30PM. 

Tuesday - Thursday -

June 28-30

A buffet style breakfast will be served (this will be available every morning.)

9AM we meet in the main living space for MYP sessions 

1-2PM - Lunch will be available on the terrace

Afternoons will involve excursions as we continue Mapping Our Path through Tuscany - a great way to do a day trip to Siena or Florence or a few of the famous Tuscan hill towns like Montepulciano.

We will have dinner reservations each evening for the group. You can choose to join or find a spot on your own. 

friday - 

July 1


7-9AM - buffet style breakfast in the main dining room

9AM - Final morning session

12-2PM - Lunch will be available on the terrace

Tonight we have a special farewell dinner. We will all be preparing our dinner together with the guidance of a chef in the villa's spacious kitchen and enjoy our feast as we reflect back on the week.

saturday -

July 2

We say our goodbyes. Transportation to airports/train stations will be arranged. 



Villa Lavacchio is a charming and elegant villa with a private pool. Located in a serene and spectacularly beautiful setting, just a few kilometres from the village of Montalcino. 


The quiet location allows for maximum relaxation while enjoying the outstanding views, taking in the Val d'Orcia and Crete Senesi that are considered the most beautiful parts of Tuscany. The villa has a large great room (where will have our daily Mapping Your Path sessions) and several smaller living areas allowing for private hideaway space and perfect spots for great conversation. In addition, it has a large kitchen (where we will all take a cooking class!) and two indoor dining areas as well as plenty of outdoor space for dining and lounging.


The grounds are surrounded by vineyards and walking trails and, don’t forget, the pool with views for days.


The villa is ideally situated for exploring the best of Tuscany. The closest village is beautiful Montalcino, just 5 miles from the villa. Also nearby are San Quirico d’Orcia, Pienza, Monticchiello, Bagno Vignoni, Chiusi, Montepulciano, and Buonconvento. Siena, Arezzo, Montepulciano, Monteriggioni, Pitigliano, Cortona, Arezzo, San Gimignano, and Florence are all within easy driving distance of 45 min to 1 hr.


In addition to exploring the nearby villages, there are options for wine tastings, long walks through the vineyards, and additional cooking classes, vespa tours or painting classes we can assist you with setting up.



Each retreat can accommodate up to 7 participants.

$5300 per person - Private Accommodation

There is one shared room accommodation option (two beds) $3800 per person

$1000 non-refundable deposit is due to secure your spot. The balance is due by May 27, 2022

* Please note: To help protect our travelers and the places we are visiting, all travelers must be fully vaccinated and upload proof of vaccination upon booking. 


The Villa Lavacchio is located just outside Montalcino in Southern Tuscany. 

FLIGHTS: If you are traveling from the US, it is easiest to fly into Rome  Fiumicino (FCO).  If you are traveling within Europe you may choose to fly in to Florence (FLR) and take the train to Montalcino.

We will coordinate with each of you to arrange transportation from the airport in Rome villa. It is about a 2.5 hour drive from Rome.

TRAIN: If you would like to take the train, the nearest station is Montalcino and it is about a 15 min drive from the Villa. TrentItalia tickets can be purchased here. Transportation from the train station to the villa will be provided.




Villa (5 nights). All room are en-suite. 


Breakfast & Lunch each day

Welcome cocktail hour and dinner 

Snacks & drinks throughout the day

Farewell dinner on the last night


Pick up and drop off at airport in Rome or local train station - Montalcino

Private driver available throughout the week for excursions


A cook and housekeeper will be on hand each day to prepare breakfast and clean common areas. Rooms will not be cleaned each day.


Four days of Mapping Your Path workshops and excursions


Because our retreats have lots of moving parts in terms of room combinations at the villa and other group considerations, we ask that you fill out the Booking Form below to ensure we can accommodate everyone and offer the best possible experience. 

Once we receive your Booking Form we will be in touch right away to let you know if there is space available and if so send you a link to book via PayPal or credit card. 


Frequently asked questions

How do I know if this trip is a good fit for me?

Do you keep rereading the page but keep making excuses not to sign up but really want to, then it's probably for you. You may also want to read Anne’s Biz Blog, Prêt à Voyager, or check out her social media if you're not familiar with her work. You also can reach out to Anne or Ashley with specific questions and we’ll do our best to help.

Will all of the time be structured or will there be free time as well?

We will have a Mapping Your Path session each morning and afternoon. These will take place at the villa and in surrounding villages so we get a chance to explore in beautiful Tuscany! While there will be structure, you will also have free time to relax at the villa and explore a bit on your own as well. If you choose to opt out of a session one day, that is perfectly fine. Transportation will be provided for all retreat related excursions but you will need your own transportation if you choose to go out on your own. We will have a group olive oil and wine tasting tour one day as well as a cooking class at the villa. 

Please note that the villa is in a rural area. It is beautifully situated in the middle of rolling vineyards that are great for long walks but it is not walkable to a town center. 

What is your cancellation policy?

We understand that flexibility is required for travel planning in the current COVID-19 scenario. Therefore, in case of travel restrictions (closure of borders and/or travel bans) imposed by the Country where the "party leader" (the person in whose name the booking is made, to whom all correspondence is addressed) resides or by the Italian Government, it will be possible to cancel the reservation free of charge. Travel Parallel will reimburse the amount paid.

Please note that travel restrictions do not include the requirement of a Covid test or Covid-vaccination entering in Italy or returning to your Country.


For instances not related to a border shut down, once your spot is booked, a refund is not possible. We will do our best to fill your spot and if we are able to do so, you would be refunded the full price minus a $100 cancellation fee.


Please note that testing positive for COVID immediately before traveling is not a condition for cancelling.

What is Italy's current COVID protocol?

As of 4/20/2022 per the US Embassy in Italy


*** Effective December 6, 2021, all air passengers 2 years or older (citizens of all nationalities, including U.S. citizens, whether vaccinated or unvaccinated) with a flight departing to the US from a foreign country, are required show a negative COVID-19 viral test result taken no more than 1 day before travel, or documentation of having recovered from COVID-19 in the past 90 days, before they board their flight. Air passengers will also be required to confirm in the form of an attestation that the information they present is true. Please visit the CDC webpages for more information on the requirement for proof of negative COVID-19 test or recovery from COVID-19 for all air passengers arriving in the United States.

What  airport should I fly into?

Flying into Rome (FCO) is the closest airport with direct flights from the US. The villa is a ~ 2.5 hours drive from the airport. We will provide transportation to and from the airport in Rome. Once you book we will coordinate directly with you about details.


If you are traveling from within Europe, you may choose to fly into Florence (FLR) which is a bit closer to the villa - ~ 1 hr 45 min drive or you can take the train to Montalcino ~3 hour 20 min - and we can pick you up from the train station.


Once you book we will help you with a plan for getting to the villa!

Do I need to be vaccinated?

Yes. In order to respect others on the trip as well as those we are visiting, everyone will be required to show proof of vaccination before booking can be completed. We will reevaluate testing protocols closer to the trip dates.