Courageous Destination Coaching
Courageous Destination Coaching
  • Home
  • About Your Coach
  • Coaching FAQs
  • Contact Us
  • Courageous Retreats
  • Retreat in Puglia, Italy
  • Courageous Testimonials
  • Courageous Blog
  • More
    • Home
    • About Your Coach
    • Coaching FAQs
    • Contact Us
    • Courageous Retreats
    • Retreat in Puglia, Italy
    • Courageous Testimonials
    • Courageous Blog
  • Sign In
  • Create Account

  • My Account
  • Signed in as:

  • filler@godaddy.com


  • My Account
  • Sign out

Signed in as:

filler@godaddy.com

  • Home
  • About Your Coach
  • Coaching FAQs
  • Contact Us
  • Courageous Retreats
  • Retreat in Puglia, Italy
  • Courageous Testimonials
  • Courageous Blog

Account


  • My Account
  • Sign out


  • Sign In
  • My Account

Choose Courage Over Confidence: A Journey to Empowerment in Italy

DATES TBD

Transform Your Life on our Puglia Retreat!

For $3,565 per person (single occupancy), you will become a special member of the Choosing Courage Over Confidence journey! Your $500 non-refundable (see our cancellation policy in the FAQs for more information) will reserve your spot on this once-in-a-lifetime experience. And, if you sign up before [DATE], you qualify for our early-bird pricing of $3,265! 

Reserve My Spot!

Our Itinerary

Day 1

We'll all arrive by 3:00 p.m. at Masseria Aprile on [DATE TBD]. Once we're settled in, we'll get to know each other, meet our hosts so we can learn about our home away from home, and talk about the upcoming week. That evening, we'll enjoy a Welcome Dinner, which is included in the retreat price. 


We'll start each day with homemade breakfast (included) before getting together for a workshop and group discussion. Each workshop will conclude with a journal prompt. After the workshop, we'll take a day trip to a nearby town before returning to Masseria Aprile  to rest and get ready for dinner.


Lunches and dinners will take place in various restaurants in Locorotondo or another nearby town. You are welcome to eat with the group or on your own, if preferred. Unless otherwise indicated, participants will pay for their own lunches and dinners.

Day 2

In our first workshop, we will Define Courage, discuss Courageous Examples, and explore ways we can try Courageous Acts. After our workshop, we'll have lunch in Alberobello and wander through the town. 

Day 3

Our second workshop will outline the Seven Courageous Traits. We'll begin with Intentionality and Purpose before we go to Polignano a Mare for a spectacular, scenic lunch in a cliff-side restaurant.

Day 4

Now it's time to delve into Curiosity & Openness and Risk-Taking, the next two Courageous Traits. Then we will head to Lecce for lunch and a walking tour.

Day 5

Acceptance, Adaptability and Commitment are today's Courageous Traits and will help us learn how to embrace what is and let go of our expectations for specific outcomes. We'll then make our way to Martina Franca for lunch before our wine tour at I Pastini Winery.

Day 6

Facing Your Fears and Limiting Beliefs is today's workshop. This can be one of the most powerful discussions of the retreat, so from here, we'll spend time wandering the grounds  of Masseria Aprile to soak up the natural energy around us before we go to Cisternino.

Day 7

We've worked hard. We've dug deep. Today we're going to take it slow. Rather than have a workshop, we'll start our day with gentle yoga before we spend the day in Matera. One of the oldest cities in the world, Matera has captivated artists and continues to enchant us with its Sassi (cave dwellings carved into limestone cliffs). We'll take our courage to this ancient city as we connect with its history before we relax and reflect over dinner.

Day 8

Our final workshop will focus on ways we can Practice Courage Everywhere. We'll focus on our Strengths & Accomplishments, learn how to Reframe Negative Self-Talk, and discuss ways to Practice Self-Compassion & Patience. This workshop will help set you up for success when you get home and it will remind you that you have connected with an amazing group of women who have your back and will support you going forward!

Day 9

Homeward bound!

How did I get this far without signing up?!

Frequently Asked Questions

Please reach us at courageousdestination@gmail.com if you cannot find an answer to your question.

  • Any cancellation will result in a total loss of the $500 USD registration deposit.
  • Any cancellation made between: [DATE] and [DATE] will result in a loss of 50% of the trip price.
  • Any cancellation made between: [DATE] and the trip departure will result in a total loss of funds.
  • We reserve the right to cancel the trip if it is not meeting the trip minimum (if we do so, your deposit will be refunded in full).
  • Trip cancellation insurance is always highly recommended whenever making travel plans. You can use our suggested Travel Guard Insurance online and choose from several policy options or find your own policy.
  • The tuition for this retreat is based on the currency rates of exchange in effect at the time of the publication of this retreat. We reserve the right to adjust the trip price if the exchange rate varies more than 5% from our published price.
  • After making your deposit, you will have a Clarity Call on Zoom with Sheryl. If for any reason during this conversation you both agree that you are not a fit for the retreat, your deposit will be refunded in full. If however, you both agree it is still a fit, the deposit remains non-refundable.


Unless otherwise indicated, breakfast is served each day at the villa. Free time is your choice — you can explore the nearby town or relax/reflect on the villa grounds. 


There are six (6) day trips (see below) included on this retreat (dates/times to be confirmed). Transportation costs for day trips as well as the cost of any guided walking tours are included in the cost of the retreat. Unless otherwise indicated, the cost of any meals eaten while on a day trip — shared as a group or individually — are the responsibility of each participant. Any other costs (beverages, food, souvenirs, other shopping, etc.) incurred while on a day trip are the responsibility of each participant.

  • Alberobello
  • Polignano a Mare
  • Lecce or Matera
  • Cisternino
  • Martina Franca
  • Ostuni

Italian-inspired activities (all costs included in the price of the retreat)

Cooking Class in Locorotondo

  • Winery Tour at I Pastini in Martina Franca
  • Wine & Food Tastings at Masseria Aprile in Locorotondo
  • Visit to Fondazione Museo Pino Pascali (modern art center) in Polignano a Mare
  • Visit Local Markets
  • Yoga Class at Masseria Aprile


Yes, you will have time to relax or explore between our scheduled activities. While we recommend you use some of your free time to rest and reflect, you are more than welcome to explore the area. Please note: Transportation will be provided for retreat activities only; we can help arrange transportation, if needed, but you are responsible for the cost.


You are more than welcome to bring a friend who is interested in joining this retreat and you two can room together. However, if you need a roommate, we’d be happy to match you with another retreat participant who is also interested in sharing a room. Please note your request for a roommate in the registration form.


This retreat is for adult women seeking to transform their life into one of peace, growth and deeply fulfilling relationships. To ensure you — and all participants — enjoy the best possible retreat experience, please leave your kids and partners who are not participating in the retreat at home.


We highly recommend you purchase travel insurance in the event you have a sudden change in plans or an unexpected emergency. Please make sure you review and agree to our cancellation policy.


  • Please fly into the Brindisi Airport (BDS, Contrada Baroncino, 72100 Brindisi BR, Italy), which is about one hour away from our accommodations at the Masseria Aprile in Locorotondo. 
  • Please arrive on or before November 1, 2025. If possible, please try to land between [TIME] and [TIME] so you can take advantage of the pre-arranged ground transportation (details to be provided). If you arrive outside of this time frame, please contact Sheryl at 781-724-2527 or at courageousdestination.com for information about ground transportation options.
  • If you arrive prior to the start of the retreat, you are responsible for your lodging costs and you must arrange for your own ground transportation to the Masseria Aprile on November 1. Please arrive at the villa by [TIME].


Yes, the villa’s hostess can accommodate dietary restrictions. Please use the registration form to indicate any dietary restrictions.


Copyright © 2025 Courageous Destination Coaching

All Rights Reserved.


Powered by

This website uses cookies.

We use cookies to analyze website traffic and optimize your website experience. By accepting our use of cookies, your data will be aggregated with all other user data.

Accept