A women-only ‘week away’ in Puglia designed to nourish and rejuvenate through the practice of pilates and learning the Italian art of being present.

Recover a Slower Pace of Life

Like stepping back in time, the landscape of southern Italy is an invitation to observe an older, more connected world where shepherds are seen grazing their sheep, homemade pasta is a daily ritual, and wealth is measured by the hours spent with friends around the dining room table or sharing a glass of wine.

Largely undiscovered by travelers outside Italy, the region of Puglia preserves an approach to life where traditional Italy still thrives. Unlike a tour spent hurrying from one site to another, you'll spend the week in a masseria, a southern Italian villa, where you'll connect to the rhythms of Puglia, have time to stroll through the olive trees, and focus on the nourishing power of beauty.

Each day will begin with Pilates followed by activities that embrace a Pugliese approach to nourishing and strengthening the body. Throughout the week you'll take time to connect with cheese makers, wine-makers, and olive farmers; you'll cycle between seaside towns, create ceramics with local artisans, and learn traditional Puglian recipes in cooking lessons; you'll also find time to unwind and reflect whether by the pool or among the olive groves, or while hiking the coast, sailing the adriatic, or enjoying candlelit dinners with friends.

Reconnect and Restore

For those seeking to disconnect from work, technology, or the constant noise of modern life, this week in Puglia will provide an opportunity to embrace the daily rhythms of Puglia. Grounded in the practice of both Pilates and the 'dolce vita' the goal of this retreat is not just to get away but to strengthen both body and soul, to let exterior voices grow quiet, and to return home stronger, and more present to yourself and to those you love most.

Body Awareness, Movement, and Intention

Inspired by Joseph Pilates' vision that 'everyone is the architect of their own happiness', daily Pilates will introduce body and movement awareness while daily activities will encourage the Italian art of living in the moment.

Just as Pilates trains your body to make intelligent movements that support your body all day, every day, travel encourages a perspective of awareness, of stepping into the new and beautiful in order to rediscover the new and beautiful within yourself. From this perspective, the goal of practicing Pilates in Puglia is to strengthen this 'connectedness' to yourself and the world.

Jennifer Olsberg

Jennifer doesn’t just teach Pilates—she lives it. A former dancer and lifelong student of movement, she has traveled the world and returned each time with more clarity, depth, and understanding—not just of the body, but of people, patterns, and purpose. Now, she’s inviting you to join her in Puglia for a Pilates retreat that’s about far more than exercise.

Expect a week that’s part reset, part celebration. You’ll move, stretch, laugh, and slowly return to yourself—healthier in your body, clearer in your mind, and more grounded in your life. Jennifer’s classes are not about perfection. They're about presence. About meeting yourself exactly where you are and opening the door to where you might go next.

With over 20 years of experience bridging the East and West Coast traditions of Pilates—from the classical rigor of Romana Kryzanowska to the deeply therapeutic work of Marie-José Blom—Jennifer guides with intuition and insight. She sees people. She reads energy. And she finds the path that helps each person reconnect with strength, breath, and self-awareness.

This is movement as relationship building, as joy. As a way to remember who you are beneath all the noise.

Come to Puglia. Jennifer will meet you there—with humor, with honesty, and with just the right push to help you discover what’s waiting for you in Italy.

Next Departures

SEPT. 27 - OCT. 4, 2025

Starting Price

$4,995

per person

Group Size

16

Travelers Max.

Reconnect and Restore

For those seeking to disconnect from work, technology, or the constant noise of modern life, this week in Puglia will provide an opportunity to embrace the daily rhythms of Puglia. Grounded in the practice of both Pilates and the 'dolce vita' the goal of this retreat is not just to get away but to strengthen both body and soul, to let exterior voices grow quiet, and to return home stronger, and more present to yourself and to those you love most.

Body Awareness, Movement, and Intention

Inspired by Joseph Pilates' vision that 'everyone is the architect of their own happiness', daily Pilates will introduce body and movement awareness while daily activities will encourage the Italian art of living in the moment.

Just as Pilates trains your body to make intelligent movements that support your body all day, every day, travel encourages a perspective of awareness, of stepping into the new and beautiful in order to rediscover the new and beautiful within yourself. From this perspective, the goal of practicing Pilates in Puglia is to strengthen this 'connectedness' to yourself and the world.

Jennifer Olsberg

Jennifer doesn’t just teach Pilates—she lives it. A former dancer and lifelong student of movement, she has traveled the world and returned each time with more clarity, depth, and understanding—not just of the body, but of people, patterns, and purpose. Now, she’s inviting you to join her in Puglia for a Pilates retreat that’s about far more than exercise.

Expect a week that’s part reset, part celebration. You’ll move, stretch, laugh, and slowly return to yourself—healthier in your body, clearer in your mind, and more grounded in your life. Jennifer’s classes are not about perfection. They're about presence. About meeting yourself exactly where you are and opening the door to where you might go next.

With over 20 years of experience bridging the East and West Coast traditions of Pilates—from the classical rigor of Romana Kryzanowska to the deeply therapeutic work of Marie-José Blom—Jennifer guides with intuition and insight. She sees people. She reads energy. And she finds the path that helps each person reconnect with strength, breath, and self-awareness.

This is movement as relationship building, as joy. As a way to remember who you are beneath all the noise.

Come to Puglia. Jennifer will meet you there—with humor, with honesty, and with just the right push to help you discover what’s waiting for you in Italy.

Il Dolce Far Niente: A Southern Italian Villa

Throughout the week you'll stay in a masseria, a working Italian farm converted into a beautiful hotel. Surrounded by olive groves and equipped with its own restaurant, spa, and pool, your masseria operates like a traditional Italian family, welcoming guests as if they were returning home. The antidote to large, impersonal hotels in cities, every room in the masseria is slightly different, has its own story and expresses the hospitality of authentic Italy.

Itinerary

Day 1

Welcome to Puglia

After arriving at your Pugliese masseria, operating as a farm from the 1700's, you'll check into your room and be free to relax by the pool with a glass of wine or visit the spa. At 4:00 pm you'll gather for an orientation to Alithea's style of slow travel in Puglia while meeting the ladies you'll be hiking, cycling, and relaxing with over the coming week.

This evening you'll have dinner together at the masseria—your first taste of Puglia's hospitality and the pleasure of being connected to nature through food and wine.

Day 2

Cycling in Salento

At 8:00 am your day will begin with an hour of Pilates followed by breakfast.

Mid-morning, you'll set out for a day of cycling as you cover the territory that reveals the DNA of Puglia in the traces of Greek and Byzantine history, beautiful seaside towns, and medieval castles and marvelously frescoed churches. While moving at the speed of a bicycle you’ll have more time for conversation, observation, and the feeling that slowing everything down means seeing more of the world around you, not less.

In the late afternoon, you’ll return to the masseria in time for an aperitivo followed by a free evening.

‍

Biking: ~ 4 hours

Day 3

A Ceramics Workshop and Pugliese Wine

After your morning of Pilates and breakfast, you’ll give your glutes a rest with a day dedicated to ceramics and wine. Your first stop this morning will be a ceramics workshop where you’ll have a chance to throw clay with a local potter before heading out for a late lunch at a nearby vineyard where you’ll taste the great Pugliese wines.

You’ll be free for dinner this evening, either at the restaurant of the masseria or in town a twenty-minute walk from the farm.

‍

Bus time: ~1 hour

‍

Day 4

Hiking and Swimming along the Salento Coast

After a morning of Pilates dedicated to body-awareness and the practice of intelligent movements, you’ll set out for a day of hiking and swimming along the coast.

In the late afternoon you’ll return to the masseria for a cooking lesson where you’ll learn to make orecchiette, i maccheroncini, e le sagne ncannulate, the home made pastas of Salento, followed by dinner.

‍

Hiking: ~ 5 hours

Day 5

Lecce: ‘the Florence of the South’

After Pilates and breakfast, you’ll depart for nearby Lecce, the jewel of Puglia, as rich in baroque architecture as in its thousands of years of history dating back to the Trojan War.

This morning you’ll walk through the civilizations from the Greeks, Romans, Normans, to the Holy Roman Empire and modern Italian state with a walking tour through the city followed by free time for lunch.

In the mid-afternoon you’ll return to the masseria in time for a quick swim before dinner.

‍

Day 6

Sailing the Adriatic

After Pilates and breakfast this morning, you’ll depart for the coast for an afternoon of sailing. Moving at the speed of the wind, you’ll observe the coastline and caves from the sea, taking time to swim and to enjoy Pugliese food and wine.

Day 7

Cheese Making, Olive Oil, and the Music and Dancing of Puglia

After Pilates and breakfast, you’ll hop back on bikes to cycle to a nearby farm where you’ll learn to make mozzarella or another local cheese that you’ll be able to make again when you return home.

Your next stop this morning will be a traditional frantoio where you’ll taste the local olive oil of a local farmer that still speaks griko or the ancient language of the Greeks.

This afternoon you’ll have some free time to relax by the pool or visit the spa before this evening’s celebrations where you’ll learn the traditional dance and songs of the pizzica with the women of Puglia.

‍

Biking: ~1.5 hrs

Day 8

Pilates in Puglia to Bring Home

This women’s retreat concludes with a final Pilates practice and breakfast. Your guide and pilates instructor will be available to help with the next leg of your journey as you continue to practice the intentionality of movement and the art of being present everywhere you go.

Day 9

Day 10

Day 11

Day 12

Day 13

Day 14

Day 15

What people say

No items found.

What's Included?

All breakfasts and six additional meals

All transportation throughout the trip

Seven days accommodation, activities, and logistics management

The cost of all entrances, local guides, and 10 tour activities

Your friendly Alithea tour manager for the duration of the tour.

All breakfasts and six additional meals

Daily sessions with your Pilates instructor, Amanda Marley

Optional private consultation with onsite nutritionist, Sarah Weiss

No items found.

Jennifer Olsberg

Jennifer doesn’t just teach Pilates—she lives it. A former dancer and lifelong student of movement, she has traveled the world and returned each time with more clarity, depth, and understanding—not just of the body, but of people, patterns, and purpose. Now, she’s inviting you to join her in Puglia for a Pilates retreat that’s about far more than exercise.

Expect a week that’s part reset, part celebration. You’ll move, stretch, laugh, and slowly return to yourself—healthier in your body, clearer in your mind, and more grounded in your life. Jennifer’s classes are not about perfection. They're about presence. About meeting yourself exactly where you are and opening the door to where you might go next.

With over 20 years of experience bridging the East and West Coast traditions of Pilates—from the classical rigor of Romana Kryzanowska to the deeply therapeutic work of Marie-José Blom—Jennifer guides with intuition and insight. She sees people. She reads energy. And she finds the path that helps each person reconnect with strength, breath, and self-awareness.

This is movement as relationship building, as joy. As a way to remember who you are beneath all the noise.

Come to Puglia. Jennifer will meet you there—with humor, with honesty, and with just the right push to help you discover what’s waiting for you in Italy.

Tour tips

Pack Light

This is some text inside of a div block.

Come Prepared

This is some text inside of a div block.

Bus and Travel Time

This is some text inside of a div block.

FAQ

For further questions don't hesitate to reach out to us directly.

explore@alitheatravel.com

Do I need to be proficient at pilates in order to sign up?

Previous pilates experience is not necessary; however, pilates is a cornerstone of the experience and we recommend some familiarity with basic movements before arrival.

How physically demanding will the trip be?

This is an active trip with physical activities planned each day. In addition to the morning pilates practice, you will spend considerable time walking, hiking, and cycling throughout the week. If you do not lead an active lifestyle or would like recommendations on how to prepare physically for the trip, please write to us before signing up.

This is some text inside of a div block.

The masseria is about one hour by car from Brindisi (BDS), the closest airport. You can also fly into Bari (BRI) or other Italian cities and take the train to Lecce. From Lecce it’s about 30 minutes by car to the masseria. Wherever you choose to arrive, we recommend setting up a transfer service with Daniele Scodari (danieletransfer@libero.it).

Is it possible to book additional nights at the masseria before the start or after the end of the trip?

There is much more to see in Puglia and spending a little extra time in the masseria is a great way to settle into the rhythms of southern Italy. If you wish to extend your stay before or after the trip dates, let us know and we’ll help coordinate the additional nights.

A Christian Classical Approach to Travel

Travel encourages a living experience of art, history, and ideas that transforms the classroom into an immersive experience of truth, beauty, and goodness. Museums, meals, archeological sites, and foreign languages are not merely artifacts that help students consider the world, they cultivate a love of wonder, moral imagination, and a rich understanding of the truth. More than a student trip, travel is an invitation to become a lifelong practitioner of the loves that shape the soul.

The Prayerful Traditions of Europe

Rather than treating churches and monasteries as defunct historical monuments, Alithea and Oakdale Academy invite students to approach them as places of prayer and worship

Your Cart

Pilates in Puglia with Jennifer

Next Departures

Starting Price

Group Size