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ITALY RETREAT

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Experience Italy Like a Local

Join us for an unforgettable week in one of Italy’s most beautiful and undiscovered regions. Nestled between rolling vineyards, medieval hilltop villages, olive groves, and the sparkling Adriatic coastline, La Marche offers everything we love about Italy (without the crowds!).

This retreat is designed for travelers seeking the perfect balance of movement, relaxation, culture, and connection. Our home for the week, Oliveto Estate, provides an intimate and authentic setting where you’ll slow down, savor incredible local cuisine, move your body daily and immerse yourself in the rhythms of Italian life.

Whether you’re enjoying a morning pilates workout overlooking the countryside, wandering cobblestone streets in a nearby village, learning to make fresh pasta from local chefs, or spending an afternoon at the beach with new friends, every day is intentionally curated to help you reconnect with yourself while experiencing the magic of Italy.

Leave feeling nourished, inspired, and deeply restored.

Retreat Details

When:

June 26 – July 3, 2027
7 nights / 8 days

Where:

Oliveto Estate: La Marche, Italy

The Investment:

-Seaview Suite:
$4,850 per person | shared room
$5,950 per person | private room
-Garden View Suite:
$4,650 per person | shared room
$5,800 per person | private room

$800 non-refundable deposit due to secure your space. Payment plans available.

Person doing yoga on a wooden deck outside a modern house under the sun.
Person in infinity pool at sunset, overlooking a scenic view.
People share a meal with pizza, salad, pastries, and drinks on a wooden table.
Person holding uncooked pasta strands with both hands.
People dining on a deck with a scenic landscape view at sunset.
Luxurious house with large windows, pool, and landscaped yard under a blue sky.
Scenic beach with cliffs, turquoise water, and land formations in sunlight.
Group cooking class outdoor, instructor at the table's end with participants on both sides.
Person using a peel to remove a pizza from a metal pizza oven.
Aerial view of a rural landscape with buildings, tennis court, pool, and trees.
Group of women sharing a meal around a dining table.

WHAT’S INCLUDED:

✔ 7 nights accommodations at Oliveto Estate
✔ Daily yoga, pilates, fitness, and wellness classes led by Jessie and Jess
✔ Brunch and dinner daily
✔ Roundtrip airport transfers
✔ Guided coastal hike and beach adventure
✔ Traditional Italian pasta-making workshop
✔ Visits to charming local villages and markets
✔ Plenty of free time to relax, explore, swim, and enjoy the Italian countryside
✔ A supportive community of like-minded travelers

WHAT’S NOT INCLUDED:

✘ International airfare
✘ Travel insurance (strongly recommended)
✘ Gratuities and tips
✘ Optional excursions and activities not listed above
✘ Alcoholic beverages and personal purchases

What To Expect

Imagine waking each morning to the sounds of nature and the scent of fresh espresso drifting through the Italian countryside. Begin your day with movement, whether it’s an energizing pilates class, gentle yoga practice, or mindful stretch session, before gathering for a leisurely brunch featuring fresh local ingredients.

Days unfold at an unhurried pace. Wander through historic villages where life still moves slowly, browse local markets, enjoy long lunches under the shade of olive trees, or spend the afternoon swimming in the crystal-clear waters of the Adriatic Sea. Learn traditional Italian cooking techniques from local experts, sip wine as the sun sets over the hills, and share meaningful conversations around the dinner table with fellow travelers.

This isn’t a retreat built around rushing from activity to activity. It’s an invitation to embrace the Italian art of la dolce vita—to savor each moment, prioritize connection, and experience Italy the way locals do.
Expect movement without pressure, adventure without exhaustion, and plenty of space to simply be.

Come for the beauty of Italy. Leave with new friendships, renewed energy, and memories that will stay with you long after you’ve returned home.

Meet Your Instructors:

Jessie Benson doing yoga on a beach at sunset, balancing on one leg.

Jessie Benson

Jessie Benson is a retreat curator, mom, yogi, fitness instructor and adventure enthusiast passionate about helping people explore the world with intention. After years in corporate marketing, Jessie followed her love of travel and wellness to lead more than 45 retreats across the globe — from South Africa’s savannas to the Greek Islands and beyond. As the founder of FloYo Travels, she combines movement, community and meaningful cultural experiences to create transformative journeys that last long after the trip ends.

Jessie will lead daily yoga practices while we are in Italy. From energizing power vinyasa classes to restorative evening sessions under the stars, her classes will spark inspiration and leave your body feeling refreshed.

Jessica Newshel sitting cross-legged, holding a circular exercise ring over their face.

Jessica Newshel

Jessica has been a certified Classical Pilates instructor since 2011. An outdoor enthusiast, Jessica enjoys tennis, skiing, hiking, running, and paddleboarding. She started to focus more on Pilates in order to rebuild core strength after childbirth. Through doing so, she experienced firsthand how Pilates transforms posture, relieves low back pain, and enhances functional strength for athletic performance as well as daily movements.

Jessica is excited to bring classical Pilates our Italy Retreat. At Oliveto, you will be able to enjoy daily, small group Pilates classes perfect for both newbies and those with prior experience. Jessica offers thoughtful modifications to ensure every class feels tailored to each participant’s body. By the end of the week, you will note how Pilates not only improves core strength, mobility, balance, flexibility, and movement quality but also helps reduce injury risk and support recovery.

About our Accommodation:

Sample Itinerary

Join Us In Italy
Outdoor patio with wooden pergola, white sofa, chairs, table, and view of garden under blue sky.
Indoor dining area leads to outdoor table on patio with scenic view.
Infinity pool with deck chairs and ocean view.
Cozy living room with large window, sea view, and modern furniture.
Outdoor patio with wicker sofa, white cushions, fabric canopy, and wooden slat walls in sunny garden setting.
Bright bedroom with large bed, ornate mirror, and balcony view.
Outdoor dining table set with white cloth, glassware, near an outdoor kitchen with a pizza oven.
Minimalist bathroom with oval sink, mirror, and light beige walls.
Cozy living room with large windows, sofas, armchairs, and a view of nature.
Spacious kitchen with a long island, stools, pendant lights, and a view of a dining area.
Elegant dining room with a long wooden table, black chairs, and large windows overlooking a garden.
Outdoor dining setup with plates, glasses, a lit candle, and cushions under a tree at dusk.
Modern bedroom with a gray upholstered headboard, white bedding, and a small bedside lamp.