Overview

You, Me, & Tuscany: The Wine Retreat
54100 Massa, Province of Massa and Carrara, Italy
Jun 5 - 12, 2027
The Self Care Retreats image
The Self Care Retreats
$5,999
Deposit: $500

About your trip

There are some experiences a woman dreams about for years.

Sipping wine beneath the Tuscan sun. Wandering cobblestone streets in Florence. Riding a Vespa through rolling hills lined with vineyards. Dressing up for long dinners under the stars. Feeling beautiful, free, rested, and deeply alive.This isn’t just a retreat—it’s a reset. A soft landing for your spirit and a powerful reminder of the gem you already are.

This is your invitation to indulge in beauty, pleasure, softness, and unforgettable memories in one of the most romantic places in the world.

A Luxury Wine & Wellness Retreat

Join an intimate group of women for 7 nights in Tuscany at a breathtaking countryside estate surrounded by olive groves, vineyards, cypress trees, and panoramic views. Think timeless Italian elegance, serene luxury, sun-drenched mornings, wine-filled afternoons, and evenings that feel like scenes from a movie.

whisk me away to wine country

❋ A Dreamy Tuscan Escape

Nestled in the hills of Tuscany, our private luxury estate offers the kind of beauty women dream about—stone villas, elegant interiors, lush gardens, and sweeping countryside views.

❋ Rest in Beautiful Surroundings

Wake each morning to birdsong and golden sunlight, sip espresso overlooking the hills, and enjoy peaceful spaces made for journaling, reflection, and true relaxation.

❋ Luxury Without Pressure

Spend your days laughing with new friends, exploring Italy, lounging by the pool, or simply resting in softness. This is beauty without rush and luxury without stress.

❋ Curated Experiences Included

Your stay includes 7 nights accommodations, daily breakfast, select dinners, wine tastings, transportation for excursions, a Vespa countryside tour, Florence and Pisa day trips, self-care moments, sisterhood, and a special retreat gift bag.

What's included

Accommodations

All 5 star living accommodations

Transportation

All transportation

Meals

Majority of meals with the exception of 1-2 (your lunch or dinner will be your expense on free days)

Sessions

All tours, excursions, workshops, and classes

What's not included

Flights

Roundtrip flight to/from Italy

Spa services

Free Day Meals

For self exploration days, attendee is responsible for covering their meals while out.

Hot Air Balloon

This is an optional activity at cost to attendee

Day 1: June 5th

Day 1: June 5th image

Arrival To Tuscany

Welcome to Italy. Arrive at our countryside estate, settle into your beautiful room, and exhale into the beginning of something special. That evening, we’ll gather for a chic welcome dinner filled with wine, laughter, and connection as the sun sets over the Tuscan hills.

Welcome to Italy

Arrive in Tuscany and begin your unforgettable retreat experience.

Countryside Estate Check In

Settle into your beautiful room surrounded by rolling hills and timeless beauty.

Time to Exhale

Unpack, refresh, and ease into the slower rhythm of Italy.

Chic Welcome Dinner

Gather for wine, laughter, and introductions as the sun sets over Tuscany.

Theme: Arrival, Softness, Intention

Begin the week grounded, open, and cared for.



Day 2: June 6th

Day 2: June 6th image

Slow Morning & Tuscan Wellness

Ease into the rhythm of Tuscany with a slow morning, breakfast, and time to simply be. Spend the day lounging poolside, journaling, resting, or connecting with the group before enjoying a beautiful dinner together that evening.

Sleep In & Savor The Morning

Enjoy a relaxed start with breakfast and slow living.

Poolside Peace

Lounge by the pool overlooking the countryside.

Journal & Reconnect

Take time for reflection, rest, or conversation.

Evening Group Dinner

Share a beautiful dinner with the group nearby.

Theme: Rest, Receive, Reset.

Let yourself soften into ease.


Day 3: June 7th

Day 3: June 7th image

Chianti Wine Country Escape

Today we journey to the iconic Chianti region for a dreamy day in wine country. Enjoy scenic drives, breathtaking vineyard views, a curated wine tasting, and a leisurely lunch surrounded by the beauty of Tuscany.

Journey To Chianti

Travel through scenic Tuscan hills to wine country.

Dreamy Vineyard Views

Spend the day surrounded by iconic landscapes and vineyards.

Curated Wine Tasting

Enjoy a luxurious tasting at a beautiful winery estate.

Lunch with a View

Savor lunch overlooking the countryside.

Theme: Pleasure & Abundance

Indulge in beauty, flavor, and joy.


Day 4: June 8th

Day 4: June 8th image

Vespa Through Tuscany

Experience Tuscany the unforgettable way—on a Vespa ride through the hills. Cruise through charming villages, winding roads, and postcard-worthy landscapes while embracing the joy, freedom, and fun of Italian adventure.

Main Character Energy

Today is all about freedom, fun, and unforgettable moments.

Guided Vespa Tour

Explore Tuscany the iconic way—on a Vespa.

Postcard Worthy Villages

Ride through charming villages and winding roads.

Scenic Countryside Views

Take in vineyards and breathtaking landscapes.

Theme: Joy & Adventure

Feel alive, playful, and fully present.


Day 5: June 9th

Day 5: June 9th image

Free Day in Florence

Spend a full day in Florence exploring exactly how you choose. Shop luxury boutiques, wander historic streets, sip wine in a piazza, visit museums, or simply enjoy the beauty of living slowly in one of Italy’s most iconic cities.

Your Day Your Way

Enjoy a full free day in Florence.

Shop & Explore

Browse boutiques, leather markets, and hidden gems.

Culture & Beauty

Visit museums, historic streets, and piazzas.

Wine & Dining

Sip wine and enjoy unforgettable meals.

Theme: Beauty & Freedom

Romanticize life on your own terms.


Day 6: June 10th

Day 6: June 10th image

Pisa & Coastal Charm

We’ll take a stylish day trip to visit the famous Leaning Tower of Pisa and explore the charm of the surrounding town. Expect beautiful architecture, cafés, photos, and a playful day discovering another side of Italy.

Day Trip to Pisa

Visit one of Italy’s most iconic landmarks.

Leaning Tower Moments

Capture photos at the famous Leaning Tower of Pisa.

Explore the Town

Wander charming streets and beautiful architecture.

Cafe & Leisure

Enjoy a lighthearted day with coffee and culture.

Theme: Wonder & Play

Stay curious, light, and joyful.

Day 7: June 11th

Day 7: June 11th image

Choose Your Magic Day

Today is yours to enjoy at your own pace. Relax at the estate, lounge by the pool, book a massage, or choose our optional hot air balloon experience over the Tuscan hills. We’ll close the retreat with a beautiful farewell dinner.

Your Perfect Day

Spend the day exactly how you choose.

Relax at the Estate

Enjoy the pool, peaceful grounds, or quiet rest.

Optional Hot Air Balloon Over Chianti

Float above vineyards and hills at sunrise.

Farewell Dinner Celebration

Gather one final time for a beautiful closing dinner.

Theme: Celebration

Honor the joy and memories created.


Day 8: June 12th

Day 8: June 12th image

A Beautiful Farewell

Enjoy one final espresso and one last view of Tuscany before departure. Leave feeling fuller than you arrived—rested, radiant, inspired, and deeply connected.Today is yours to enjoy at your own pace. Relax at the estate, lounge by the pool, book a massage, or choose our optional hot air balloon experience over the Tuscan hills. We’ll close the retreat with a beautiful farewell dinner.

One Last Espresso

Enjoy one final slow Tuscan morning.

Final Views

Take in the beauty one last time.

Heartfelt Goodbyes

Say farewell to new friends and memories made.

Leave Renewed.

Return home rested, radiant, and inspired.

Carry Tuscany with You

Let the magic stay with you long after departure.


Location

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1. 54100 Massa, Province of Massa and Carrara, Italy

54100 Massa, Province of Massa and Carrara, Italy

About your organizer

A travel destination company for women of color to release, relax, and unwind.

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