A Sweet Life Retreat

Legacy +
Leisure

Reclaim. Radiate. Return.

SEPTEMBER 17 – 20, 2026 · OAK BLUFFS, MARTHA'S VINEYARD

ONLY 8–10 WOMEN · BY DESIGN

WHY THIS PLACE

This island has held
Black joy for over a century.

Before we talk about this retreat, we need to talk about this place because where you rest matters as much as how you rest.

Oak Bluffs, Martha's Vineyard has been a sanctuary for Black Americans since the late 1800s. At a time when most of America refused to welcome us, Black families, artists, writers, and visionaries found refuge here, building community, buying land, and passing both down through generations.

The Inkwell, Oak Bluffs' legendary beach, became a symbol of Black joy reclaimed. Harlem Renaissance writers walked these shores. Civil rights leaders gathered in these cottages. Dorothy West wrote here. The Obamas vacationed here. And every summer, Black families return - by tradition, by inheritance, by choice.

This is not just a beautiful island. It is hallowed ground. A place where Black people have always known how to rest, gather, and thrive and where that legacy lives in every ocean breeze.

"When we gather here in September, we are not just on a retreat.
We are standing in a lineage of Black women who chose themselves."

Sweetness is your birthright.

This retreat is your invitation
to live inside it.

Over four intentional days on the storied shores of Martha's Vineyard, you'll rest deeply, reconnect gently, and return to yourself without urgency or expectation. Held at the Summercamp Hotel in Oak Bluffs - a beautifully curated space in the heart of this historic community - every detail has been chosen to honor your fullness.

This is not a getaway. This is a return - to yourself, to ease, to the kind of leisure that has always been your inheritance.

Photo by Christine Sargologos | Edited by Noah Rosenberg

A large Victorian-style house with blue shingles and multiple windows, featuring a porch with white columns and lounge chairs. There are flowers and plants in front of the house. A sign reads 'Summercamp, Oak Bluffs Hotel - M.V.' indicating a summer camp or hotel setting. The sky is clear and blue, and the grass is green.

Planning to bring a friend?

We have a special Circle Rate available for women joining together. This retreat is even sweeter when shared with someone who knows your heart. Email us at retreats@holistree.comfor details - we'd love to hold space for you both.

Two queen beds with yellow and green pillows, a nightstand with a lamp and plant, a chair with a pillow, window with patterned valance, and a green throw blanket in a beachside room.
A bedroom with a floating bed suspended by thick ropes, a blue and white color scheme, decorative pillows with green, yellow, and black patterns, a nightstand with plants and decor, a water-themed mural on the wall behind the bed, and minimalistic wall decor.
Reserve your spot

WHO THIS IS FOR

For Black women who hold everything and are ready to be held.

  • You lead, nurture, and give so much to everyone else and rarely take time to pour back into yourself

  • You are ready to experience leisure not as a reward, but as a way of life

  • You crave rest that actually restores surrounded by beauty, depth, and community

  • You want to be in a space that honors the fullness of who you are

  • You are drawn to experiences rooted in culture, legacy, and meaning

  • You desire connection with women who understand your rhythm and your power

Woman smiling, wearing sunglasses and a black sweater with 'Summer Vibes' written on it, standing outdoors next to a windowed building, with a large white and orange duffle bag labeled 'ESCAPE' and a black rolling suitcase.

"You'll leave feeling restored, clear, and quietly radiant - connected to yourself and to a circle of women who understand the power of ease."

"What I love most about these retreats is the intentionality. I always feel like they've created the moment exactly for me."

-DIONNA M., SWEET LIFE RETREAT

YOUR EXPERIENCE INCLUDES

Everything held.
Everything intentional.

Your investment wraps you in the essentials of a fully curated Sweet Life experience. Meals outside of our group gatherings are yours to explore freely - Martha's Vineyard has a rich landscape of Black-owned restaurants and local gems waiting for you.

4 days / 3 nights at the Summercamp Hotel, Oak Bluffs

Sweet Life Welcome Ritual + curated gift set

Welcome Dinner - communal, intentional, abundant

Lunch on our island outing day

Slow farewell morning to close our time together

Daily grounding practices - meditation, gentle movement, reflection

Sweet Life signature workshops + sessions

Curated island outing rooted in legacy, culture, and leisure

Sweet Life retreat workbook + themed practices

Curated guide to Black-owned local gems on the island

Professional retreat photography - your Sweet Life moments, captured

Closing circle + blessings for your return home

SAMPLE ITINERARY- Four days on the island.

DAY 1 · THURSDAY, SEPTEMBER 17

Arrival & Soft Landing

  • Arrival at Summercamp Hotel, Oak Bluffs

  • Sweet Life Welcome Ritual + curated gifting

  • Opening circle + intention setting

  • Sunset Welcome Dinner — communal, candlelit, abundant

  • Evening wind-down + porch conversations by the water

DAY 2 · FRIDAY, SEPTEMBER 18

Legacy & Leisure

  • Morning meditation + gentle movement

  • Sweet Life Session: Rest, Sweetness & Power

  • Curated island outing - exploring the legacy of Oak Bluffs, the Inkwell, and the African American Heritage Trail

  • Lunch at a Black-owned island restaurant

  • Afternoon spaciousness - rest, journal, wander

  • Evening gathering + reflections

DAY 3 · SATURDAY, SEPTEMBER 19

Integration & Radiance

  • Morning grounding + intention renewal

  • Sweet Life Signature Session: Reclaiming Your Rhythm

  • Free afternoon - the island is yours to savor

  • Closing Dinner - communal toast, storytelling, celebration

  • Evening reflection + sweetness cards

DAY 4 · SUNDAY, SEPTEMBER 20

Return Renewed

  • Slow farewell morning — unhurried, spacious, sweet

  • Closing circle + blessings for the journey ahead

  • Departures feeling full, grounded, and quietly radiant

*Itinerary subject to minor changes to preserve flow and spontaneity.

"The thing that touched my heart so deeply was the love and celebratory manner in which I was received. I felt heard. I felt valued."

CHANIKA M., SWEET LIFE RETREAT

YOUR INVESTMENT

Legacy is not only
what you leave behind.
It is how you live now.

This retreat is intentionally limited to 8-10 women to preserve intimacy, depth, and a high-touch experience. A small number of spots are available.

Most Popular

SINGLE ROOM $3,850

Your own private sanctuary for rest and restoration.

Save 5% when paid in full.

SHARED ROOM$2,925

Per person, for two guests traveling together.

Per person, for two guests traveling together - each with their own bed.

Flexible installment plans are available to make your investment feel spacious.
A non-refundable deposit of $750 secures your spot.
Remaining balance is due in full by September 3, 2026.

Only 8-10 women will gather here - by design and by intention.

Reserve your spot

SWEET LIFE SOCIETY MEMBERS

You have first access
and locked pricing -always.

Sweet Life Society members receive priority access and their locked member rate on all 2026 retreats. If you're not yet a member, the Society is your year-round home and your gateway to every Sweet Life experience before the doors open to the public.

Learn about the society

Meet the Curator

I created Sweet Life retreats as spaces where Black women can rest without justification and be held without performance.

Martha's Vineyard has always called to me because this island understands something about Black joy that most places don't. It has held us. It has welcomed us. It has watched generations of Black women exhale on its shores.

This experience is about honoring who you already are and allowing ease to support the woman you are becoming. You deserve to walk where our ancestors walked and feel the fullness of what they built for us.

I cannot wait to welcome you to the island.

Rakita Lillard- Brown Founder + CEO, Holistree LLC

Woman with curly hair leaning on a black railing holding a bouquet of baby's breath flowers on a city sidewalk with brownstone houses in the background.
A young woman with curly hair standing in the middle of a street with parked cars on either side, holding a purple handbag and smiling at the camera, with trees and houses in the background. 
If you feel genuinely called to join us and simply need the investment to meet you differently in this season, reach out to us directly at retreats@holistree.com. We hold space for aligned women in every season and we are always willing to have that conversation with care and discretion.

QUESTIONS

Everything you need to know.

  • Your investment covers 3 nights at the Summercamp Hotel in Oak Bluffs, your Welcome Dinner, island outing lunch, all workshops, sessions, and curated experiences, retreat photography, welcome gifts and keepsakes, and a community of women ready to pour into you. Travel to and from Martha's Vineyard is not included.

  • Outside of our Welcome Dinner and outing day lunch, meals are yours to explore. Martha's Vineyard has a beautiful landscape of Black-owned restaurants and local favorites - your curated island guide will be your companion for every meal.

  • Yes. A non-refundable deposit of $750 secures your spot. The remaining balance can be paid in flexible monthly installments, with the full balance due by September 3, 2026. A 5% discount applies to single room registrations paid in full.

  • Shared rooms at the Summercamp Hotel have two separate beds so you each have your own space to rest. This option is designed for friends, sisters, or partners who are joining the retreat together. We do not pair strangers in shared rooms.

  • Because of the intimate nature of this retreat and the planning involved, payments are non-refundable. However, your registration is transferable if you find someone to take your place with prior approval. We strongly recommend purchasing travel insurance to protect your investment.

  • Martha's Vineyard is accessible by ferry from Woods Hole, Massachusetts, or by small regional aircraft. The Steamship Authority ferry runs regularly and is the most popular option. We'll include detailed travel guidance in your welcome email upon registration.

  • Email us directly at retreats@holistree.com and we'll respond within 72 hours.

THE ISLAND IS WAITING

You were made for
this kind of ease.

8-10 women. Four days. An island that has held Black joy for over a century. Come stand in that lineage. Come rest in that legacy. Come taste the sweetness that has always been yours.

reserve your spot

Past Retreat Reviews

Dionna M.

“What I love most about these retreats is the intentionality. I always feel like they’ve created the moment exactly for me!”

Chanika M.

“The thing that has touched my heart so deeply was the love, enthusiasm and celebratory manner in which I was received by my fellow retreaters! I felt heard. I felt valued.”