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.
"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
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
The Experience
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
Closing circle + blessings for your return home
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.
SINGLE ROOM $3,300
Your own private sanctuary for rest and restoration.
SHARED ROOM$2,500pp
Per person, for a shared occupancy- double queen beds.
Flexible installment plans are available to make your investment feel spacious.
A non-refundable deposit $750 of you total 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.
Legacy +
Leisure
Reclaim. Radiate. Return.
SEPTEMBER 17 - 20, 2026 · OAK BLUFFS, MARTHA'S VINEYARD
4 Spots Remaining
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."
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
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.
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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.
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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.
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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.
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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.
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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.
Holistree LLC, in its sole discretion, reserves the right to cancel a retreat for attendees' safety, acts of God, government policies, or any other unforeseeable reason.
Upon the occurrence of such cancellation, Holistree LLC will provide a credit for a future retreat, valid for up to one year from the date of the original retreat.
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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.
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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.
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.