Sept 29 - Oct 5, 2024

Let's Get "Naked"
In Jamaica

The third annual all-women Retreat for entrepreneurs, creators, and career focused besties.

"I don't need therapy, I need Jamaica!" (but, we'll take both!)

7 Days of Mindset, Money, and Connection
at a Private Caribbean Estate 🇯🇲

3rd Annual Jamaica Retreat

Let's Get "Naked"

We spend our lives COVERING UP.  Hiding who we are, what we think, and what we want. Join us in Jamaica for a week of GETTING NAKED: Emotionally, financially,  mentally and even physically!  Let’s strip away what’s stopping us from hitting our goals and our highest potential, and find who WE are. 

We’ve met many amazing women from different backgrounds at our Jamaica Retreat, leaving refreshed, inspired and empowered!

Plus, it doesn’t hurt that we’ll do this in our most magical location ever – a private luxury compound with 3 majestic stone villas, a private river and beach, a concierge, chefs, swimming pool, horses, ALL THE THINGS!  This location has hosted the greats: Martha Stewart, Robin Sharma, Harrison Ford, and now YOU.

This is truly a Grown Up Wonderland.   

This week, I want us to do 3 things:

PS: OUR RETREATS FILL FAST. Rooms first come first serve. Apply now to confirm your spot!

*Schedule and day trips are subject to change (and most likely will)

The best thing you can invest in is yourself.

Hello, Jamaica! 🇯🇲

Welcome to the Caribbean island rich with history, energy, and THE SPICE OF LIFE. A short 90 minute flight from the US, it feels a world away, with white sand beaches, tangy flavors, a true tropical paradise. This is an island where plant medicine is embraced, all bodies are celebrated, and eating fresh food from the earth is a way of life. Our location is one of a kind, a safe haven and heaven on earth. 

Expect your days to be filled with both activity and spaciousness – to explore yourself as well as the epic villa, island, and country. Our villa -where we’ll spend most of the week- is located in Trelawney, Jamaica, just outside the tourist capital, Montego Bay.

“I hit my first $30,000 month I now can make what I made in a YEAR in one month, and I love what I do.”


Content Creator

Our Retreat Details

Jamaica retreat at a glance.


Who Can Join?

Due to the intimate setting of this retreat, this is exclusively a WOMEN ONLY retreat! (We define "women" in the FAQ!)


What are the dates?

Sept 29 - Oct, 5 2024 (Schedule is subject to change - and most likely will)


A very 2000 acre heritage private estate 😎 in Montego Bay, Jamaica☀️

Closest Airport

Donald Sangster International Airport in Montego Bay (MBJ)

jamaica retreat

What will we do?

🔥Hot Seats (your problems solved, in minutes)

⭕️Women’s Circle – Emotions on steroids

💸Financial Workshops: work less, and make more

🧘‍♀️Staying sane – Meditation, Yoga, and breathwork

💅Stay Young – Beauty secrets, shared

🌿Live Longer – stress less, eat better, enjoy moving

👯‍♀️Level Up Your Friendships – become besties with women you admire

“I have multiplied my income by 4x and I even brought my girlfriend to a retreat and it improved our entire relationship.”


Alumni for 5 Retreats

Your private Jamaican ranch home for the week

Luxury Accommodation

We will spend our week in this piece of heaven. I mean, the photos speak for themselves! Come RELAX, RESET, AND RECONNECT  in a private 2000 ACRE tropical paradise. This 3 villa compound with a staff of 5 boasts a jungle infinity pool to splash around, another private pool, endless privacy to shoot content in the sunshine, and large shared spaces to enjoy workshops in the Gem of the Caribbean. On the land is a private ranch with Horses, Cattle, and cats to pet. 

You will stay in a spacious double occupancy room with an amazing new bestie,  with an ensuite bathroom and jungle views (There are single-room upgrades available! We recommend sharing, but once accepted you’ll be emailed availability).

What to expect:


“I increased my salary by 50% and tripled the amount I was investing. I now view money in positive way and the retreats inspired me and now I’m an inspiration to my entire family. 


Returning Alumni for 7 Retreats

So what's the plan?! ( expect changes + surprises)

Jamaica Retreat

Check in to your luxury home

We will spend our week in this piece of heaven. I mean, the photos speak for themselves! Come RELAX, RESET, AND RECONNECT  in a private tropical paradise. This 3 villa compound with a staff of 5 boasts a jungle infinity pool to splash around, another private pool, endless privacy to shoot content in the sunshine, and large shared spaces to enjoy workshops in the Gem of the Caribbean. On the land is a private ranch with Horses, Cattle, and cats to pet. 

You will stay in a spacious double occupancy room with an amazing new bestie,  with an ensuite bathroom and jungle views (There are single-room upgrades available! We recommend sharing, but once accepted you’ll be emailed availability)

Enjoy a private shuttle from the airport to your beautiful VILLA in Montego Bay! It’s gonna be a place to Relax and and have the BEST time of your life!

💸 Financial Workshops

Personal Finance, Investing, Manifestation, Meditation – deep dives that you can apply to improve your life, instantly

🔥 Hot Seats

Get the full focus of the entire group on you and your problem – this is always a group favorite and can help you solve problems you’ve been worrying about about for months in minutes!

⭕️ Women's Circle

Alyne’s favorite experience! The ancient, powerful, simple art of women gathering and sharing in circles. Emotions, epiphanies, and euphoria expected.

🧘‍♀️ Yoga & Meditation

Daily yoga, breathwork, and meditation to slow down and reset your nervous system and stay sane. Create routines that you can take home with you.

💃 Jamaican Dance Hall

Sensuality and Sexuality – learn how to feel accepting, safe, and loving towards your body, along with a dancehall reggae class to get into the zone of loving and owning ourselves. Plus learn what “Dagga” means

🤫 Surprise Workshops from Special Guest Experts

Our best workshops always happen organically. Perhaps from our participants themselves (from girlies who made 300k-1M+ a month profit) to Alyne’s friends in town (one, a CEO who recently married a girlie he met at his talk at the retreat!)

💅 The Famed “Chisme Hour”

Chisme means “gossip” in Spanish, and with all our Latina girlies, our late nights have degenerated (or developed) into our best chats yet, with secrets, sex tips, relationship insights and more

I cant believe I spent 3 days debating and worrying and I don’t even want to think about if I hadn’t come.”


Creative Agency Owner

Retreat Details

What's included?

Stunning Luxury Villa for 7 days

This tropical 3 villa compound is all ours for the week! Private swimming pool, river, beach, and acres of land. Enjoy an experienced on staff Concierge, Cleaning Crew, Chef, Property Manager, and Beach Guide.

Private Chef, Airport Transfer, Island Activities

This is an ALL INCLUSIVE retreat. That means from the moment you land, until the moment you leave, you won't need to touch your wallet or worry about a thing. ALL meals are included, island activities, transportation and accommodation.

Jamaican Dance Hall Classes

You will GROOVE to the irresistible beats of Jamaica Dancehall! Dive into the heart and soul of dancehall culture -Jamaica's dancehall maestro. Discover your sensuality, and prepare to surprise everyone with a coordinated group dance experience that will leave you in awe!

Workshops and Experiences

Enjoy daily yoga in an open air shala, workshops, and tours in Jamaica that challenge your mind and help you grow. Have something to share? Let us know and maybe you can teach a workshop on a magical island!

What's not included:

Your flights or personal purchases.

That's all!

Who is this for?

This Retreat is perfect for you if:

Starting your day with a red light mask makes you happy

You want to make your work revolve around your life (and not the other way around)

Creating a “flow” state in life is your dream

Longevity is a lifestyle you prioritize

Smart business girlie friends are your goal

Emotional connection is a priority in your life

Taking risks personally and professionally excites you

This Retreat is NOT for you if:

Your focus is on going deep on specific personal traumas

We are not licensed therapists or trauma trained professionals.

You’re looking to completely and EXCLUSIVELY focus on business growth

We believe true business growth comes from a holistic approach

You are looking for a lot of FREE TIME

This is a highly scheduled event.

You want a thorough tour of JAMAICA

We will see some of Jamaica but this is not a tour

“I felt the retreat paid for itself just after the first day. If you’re thinking about coming, stop thinking and JUST BOOK IT!”


Celebrity Household Manager & Newborn sleep training expert

Our Retreat food

Jamaican Vegetarian Heaven

Local & fresh chef cooked vegetarian meals

As always, Dear Alyne Retreats are 100% vegetarian with vegan options. Are you Gluten Free, or have allergies? Just let us know! 
Indulge in the magic of vegetarian cuisine. 🤩
From spicy Jamaican stews to refreshing tropical salads, our on-site chefs will take you on a flavor journey like no other.
All daily meals and drinks are included, that’s 20 delicious, wholesome meals eaten poolside in Paradise!

"One year from now, you will wish, you had signed up for the Jamaica Retreat today!"

-Amelia Earheart  -Abraham Lincoln  -Mahatma Gandhi

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“I hit my first 5k week after years of trial and error, and now I’ve completely replaced my income as a travel nurse and can work from anywhere. Plus, I’m teaching my mom!”


Alumni for 5 Retreats

“DearAlyne Retreats are my safe space for open up and ease my mind and help my mental health. It is absolutely life changing, and this is why I will sign up for my 3rd retreat!!”


Quality Management & Robotic Systems

“The Jamaica retreat was far from ordinary; it was an extraordinary event meticulously curated for an immersive experience… Participants embarked on a transformative journey of self-perception.”


Founder of Womennovator

Sept 29 - Oct 5 2024
7 Day Luxury Reset in Jamaica


Meet your hosts

Alyne Tamir @DearAlyne

Content Creator & Entrepreneur

An only child, Alyne started Dear Alyne retreats so she could have her own “Sisterhood of the traveling pants” and build what she hopes will be a lifelong community. 

Named by Forbes “The top influencer pioneering online to offline!”, Alyne is a Content Creator and Entrepreneur with over 3 million-plus followers and more than a billion views across all her social media platforms.  Raised both Mormon and Jewish, Alyne attracts an audience of people with mixed identities.   Alyne’s passions include social issues, women empowerment, animal rights, and she has travelled to over 90 countries.

When not creating content, she runs Dear Alyne Retreats, Success Circle Mastermind, and on-demand courses, with over 2000 graduates, where she continues to transparently enable people to grow in their professional and personal lives.

Alyne has worked with global brands such as Disney, The United Nations, Abu Dhabi Tourism Board, Taiwan Tourism Bureau, and many more.


Tupu Wheeler @Auntytupu

Social Director/ Retreat Concierge

Cultural Explorer of 35+ countries. Women’s empowerment mentor. Foodie & Environmental Activist. Music & college prep teacher. Super mom to 6 and Community Cheerleader to all.

An early path to becoming an LAPD police officer became the jumping off point to being a lifelong student of many subjects & mentor on how to best live a life of purpose, on purpose, while looking out for youth who need encouragement to overcome challenges to reach for their dreams. 

Diversity & Adversity being life’s greatest teachers, childhood health challenges & tragically losing her parents too early in life became the prompt for raising the bar higher to live a conscious life & take charge of her destiny, thereby inspiring others to also prioritize health, wellbeing & a life of learning. 

Let’s just say… if there’s a PhD in adventure, wellness & serving the Greater Good, Tupu has 2! 

If ever in Hawaii, visit the staff at The Polynesian Cultural Center & ask for “Miss Aloha,” herself, or as she’s affectionately known by many on island, “Aunty Tupu


Business Mentor & Entrepreneur

Dallen Levitan is a dynamic business counselor and entrepreneur whose passion for nurturing talent and innovation has made a significant impact on the entrepreneurial landscape in South Africa. As the founder and owner of “The Human Resource,” a thriving business incubator, Dallen has been instrumental in the growth and success of over 100 businesses, fostering a community of creativity, resilience, and sustainable growth.

With a diverse portfolio that includes seven businesses across various industries—ranging from digital marketing to talent management, and event production—Dallen embodies the spirit of a true hippie businessman. His approach to entrepreneurship is as eclectic as it is effective, always driven by a genuine desire to connect people and ideas.

One of Dallen’s standout achievements is his unique insight into achieving a healthy work-life balance, a “hack” that he passionately shares with others. His full-time travel lifestyle is a testament to his belief that success in business should not come at the cost of personal well-being. Whether he’s sailing the seas or exploring new cultures, Dallen’s adventures are fueled by a relentless curiosity and a quest to discover the world’s best chocolate milk.

Known for his friendly and humble demeanor, Dallen Levitan is more than a successful entrepreneur; he is a connector, a mentor, and an advocate for a balanced, fulfilling life. His mission is to inspire others to chase their dreams without compromising their happiness, and his journey continues to inspire and motivate successful business leaders around the globe.


Author, CEO & Founder of "Travel Off Path"

Kashlee is a Retreat Graduate and travel industry powerhouse. She built a 7-figure online Business from scratch and loves traveling around the world in Business Class.

As the co-founder and CEO of Off Path Enterprises, she has built a global travel empire, including Travel Off Path, one of North America’s largest travel news websites with over 4 million monthly readers. 

After attending the Dear Alyne Retreats in Albania, Turkyie and Scotland, Kashlee saved $400k a YEAR on taxes by realising she should move tax residency 

Born in Canada, home-based in Mexico, and kind of living in multiple countries a year. Her friends says she’s like a geeky kid in a hot girl disguise!

Kash is also a Manifestation Queen, she loves sharing her secrets on how to manifest a life in your own terms and build the Money Mindset that will take you where you want to be.


No Excuses, Just Retreats!



This retreat will take place from September 29 to October 5, 2024 (Schedule is subject to change – and most likely will)

Any woman (+18) is welcome to our retreat. That includes women, and everyone who identifies as a woman. community. Young or old, employees or CEOs. All you need is the will to learn and better yourself!

The average high temperature in Jamaica in October is 89 degrees Fahrenheit or nearly 32 Celsius. The average low is 74 degrees Fahrenheit. 

When you come to the retreat, specially one in Jamaica, leave work where it belongs (back home!) 😁 We want this experience to be a relaxing and detoxing experience for you, that’s why we discourage you to bring work at this retreat. If you need to check emails etc you’ll have time in your room, but please NO work calls during retreat activities. 

We debated opening this to both genders but ultimately decided because of the intimate setting to keep it women only.  The word woman is fluid, so imagine it as “feminine energy”. If you are a man that’s LGBTQ+ please feel free to apply.

Most girls will share a fresh, beautiful room in one of the 3 STUNNING stone villas at the private property at double occupancy with ensuite bathrooms. However, there are limited single-room upgrades available. There are photo examples under the accommodation section. Those are from our villa.   

ALL rooms are beautiful but  they will be assigned based on 1st come 1st serve basis. Room priority is  given to people who complete payments first, so if you want a better room we recommend to fully book your retreat spot as soon as possible!

Rooms have different bed sizes and types (kings, queens, twins) and as always, those who register first, get first priority (aka the larger beds).  

Upgrades: There may be a few single room available at a premium cost – we’ll let those accepted know closer to the retreat date.

p.s. Each bedroom is fitted A/C’s, fans and en-suite bathrooms. The property has wifi. 

  • We have a no refund policy, but you can find a replacement and transfer your spot! Please do not book if you are not sure you’ll be joining. As there are costs associated with the retreat that we must pay prior to the start date. This includes but is not limited to the reserving the villa, staff, activities, aligning of vendors, van rentals, chefs, staff, and other relevant arrangements.
  • Cancellation needs to be in writing, to be sent to us on email at, NOT on Whatsapp. The cancellation needs to be acknowledged back, in case you do not receive an acknowledgment the cancellation is not valid, so ensure to get a confirmation email back.

No. We typically require payments to be made in full at the time of booking. While we don’t offer specific payment plans, we can provide an option to split the payment into two installments upon request

“What a trip! (IYKYK) An indescribable week of laughing, crying, manifesting, ass-shaking, yoga, headstands, inspiration, hugging and breaking wide open.”


Director at Wooton Properties

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“We need each other as women”

Before this retreat, I felt good about myself and my life. Coming here gave me so much confidence and understanding that I am on the right path. We need each other as women, and knowing that somebody will hold my hand, somebody will hold me accountable, and somebody will love on me.

But the best thing is that somebody will call me when I need them. And this is the most beautiful thing. So, if you’re thinking about coming to the retreat, don’t think twice, because you’re going to get SO MUCH MORE than you’ll actually pay for.