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Overview

Creative Escape in Paradise: Art, Yoga & Wellness
Puerto Rico
Jan 24 - 31, 2026
Paint With Gayle and Jennifer image
Paint With Gayle and Jennifer
$4,650
Deposit: $500

About your trip

  

Join artists Jennifer Orkin Lewis (August Wren) and Gayle Kabaker for a transformative week of creativity, relaxation, and connection. This Tropical Painting, Yoga & Wellness Retreat is more than just a getaway—it’s a chance to immerse yourself in art, nature, and self-care.

This year, we are thrilled to welcome yogi goddess Chloe Ward, who will guide us through daily morning yoga, evening meditation, and Yin yoga sessions.

A Place to Reconnect with Nature

  

Whether painting under the shade of a mango tree, meditating in the peaceful valley, or taking a refreshing dip in the saltwater pool, this retreat is designed to inspire and rejuvenate. 

What to Expect

  

Daily morning yoga to awaken your body and mind, as well as evening meditation and Yin yoga

Painting and drawing sessions inspired by lush tropical surroundings—vibrant foliage, delicate flowers, towering bamboo, and more

A scenic day trip to a breathtaking beach one hour away, where we’ll paint, draw, and soak in the beauty of the ocean

Exploring the art of painting water and deep dives into other topics that inspire the group

A community of like-minded artists who find joy in discovering new colors, forming meaningful connections, and sharing creative energy

Incredible chef-prepared meals, fresh, organic, and locally sourced. The on-site restaurant offers delicious vegan, vegetarian, and pescatarian options

Opportunities for relaxation and self-care, including massage, reflexology, facials, Reiki, card readings, and private yoga sessions with Chloe

Location

  

Once a thriving coffee plantation, this enchanting mountainside retreat, 2 hours from San Juan, is now the perfect haven for artists seeking inspiration. Surrounded by lush greenery and bathed in golden light, the landscape itself is a masterpiece waiting to be captured in your sketchbook. The rustic charm of rough-hewn wood and natural textures creates a warm, inviting atmosphere, while the gentle murmur of the river and the chorus of tree frogs provide a soothing soundtrack to your creativity. Each cozy cabin features a private porch with a hammock—ideal for sketching, daydreaming, or simply soaking in the tranquil surroundings. Come immerse yourself in nature’s beauty and let your creativity flow in this truly inspiring setting. 

What to Pack

  Art supplies (a suggested materials list will be provided)

   Yoga gear (comfortable clothing for movement)

   Layers for the evening

   Swimsuit (for the pool and beach trip)

   Hiking shoes/sneakers (for nature walks)

   Sandals (for lounging)

   Sunscreen (a must-have!)

This is a very casual retreat—you can even paint in your bathing suit!

Weather

  

In January, Puerto Rico offers the perfect climate—warm days in the 70s and 80s°F, cooler breezy nights, and occasional refreshing rain showers.

Extras (Available On Site)

  

Shamanic Healing with Chloe

Reiki with Chloe

Massages, reflexology & facials 

Chloe Ward Yogi and Healer

Hi, beautiful souls! I’m Chloe, a holistic guide here to support your wellness, growth, and healing. Whether you’re seeking clarity or deeper connection, I’m honored to walk this journey with you.


Connection is truly at the heart of everything I do. Whether it’s helping you deepen your connection with yourself, others, or the world around you, my purpose is to guide you on a journey of healing, growth, and transformation. Through ancient wisdom and modern holistic practices, I’m here to support you in unlocking your magic within. 

What People are Saying

  

Jennifer and Gayle are AHHH-mazing! Their different styles complement each other so well, and it was inspiring to watch them paint the same subject with unique approaches. Whether you’re a beginner or an experienced artist, you’ll learn so much while having a blast. I can’t wait for my next retreat with them!”

“Gayle and Jennifer’s teaching philosophy—‘play and have fun’—helped me move past self-judgment and truly enjoy experimenting with my art. Their support and encouragement made this an unforgettable experience.”

“As a teacher who incorporates art into my core curriculum, I find endless inspiration in Jennifer and Gayle’s workshops. Their passion, experience, and warmth make learning from them an absolute joy.”

“Jennifer and Gayle are a perfect pair—like peanut butter and jelly! Their different styles complement each other beautifully, and their workshops are both playful and deeply inspiring.”


What People are saying about Chloe Ward


 

We were lucky to have  at our Portugal retreat last year. We found that starting each day with her amazing yoga classes & meditation, we were open to so much inspiration! Here’s what some of our participants had to say about her:

“Starting each day with Chloe’s yoga set the perfect tone. By the second session, I knew I could trust her to help me rebalance my energy, which allowed for greater creative freedom in my art. This combination resulted in magic that lasted long after the retreat.”

“Chloe’s positive vibe is infectious! She has a truly unique life force that draws people to her. Yoga and meditation with her is an experience not to be missed.”

“With Chloe’s patience and guidance, I embraced yoga for the first time during an art retreat in Portugal. It became a transformative practice for me, helping me work through grief and improve my overall well-being.”


Transportation

  

The transport to the venue will leave at 3 pm from the  Luis Muñoz Marín International Airport on Jan. 24. 

It will pick guests up at 10 am on Jan 31 at 10 am and be at the airport around noon. 

If your flight doesn’t get in by 3PM, you can either come into San Juan the day before and stay over to make the timing of the transport bus - or you can hire a private car at your own expense to get to the venue. The cost would be $200 for 1-2 people. 


We can suggest a few lovely hotel suggestions in San Juan near a great beach! Old San Juan is fun to explore and the beach is gorgeous. 

Participating painters only

To keep the incredible energy of creativity and inspiration this retreat is for participating painters only. We welcome all levels and listen closely to the vibe of the group to make it an amazing experience for everyone. All ages welcome.

Mobility

You must be mobile to come to this retreat. There are steps and paths to navigate. If you choose to hike the trails, they are advanced, rocky, steep, and slippery. There is also a flat road with very little traffic that is perfect for for a good long walk or run.

Non-Refundable Booking

Kindly be aware that all bookings are nonrefundable. Once payment has been made, it is regarded as final.

Retreat cancellation:
If the retreat is canceled by Gayle & Jennifer  due to force majeure events or circumstances out of their control, they will let you know as soon as possible and refund the total cost of the retreat.

Cancellation insurance:
Participants are required to purchase travel, medical, and cancellation insurance for protection against any circumstances that might require cancellation or change of travel arrangements. This insurance should cover any potential losses incurred due to cancellation or no-show, including but not limited to medical emergencies, travel disruptions, or personal circumstances. We are not affiliated with any travel insurance providers. It is your responsibility to secure appropriate insurance coverage that includes trip cancellation and interruption protection. We highly recommend reviewing the terms and conditions of your chosen insurance provider to understand the coverage and claim process.

Gayle and Jennifer Bios

Gayle Kabaker


Gayle Kabaker is an award-winning illustrator, writer, and visual storyteller. She has created 10 New Yorker covers, including the iconic June Brides. Her work explores femininity and beauty, often documented in her sketchbook. She wrote and illustrated the column Sketching My Way Through Crisis for The Washington Post and illustrated 100 portraits of women for the book Vital Voices – 100 Women Using Their Power to Empower. Gayle uses her sketchbook to document her life and her current favorite muses are her granddaughters Mona and June. Gayle lives in Western Massachusetts with her husband and dog, Charlie.

Website | Instagram

Jennifer Orkin Lewis / Augustwren

Jennifer Orkin Lewis is an artist, illustrator, and author known for her vibrant gouache paintings inspired by nature, color, and pattern. Her daily sketchbook practice became the foundation of her distinctive style, leading to collaborations with Anthropologie, Abrams Books, Kate Spade, and more. She has authored two sketchbook journals encouraging creative practice. Jennifer studied at RISD and spent years as a textile designer before transitioning to illustration.

Website | Instagram

What's included

Daily Art Classes

You will create a sketchbook full of memories, sketch on location and on the patio’s outdoor studio. It’s a chance to grow and learn without judgment, gaining confidence in your artistic choices

Instruction and Demo's

There will be daily demo’s, new techniques, tailored feedback, and, most importantly, expanding your self-expression. There will be lessons on color mixing, painting water, faces and more!

7 Nights Accomodation

Stay in a charming shared or private cabin with modern décor, en suite bath, ceiling fans, and a private porch with a hammock—the perfect cozy retreat to relax and recharge between painting sessions!

Exclusive Retreat Venue

Enjoy exclusive access to our serene retreat, just for our painting group. With total privacy and tranquility, you’ll find the perfect space to relax and immerse yourself in artistic inspiration.

All Meals

Enjoy fresh, organic farm-to-table meals. Vegan, vegetarian, and pescatarian dishes are crafted daily by Chef Eduardo.Delicious, artfully inspired and healthy dining to fuel your creativity!

Welcome and Farewell Din

Daily Yoga

Daily morning yoga to awaken your body and mind, as well as evening meditation and Yin yoga with Chloe, a holistic guide here to support your wellness, growth, and healing.

Day Trip to the Beach

Mid-week day trip to a stunning beach an hour away, where we will paint, relax, and soak in the beauty of the ocean. It features a small, quiet turquoise cove for safe swimming.

Bus from SJ to Venue

Round-trip transportation from Luis Muñoz Marín International Airport (Jan 24 & 31 at preset times)

Private Whats App Group

One month before the retreat a What's App group will be set up for all participants

Pre-Retreat Zoom Call

Two months prior to the retreat we will meet on Zoom to answer questions and start to get to know each other

What's not included

Airfare

You are responsible for your RT Airfare from home to San Juan

Travel Insurance

We strongly recommend that you get travel Insurance in case of any reason for your cancellation for personal reasons

Art Materials

A detailed list will be sent five months before the retreat

Tips for Staff

at your personal discretion

Personal Expenses

We will offer one glass of wine or beer at the 5pm painting happy hour. Cash bar option during dinner.

Day 1

Day 1 image

Arrival and Opening Ceremony

  

4:00 PM – Check-in & introductions

Evening Meal

New Moon Ceremony – A special ritual to set intentions and prepare for the retreat

Day 2 and 3

Day 2 and 3 image

Daily Flow (subject to change depending in inspiration of the day)

  7:30–8:30 AM – Morning Yoga & Movement

   8:30 AM – Breakfast

   9:30 AM–1:00 PM – Painting & Drawing

   1:00–2:00 PM – Lunch

   2:00–4:30 PM – Free time (swimming, hiking, wellness treatments, rest)

   4:30–6:00 PM – Afternoon Painting & Drawing

   7:00 PM – Evening Meal

   8:00 PM – Evening Reflections, Meditation & Yin Yoga

Day 4

Day 4 image

Full Day Beach Day Trip

Bag Lunch Provided 

Sketching people and scenes on the beach and general relaxation and swimming

7:00 PM – Evening Meal

8:00 PM – Evening Reflections, Meditation & Yin Yoga

Day 5 and 6

Day 5 and 6 image

Daily Flow (subject to change depending in inspiration of the day)

  

7:30–8:30 AM – Morning Yoga & Movement

8:30 AM – Breakfast

9:30 AM–1:00 PM – Painting & Drawing

1:00–2:00 PM – Lunch

2:00–4:30 PM – Free time (swimming, hiking, wellness treatments, rest)

4:30–6:00 PM – Afternoon Painting & Drawing

7:00 PM – Evening Meal

8:00 PM – Evening Reflections, Meditation & Fire Ceremony of releasing on last night

Day 8

Day 8 image

Departure

7:30–8:30 AM – Morning Movement

8:30 AM – Breakfast

10:00 AM – Transport to Airport

About your organizer

Photo gallery

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© 2026 Paint With Gayle and Jennifer