
Portland, Jamaica
SATURDAY
February 21, 2026
About Holy Sip Jamaica
Since 2018, we’ve gathered a small group for a journey to Portland, Jamaica — far from the resorts and deep into a community where the pace slows and the flavors speak. Here, we share drinks that carry meaning and dishes rooted in the spirit of the place.
There’s no focus on perfect glassware or polish. What matters is the conversation, the connection, and the way time slows when we’re together.
The Holy Sip Jamaica dinner is an annual pilgrimage—an invitation to leave with more than you arrived with.

Frequently Asked Questions
Here are the answers to some of the questions we’re asked the most. If we missed something, please send us a message.
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Portland is a trek to get to, but it’s one of the most beautiful parishes in Jamaica. The main city, Port Antonio, has a long history of being home to the original Hollywood jet-set crowd.
There are no all-inclusive properties and only a few hotels. The widespread tourism that saturates other areas of Jamaica, like Montego Bay and Negril, doesn’t exist in Portland. Instead, you’re offered untouched beauty and homestyle hospitality. It will capture you. -
Norman Manley International Airport (KIN) in Kingston is three hours away. Sangster International Airport (MBJ) in Montego Bay is 4 hours away. Due to the distance, we recommend finding a flight that arrives early and departing on an evening flight.
To get to Portland from the airport, you can rent a car, hire a taxi or take the Knutsford Express. -
We get this question often. Especially in the early days when there wasn’t a built-out website with some details. The answer is the same then as it is now: The guests choose themselves. Portland isn’t easy to get to and it’s not the most convenient while you’re there. However, its beauty is unmatched. If something about this speaks to you, you’re the right person and you’ll find other like-minded people as your dining companions.
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Most guests stay in Portland from Weds-Mon. We’ve also had people explore other parts of the island and come to Portland just for the dinner. There’s no wrong way. Our recommendation is that you give yourself a minimum of two full days so you have time to explore the area. There’s a reason that we picked this area for the dinner. There are remarkable beaches, waterfalls, rafting, stillness and much more.
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We’ve dubbed this the anti-group group trip. There’s no set agenda besides the dinner. However, we often have optional activities on Thursday and Friday that give people the chance to get together. These will be announced two weeks before the dinner. We also create a platform for guests to connect and make plans together.
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For places to stay in the Portland area, please connect with Yvonne Blakey, our travel partner, to secure accommodations. We’ve worked with Ms. Blakey for the past 6 years. She represents the best villas and guesthouses in the area. More information is available under our Travel Partners section.
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The menu is crafted by Chef India and isn’t revealed until the day of the dinner. It’s inspired by local ingredients. The meal is paired with a variety of drinks (alcoholic and zero proof).
If you have any dietary restrictions, please note that when you purchase your ticket. We will accommodate you. -
Start planning your trip! Book a flight and secure your accommodations. If you have any questions along the way, please don’t hesitate to reach out. Three weeks before the dinner we’ll send an email with the final dinner details, things to do in the area, packing resources and more.

Chef de Cuisine
Chef India Johnson
Born into a Trinidadian and African American family, Chef India is originally from Queens N.Y. Much of Chef India’s cooking style; a fusion style and interpretation of Caribbean and Southern cuisines, has been inherited from her Trinidadian father who is also a creative and experimental chef.
Focusing on the ideal of accessible and sustainable food, much of Chef India’s products and offerings are based on fresh, local, and classic ingredients made with cultural and exotic twists.

TICKETS
Step into an evening where every detail — from the first sip to the last conversation — is rooted in the spirit of Jamaica and shared with good company. Your ticket includes:
Welcome drinks on arrival — something local, seasonal, and meaningful to start the night.
A multi-course dinner with ingredients sourced from local farmers and markets, highlighting the flavors of Portland, Jamaica.
Thoughtfully paired drinks — from classic cocktails to root tonics and teas
Curated storytelling throughout the evening, sharing the history, culture, and flavors behind each course.
An intimate setting with a small group of guests, designed for conversation and connection.
A sense of place — hosted far from the resorts, deep in a community where the pace slows and the flavors speak.
A curated playlist inspired by the island to take home with you.
Personal recommendations for exploring Portland, Jamaica — from hidden beaches to favorite roadside stops.
Memories not just of what you tasted, but who you shared it with.
*All ticket purchases are non-refundable.
Chef de Cuisine
Our focus is on bringing you a great dining experience with the vibes to match. We encourage you to make this trip what you’d like it to be. If you need assistance along the way, we’ve assembled a team of trusted friends that will help you with your stay in Portland or anywhere else on the island.
YVONNE BLAKEY
We’ve worked with Ms. Blakey for the past six years. She’s from Portland and knows everything about the area including the best villas and guesthouses. If you need help finding a place to stay, please reach her on WhatsApp at +1(876) 276-7019.
BEING JAMAICAN / TEIKA SAMUDA
Our friend Teika Samuda is a frequent guest of the dinner and the owner of Being Jamaican Tour Company. If you’d like a curated, authentic tour of any part of the island, please reach out to her by email (tours@beingjamaican.com) or on WhatsApp (+1 876-855-0232).













