WHAT IS CARIBBEAN POSH WEEKEND?
Caribbean POSH Weekend is an award-winning, boutique-style regional experience designed for Caribbean women who are building, leading, and shaping the future.
Guided by this year’s theme—The Future of the Caribbean: Connection, Collaboration and Growth—the experience is intentionally curated to spark meaningful dialogue, unlock opportunity, and strengthen how we move as a region.
At the intersection of business, culture, and community, this is where visibility becomes currency, connections turn into collaboration, and ideas evolve into opportunity.
More than an event—it’s a movement rooted in purpose, created to elevate Caribbean voices on a global stage.
WHY ATTEND?
Step into a curated, high-impact environment designed for growth, connection, and expansion.
- Future-Focused Conversations
- Real, solution-driven discussions centered on connection, collaboration, and sustainable growth
- Meaningful Networking
- Build relationships that lead to partnerships across islands and industries
- Business & Brand Visibility
- Gain exposure within a powerful Caribbean and diaspora network
- Immersive Experiences
- Culture, luxury, and connection—woven into every moment
THE EXPERIENCE
Caribbean POSH Weekend is rooted in intention and impact—inspired by Caribbean women, built for Caribbean women, and designed to move the region forward.
What to Expect:
- ICON Woman Awards Gala
Honoring excellence while amplifying the stories and leadership shaping the Caribbean - POSHgirl POWER Brunch & Marketplace
Where conversation meets commerce—creating direct pathways for visibility and growth - Curated Panels & Fire Chats
Focused on real solutions across business, legal strategy, tourism, innovation, and regional collaboration - Cultural Experiences & Island Tours
Grounded in identity, heritage, and the richness of the Virgin Islands - PINK Sunday Sunset Sail
A signature celebration of connection, community, and culture
This is where ideas are exchanged, partnerships are formed, and the future of the Caribbean is actively shaped.
TRAVEL PERKS FOR ATTENDEES
Getting to Caribbean POSH Weekend has never been easier—or more rewarding.
Regional Air Travel
Registered attendees receive 25% off flights with interCaribbean Airways. We encourage early booking to secure preferred routes and availability.
Ferry Access from St. Thomas
Guests traveling via St. Thomas enjoy a special ferry rate of $75 round-trip with Smith’s Ferry Services, plus applicable port fees and departure tax, for seamless access to the British Virgin Islands.
Exclusive Booking Access
Travel discounts are available to registered attendees only. Select your travel requirement during registration to receive your exclusive booking code.
BECAUSE WHEN CARIBBEAN WOMEN MOVE, THE REGION MOVES WITH US.
SCHEDULE
Heritage, Rum & Rhythm: A Curated Island Experience
(Optional – Pre-Registration Required by June 23)
Step into the soul of the Virgin Islands through a thoughtfully curated journey blending history, culture, and flavor.
Experience includes:
A guided visit to Old Government House, uncovering the legacy and stories that shaped the territory
A cultural stop at Callwood Rum Distillery, one of the Caribbean’s oldest distilleries, for an authentic taste of tradition
Curated island exploration featuring local gems, artisan touches, and a relaxed lunch experience
Picture-perfect moments at iconic island murals and cultural landmarks, designed for storytelling, content creation, and capturing the essence of Caribbean creativity and identity
This is more than a tour—it’s an immersive cultural experience designed to connect you with the rhythm, heritage, and visual beauty of the Virgin Islands.
Boarding & Departure
Guests will board the designated event ferry at the Road Town Ferry Terminal for transportation to Ocean 7, Peter Island.
Cocktail Reception & Pink Carpet Arrival
Guests arrive in elevated Caribbean glamour (dress code: Island Icons) for a signature pink carpet experience featuring welcome cocktails, photography, media interviews, and networking against the stunning backdrop of Peter Island.
Caribbean POSH ICON Woman Awards Gala
An elegant and inspiring fundraising gala benefiting Empower Caribbean, celebrating exceptional Caribbean women across more than 17 award categories. Through powerful storytelling, thought leadership, and recognition of excellence, the evening honors women who are making a lasting impact throughout the region while helping to fund grants, mentorship opportunities, and entrepreneurial support for emerging female leaders.
Post-Awards Celebration & Networking
Continue the celebration with music, meaningful connections, media moments, and networking with honorees, nominees, sponsors, dignitaries, and guests from across the Caribbean and diaspora.
Return Ferry Departure
Guests depart Ocean 7, Peter Island for return transportation to the Road Town Ferry Terminal.
POSHgirl POWER Brunch & Marketplace Experience
Dress Code: Islands Full Bloom
10:00 AM | Ferry Departure
Guests will depart from the Road Town Ferry Terminal aboard the designated event ferry for transportation to Ocean 7, Peter Island.
10:00 AM – 10:45 AM | Guest Arrival & Welcome Experience
Marketplace browsing, refreshments, networking, media moments, and opportunities to connect with fellow attendees, speakers, and featured brands.
10:45 AM – 11:00 AM | Seating & Opening Flow
11:00 AM – 11:15 AM | Brunch Service Begins
11:15 AM – 11:30 AM | Opening Remarks & Welcome
11:30 AM – 12:10 PM | Keynote Address
Featuring Hon. Cora Richardson-Hodge, Premier of Anguilla
An inspiring keynote exploring the power of regional collaboration, leadership, innovation, and the opportunities that lie ahead for Caribbean women, entrepreneurs, and communities.
12:10 PM – 12:20 PM | Transition & Audience Reflection
12:20 PM – 1:00 PM | Featured Panel I
Tourism Reimagined: Building Caribbean Ownership & Economic Independence
Exploring how tourism can become a stronger catalyst for entrepreneurship, local ownership, economic independence, and long-term prosperity throughout the Caribbean.
1:00 PM – 1:10 PM | Networking & Marketplace Break
1:10 PM – 1:40 PM | Featured Panel II
Position, Protect & Prosper: Building Caribbean Businesses That Last.
A dynamic discussion focused on business growth, legal protection, strategic partnerships, succession planning, and creating sustainable Caribbean enterprises that thrive for generations.
1:40 PM – 2:10 PM | Caribbean POSH Future Makers
Featuring the 2026 Miss BVI Contestants
An inspiring conversation spotlighting the next generation of Virgin Islands leaders as they share their aspirations, perspectives on leadership, entrepreneurship, community impact, and their vision for the future of the Virgin Islands and the Caribbean.
2:10 PM – 2:50 PM | Featured Panel III
The Future of the Caribbean: Food, Energy & Climate Resilience
Exploring innovative solutions, emerging opportunities, and practical strategies to strengthen food security, energy independence, climate resilience, and sustainable economic development throughout the Caribbean.
2:50 PM – 3:20 PM | Marketplace Fireside Chat: Founder Spotlight
An intimate, high-energy conversation featuring standout entrepreneurs from the Marketplace sharing their journeys, lessons learned, challenges overcome, and insights on building and scaling Caribbean brands.
3:20 PM – 3:25 PM | Audience Engagement Giveaway #1
A fun, interactive audience engagement moment featuring a special prize giveaway courtesy of Caribbean POSH and event partners.
3:25 PM – 3:40 PM | Networking Interlude & Marketplace Engagement
Guests connect directly with featured entrepreneurs, explore Marketplace brands, capture content, make purchases, and build meaningful relationships within the Caribbean POSH community.
3:40 PM – 3:45 PM | Audience Engagement Giveaway #2
Another exciting audience participation opportunity with prizes and surprises for attendees.
3:45 PM – 3:55 PM | Fashion Showcase: Caribbean Style in Motion
A curated runway experience featuring Marketplace designers and regional fashion brands, celebrating Caribbean creativity, culture, and style.
3:55 PM – 4:00 PM | Audience Engagement Giveaway #3
Our final audience engagement giveaway of the afternoon, celebrating community, connection, and the spirit of Caribbean POSH.
4:00 PM – 4:10 PM | Closing Reflections & Call To Action
A final opportunity to reflect on the day's conversations, celebrate connections made, and challenge attendees to take action in their businesses, communities, and careers.
4:10 PM – 4:30 PM | Extended Networking & Marketplace Experience
Continue conversations, connect with speakers and entrepreneurs, explore featured brands, and celebrate the power of Caribbean women in business.
4:30 PM | Return Ferry Departure
Guests depart Ocean 7, Peter Island for return transportation to the Road Town Ferry Terminal.
PINK Sunday Sunset Sail
Departure: Road Town Ferry Terminal, Tortola
Boarding: Begins at 1:30 PM
Departure Time: 2:00 PM sharp
Dress Code: Pink Paradise
Set sail for an unforgettable afternoon of music, networking, island views, and elevated experiences aboard the Caribbean POSH PINK Sunday Sunset Sail. Connect with fellow attendees, speakers, entrepreneurs, and professionals while enjoying curated vibes, refreshments, and the beauty of the Virgin Islands at sunset.
Embrace the Pink Paradise theme with your favorite shades of pink, tropical elegance, resort-chic fashion, and vibrant island style as we celebrate connection, collaboration, and Caribbean excellence on the water. The perfect finale to Caribbean POSH Weekend—where business, sisterhood, and celebration meet against the backdrop of a Caribbean sunset.
Optional POSH Meetups (Curated & Informal)
Brunch meetups, beachside networking, founder circles, and content sessions.
2026 HONOREES
2026 SPEAKERS
EVENT PACKAGES
Your experience is designed with flexibility—
whether you’re joining for a moment or stepping fully into the movement.
FULL WEEKEND INSIDER PASS (BEST VALUE)
[$520 USD]
The complete Caribbean POSH experience.
Designed for women ready to fully immerse themselves in a weekend of connection, visibility, and growth—across every signature moment.
ICON WOMAN AWARDS EXPERIENCE
[$200 USD]
An elegant evening celebrating Caribbean excellence.
A powerful gathering honoring women who are shaping industries, communities, and the future of the region.
POSHGIRL POWER BRUNCH EXPERIENCE
[$190 USD]
Where conversation meets opportunity.
A dynamic daytime experience featuring a keynote conversation, curated panel discussions, and full access to the Caribbean POSH Marketplace — plus a signature Caribbean POSH designer bag.
STUDENT RATE
[$95 USD]
Designed to support emerging leaders and future changemakers.
PINK SUNDAY SUNSET SAIL
[$150 USD]
A vibrant celebration on the water.
A high-energy, culture-forward experience designed for connection, release, and unforgettable moments to close the weekend.
GROUP EXPERIENCE (5+ ATTENDEES)
STARTING AT [$180 USD] PER PERSON
Because growth happens in community.
Perfect for teams, sister circles, and organizations looking to experience either the ICON WOMAN Awards or POWER Brunch together, while building meaningful connections.
HERITAGE, RUM & RHYTHM: A CURATED ISLAND EXPERIENCE
[$65 USD]
(OPTIONAL – PRE-REGISTRATION REQUIRED BY JUNE 23)
A guided visit to Old Government House, uncovering the legacy and stories that shaped the territory. A cultural stop at Callwood Rum Distillery, one of the Caribbean’s oldest distilleries, for an authentic taste of tradition.
A MOVEMENT, NOT JUST A MOMENT
Caribbean POSH Weekend operates with purpose. Proceeds support Empower Caribbean, providing grants and mentorship to emerging female entrepreneurs. This is not just about attending an event.This is about investing in the future of Caribbean women—and the region as a whole.
THANK YOU TO OUR PARTNERS
