Sip & Speak Social

Leaders in Conversation. The room that keeps selling out.

An afternoon where the right people get in a room, real conversations happen, and you leave with sharper insight, stronger connections, and the kind of energy that stays with you long after the last sip.

This is not a conference. Not a workshop. Not a networking happy hour.

Sold Out - Sip and Speak Leaders in Conversation, June 13, 2026

Saturday, 13 June 2026

Cascadia Hotel · St. Ann's · Trinidad & Tobago

4:00 PM – 7:00 PM

Arrival

3:45 PM

Programme

4:15 PM

Dress

Caribbean Business Chic; national dress welcomed

First time at Sip & Speak

One evening. One room.

Sip & Speak is not a panel. It is not a networking event. It is a curated room of senior professionals from across the Caribbean who rarely sit down in the same space casually.

Small on purpose. Intentional by design. The kind of conversation you usually only get behind closed doors.

A moderated conversation with the people you’ve been trying to get into the same room as.

Senior executives, founders, and leaders who’ve navigated the rooms most of us are still trying to get into. Not a lecture. A real conversation, and you get a front-row seat.

Candid insight on executive presence, leading under pressure, communicating with authority, and what it actually takes to command a room at the highest level.

Sip and Speak Leaders in Conversation, June 13, 2026

01 · The Keynote

Samantha J. Best

A signature talk on executive presence and high-stakes communication. Twenty-four years of broadcast distilled into something practical, punchy, and immediately applicable.

02 · The Panel

Leaders in conversation

Senior voices, unfiltered. Honest, high-value insight you won't find in a training manual.

03 · The Networking

Structured. Purposeful. Fun.

Past attendees consistently say the networking at Sip & Speak is unlike anything else on the T&T professional calendar. Real connections. Not just business cards.

04 · The Extras

Giveaways & surprises

Past editions have sent guests home very happy. That's all we'll say. Because it wouldn't be Sip & Speak without a few surprises.

A curated room. Always has been.

Opening Remarks: His Excellency Diomedes Carles, Ambassador of Panama

Opening this Edition

His Excellency Diomedes Carles, Ambassador of Panama

The June 13 edition opens with remarks from His Excellency Diomedes Carles. The kind of presence that sets the tone for the room before the first conversation begins.

Cultural Performance

The Panama Folklore Group

Through the Embassy of the Republic of Panama in Trinidad & Tobago, the Panama Folklore Group joins this edition as the cultural anchor of the evening.

A 20-member ensemble travelling from Panama. Traditional polleras. Live performance. A reminder that the rooms worth being in are the ones where culture and conversation move together.

Panama Folklore Group performing at Sip and Speak Leaders in Conversation, June 13, 2026, Cascadia Hotel

The Leadership Panel

Two voices. Two scales of presence.

The conversation moves from regional security to personal authority and back, mapping how leadership is built and held at every level.

Commander Jason Kelshall (retired), Regional Coordinator for the Caribbean, EU SEACOP, panelist at Sip and Speak June 2026

Commander Jason Kelshall (retired)

Regional Coordinator for the Caribbean, E.U. SEACOP

Nicole-Anastasia Thomas, Image Consultant and Fashion Stylist, panelist at Sip and Speak June 2026

Nicole-Anastasia Thomas

Image Consultant & Fashion Stylist

Past editions have welcomed

The kind of room you walk into knowing the conversation will sharpen you.

  • The diplomatic corps
  • Senior government & public-sector representatives
  • C-suite executives
  • Founders & entrepreneurs
  • Regional business leaders
  • The Caribbean’s quiet operators

The brands choosing to be in the room.

Sold Out - Sip and Speak Leaders in Conversation, June 13, 2026, Cascadia Hotel

JMMB Bank · BOLLA Wines · Voyant Media Solutions Limited

FK Jackie Consultancy · B’s Ice Cream · GAK Electrical and Plumbing Limited

Huggins Shipping · Renaissance Energy Limited

Cultural Partner

Embassy of the Republic of Panama in Trinidad & Tobago

Limited Gold sponsor packages remain. Brand placement in a prestige room.

Become a partner

What Leaders Say

“Sip & Speak was not only useful but also highly enriching. A well-structured environment for learning and exchanging ideas, and it has positively contributed to my own communication approach.”

H.E. Álvaro Enrique Sánchez Cordero

Ambassador of Venezuela · Dean of the Diplomatic Corps, Trinidad & Tobago

Take your seat

The room only fits so many.

Three for three. The June 13 room is full. Join the waitlist to be first to know when the next edition opens.

Between gatherings

The Sip & Speak Podcast

The same standard of conversation, every week. Listen between the live editions.

Sip & Speak is going where the conversations need to happen next.

Trinidad & Tobago first. The Caribbean and beyond next. Subscribers know first.