Trinidad & Tobago EXPEDITION
For Accomplished Professionals Ready to Explore their Second Act
March 6-13, 2027Â |Â Exclusive VIP Experience March 13-16, 2027
You spent a career making things happen.
Now what?
The title is gone and the calendar is quiet.
You don’t want another vacation.
You want to give back, to sense purpose again, and to spend time with a community of people who get it.Â
Welcome to Trinidad and Tobago.
Welcome to what becomes possible when community, meaning, and making a difference become real.Â
This is a small-group week of service, culture and adventure, designed to help you find where your purpose lies next.
What you’ll come home with
- A clear plan for where you’ll make a difference next
- Firsthand experience of service that actually helps
- A new community of friends who want the same thing
- A renewed answer to “So what are you doing now?”
- Unforgettable adventures you’ll talk about for years.
Why Trinidad
A mosque, a cathedral and a Hindu temple within minutes of each other. Five heritages in one island culture. Local leaders doing remarkable work in their neighborhoods. And this year, Eid al-Fitr falls during our week, when families of every faith open their homes.
Why Trinidad & Tobago?
Long before Columbus arrived, the indigenous Arawak and Carib peoples honored these islands as sacred ground, viewing nature as a source of powerful, guiding spirits. When you step onto this soil, you are walking on land that has known deep spiritual practice for 7,000 years — a history that doesn’t shout but whispers, inviting you to connect to a deeper, more grounded sense of self.
But the story doesn’t end with the ancient. After centuries of colonial rule, after the brutal machinery of slavery was finally dismantled, Trinidad and Tobago became something extraordinary: a destination for the world. Hundreds of thousands of people arrived from Africa, India, China, Portugal, Syria, and Lebanon — each carrying their own language, faith, cuisine, music, and way of mourning and celebrating. What could have become a story of fracture became, instead, a story of fusion.
This is not a history of tolerance. Tolerance is what happens when people endure each other. This is a history of integration — what happens when people genuinely learn from one another. Trinidad and Tobago is arguably the world’s most successful living experiment in coexistence. A place where the call to prayer, the church bell, and the Hindu chant are not competing sounds but a single, astonishing symphony.
The striking beauty of the country is also riddled with challenges – and people who are trying to solve them even in extraordinary circumstances. Â You will have conversations with some of them, and begin to ask different questions – to others and to yourself, diving into what your Second Act will be. Â
The Cuisine
A Heritage on a Plate
The first scent will find you before you find the kitchen.
It’s Green Seasoning — that fragrant, irreplaceable blend of fresh chadon beni, pimento peppers, garlic, and thyme that is the beating heart of nearly every savory Trinbagonian dish. One breath and you’ll understand: in this country, food is not fuel. It is identity. It is history. It is love made visible.
Trinidad and Tobago is famous across the Caribbean and beyond for a cuisine that tells the story of every culture that ever called these islands home. What lands on your plate is a living fusion of West African, Indian, Creole, and Chinese traditions — each dish a direct line to the generations of ancestors who blended these flavors into something entirely new.
Breakfast may greet you with bake and saltfish — that perfect marriage of salty and savory that Trinbagonians wake up craving — alongside fresh tropical fruits and strong local coffee.
Lunch might be doubles, the island’s beloved street food: soft, warm flatbread cradling spiced chickpeas, topped with fiery pepper sauce if you dare. The vibrant yellows of curry, the ruby red of sorrel drink, the deep greens of the surrounding rainforest — even the colors here taste like something.
Dinner becomes a feast: hearty pelau studded with caramelized chicken, coconut-rich callaloo, tender stewed meats sweetened with local cane sugar, and roti so warm and layered it practically tells you its life story. Every bite is a connection to this island — not as a tourist, but as a guest at the family table.
Your dietary preferences and allergies will be thoughtfully accommodated. During meals with local community members, we’ll do our best to honor any restrictions, and our hosts will welcome you with the generosity that defines Trinbagonian hospitality.
Our Journey
Saturday, March 6: Arrival & Welcome
You arrive at Piarco International Airport and step into the warm Caribbean air for the first time. Your transfer is waiting — along with a cold bottle of water and a smile. Welcome dinner to come.
Sunday, March 7: Contradictions & Conversations
Mosque, cathedral, and temple: what it takes to live side by side, what it takes to move from a career to the Second Act.
Monday, March 8: Meaning at the Margins
Mangroves by boat. Sharing a meal with families in a Hindu village.
Tuesday, March 9: Community Calling
Local innovators and a neighborhood sports program. Â How to give in ways that last, that matter.Â
Wednesday March 10: Eid-ul-Fitr Celebrations
A remarkable day in a family home over Eid-ul-Fitr.Â
Thursday, March 11: Music and Movement
Steelpan in Port of Spain. Â Rhythm and storytelling.
Friday, March 12: The Art of Discovery
Creative studio, closing gathering, and farewell dinner.Â
Saturday, March 13: Departure/Optional Tobago Extension
Returning home or onward to Tobago.
There is nothing else like this.
This experience is learning how to make the Second Act count.
It’s about rekindling a life of purpose and genuine excitement.
It’s reconnecting with a sense of adventure.
It’s rediscovering the joy of a community of peers, engaged with the world, asking the same questions you are.Â
It’s moving from “what do I do now” to “I can’t wait to get started.”
Executive Coaching wraps around this journey – essential to lay the foundation and to take action on decisions.
Bonuses
- Two Coaching Sessions before and after the immersion. These calls are 1:1, tailored to you.
- Pre-Departure Group Call — You will meet your group prior to departure, making connections early.Â
- Access to a Private Community Group — Share excitement before the trip, make connections with new friends, ask questions, receive up-to-date trip info, stay connected post-trip, and use the group as a photo dump to share every captured moment!
- A Post-Retreat Group Call — Celebrating our newfound community and creating ideas for how to continue our shared time together.
What’s Included
- 7 nights lodging.
- All delicious breakfasts, lunches, and dinners made with local natural ingredients — including excursion meals, the Eid al-Fitr celebration, and homecooked meals with local families.
- All local ground transportation, including all airport transfers.
- All entrance fees and private tour guide fees.
- All donations made to local organizations we visit.
- All tips and gratuities (you are welcome to add a personal note of thanks if desired).
- All group coaching and facilitated reflection throughout the journey.
- Two coaching calls before and after the immersion.
- All yoga and meditation sessions.
- All activities offered throughout the experience — cultural immersions, community visits, steelpan workshop, creative work, and more.
- Access to a private community group for pre/post-trip connection.
- Special welcome gift upon arrival.
What’s Not Included
- Your round-trip airfare to and from Piarco International Airport (POS) in Port of Spain.
- Alcoholic beverages.
- Souvenir shopping, personal phone calls, and personal items.
- Personal, medical, or trip cancellation insurance (strongly recommended).
Flights
Arrive at Piarco International Airport (POS) in Port of Spain on March 6, 2027, before 4:00 PM so you can settle in before our welcome dinner and Opening Evening.
Your departure on March 13 should be scheduled no earlier than 12:00 PM, unless you are remaining for the Exclusive VIP Experience in Tobago.
All airport transfers are included. If you would like to arrive earlier than March 6 or stay longer in Trinidad and Tobago after March 13 on your own schedule, we are happy to provide resources and recommendations for lodging and activities.
​The Host Team
Stephanie Mikulasek
A former U.S. Diplomat and founder of The ServantEDGE, Stephanie brings 20+ years of experience igniting transformation through immersive experiences across six continents. A certified executive coach, mindfulness meditation teacher, and PhD candidate researching how transformational leaders are developed through immersion, she blends wisdom, wit, and depth in a way that makes you feel simultaneously challenged and completely safe. Stephanie will guide the journey’s coaching, reflection, and leadership arc — and is available for optional 1:1 sessions to help you gain clarity on what matters most.
Ryan Assiu
A Trinbagonian and former USAID Foreign Service National, Ryan is the Founder of Advisors Next Door. He brings an unparalleled depth of local knowledge, deep community relationships, and a contagious passion for Trinidad and Tobago and community-led development. Ryan is the reason doors open that don’t open for tourists — and the reason every encounter feels genuine, not curated. His presence ensures you experience the real island, not the brochure version.
Deanna Albert
A Trinbagonian and Principal Consultant at Advisors Next Door, Deanna is an artist, masquerader, and sustainability champion with a deep understanding of local culture, history, and community. She is the warmth you feel before anyone says a word — the person who ensures you are not just welcomed into this experience, but truly embraced by it. Her knowledge of Trinidad and Tobago’s creative and cultural traditions will add dimension to every day of the journey.
The Exclusive VIP Experience: Tobago
March 13–16, 2027
For a very select few guests.
If you are looking for consequential 1:1 time, if the week in Trinidad opens something in you that wants more space — more reflection, more integration, more time to let what emerged actually settle — Tobago is available for a highly limited number of guests.
Tobago offers white sand, turquoise water, and the sound of your own thinking. A gorgeous beach villa or resort becomes your base. The pace shifts entirely. The agenda is around your needs.
What Unfolds
Each day is co-designed around your specific needs, questions, and objectives — built during a dedicated pre-trip call with Stephanie focused solely on you.
Tobago VIP Day 1
A short flight carries you from Port of Spain to Tobago, where airport transfers whisk you to your resort. Executive coaching, relaxation, and an hurried dinner unfold.Â
Tobago VIP Day 2
Between coaching sessions, you may find yourself snorkeling with sea turtles, walking barefoot on a beach that feels like it was made just for you, or reading by the pool while the breeze does the rest.Â
Tobago VIP Day 3
The week’s influence is becoming an action plan. The excitement of returning home with real clarity begins to build.Â
Tobago VIP Day 4
An early flight returns you to Port of Spain and onward to home. You’ve already sent photos and notes to the Alumni group, sharing the magic of what emerged on this island.Â
What's Included
- Three nights lodging at a gorgeous beach villa or resort.
- Round-trip flights from POS to Tobago and all airport transfers.
- Breakfasts and dinners.
- A personalized, tailored itinerary of coaching and reflection activities.
- A separate 50-minute planning call prior to departure.
- Six 50-minute 1:1 coaching sessions with Stephanie.
- A snorkeling trip.*
- A follow-up coaching call within fifteen days of returning home.
*The snorkeling trip is not private and will be with other travelers. Subject to weather and conditions.
What's Not Included
- Additional activities (boat excursions, town outings, etc.) — coordinated directly with the resort or a local guide (separate expense).
- Lunches.
- Alcoholic beverages.
- Personal items (souvenirs, phone calls, etc.).
Frequently Asked Questions
What is included in my registration?
Is this a volunteer trip?
Not the build-something kind. Â You’ll spend time with local organizations as a partner, and part of your investments goes directly to their efforts.Â
Will I have internet access?
Yes, during most of the trip. However, on the river in boats or in more remote areas, service may be limited. We recommend contacting your phone carrier to inquire about international options.
Where do I fly into?
Do I need a visa?
Not at the time of this publication — U.S. citizens need only a passport with at least six months of validity beyond the intended stay. This means your passport must not expire before September 13, 2027.  For other nationalities, please check Trinidad and Tobago government visa requirements.
Is there transportation from the airport?
How active is this immersion?
Moderate: daily walking in the heat (hats recommended), some uneven paths, and boat trips in sometimes small canoes.
Can you accommodate dietary restrictions?
Generally, yes — our private chefs can accommodate gluten-free, vegetarian, and most other dietary needs.  Vegan travelers may have more difficulty; please reach out to us in advance. During meals with local community members, we have significantly less control of the menu but will do our best to honor any restrictions. Rest assured: Trinidad and Tobago is famous for its cuisine — a genuine feast for the senses.
Is it safe to travel to Trinidad and Tobago?
Your safety is paramount. We travel in safe, private transportation at all times and remain vigilant of travel advisories. As with any destination, we strongly recommend leaving expensive jewelry and valuables at home and exercising normal precautions.
What is the weather like?
What Do I Pack?
What are the physical requirements?
This journey requires reasonable physical fitness. You’ll walk on varied terrain including city streets, uneven paths, and dock areas for boat excursions. Expect warm Caribbean temperatures throughout. This is not an extreme adventure, but it does involve daily movement and engagement. Please contact us with any questions.
What is the cancellation policy?
A $500 non-refundable deposit is required at time of registration. Any cancellation will result in a total loss of the $500 deposit. Any cancellation made prior to January 2, 2027, will result in a loss of 50% of the trip price. Any cancellation made between January 2 and trip departure will result in a total loss of funds. We reserve the right to cancel the trip if it is not meeting the minimum (if we do so, your deposit is refunded in full). Trip cancellation insurance is always recommended. Common options include Wanderwell Insurance Company or Travel Guard Insurance Online. If we find that the trip is not a good fit for you, we reserve the right to cancel your reservation, in which case your payments will be fully refunded.
Destination Trinidad & Tobago
Trinidad & Tobago, West Indies
Nestled at the southernmost tip of the Caribbean, just off the coast of Venezuela, Trinidad and Tobago is unlike anywhere else in the region — or the world. This twin-island nation is a place of staggering contrasts held in extraordinary balance: Trinidad’s lush rainforests, cascading waterfalls, and the kinetic energy of Port of Spain exist alongside Tobago’s pristine white-sand beaches, coral reefs, and a quietude so deep it feels like the island is keeping a secret just for you.
This is where steelpan music was born — hammered into existence from discarded oil drums by people who refused to let their creativity be silenced. The infamous Carnival is a communal act of joy so powerful it rewrites the body’s memory of what celebration can be. Street corners offer a myriad of flavors, rhythms, and local stories over doubles and pepper sauce.
But beyond the beauty and the music lies the real magic: the spirit of the people. Trinbagonians carry a warmth and generosity of spirit forged by centuries of learning to see the humanity in difference. By the time you leave, you’ll understand that paradise isn’t a place: it’s a way of being with one another.
Your Investment
Executive Coaching (four 1:1 sessions); group coaching (2 sessions) plus an Eight Day Immersion: March 6-13, 2027Â
- Double Occupancy: $8,795 USD per person
- Single Occupancy: $9,495 USD per person
How To Join Us:
- Choose your room type, then place your non-refundable deposit of $500 USD below.
- 50% of your balance is due by January 2, 2027
- The balance is due in full by February 1, 2027
Not sure if this trip is for you? Or need a custom payment plan?
Feel free to email Stephanie at support@theservantedge.com for help or book a call with her here!
✦ Early Bird: Save $500 when you register by November 15 ✦
Register for the Trinidad & Tobago Immersion
Space is limited. For queries, contact us at support@theservantedge.com.