Live from the Caribbean: Our Island-Hopping Adventure to Find The Perfect Business Location

How we’re scouting Grenada, Bequia, and Barbados for The Holmestead Bar & Retreat

When most people dream of starting a Caribbean business, they picture endless beaches and rum punches. The reality? It’s “like driving in the worst ice storm for three hours” while navigating narrow mountain roads and evaluating seasonal tourism patterns.

That’s exactly what Angel and Brian Holmes discovered during their recent Caribbean research trip, documented in Episode 19 of the Never Stop Dreaming BIGGIE podcast. The entrepreneurial couple is scouting locations for The Holmestead Bar & Retreat, and their unfiltered journey reveals what it really takes to build an international business.

Island #1: Grenada – Amazing People, Challenging Infrastructure

The Good: Grenada immediately won their hearts with incredibly friendly locals and stunning scenery. “The people are amazing,” Angel shares. “I already hired like five or ten people if we could stay here.”

The Challenge: Those picturesque mountain roads come with a price. After 140 near-misses navigating the island, Brian concluded that future guests would need transportation solutions rather than rental cars.

The Verdict: Grenada offers authentic community connections but requires creative logistics planning.

Island #2: Bequia – Sailing Paradise with Seasonal Concerns

Bequia delivered on the sailing culture they’d envisioned. “It’s beautiful and smells great, sounds great, looks great. It’s top-notch all the way around,” Brian observed.

The couple even found their dream location – an undeveloped cove with sailboats and land for sale. But like many Caribbean destinations, Bequia faces a significant challenge: a short, intense tourist season from November to April, followed by much quieter months.

Island #3: Barbados – Great Infrastructure, Wrong Vibe

While Barbados offered better roads and infrastructure, it didn’t match their vision for an intimate, community-focused retreat. The larger, more commercialized island felt too much like a party destination rather than the meaningful experience they want to create.

The Bigger Picture: Building with Purpose

What stands out in their journey isn’t just location scouting – it’s their commitment to community impact. “We want to be part of the community. We want to be an asset,” Angel emphasizes. “We want to contribute and be a positive thing, not a negative thing.”

This philosophy drives every decision, from transportation solutions for guests to partnerships with local operators. They’re not just looking for paradise; they’re seeking a place where their business can genuinely enhance the local community.

Key Takeaways for International Entrepreneurs

Research Seasonal Patterns: Understanding tourism cycles is crucial for year-round sustainability.

Prioritize Infrastructure: Beautiful views don’t matter if guests can’t safely reach you.

Build Local Relationships: The best insights come from people who live there year-round.

Think Like a Guest: Consider every aspect of the customer experience, including transportation.

Lead with Community Impact: Successful international businesses enhance rather than exploit local communities.

What’s Next?

The Holmes are still evaluating their options, with both Grenada and Bequia remaining strong contenders. Their decision will ultimately depend on finding the right combination of practical logistics and community welcome.

As Angel puts it: “If this is the island that God wants us at, then that’s it.”

Listen to Episode 19 of Never Stop Dreaming BIGGIE for the complete Caribbean adventure, including behind-the-scenes moments and detailed island comparisons.

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Ready to start your own location-independent business? Connect with Angel and Brian at @neverstopdreamingbiggie and learn more about The Holmestead Bar & Retreat at neverstopdreamingbiggie.com.