"Live from the Caribbean: Island Hopping to Find Our Dream Location" episode artwork

EPISODE · Jul 9, 2025 · 25 MIN

"Live from the Caribbean: Island Hopping to Find Our Dream Location"

from Never Stop Dreaming Biggie

SummaryIn this special travel episode "Live from the Caribbean: Island Hopping Adventure," Angel and Brian Holmes take you on their real-time research journey through Grenada, Bequia, and Barbados as they scout locations for The Holmestead Bar & Retreat. From navigating treacherous mountain roads in Grenada to falling in love with the sailing culture of Bequia, and experiencing the party atmosphere of Barbados, they share unfiltered insights about each island's potential. The couple discusses the realities of seasonal tourism, infrastructure challenges, and what it really takes to build an international business. Angel reveals her vision for each location while Brian provides his practical "Director of No Fun" perspective on the logistics and financials. They share honest pros and cons, from Grenada's amazing people and stunning scenery to Bequia's perfect sailing community and Barbados's party scene. Their adventure includes everything from rum punches at 8 AM to hiring local drivers as tour guides, showcasing both the excitement and exhaustion of location scouting. This episode proves that turning dreams into reality requires boots-on-the-ground research, cultural sensitivity, and the flexibility to adapt when plans don't go as expected.FOLLOW US:Instagram: @neverstopdreamingbiggie and @angelpholmesLearn more at https://neverstopdreamingbiggie.com/spiritsFollow us at https://www.instagram.com/neverstopdreamingbiggie/Learn more about The Holmestead Bar at https://neverstopdreamingbiggie.com/the-holmestead-bar-retreatPlaces we loved during our stay:True Blue Bay Resort: https://www.truebluebay.com/Bequia Plantation Hotel: https://bequiaplantationhotel.com/The Cocktail Lab Bequia: https://www.instagram.com/thecocktaillabbequia/?hl=enFrangipani: https://frangipanibequia.com/Sweetfield Manor: https://sweetfieldmanor.com/TakeawaysResearch seasonal tourism patterns before committing to international business locationsBuild genuine relationships with locals when scouting new markets - they provide invaluable insightsConsider transportation logistics for both operations and customer accessibilityGrenada offers amazing people and scenery but challenging roads and short seasonBequia provides perfect sailing culture and community but limited year-round tourismBarbados has great infrastructure and energy but doesn't match their intimate bar visionFactor infrastructure challenges like narrow roads into business planning and vehicle choicesDocument your journey for both content creation and future business planningTrust your instincts while remaining open to unexpected discoveries and opportunitiesPlan for multiple transportation scenarios when international travel is involvedPrioritize becoming an asset to the community rather than just extracting valueOff-season visits reveal the true local culture and business sustainability challengesChapters00:00 Welcome from Grenada - First Impressions02:30 Grenada Pros and Cons Discussion07:39 Traveling to Bequia via Multiple Transportation Methods09:15 Bequia Beauty and Sailing Culture12:45 Finding Potential Locations and Meeting Locals15:15 Barbados Reality Check from the Hotel Room17:30 Why Barbados Isn't Their Scene19:45 Overall Trip Reflections and Next StepsHave ideas, questions, or comments? Email us at [email protected].

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"Live from the Caribbean: Island Hopping to Find Our Dream Location"

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This episode was published on July 9, 2025.

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SummaryIn this special travel episode "Live from the Caribbean: Island Hopping Adventure," Angel and Brian Holmes take you on their real-time research journey through Grenada, Bequia, and Barbados as they scout locations for The Holmestead Bar &...

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