Opening a Bar in the Caribbean: Our Real Story from Grenada (Episode 41)

It was all a dream… but what happens when you actually start making that dream a reality?

If you’ve ever dreamed about opening a bar in the Caribbean, let me tell you what it actually looks like — because it’s nothing like what you see on Instagram. It’s December 8th, 6 PM, 80 degrees, and I’m sitting beachside in Grenada with Brian, recording our podcast with actual sailboats and crashing waves behind us. Not a fake Zoom background. Not a staged photo. This is real life, and we are actively in the process of opening a bar in the Caribbean.

We’re here on a mission — to find the perfect location for The Holmestead Hideaway, our Caribbean retreat and bar launching in 2028. And turning your biggest dreams into reality looks nothing like what you expect.

From Charleston to Grenada: What Opening a Bar in the Caribbean Really Requires

When most people think about opening a bar in the Caribbean, they imagine warm breezes and easy living. The reality? It’s narrow mountain roads where you almost crash your rental car, meetings with government officials while sweating through your clothes, and praying constantly that you’re following God’s plan and not just your ego.

Brian and I have narrowed down our top two locations: Grenada and St. Vincent/Bequia. This trip was all about getting serious — really serious — about making this happen. We’re talking meetings with real estate agents, attorneys, government officials, and local community leaders. This isn’t vacation mode. This is entrepreneurship in action.

Three Properties, Three Very Different Lessons About Caribbean Real Estate

Our incredible realtor Lucille from Century 21 Grenada — who’s already a gift from God and will be joining The Brighter Side Society, she’s that amazing — took us to three properties. Here’s what we learned about finding the right home for opening a bar in the Caribbean:

Property 1: Automatic Bay — Beautiful But Not the Vision

Sometimes a place can be gorgeous and still be wrong for you. This property was stunning, but it just didn’t fit what we’re building. Lesson learned: don’t settle for “pretty good” when you’re meant for “absolutely perfect.”

Property 2: Mourn Rouge — Too Much, Too Steep, Too Expensive

This was on our radar from before, but seeing it again with fresh eyes showed us the truth. Yes, we thought we needed three acres. But massive land on a steep slope that we can’t actually build on? That’s not opportunity — that’s a money pit. Plus, it was way out of budget. We’re building something sustainable, not going broke chasing a fantasy.

Property 3: The One — Our Caribbean Bar Location

This is the property we fell in love with last year when we first visited Grenada. Coming back confirmed it: this could be home.

Here’s what makes it the right location for opening a bar in the Caribbean:

• The right amount of land — not too much to manage
• A manageable slope, which is crucial for building
• Gorgeous jungle features we can preserve
• Stone gates and structures that add real character
• Amazing neighbors who’ve already done incredible work with their land
• Located in an up-and-coming area — perfect timing
• A price point we can actually work with and negotiate down

The best part? We walked up these incredible stone stairs to the top of the property, looked out at the jungle canopy, and both felt it: this is where The Holmestead Hideaway comes to life.

The Real Considerations When Opening a Bar in the Caribbean

Let me be honest about what goes into a decision like this, because if you’re dreaming about international business expansion, you need to know the truth.

The Tourism Factor

Grenada is 12 miles from Venezuela. With political unrest happening there, some tourists — especially Europeans — are nervous about visiting the region. Is it actually dangerous? No. We feel completely safe. But perception affects tourism, and tourism affects business. We have three years before we open, so we’re not panicking, but it’s something to watch closely.

The Practical Reality of Opening a Bar in the Caribbean

• Driving on the left side of the road is genuinely terrifying — we almost got in a wreck
• Grocery stores have everything you need at decent prices
• Drinks cost $10–15 USD versus $15–17 in the US
• The Christmas market and local festivals are incredible
• It’s actually more affordable than building in the States
• The local community is welcoming, friendly, and ready to work with us

The Strategic Side

We’re meeting with government officials and attorneys, and we have a tour guide set up by our advisor David — another angel God brought us — to really understand the local culture and community. Because here’s the thing: we’re not just buying land. We’re joining a community.

We’re committed to using local contractors, local artisans, and local community members for everything we build. This isn’t about Americans coming in and taking over. This is about partnership, collaboration, and lifting up the people who call this island home.

What Opening a Bar in the Caribbean Taught Us About Big Dreams

You might not be shopping for Caribbean real estate, but if you’re sitting on a big dream wondering whether you should actually go for it, here’s what this journey has taught us:

1. You have to show up in person Virtual tours and Zoom calls will only get you so far. At some point, you have to be willing to get on the plane, drive the scary roads, and see things with your own eyes. Stop hiding behind “research” and start taking action.

2. Build relationships before you make decisions The best thing we did was connect with people like Lucille and David before we started making major decisions. They know the market, the culture, and the community. They’re helping us avoid expensive mistakes and find incredible opportunities.

3. Not every good option is the right option Property 1 was beautiful. Property 2 had potential. But Property 3? That’s the one that feels right in our spirits. Don’t settle for good enough when something absolutely perfect is waiting for you.

4. Your timeline matters We’re launching in 2028. That three-year timeline keeps us grounded, realistic, and patient. We’re not rushing. We’re not panicking. We’re building something that will last.

5. Faith and business work together Every step of opening a bar in the Caribbean, we’re praying, surrendering, and trusting that if this is God’s plan, He’ll make it clear. If it’s not, He’ll close the door. That takes the pressure off and puts it where it belongs.

What’s Next for The Holmestead Hideaway

Tomorrow: government officials and attorneys. More exploring. More praying.

Wednesday: a local tour to really understand the community and culture.

Then we head to St. Vincent and Bequia for part two of this adventure — meetings with realtors, an architect, and possibly even the Prime Minister of St. Vincent.

By the end of this week, we’ll know where The Holmestead Hideaway will call home.

Follow the Journey

Episode 41 of Never Stop Dreaming Biggie gives you the full behind-the-scenes of our Grenada adventure — complete with the actual sounds of the ocean, our real conversations, and all the unfiltered truth about what it takes to start opening a bar in the Caribbean.

Episode 42 takes you to St. Vincent and Bequia, and we share our final decision about where we’re building.

If you’ve been waiting for permission to dream bigger, consider this it. Your dreams aren’t too big. Your vision isn’t too wild. And you are absolutely capable of making it happen.

It’s December. It’s 80 degrees. And this could be yours in 2028 at The Homestead Hideaway.

Until then, keep dreaming Biggie.