Why I Started Middle of the Vines

If you had told me five years ago that I would quit my job and start a vineyard tour company, I probably would have laughed, mostly because I don't even like wine that much. Sure, I'll enjoy a glass now and then, but wine was never really the point. The point was always the experience.

My husband Mike and I travel whenever we can, and one of our favorite things to do is book local excursions. We've done history pub crawls, ghost tours, wine tours, food tours, and sightseeing tours everywhere from Savannah and Key West to Montreal, Denver, Charleston, Galveston, Salem, and Napa Valley. We love meeting people, hearing stories, and seeing a destination through the eyes of someone who knows and loves it.

For years, we joked that when we retired we'd move somewhere like Savannah or Key West and I'd become a tour guide. I love people. I love stories. I love making people laugh. It seemed like the perfect retirement job.

Then one evening after spending yet another day at Stonington Vineyards, I asked Mike a simple question:
"Why are we waiting until we retire?"

At the time, we seemed to end up at Stonington every other weekend. After the kids grew up and moved out, our lives got quieter. There were no more soccer games, dance competitions, school events, or busy family schedules. Suddenly it was just the two of us trying to figure out what to do with a Saturday afternoon.

Stonington Vineyards became our version of Cheers.

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We know the staff. They know us. If it is cold outside, they save us seats by the fireplace. They know I prefer their Summertime Sangria when it is available and Seaport White when it isn't. We bring trivia games and before long the people at nearby tables will start shouting out answers. We've been invited to staff birthday parties and after-parties. One year when Mike was out of town during a vineyard festival and I didn't want to spend the day by myself, they found me a volunteer role so I could still be part of the fun. 

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Somewhere along the way, they stopped feeling like a business and started feeling like friends.
That night over dinner, I looked at Mike and said, "There are six vineyards within thirty minutes of Mystic, one of the biggest tourist destinations in Connecticut. Why can't we do vineyard tours now?"
His response was simple.
"What would you call it?"
I already had a tiny side hustle travel agency side business called Middle of the Blue, so the answer came immediately.
"Middle of the Vines, obviously."

Before dinner was over, I had purchased the domain name.
By the next day, I had formed the LLC.
That's usually the point in the story where everything falls into place.
It did not.
Everyone loved the idea. Then they immediately gave me a list of reasons why it couldn't work.
The licensing would be impossible.
The insurance would be outrageous.
The van would be too expensive.
Connecticut only has tourists a few months a year.
I heard story after story about people who tried similar businesses and gave up.
I researched anyway. I spoke with another tour operator in Washington, D.C., who generously spent nearly an hour answering my questions. I met with the Women's Business Development Council and started building a business plan.
Then I got my first insurance quote.
The number was so high that I honestly thought everyone else had been right.
Maybe that was why nobody was doing it.
Maybe the business simply didn't make financial sense.
For a while, I put the idea aside.
Then I attended a Chamber of Commerce networking event and met the owner of a local limousine company. I told him about the idea and the challenges I'd run into.
He listened for a few minutes and then said something that changed everything.
First, I didn't need the license everyone said I needed.
Second, the insurance quote I had received was completely unreasonable.
He handed me the contact information for someone who actually specialized in commercial transportation insurance.
Suddenly, the impossible started looking possible again.
I signed up for the Chamber's Entrepreneur Academy. I worked on my business plan. A friend from the advertising agency where I worked helped me create the logo and marketing materials. The website began taking shape.
And then I started looking for the van.
At first, I thought I wanted a Mercedes Sprinter set up like a party bus. The more I researched, the more I realized I wanted something entirely different.
I wasn't building a party bus business.
I wanted small groups. Couples. Solo travelers. Friends who might not know each other yet.
I wanted people to be comfortable.
I wanted them to have room.
I wanted storage for umbrellas, blankets, coolers, snacks, and all the little details that help create a great day.
Most importantly, I wanted a tall van so nobody felt cramped.
In January, I found it.
A 2018 Ford Transit.
Tall.
Long.
Executive-style seating.
Leatherette seats.
Not flashy. Not extravagant.
Just right.
It was sitting in New Jersey, about two and a half hours away.
Mike happened to be driving nearby on a business trip, so he stopped to look at it. He called me afterward and said it was beautiful.
A few weeks later, we went to see it together.
The moment I stepped inside, I knew.
That was the van.
That was the vehicle that would become Middle of the Vines.
It still took another five months to make it happen. I used money I had saved. My mom helped. My oldest daughter helped. Mike helped. I found better insurance options. The Women's Business Development Council connected me with Michelle from Connecticut Beer Tours, who spent two hours answering every question I could think of.
Looking back, one of the things that strikes me most is how many people helped along the way.
Middle of the Vines may have been my idea, but it was built with the encouragement, advice, expertise, and generosity of a whole community of people who wanted to see me succeed.
People often ask whether I was scared to leave my job.
The truth is, not really.
I had spent years paying off debt and building savings. I had a plan. If the business didn't work, I would sell the van, get another job, and pay everyone back.
That was always the worst-case scenario.
But honestly, I never spent much time thinking about failure.
I spent my time thinking about the experience I wanted to create.
Because Middle of the Vines was never really about wine.
It's about that feeling you get when you're completely relaxed.
It's about sitting in a beautiful place with people you enjoy.
It's about meeting strangers who might become friends.
It's about discovering places you never knew existed.
It's about spending a day without worrying about directions, schedules, traffic, or who's driving home.
It's about enjoying the moment.
When people visit Mystic, they often ask their hotel staff what there is to do in the area.
I've been that traveler.
I've stood in a hotel lobby wondering what hidden gems I might miss if nobody pointed me toward them.
Middle of the Vines is my answer to that question.
It's me saying, "Come on. Let me show you some of my favorite places."
And every time I climb into that van, I still feel the same thing.
Pride.
I have ADHD. I have bright ideas all the time. Most of them never make it past the idea stage.
But this one did.
Just the other day, I was walking through downtown Mystic introducing myself to local businesses. I stopped into a bakery and said, "Hi, I'm the owner of Middle of the Vines Vineyard Tours."
Then I pointed to the van outside.
And for a second, my heart felt like it might burst.
Because I own it.
I don't work for it.
I'm not consulting for it.
I'm not helping someone else build it.
I built it.
And I can't wait to share it with you.