Ian spent his childhood summers chasing bonefish through the flats around Islamorada. Cheeca Lodge was always part of that story. So when he started planning a Cheeca Lodge wedding of his own, he didn’t have to think twice about the venue. He already knew.
Steffanie and Ian met back in elementary school. They lost touch the way most of us do, then found each other again years later in their hometown. That’s the kind of timing you can’t plan for. Ian proposed at Cheeca Lodge, the same resort his family had visited for years because of its deep ties to competitive fishing. A little over a year later, the two came back to the same property to get married. I got to photograph the whole thing, and it’s exactly the kind of full circle story that makes this job worth doing.
How Steffanie and Ian Found Their Way Back to Each Other
They knew each other as kids. Then life happened. They grew up, moved on, and their paths didn’t cross again until adulthood brought them back to the same hometown. Some couples have a meet cute. Steffanie and Ian had more of a “we already knew this was right” moment, which honestly might be rarer.
By the time Ian was ready to propose, there was only one place that made sense to him. He’d been coming to Cheeca Lodge his whole life. His family’s connection to the resort runs through its history as one of the most established fishing destinations in the Florida Keys. That place held enough meaning that he wasn’t going to propose anywhere else.
Why Do Couples Choose Cheeca Lodge for a Wedding?
Cheeca Lodge has been pulling in visitors for its fishing long before it became known as a wedding destination. The resort has hosted presidents over the decades, including George H.W. Bush, who was a regular guest and even co-founded a fishing tournament on the property. That history gives the place a certain weight, even though the buildings have been renovated many times over the years.
What draws couples now is less about the architecture and more about the setting. Cheeca sits on one of the largest stretches of beach in the area. Palm trees and that unmistakable Keys landscape frame the whole property. Add a full spa, multiple pools, and a golf course, and you’ve got a resort that can host a wedding weekend, not just a ceremony.
What Does a Wedding at Cheeca Lodge Actually Look Like?
Steffanie and Ian got married right on the beach, which is what most couples choose here. There’s something about saying vows with the ocean right behind you that photos can’t fully capture. We sure try, though.
Their cocktail hour ran straight into sunset, and that light did most of the work for us that evening. Golden hour on an Islamorada beach is about as good as it gets for photography. I’d plan a Cheeca timeline around that sunset every single time if a couple let me. After the beach, the celebration moved inside. My favorite frame from the whole day might be the two of them sneaking bites of cake in the hallway between events. Not posed. Not planned. Just them.
Their vendor team helped set the tone too. Key Largo Flowers handled the florals. Phil Santos kept the dance floor going as DJ. Caroline Waterman ran the day as month of coordinator. A wedding this smooth doesn’t happen by accident.
Is Islamorada Easy to Get to for Out of Town Guests?
Here’s something I tell every couple looking at Islamorada versus Key West. Cheeca Lodge is a much shorter drive for guests flying in. Key West sits about four and a half hours from Miami by car. Islamorada is a fraction of that distance. If you’ve got guests coming from out of state, that shorter drive from Miami International can be the difference between a full RSVP list and a lot of regretful declines.
For couples weighing a Cheeca Lodge wedding against other Keys venues, that accessibility is worth factoring in early. This matters most if your guest list skews toward people who’ve never been to the Keys before.
Planning Your Own Wedding at Cheeca Lodge
If Steffanie and Ian’s day tells you anything, it’s that Cheeca Lodge rewards couples who lean into what the property already does well. Get married on the beach. Let the sunset run the cocktail hour. Don’t overthink the reception details when the setting is already doing the heavy lifting.
I’ve photographed weddings all over the Florida Keys. Cheeca Lodge remains one of my favorite venues to shoot, precisely because it gives me so much to work with in a single afternoon. If you’re planning a wedding here and want a photographer who already knows the property, I’d love to hear about your day.
FAQs
Pricing varies by season, guest count, and package, so Cheeca Lodge doesn’t publish a flat rate. As a luxury oceanfront resort in Islamorada, expect the investment to reflect that positioning. The most accurate way to get a number is to request a custom quote directly from the resort’s wedding team, since packages are fully customizable.
Not in the traditional all-inclusive sense, but it comes close. Cheeca Lodge offers full-service wedding planning that includes catering, vendor management, décor, and event setup handled by their on-site team, which makes the planning process feel far simpler even though the pricing structure works differently than a true all-inclusive resort.
Yes, a beachfront ceremony is one of the most popular options at Cheeca Lodge, and it’s exactly where Steffanie and Ian said their vows. The resort’s oceanfront setting makes an outdoor beach ceremony followed by a sunset cocktail hour one of the most requested formats for couples getting married here.
Yes. Islamorada, where Cheeca Lodge sits, is a significantly shorter drive from Miami than Key West, which runs about four and a half hours by car. For couples with guests flying into Miami from out of state, that shorter drive can make a real difference in how many people actually show up.
Cheeca Lodge & Spa sits oceanfront in Islamorada, in the upper Florida Keys, making it one of the more accessible Keys wedding venues for guests traveling from South Florida. Its beachfront setting and Keys landscape are a big part of why couples choose it for a wedding.
