One of the core facets of Inspirato is to help families spend more time together, allowing them to create lasting memories amid a beautiful setting. And when Inspirato members Skip and Janet Pawul gathered their family for a multigenerational reunion, they chose the Florida Keys to do just that. Booking next door units Palomar and Arbor at the Isles of Islamorada resort, they prepared to gather 16 family members together for the first time in three years.

“Our kids live in New York, Connecticut, and Texas, and we have eight grandchildren, so it’s a great thing to get everyone together,” Skip said. “We’ve been to the Keys before, loved the casual atmosphere, and thought it would be the perfect setting.”

(All photos courtesy of Skip Pawul.)

But right before the trip—which had already been rescheduled for a year later due to COVID—the family suffered a profound loss.

“My dad passed away the day before we left,” Janet shared. “We all came together and honored him, and he would have wanted that. … I always feel like he was looking down and giving us his blessing.”


“Everyone wondered if we should still go,” Skip continued. “I went in to talk to him—he was in hospice—and said, ‘You have to let us know what you want us to do.’ He heard what we were saying, and he was a big family guy; it was everything to him.” Skip said

“We went to say goodbye to him the night before we left, and he had just passed away before Skip and I walked in,” Janet said. “It was profound.”


What was once just a family reunion became an ode to the family patriarch. Together, all 16—Skip and Janet, their three children and their spouses, and all eight grandkids—were able to both mourn and celebrate his life.

One of the most special moments of the trip, a sunset catamaran cruise, served as a memorial service to Janet’s father. “We played my dad’s song and threw golf balls into the water,” she said—they checked beforehand to make sure it was okay for the environment, they mentioned with a laugh—“Captain Lolly, who’s a little bit of a tough character, even cried.”


Among other highlights of the trip were swimming with dolphins, a family photoshoot—complete with hair and makeup—hobie cat adventures, a private chef who serenaded them under the stars, and pool time at Islamorada.

“I was able to relax and really enjoy the kids in between making funeral arrangements,” Janet said. “And of course, the Inspirato team is always so supportive.”


“We’ve done a lot of Inspirato Only experiences … and the one thing you know about Inspirato is that you never under deliver,” Skip continued. “That’s one of the reasons that we chose to do the trip with Inspirato, because with that many kids and that much stuff to plan, the concierge team is amazing at Islamorada.”

The concierge even helped all the kids get pumpkins to carve, as the family was there over Halloween. She also recommended a trusted babysitter whom the kids loved—Janet said she had the magical air of Mary Poppins.


“It all seemed perfect in every way. That’s how special it was. All eight kids got along—they never fought at all,” she said. “It was really amazing.”

Skip rounded out the trip by giving awards to all the grandkids on the last night—accolades like “best swimmer”—and a $20 bill for each. “Their faces just lit up,” Janet said.

Our motto is to create magic moments for our kids and grandkids, and the Inspirato homes make it easy. You never have to worry that the home is not going to be big enough or clean enough or beautiful enough, or that the support team would ever let you down in any way—that’s the magic of Inspirato.

Skip Pawul

Even with—or perhaps because of—the tragedy that befell the family the night before their trip, it became one of the most important of their lives. “It just seemed perfect in every way,” Janet said. “I said to Skip, ‘I don’t even know if we should ever do this again. I don’t think we could ever duplicate this. That’s how special it was.”


Inspirato was honored to be a part of the Pawuls’ incredible reunion-turned-memorial trip. To find out more about how Inspirato can make your next vacation once in a lifetime, contact your Care team.

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