For decades, the default setting for corporate retreats in the United States was a predictable mix of hotel ballrooms, boxed lunches, and evening cocktails in the lobby bar. That formula worked well enough in an era when business travel was built around convenience and cost. Today, though, many executives are asking a different set of questions. Where can a team truly connect? How do you create an environment that feels less like another meeting and more like a reset?
Increasingly, the answer is not found in a hotel. It’s coming from luxury private estates.
Drip Castle Estate Collection, which manages four sprawling properties across Florida, Vermont, and New Mexico, has seen corporate bookings rise sharply. The company’s founders, Michelle and Greg Barry, say executives are less interested in traditional conference packages and more focused on spaces that feel both private and personal.
“We are seeing an increase in corporate-based groups trying to stay out of the hotel and bar scene,” Michelle Barry explained. “Teams want true connections. They don’t get that from crowded lobbies or ballroom seating. ”
That practicality is driving demand. At Drip Castle’s estates, groups stay under one roof. Every guest has a private bedroom and bathroom, but shared kitchens, terraces, and lounges encourage natural interaction. Instead of scattering after hours, colleagues might find themselves grilling dinner together, playing pickleball, or gathering around a firepit.
Greg Barry puts it simply: “Instead of meeting in a corporate boardroom, it could be a meeting on the beach.
Executives who have made the shift from the hotel scene say it is not only about luxury but about avoiding the limits of the traditional model. When meetings end at a hotel, the group usually disperses: some head to their rooms, others to the bar. The dynamic quickly fragments. For those who don’t drink — a growing number of younger professionals — the lobby cocktail hour can feel more isolating than inclusive.
At a private estate, the environment is closer to a home than a convention center. The atmosphere is quieter, more relaxed, and better suited for building trust. Meals are eaten together. Breaks spill naturally into a round of paddle boarding or a walk along the beach. These small, unscripted moments become the glue that keeps a team connected.
A corporate client’s view : Marty Franchi, CEO of trading platform NinjaTrader, has hosted his leadership team at Drip Castle’s Sea Oats Luxury Estates property on Captiva Island. He describes the experience as offering “the perfect balance of collaboration and retreat.”
For him, the difference comes down to how the estate is set up. The layout, he explained, includes ample private rooms and bathrooms, which makes extended stays practical. But what struck him most were the opportunities for his team to connect outside of formal meetings. “Kayaking, paddle boarding, fishing, the beach, the sports court, the gym — those activities created natural ways for my team to bond,” he said. And when they needed focus, the privacy of the estate gave them the right setting for strategy sessions without distraction. He also pointed to the concierge team, whose “creativity and ability to make anything happen” turned the retreat into something his executives still talk about long after returning to the office.
Part of the appeal lies in the details. “When a corporate team arrives, the bar is stocked, their rooms are labeled, their chef is booked, events and tours are planned,” Michelle Barry said. “That means they don’t waste half a day checking in or organizing. They can relax knowing everything is taken care of, and get right to the purpose of the trip.”
This kind of planning has real value for executives trying to maximize both budgets and time. With hybrid work dispersing teams across regions, retreats are often the only time some colleagues see each other in person. Wasting hours in transit or on logistics is no longer acceptable.
The usage of the luxury estates is perfection – somehow, they seem built for teams. Each of Drip Castle’s estates offers a distinct backdrop. Sea Oats and Sea Palms on Florida’s Captiva Island place teams directly on the Gulf, with pools, private docks, gyms, and large indoor-outdoor gathering areas. Meadowstone Manor in Stowe, Vermont sits on 30 private acres with its own pub, yoga studio, tennis courts, ski valet and seasonal pool. Gem Hacienda in Taos, New Mexico, is an adobe-style retreat with sweeping mountain views, offers fireplaces, hot tubs, and easy access to both ski slopes and the local arts district.
These properties are not hotels repurposed for business. They are homes on a grand scale, configured from the start to host large groups while still giving each individual privacy.
The move toward estates reflects larger cultural changes. Employees want clear boundaries between work and personal life. They also want experiences that feel meaningful, not obligatory. A weeknight dinner on a terrace in Vermont, or a morning paddle off the coast of Florida, delivers more value than another generic banquet. For companies, this shift is more than a perk. It is a way to strengthen retention and reinforce culture at a time when both are fragile. Leaders are finding that problems once hashed out over weeks of emails can sometimes be solved in a single weekend when teams live and work side by side.
Drip Castle has tapped into this new reality, positioning its properties as the stage for that kind of work. The Barry family does not talk about ballrooms or packages. They talk about provisioning – grocery deliveries, stocked kitchens, rooms prepared and specially labeled for each guest, and chefs who understand how to cook fine food for thirty people.
It is the small touches that make the estates feel less like rentals and more like a temporary headquarters for ideas.
For now, hotels still dominate the corporate retreat market. But the growth of estates like those in the Drip Castle collection shows a clear change in executive preferences as they become increasingly aware of the alternatives. Privacy, inclusivity, and immersion are replacing conformity as the drivers of choice.
The boardroom is no longer the center of a corporate retreat. Increasingly, it is the backyard, the beach, or the kitchen table.
If hotels once symbolized business travel, private estates now symbolize the business of culture — teams leave not just with notes, but with memories that last.
