One of the unique perks of owning or working with a captive insurance company is the opportunity to attend board meetings in destinations that are not only practical but also enjoyable. Being based in Grand Cayman, I am very fortunate to not only call this beautiful island my home, but I also get to welcome my clients here for their Board meetings year after year. However, sometimes captive boards may want to travel further afield. Many destinations outside of the U.S. make a routine board meeting a great way to connect with other board members and captive industry professionals, combining business with a touch of leisure. I recently asked some of my peers and colleagues across the industry about their preferred places to meet and the little things that make all the difference. The answers painted a picture of some truly special spots.
Top Meeting Locations and Hotels:
Central America
Costa Rica - Four Season Guanacaste
Think rainforest backdrops, monkeys swinging through the trees, and black sand beaches, not to mention five-star service. With just a three-hour flight from many East Coast hubs, Costa Rica can be reached by multiple direct flights daily from major U.S. cities like Miami, Houston, Atlanta, and New York.
Europe
Portugal – Ritz Carlton - Penha Longa Resort, Sintra
Set in the Sintra Cascais Nature Reserve, this luxury resort features two championship golf courses, and not one but two Michelin-starred restaurants. Sintra, a UNESCO World Heritage Site, enchants visitors with its fairytale-like palaces, lush forests, and mystical atmosphere. A dream for golf lovers, foodies and explorers alike.
Rome - The Bernini Hotel
Just steps from the Trevi Fountain, where every corner whispers history and the food is always perfection. As one peer put it: “You could sense how old and historic it truly is.”
London - Pan Pacific Hotel
One of our peers told us he loved the history of London and its prominence in the insurance business, noting that the Pan Pacific Hotel is in a great location for exploring the historic city on foot during down time.
Canada
Short, direct flights from most U.S. cities make Canada an incredibly convenient option.
Vancouver – Rosewood Hotel Georgia 
Mountains, water, and a city vibe all in one — plus an easy spot for West Coast clients to meet.
Banff and Whistler
From the iconic Fairmont Banff Springs to Whistler’s charming alpine village, these destinations deliver jaw-dropping scenery and plenty of activities.
Quebec City – Fairmont Le Chateau 
Old cobbled streets, boutique shops, and a heritage hotel that feels straight out of a postcard.
What Matters Most When Picking a Location
After a flight, no one’s excited about a two-hour bus ride. That’s why ease of travel was the #1 factor across the board — direct flights, short transfers, and quick airport connections. Beyond that, peers mentioned the importance of good weather, safe surroundings, dining options, and hotels that know how to host business groups. Making sure the meeting room and facilities are to the Board’s expectations is paramount. One peer noted the importance of having meeting rooms that are of a size consistent with the in-person attendance, down to the table space per participant being at least 36 inches, preferably 48 inches. One of our peers recalled a meeting where the meeting room was on a terrace outdoors, in the Caribbean heat, which is never a good idea.
The Smoothest (and Trickiest) Immigration Experiences
When it comes to immigration, every minute counts. Some of the easiest entries? St. Thomas, the Bahamas, Cancun, and Canada (with Nexus). On the flip side, a few airports got called out as ones to avoid if you can — Tortola for long lines, Chicago O’Hare for winter delays, and Miami International for its endless immigration queues.
Frequent Locations
In the past year, some destinations popped up over and over again: Vancouver, Toronto, Cayman, Bermuda, and Cabo San Lucas were the most-visited meeting hubs.
Recommendations
If you’re planning your next meeting and need inspiration, our peers had plenty of other ideas:
- The Hazelton Hotel, Toronto, Canada
- The Hilton, Cabo San Lucas, Mexico
- The Cove, Paradise Island, Bahamas
- Ritz Carlton Montreal, Canada
- Four Seasons, London, UK
- Even Barcelona (Hotel Arts), Lisbon (Corpo Santo) and Iceland (Fosshotel) got shout-outs as unique, affordable, and surprisingly accessible spots.
Mixing Business with a Bit of Pleasure
Captive board meetings don’t have to be all business. Choosing the right destination can set the stage for productivity while also giving board members the chance to network and recharge in a relaxed setting. Whether it’s a stroll through Rome’s ruins, a round of golf in Ireland, or a drive up the Sea-to-Sky Highway to Whistler, sometimes it’s those little detours that make a work trip truly memorable.
Contributors
For their thoughtful responses to our survey, I would like to thank Tom Adams (Former President of Owners Operators Services Inc.), James Trundle (GCM), Bill Hochkammer, Greg Nowakowski and Mark Kleinline (all Honigman), Gillian Hall (Aon), Anna Ghandilyan (Kensington), and our very own Paul Macey and Rob Leadbetter (USA Risk Group).
