16. The Upgrade | Weekly - Succession: The Millennial Heirs in Hospitality Families Stepping up the Plate
An interview with Ian Swain II on taking over his parent’s company, Swain Destinations. Other millennials taking the helm.
🗝️ The Upgrade | Weekly by Anne Marie Brown
Issue 16 · Succession: The Millennial Heirs in Hospitality Families Stepping up the Plate
In The Upgrade this week:
Pre-Departure – An interview with Ian Swain II on taking over his parent’s company, Swain Destinations. Other millennials taking the helm.
The Room Report – Naviva, Four Seasons Punta Mita
The Lobby Bar – This week: Hoshinoya opens inside a 1908 prison in Nara, Fouquet's plants its first flag outside France on Paraga Beach in Mykonos, and Explora Journeys becomes the first luxury cruise line to join Hilton Honors. Also - a list of 2026 luxury hotel openings
By Anne Marie Brown | Alpenglow Travel
Travelers,
Luxury hospitality is built on legacy. Our own family successfully passed the hotel company my grandfather founded, Outrigger Hotels, to my father and his sisters, then to my brother-in-law and my half siblings, before we sold the company in 2016 to private equity firm KSL.
The properties with the most devoted guests tend to be family-owned, with ownership structures that take a stewardship view rather than a transactional one. Right now, the generation tasked with inheriting those foundations has moved into the chair, and I’m watching my millennial peers that I grew up with step into leadership roles at their family companies.
Across luxury hotels, safari companies, and high-end travel brands, millennial leaders are running businesses their parents or grandparents built.
In The Upgrade this week, I sit down with my friend and new CEO of Swain Destinations, my go-to tour operator for Alpenglow Travel clients in New Zealand and Australia. As soon as I saw his announcement on LinkedIn, I reached out to interview him.
Yours truly, a millennial, via ChatGBT. There are some things AI is good for.
🗝️ Pre-Departure — Hospitality Hot Takes
Millenial Succession:
A Conversation with
Ian Swain II of Swain Destinations
Ian Swain II
Ian Swain and I grew up in parallel corners of the travel industry. His parents built Swain Destinations, a luxury FIT (free independent travel) tour operator for Australia, New Zealand, Africa, and the Middle East. My dad ran Outrigger Hotels. The two of them were friends, part of a generation of founders who launched international leisure travel for Americans. They sat on the board at WTTC (the World Travel and Tourism Council) together, and Ian and Linda flew out to attend my father’s funeral when he passed away. Ian II and I are the same age, and both come from large families with a veritable basket of other siblings. We could probably field a soccer team.
Ian II and I talked about family succession, the pressure of a founder’s shadow, what luxury means to our generation, and the legacy we hope to pass to our own kids.
AM: Give me an overview of Swain Destinations and a little history of your family.
Ian: Swain Destinations is a luxury FIT tour operator. We build itineraries customized for North Americans to Australia, New Zealand, Africa and the Middle East. The company is about forty years old, started by my parents. My father is Australian; my mother is American. They met, fell in love, and decided the path forward was to bring Americans to my father’s homeland. They have been selling travel and building it ever since. I am one of six kids in a big family.
AM: When did you first decide you wanted to actually run the company, not just work in it?
Ian: As a kid, you look up to your parents, especially when they’re building a company. The dinner time conversations are often about the business. It is a different dynamic than most children are exposed to because you are hearing about growth problems and strategic decisions being made as if it is a normal family conversation. Maybe that’s where it started.
Even before I worked here, just traveling with the family, I’d watch my mother and father go to Australia or New Zealand, and they already knew people everywhere. That’s this industry. You build colleagues and friends all over the world, so anywhere you are, there’s someone to say hi to. The industry itself is what drew me in.
As I got older, I realized how impactful travel is. It changes your world and how you see things. Being part of a company that does that is inspiring. Now I get to help steer where it goes next, and doing that alongside this team is what I love.
AM: How did the transition happen with so many siblings?
Ian: My siblings all have their own lives and careers. I was the one actively pursuing it. It was a private conversation between my parents and me. I approached them and we talked it through over a few months. Once it started to feel real, we moved down the path as best we could. When it was announced, all my siblings were genuinely excited and happy for me. I’ve been with the business the longest, and only a couple of the others have worked at Swain. It was organic in a way, but it was something I went after.
AM: What did your dad do to prepare you to take over?
Ian: : I am very fortunate to live close to my father, and our relationship has a large business component, which I like. Between working for the company and traveling with him for years, he’d been preparing me without either of us realizing it, or at least I didn’t.
The best thing he did was build such a great team. We have some industry legends at Swain, people who’ve been here for decades and know everything. Coming back after a few years in other industries, I’ve leaned on them constantly. Some of them have known me since I was a kid, so there’s a real familial feel here.
He’s all still here supporting through the transition. We talk business every day, and we have complementary skill sets. A forty-year-old company has a lot of ways it works and flows that take time to learn, even having been here before. Building the right team and keeping them is absolutely the best thing he’s done.
AM: What advice would you give other millennials waiting in the wings to take over a family business?
Ian: Stop waiting. If you’re holding yourself back and there’s a path, pursue it. If you want it, go after it.
If it’s not time yet, don’t sit still. Build your skills, inside or outside the brand, and keep a pulse on the business. And when you are ready, and they are ready, make sure you really want it. Emotion is a huge part of this. Everything is personal, and no matter how objective you think you are being, it hits you emotionally. You must be ready to weather that.
Ultimately, go for it. There’s so much opportunity in being the child of a founder, so much to learn and build. Not everybody gets that. Take advantage of it..
AM: What have been some of the challenges of coming in as the son of the founder?
Ian: The hardest part back then was proving myself. Being the second Ian Swain to an Ian Swain founder, you carry a self-imposed pressure to show people you’ve earned your place and you’re not just there because of the name. In a strange way, that pressure helped. It built my work ethic and my focus on executing, because I wanted to prove I could do it myself.
After you execute enough, you get more confident and you stop worrying about what people assume. As you get older, you have your family, your team, your clients, and everything else becomes noise. If someone questioned whether I belonged here today, I’d say okay and move on. There’s enough real work to focus on. When I was younger, that pressure created the work that got me where I am, so I don’t resent it at all. It pushed me to grow.
AM: You left the company for a few years. Did that time outside change things?
Ian: I left for some time to work outside the company . Before I did, I did not realize how valuable it would be. Going outside and back gives you a completely different perspective, and was one of the most valuable educations I’ve had.
AM: What makes Swain Destinations special? Tell me about “luxury with heart” and the Swain sauce.
Ian: Australia and New Zealand are where it all started. I truly believe our travel consultants are the most knowledgeable about our destinations and the most invested in the trips they plan. They have traveled there or lived there, and it’s personal to us. Every trip matters to everyone on the team. We try to create something effortless that takes care of you the whole way through.
The knowledge runs deep. We have product team members who’ve been with us for decades and been a part of the change of the industry. As a family company, we care about our travelers and advisor partners, without question.
Swain sauce is a funny term, but it’s referenced a lot. My parents are outgoing and they love traveling, networking, and relationship building, and all of that is part of the Swain sauce. How do we get past the client relationship to a friendship, where we’re helping you see the world a little differently? That’s the mindset.
The Swain sauce is staying. I have no intentions of changing the brand. Our focus now is to grow it deliberately, open it up to more people, and keep delivering the same level of service without losing quality. That’s something that can slip in an acquisition, so it is a significant focus of mine.
AM: How do you define luxury travel for millennials versus older generations?
Ian: The simplest way I describe millennial luxury is experiential. Older generations leaned toward the white glove, the “sir,” the “madam.” I haven’t seen millennials value that as much. They want the unique tour, the speakeasy down the alley, or that sunset view you can only see if you know the right person. Rare experiences and stories they can’t wait to tell people about. That is the millennial luxury, the undiscovered place or experience.
For me, luxury is being able to take my family somewhere new and not worry about a thing.. Moving seamlessly through the transfers, the flights, the hotels, the experiences, so that my only focus is enjoying the time with my family in these new worlds. That’s luxury to me.
AM: Do you think Swain will one day pass to your kids? What do you hope for them?
Ian: My kids are the most important things in my life. When my wife and I were deciding whether to buy the company, they were the biggest factor. We knew it would take our time and affect them, that they’d see a different side of us in a business setting.”
I didn’t do this thinking about them taking over. I hope they will share my passion. I hope I can give them the opportunities I was given. If they decide they want to pursue the business, I’ll happily teach them what I can, but they’ll have to earn their spot. We have an incredible team here, and we’ll bring on more incredible people over the years. Maybe one of them takes the baton and leads the brand into the next generation after my time.
I’m not going into this expecting my children to take over or putting pressure on them, because the only pressure I had was self-imposed. I hope they are interested and I hope I grow the business big enough where there is opportunity for them if they want it.
I hope they love travel. I really do.
AM: What do you hope to pass on to them, beyond the business?
Ian: Curiosity and a sense of adventure. I hope I can impart that on them. When they travel, I hope they can take in different cultures, and I hope they can bring what they learn back to the people around them. Travel changes you in incredible ways. The world could use a lot more of that. It educates you differently than school does and shows you there is a world outside of your own. I hope I can give them that curiosity. That is all I want.
Ian Swain is the incoming owner of Swain Destinations. If you are planning a trip to Australia, New Zealand, Africa, or the Middle East, reach out to me at AnneMarie@AlpenglowTravel.com and I will connect you.
Other Millennial Successors In Hospitality
The baton is being passed to the next generation of leaders in the luxury travel and hospitality industry. Here are a few other examples of millennial leaders.
Sonia Cheng, Rosewood Hotel Group
Born in 1980, Sonia Cheng grew up inside a Hong Kong dynasty. Her grandfather built the Chow Tai Fook jewelry empire and founded New World Development. Her father runs the family’s real estate and hospitality business.
Sonia went to Harvard, worked at Morgan Stanley, and joined the family business at 28. At the same age, I graduated business school and took a mid-level role at Inspirato. Sonia bought Rosewood in 2011 for $229 million and set out to build the “Four Seasons for millennials,” properties with more character and a stronger sense of place.
Since then, Rosewood has grown from 19 hotels to 33 across 21 countries, with another 27 in the pipeline. The portfolio includes The Carlyle in New York, Hôtel de Crillon in Paris, and Rosewood Mandarina in Mexico.
Alexandre Barrière and Joy Desseigne-Barrière, Barrière Group
Barrière goes back to 1912, when François André opened a luxury resort in Deauville combining hotels, casinos, restaurants, and recreation. The company passed to Diane Barrière in 1990 after her father’s death. A 1995 plane crash critically injured Diane, who remained involved until she died in 2001.
Her children, Alexandre and Joy, are the fourth generation. In 2023, they bought out a 40% outside stake and took full control as co-chairs. Fiscal 2025 revenue hit €1.5 billion across 21 hotels, 33 casinos, and nearly 200 restaurants and bars. Fouquet’s Mykonos opened in 2026.
“They think quarter to quarter. We think generation to generation.”
Alexandre Barrière
Charles, Lydia, and Irene Forte, Rocco Forte Hotels
The Forte family lost its empire, Trusthouse Forte, to a hostile takeover in 1996. Sir Rocco rebuilt from scratch around local ownership and Italian character. His three children now run large parts of the company. Charles, 32, leads development and plans to double the business in five years. Lydia runs food and beverage. Irene leads spa and founded Irene Forte Skincare, made from ingredients grown at the family’s Verdura Resort in Sicily.
Saudi Arabia’s Public Investment Fund took a 49% stake, valuing the group at roughly $741 million. All three siblings worked hotel kitchens and housekeeping as teenagers. That sounds like the internship my dad ran for his kids and grandkids at Outrigger, summers rotating through housekeeping, maintenance, bell, and front desk.
Takeaways
In summary – millennials are stepping into leadership roles at family companies across the hospitality and travel industries.
They are bringing a sense of place, intention, and a vision for designing luxury experiences for a generation that values different things than our parents.
What this new generation of leaders will change remains to be seen, but I’m looking forward to watching as they reshape and redefine luxury travel.
🗝️ Room Report — Naviva, Four Seasons Punta Mita, Mexico
Every travel advisor keeps a bucket list of hotels. These are properties we want to prioritize visiting in the next few years, the ones that make us scroll endlessly through their online galleries and pitch to our clients like evangelists.
Naviva has been at the top of my list since it opened three years ago. I finally made it down here on an impulse, last-minute trip thanks to my angel in laws who agreed to watch my children the day after returning from Alaska, and a husband who has learned it’s best to indulge me in these flights of fancy.
Designed by the architects at Luxury Frontiers , (who also designed Nayara Tented Camp and King’s Pool Camp in Botswana, two of my favorite properties on earth), Naviva stands for “Naturaleza Viva” or “Living Nature.”
Naviva is the adults-only, tented sister property to Four Seasons Resort Punta Mita. It sits on 48 acres and has only 15 tents or “bungalows.” Guests can walk or shuttle over to the main Four Seasons for restaurants, but your all-inclusive rate doesn’t cover meals over there. You do get a room credit if you book through me, your friendly Four Seasons Preferred Advisor. We blew ours by buying overpriced yoga clothes at their boutique since we forgot ours at home.
The tents
These are basically like luxury safari tents. They have canvas roofs, hardwood floors, freestanding tubs, indoor and outdoor showers, a private deck, and a plunge pool that’s kept at a balmy 85 degrees. There are two categories:
Luxury Tent: about 1,259 sq ft of combined indoor and outdoor space
Grand Luxury Tent: 1,604 to 1,722 sq ft, most with better ocean or jungle views and larger outdoor decks
Before you worry, every tent AC.
What’s included in the rate
All-inclusive nightly rates typically run from around $3,500 to $6,000+ per tent, per night depending on season and category. Holiday weeks and Grand Tents can get even pricier, and minimum night stays apply during peak periods.
Naviva runs on an all-inclusive model, and your stay includes:
All meals and premium beverages (top-shelf spirits, curated wine list)
One 90-minute spa journey per guest, per stay
A personal guide assigned to your stay who builds a custom itinerary
Group experiences: guided hikes, snorkel outings, temazcal ceremonies, agave and raicilla tastings, watercolor workshops, yoga, wine tasting, sound baths, Mexican boxing
Naviva guests enjoy access to all of the Four Seasons Punta Mita resort’s restaurants, beaches, pools, and facilities.
Guests receive a USD $130 dining credit per person, per meal at Four Seasons Punta Mita restaurants. This allows guests to enjoy experiences such as breakfast at Dos Catrinas, a poolside lunch at Tamai, beachside dining at Manzanillas, or dinner at Aramara, just to name a few. It’s a wonderful benefit for travelers looking to explore a different ambiance while still enjoying the personalized service and intimacy of Naviva.
Preferred Partners who book through Alpenglow Travel receive a USD $200 resort credit per bungalow. Guests can apply this credit toward airport transfers, private experiences, additional spa treatments, and more.
Additionally, many special events, including the Naviva Unplugged Concert Series, are included in the nightly rate and are exclusively available to Naviva guests.
Not included: additional spa treatments beyond the first, private excursions, and the Naviva Unplugged concert series (capped at 30 guests, ticketed separately).
Food
I am still getting used to the fact that we can order literally anything here. They don’t have menus, they just tell you the special and you can take it or pick anything else you want out of thin air.
They have one all-day restaurant on property, plus in-tent dining at anytime. We had amazing ceviche by the pool. Beach picnics, cliffside dinners, and jungle breakfasts can all be arranged through your guide at no extra cost.
In terms of activities, we are partaking in the yoga, wine tasting, and temezcal ceremony.
This place is magical. It’s like a safari camp except the animal viewing are little wild pigs and some lizards. The beach feels totally private, and the staff are warm without being stuffy.
There’s an advanced purchase offer through November 30th that offers 15% off, and a $200 resort credit if you book through me. Contact me here: www.alpenglowtravel.com
🗝️ The Lobby Bar — Hospitality updates, promotions, and the occasional pun
1. Hoshinoya turned a 1908 prison into a hotel in Nara
Hoshinoya opened inside the old Nara prison this month. It’s a red-brick building from 1908, still recognizably a prison from the outside. Architect Rie Azuma knocked down walls between the original cells to make 48 suites, so the century-old masonry sits behind your bed.
Wallpaper*
2. Fouquet’s finally left France
The Parisian brand behind Hôtel Fouquet’s on the Champs-Élysées just opened on Paraga Beach in Mykonos. Sixty-one suites, three villas, Divercity Architects, and a spa with Dr. Barbara Sturm. It’s their first property outside France.
Wallpaper*
3. Explora Journeys joined Hilton Honors
Announced July 22. Explora is the first luxury ocean cruise line to plug into Hilton’s points program, meaning members can now earn and redeem on sailings.
Lifestyle and Tech
4. LVMH just unveiled a Dinner Yacht concept under the Orient Express brand, another piece of its push to turn luxury into infrastructure rather than just handbags. More on the strategy here: https://www.hotel-online.com/news/lvmh-and-accors-orient-express-sets-its-sights-on-new-tech-billionaire-class
Offers
Goldener Hirsch Deer Valley is offering a third night free for travel through December 13, 2026.
Bishop’s Lodge has a stay longer/stay more promotion on guestrooms, save up to 30% when staying 4 or more nights. Suites offer a 20% savings on select dates.
Four Seasons Naviva Advanced Purchase 15% off through Nov 30th.
Four Seasons Punta Mita:
5th Night Free Promo: Thanksgiving and January - April 2027
4th Night Free Promo: Now through middle of December
SPECIAL DEALS:
Offering 40% off Best Available Rate for 5 of their Beach Homes/Estates and Villas for stays through the month of May. Please click on the hyperlinks for more details on each of these
Casa Tesoro - 7 Bedroom Estate
FOUR SEASONS NEVIS:
Preferred Partner offers and added values:
BRAND NEW Island Breakaway package
4 night stays from $3120 including tax, service & transfers
Oceanside room (after guaranteed upgrade), plus Preferred Partner benefits
4th Night Free open for Thanksgiving & pre-Festive (until December 26th)
With triple Preferred Partner credit
Luxury hotel openings in 2026:
A few of the most-hyped luxury hotel openings in 2026, from restored European palazzos to remote wellness resorts.
Orient Express Venezia (Venice, Italy): A 15th-century palazzo in Cannaregio with 47 rooms, gilded ballrooms, and an arrival by canal.
Corinthia Rome (Rome, Italy): Corinthia’s first Italian property, in a 1914 landmark on Piazza del Parlamento. 60 rooms and a spa built inside the original Bank of Italy vaults.
The Cooper (Charleston, South Carolina): Five-star arrival on Charleston’s harbor, with private yacht charters, a full spa, and an infinity pool over the water.
The Huntington Hotel (San Francisco, California): Ken Fulk restored this Nob Hill icon top to bottom. 143 rooms, the Big Four restaurant is back, and there’s a three-level spa.
Mandarin Oriental, Desaru Coast (Malaysia): 44 suites and villas on 128 rainforest acres along the South China Sea, most with private plunge pools and yoga pavilions.
White Elephant Aspen (Aspen, Colorado): The Nantucket brand’s first mountain resort, opened this summer on Dean Street. 26 rooms and suites, private terraces, art, and Hooch, the restaurant.
Faraway Jackson Hole (Jackson, Wyoming): Faraway went west with its first Rockies property, minutes from the ski lifts.
Danieli, A Four Seasons Hotel (Venice, Italy): The Danieli reopened this summer under Four Seasons after a full restoration. Gothic landmark on the lagoon, original Sala Duca D’Aosta preserved, and a rebuilt rooftop terrace.
Park Hyatt Mexico City (Mexico City, Mexico): Opening in August. 155 rooms in Polanco with Chapultepec views, indoor-outdoor spa, and Park Hyatt’s first Mexico City address.
Aman Beverly Hills (Los Angeles, California): Aman’s Beverly Hills debut lands later this year on the corner of Rodeo and Wilshire. 40 rooms and 42 residences.
Amanvari (Baja California Sur, Mexico): Aman's Mexico debut, opening this summer inside the Costa Palmas community on Baja's East Cape. 18 pavilions and 21 residences on the Sea of Cortez, with the sensory-restrained Aman treatment applied to a desert-meets-water setting.
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Very interesting take on how the next generation of hotels you mentioned will evolve. Plus as always, a breadth of information- your newsletters are always packed with good stuff!
Thank you so much. It was a real pleasure to sit down with you. Our fathers built within this industry side by side, so getting to talk succession, family, and where travel goes next with you meant a great deal. Grateful to be included, and looking forward to reading everything you put out next!