The Millionaire Vacation Index

The number of centi-millionaires has doubled in recent years, but where do these elite travelers really go when they want to switch off? For the ultra-wealthy, leisure means more than five-star hotels or fine dining; it’s about destinations built around privacy, exclusivity, and ease of access.

Using the Henley & Partners’ Centi-Millionaire Report as our seed list, we analyzed the US destinations where millionaires and centi-millionaires (those worth $100m+) are known to spend their time. We then measured the factors that define luxury travel at this level:

• Private aviation access through Fixed Base Operators (FBOs) and heliports

• Members-only Platinum Clubs of America

• Michelin-recognized restaurants and dining costs

• Five-star spa hotels

From the cultural prestige of New York to the oceanfront glamour of Miami, these are the destinations shaping how America’s wealthiest travellers spend their downtime.

The most exclusive luxury destinations across the US

Every destination in our ranking has one thing in common: it isn’t just luxurious, it’s where America’s millionaires already choose to spend their time. If you’re hunting for an established but low-key cultural capital or a rising enclave of utter indulgence, these cities are the proven playgrounds of the ultra-wealthy.

1. New York City, New York

No city captures the millionaire living on a grander scale than New York. With 11 private aviation operators handling nearly 200,000 flights a year and five heliports, the city is one of the busiest hubs for private jet and helicopter arrivals in the US.

And for good reason, because on the ground, exclusivity runs deep through the Big Apple’s veins. New York has the highest number of Platinum Clubs of America (31) and more than 370 Michelin-recognized restaurants, from intimate omakase counters to timeless French dining. Add in world-class culture, from the Met Opera to private Chelsea gallery viewings, and it’s clear why so many millionaires call New York their second home.

Chief of Staff, Mat Kowalewski, recommends… Wander Bellport Park

A secluded sanctuary in the heart of Bellport, close to New York City, this retreat offers an elevated escape where every detail invites relaxation. Imagine evenings around the glow of a fire pit and conversations lingering under a canopy of stars.

Your stay includes privileged access to both the Tennis Club and Golf Club, perfect for leisurely mornings spent together on the courts or afternoons framed by sweeping fairway views. For a more intimate escape, a private ferry can be arranged to Ho-Hum Beach, where you can stroll barefoot along untouched sands.

2. Los Angeles, California

For millionaires, arriving in Los Angeles often means skipping the traffic and touching down by helicopter. The city has 50 heliports – the highest of any destination in our index – alongside 13 FBOs handling more than 236,000 private flights a year. This is a level of access only available to the ultra-rich.

Once on the ground, indulgence is everywhere. LA boasts 22 Platinum Clubs of America, 169 Michelin-recognized restaurants, and the unique blend of glamour, privacy, and prestige that keeps it at the top of every UHNW jet-setter’s list.

Chief of Staff, Mat Kowalewski, recommends… Wander Bel Air Crest

A hillside haven designed for gathering. With space for up to 10 guests, it combines sweeping views with resort-style amenities that make every moment unforgettable. Spend sun-soaked afternoons by the sparkling pool, then relax together in the hot tub as the city lights begin to glow below. 

Inside, a state-of-the-art game room ensures endless entertainment for all ages, balancing lively group fun with quiet corners for reflection. Blending indoor comfort with outdoor elegance, this Bel Air retreat creates the ultimate setting for families and friends to experience Los Angeles living at its finest.

3. Chicago, Illinois

The Chicago skyline is iconic, but the real story lies in the luxury woven throughout the city. It is home to 13 Platinum Clubs of America, from historic city clubs like the Union League Club of Chicago to refined spaces where you can connect over cocktails and skyline views.

Whatever opulent activities you fill your days with is up to you. Think architectural tours along the Chicago River or evenings at the Lyric Opera enjoyed from the intimacy of a box.

Going for a long weekend can feel effortless, making it an ideal city for a spontaneous escape. Chicago is exceptionally well-connected, with seven private aviation operators handling nearly 20,000 flights per facility.

4. Miami, Florida

Miami is one of the most sought-after destinations for high-net-worth travelers, and these numbers prove it. There are 13 private aviation operators, nearly 18,000 private flights per FBO, and 19 heliports to keep the city connected to the world.

Mornings on your trip might begin with yoga overlooking the Atlantic, afternoons on a dolphin tour, and nights that stretch from rooftop lounges to beach clubs.

There are also 60 Michelin-recognized restaurants throughout the city, averaging $79 per person. Enjoy the theatrical experience of Elcielo, exclusive omakase in Hiden, or addictive Mexican in Los Félix.

Chief of Staff, Mat Kowalewski, recommends… Wander Pinecrest Palms

A South Miami estate that redefines luxury living. Spanning more than 8,000 square feet, this eight-bedroom retreat accommodates up to 10 guests in comfort and style. Designed for seamless indoor-outdoor living, the property centers around a spectacular 75-foot infinity pool with an integrated jacuzzi, a sunken lounge with a fire pit, and a summer kitchen perfect for al fresco dining.

Inside, every detail speaks to elevated living. Smart home technology, a private gym, media room, and spacious den create a balance of entertainment and relaxation. The Dada Italian kitchen, complete with Wolf and SubZero appliances, is a culinary dream. Upstairs, six estate-style bedrooms each feature en-suite bathrooms, with the 1,300-square-foot primary suite offering a spa-inspired bath, expansive walk-in closet with laundry, and wraparound windows framing lush tropical views.

5. San Francisco Bay Area, California

The Bay Area in northern California combines vineyard calm with cosmopolitan energy, making it one of the most desirable destinations for wealthy travellers. And the figures back it up: the region is served by 10 private aviation operators and eight heliports, with almost 200,000 flights a year handled privately.

This connectivity supports a lifestyle built around exclusivity. There are 10 Platinum Clubs of America across the region, alongside 157 Michelin-recognised restaurants, where world-class tasting menus sit within easy reach of Napa and Sonoma’s private wine estates. It’s a millionaire’s retreat that balances business, leisure, and seclusion at every turn.

Chief of Staff, Mat Kowalewski, recommends… Wander San Rafael Retreat

A luxurious coastal escape offering unparalleled ocean views and an idyllic setting for an unforgettable vacation. Wake up to breathtaking sunrises over the expansive ocean from your private balcony, a perfect spot for morning coffee and quiet contemplation. Spend your days lounging by the sparkling outdoor pool, soaking up the sun and the mesmerizing ocean vista.

Evenings offer a tranquil ambiance, ideal for enjoying the sunset's fiery hues before retiring to the comfort of your luxurious accommodations. This retreat seamlessly blends indoor and outdoor living, creating a harmonious space where you can relax, rejuvenate, and create lasting memories.

The best places in the US for private jet and helicopter access

The most luxurious trips begin before you even arrive. It’s about the ease and discretion of the journey itself. Stepping off a private jet, taking a quick helicopter transfer, and slipping into the city without delay.

Miami is the leading destination for private travel. Thirteen private aviation operators handle nearly 18,000 general aviation flights per facility, while 19 heliports allow high-net-worth passengers to arrive and move around the city discreetly. Together, this infrastructure underlines the city’s reputation as a perfect coastal escape for the ultra-rich.

San Diego’s 10 private aviation operators and 10 heliports handle more flights per facility than anywhere else in the top three, so arriving on the coast feels seamless. Such high usage of these exclusive facilities highlights the city’s growing appeal to wealthy travelers.

Chicago has seven operators and 13 heliports, with nearly 20,000 flights per FBO, making it easy to slip away for a weekend of true indulgence and extravagance on the shores of Lake Michigan.

Methodology

We used Henley & Partners’ Centi-Millionaire Report to create a seed list of US destinations with lots of high-net-worth individuals. This report also reveals that the number of centi-millionaires has doubled in the last two decades, rising by 12 per cent.

For each destination, we collected the following data:

Private aviation access

The number of Fixed Base Operators (FBOs) was sourced from Aviation Week Network. We included all airports officially serving each metropolitan area that host one or more Fixed Base FBOs. Only airports with active FBO facilities used by private aviation operators were counted.

Private aviation volume

The number of general aviation itinerant operations at each FBO in the area, sourced from the U.S. Department of Transportation Federal Aviation Administration. 

Helipad availability

The number of public helipads, sourced from Aviation Week Network. For this factor, just helipads listed as being specifically in the city itself were counted.

Members-only clubs

The number of establishments listed on Platinum Clubs of America. For this factor, establishments within the wider metro area that would serve each city were counted.

Michelin restaurants

The number of Michelin-recommended restaurants. Note that Michelin doesn't cover some US cities, such as Boston, Las Vegas, and Seattle.

Average Michelin dining cost

For each restaurant in the previous factor, Michelin lists a price estimate. Using this, we converted each symbol to the following numeric values:

• $ - $25

• $$ - $50  

• $$$ - $75  

• $$$$ - $125

This allowed us to assign an estimated cost to each restaurant and calculate an estimated average fine-dining cost per destination.

Luxury spa hotels

The number of five-star hotels with spas listed on Tripadvisor.

Note: The total figures for both cities were taken for Palm Beach & West Palm Beach and Greenwich & Darien. For the San Francisco Bay Area, if data wasn't available for the area as a whole, totals were taken for San Francisco, Oakland, and San Jose.