
I am passport-ready!
I’m young and well-traveled, having studied abroad during college and visited Europe a few times over!
But oh, there are so many more places we could go! There is nothing more provocative than exploring together, whether it be hiking in a national park or lounging in our suits by the beach. I love accompanying you, whether it includes getting away from the stress of everyday life or being your little secret on your business trip.
A 100% deposit for my transportation/hotel fees & lodging plus a 20% deposit of my patronage is due at time of booking.
If you are interested in me being your travel companion, please email me at hello@hailey-madison.com with the details.
My transportation (business or first class roundtrip flight/train) and hotel (4-or-5-star hotel) costs are covered by you, booked by me. If it is an overnight or multi-day trip, I allow you to book our lodging.
Please take note the of following requirements for me to travel to you:
Four (4) hour minimum for dates along the East Coast, USA. Travel by train available for the Northeast
Six (6) hour minimum for dates within the rest of the contiguous USA
Twenty-four (24) hour minimum for international dates. I am passport-ready!
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I’m the perfect petite & discreet travel companion you can take anywhere 😇
Planning is key! Very rarely am I happy hiding out in a hotel—let’s go to the spa, the pool, museums, shopping, lunch, dinner, a show, the strip club…Privacy concerns? We can talk about it ✨
I do ask for at least 2 hours of personal time per day for pampering myself and catching up with my obligations outside of Hailey
I also must sleep 8 hours per night in order to function properly — you don’t want me to be snoozing at the brunch table!
First or business class travel is essential since my legs are legitimately too long to fit comfortably in coach…believe me. It’s a hard life ;)
Help fill my new passport with stamps?
My Top Picks for International Wanderlust
Malta is pure magic. We’ll start with lazy afternoons at the iconic Blue Lagoon, the turquoise water so clear it’s almost unreal. Then, off we go to explore the historic, honey-colored streets of Valletta and Mdina—every corner of these ancient cities feels like stepping into a fairytale. Picture us sipping wine in a charming piazza, the warm Mediterranean sun kissing our skin, before slipping away for a romantic dinner overlooking the sea. Malta has this enchanting old-world charm that makes it feel like our own secret escape.
Oh, Singapore… it’s where luxury meets that vibrant city buzz. We’d kick off our day with a swim at the iconic Marina Bay Sands infinity pool, high above the city, and then lose ourselves in the chic streets of Orchard Road for a little designer shopping spree. By night, it’s all about rooftop cocktails with the skyline glittering below, or maybe dinner at one of the world’s best restaurants. For the ultimate pampering experience? A stay at Raffles Hotel for its legendary service and timeless luxury. I can already picture us, darling, sipping Singapore Slings under the swaying palm trees of the courtyard.
Imagine sailing along Croatia’s sparkling coastline, basking in the sun on our own private yacht, the islands of Hvar and Korčula as our perfect playground. We’d dive into the crystal-clear waters of the Adriatic, then wander through the charming medieval streets of Dubrovnik, hand in hand, exploring the ancient city walls. Picture us toasting champagne at a beachside bar, soaking in the Mediterranean breeze, and then slipping into the night to dance beneath the stars. Croatia brings together that blissful mix of adventure and glam, all while feeling impossibly intimate.
Let’s wake up in a cozy, luxurious lodge surrounded by the rugged beauty of the Canadian Rockies. Banff offers stunning alpine scenery, and we could stay at the famous Fairmont Chateau Lake Louise, where the view from our suite would be nothing short of breathtaking. From private guided hikes through lush forests and serene lakes, to relaxing in the Banff Upper Hot Springs, we’ll reconnect with nature while indulging in the finest mountain hospitality. In the winter, we can ski or snowboard down world-class slopes (I’ll need to sign up for some lessons!), then end the day with a private fireside dinner, sipping on wine as snow falls around us.
Have you ever thought of exploring the mystical Kingdom of Bhutan? Starting with a hike through misty mountains to ancient monasteries like the iconic Tiger’s Nest, we’ll stay at luxurious, eco-conscious lodges like Amankora or COMO Uma Paro, where we can unwind with Bhutanese-inspired spa treatments. Exploring local villages, attending traditional Buddhist ceremonies, and soaking in the peaceful energy of the Himalayas would make this a spiritual and unforgettable journey.
Imagine us staying in a luxurious private villa at Trisara or Sri Panwa, both offering jaw-dropping ocean views and personalized service to spoil us senseless. We can indulge in Michelin-starred meals at PRU, unwind with decadent spa treatments at Banyan Tree Spa, or explore the vibrant culture of Old Phuket Town—its boutique shops and Sino-Portuguese architecture are a feast for the eyes. And for a little thrill, let’s take a sunset cruise through Phang Nga Bay or hit the water sports at Kata Beach. Sound perfect?
Monaco has glam written all over it! I see us soaking in the Mediterranean views at Thermes Marins Monte-Carlo, enjoying the opulence of the Prince's Palace, and getting lost in the rich history at the iconic Casino de Monte-Carlo. A stop here wouldn’t be complete without savoring high-end dining and champagne. Total elegance.
Vienna is all about grandeur, and I’m ready to dive in! Let’s kick off with a slice of the legendary Sachertorte at Hotel Sacher. The Vienna State Opera and an exclusive Schönbrunn Palace tour would satisfy my love for culture and history. And since I’m a sucker for gourmet plant-based cuisine, we can’t skip dining at Tian—it’s Michelin-starred and purely focused on plant-based creations!
For a cultural escape wrapped in luxury, Taipei is calling. Starting at the Mandarin Oriental with its insane city views, we can explore Jiufen’s quaint streets, dive into local flavors, and melt into Beitou’s hot springs. If we feel like an extra adventure, I’m all in for a trip to Sun Moon Lake for those breathtaking sunset views.
White sandy beaches, clear turquoise waters… Seychelles is the ultimate tropical paradise! Snorkeling at Anse Lazio or Sainte Anne Marine National Park is a dream, and I definitely need to see those giant Aldabra tortoises. We can hop between Praslin and La Digue islands and unwind in overwater bungalows—imagine waking up to the most magical ocean views.
St. Barts = beachy luxury! Between snorkeling, lounging on Shell Beach, and exploring the vibrant shopping and nightlife in Gustavia, it’s the perfect mix of relaxation and fun. I can already feel the island vibe taking over.
Central Europe has always fascinated me, and Budapest is right at the top of my list. Gellért Thermal Baths, with its private cabins and stunning Art Nouveau architecture, is my dream spot to unwind. Exploring Buda Castle and the Hungarian Parliament is a must, and we’ll be dining at Salt—a Michelin-starred spot that serves a 15-course tasting menu with vegan options (obsessed with the idea already)!
Volcanic landscapes, lush tea fields, and upscale resorts like the Lotte and Shilla make Jeju-do an island I’d love to explore with you. Between indulging in a traditional jjimjilbang, checking out the quirky Jeju Loveland, and visiting famous cafés, our time on Jeju will be as unique as it is luxurious.
There’s something magical about Finland, and I’m dying to find out what makes it the happiest place on Earth. With stunning architecture like Temppeliaukio Church and the serene Löyly Sauna by the Baltic Sea (Fun fact! There are as many as one sauna for every two of Finland’s 5.5 million residents), this trip would be all about relaxation. And we simply have to dine at Michelin-starred Grön—a total Nordic culinary experience. We can take a leisurely stroll through the streets of the Design District to round out our visit, shopping for elegant Finnish designs and souvenirs.
Buenos Aires is rich in culture, and I’d love to explore it in style. Starting with a stay at the Palacio Duhau – Park Hyatt in the chic Recoleta neighborhood, we’ll take private tango lessons and immerse ourselves in the vibrant art and fashion scene. Rojo Tango and the fashionable boutiques of Palermo are definitely on our itinerary.
A full adventure through Japan sounds perfect. In Tokyo, we’ll stay at Aman Tokyo, shop the luxury boutiques of Ginza, and indulge in Michelin-starred kaiseki at Ryugin and Daigo. Nights will be filled with drinks in Golden Gai and some flirty karaoke. Private rooms adorned with neon lights offer the perfect setting to get loose with each other and sip on premium sake and champagne. May I suggest booking room 601 at the Shibuya branch of Karaoke Kan? (It’s where the famous karaoke scene from Sofia Coppola’s movie ‘Lost in Translation’ was filmed!) In Kyoto, we can explore the stunning Fushimi Inari Shrine and stay at The Aman or Ritz-Carlton, savoring traditional kaiseki cuisine at Kikunoi. Let’s not forget a cheeky night at a love hotel for that unforgettable Tokyo twist.
The Maldives is paradise on Earth. Picture us staying in an overwater villa, dining underwater at Ithaa, and lounging on pristine beaches. Snorkeling with vibrant marine life will cap off a perfect day of sun, sea, and each other.
The iconic lavender fields and vineyards of Provence are calling! I’m dreaming of a luxurious retreat, where we’ll stay in boutique hotels, indulge at Michelin-starred restaurants, and soak up the culture among postcard-perfect landscapes. Plus, this region is home to my favorite rosé, Whispering Angel—perfect for a toast to our escape!
Wanna pay homage to my Italian roots with me? Imagine sipping wine on the shores of Lake Como! Staying at Grand Hotel Tremezzo, we’ll explore Bellagio’s charming streets, take in Villa Serbelloni’s gardens, and dine at Michelin-starred restaurants overlooking the lake. I can’t wait to experience the timeless beauty of Lake Como with you.
Let’s escape to Queenstown, New Zealand, where the dramatic Southern Alps and the crystal-clear waters of Lake Wakatipu set the stage for an unforgettable getaway. We’ll stay at breathtaking spots like Matakauri Lodge or Eichardt's Private Hotel, where the views of the Remarkables mountain range will leave us in awe. How about a heli-wine tour to the famous Central Otago vineyards? We can top it off with a private soak at the Onsen Hot Pools, and later, soar over Milford Sound on a private helicopter tour. Dining at spots like Rātā and Amisfield will make our adventure an incredible blend of nature and elegance.
Imagine this: we’re in Bora Bora, lounging in an overwater bungalow, surrounded by crystal-clear turquoise waters. Our luxurious escape at the Four Seasons begins with relaxation in a private villa, followed by a gourmet dinner at Arii Moana, and Polynesian-inspired spa treatments that leave us feeling rejuvenated. We’ll snorkel in the Bora Bora Lagoonarium and end the day with a sunset cruise around Mount Otemanu—champagne in hand, of course.
In Amsterdam, history and modern luxury blend beautifully. Picture us on a private canal cruise, gliding past the city’s iconic Dutch architecture. Then, we’ll visit the Rijksmuseum to admire masterpieces by Rembrandt and Vermeer. Later, we’ll indulge in a Michelin-starred dinner at Spectrum before retreating to the charming Pulitzer Amsterdam, a hotel that’s as cozy as it is grand. And who could resist a cheeky visit to the Red-Light District while we’re there? 😉
From pristine beaches to volcanic craters, Maui is pure magic. Let’s rent a convertible and cruise the Road to Hana, taking in the breathtaking scenery along the way. Snorkeling in Molokini Crater and witnessing the sunrise from the summit of Haleakalā will make our time here nothing short of unforgettable.
Nestled by the Julian Alps, Lake Bled is a serene paradise. We’ll stay at the elegant Grand Hotel Toplice or Adora Luxury Hotel, both offering stunning views of the emerald lake. A private boat ride to Bled Island, Michelin-star dining at Hiša Linhart, and a round of golf at Royal Bled will make this a truly lavish escape. And let’s not forget exploring the enchanting Bled Castle for some fairytale charm.
A safari in the Serengeti sounds like the ultimate adventure. We’ll stay in luxury tented camps, timing our visit to catch the Great Migration in all its glory. A hot air balloon safari over the vast African plains will give us a breathtaking view of the wildlife, making this an unforgettable experience.
I’ve been to Lisbon a few times, but the Azores have always been on my list. We’ll start in São Miguel, staying at the lush Furnas Lake Villas with private thermal springs. Terra Nostra Garden’s legendary hot springs will seduce us with their beauty. We’ll visit the azure waters of Sete Cidades and the majestic Islet of Vila Franca do Campo, before savoring modern Azorean flavors at Restaurant Anfiteatro and À TERRA. It’s going to be magical!
Santorini's white-washed architecture and sapphire waters make it a dream romantic destination. Exploring Oia and Fira, savoring Greek cuisine, and lounging on those famous black sand beaches will make for the most picturesque escape.
The Amalfi Coast’s dramatic cliffs, colorful villages, and world-class cuisine are calling. We’ll stay in charming boutique hotels, enjoy exquisite meals with panoramic views of the Tyrrhenian Sea, and wander through the scenic streets of Positano. A visit to the historic town of Ravello will add a touch of timeless elegance to our escape.
Feel free to whisk me away on any of these dream escapes—because what’s better than exploring the world with the one you adore? ✨