Dione Bailey
She/HerBased in California and Singapore
English
Destinations by Bailey
Ask us about
Our Story
I plan trips for people who want to stop thinking about logistics and start living the experience—wherever in the world that takes them. Based between Singapore and California, I work with curiosity, intention, and nothing left to chance.
Travel Style
For me, travel has never been about checking boxes—it’s about the moments that stay with you long after you’re home. I’ve lived on three continents, traveled to 46 countries, and learned that the destination is just the beginning—it’s the details that make it unforgettable.
I’ve planned for every kind of traveler and every kind of trip. Whatever the occasion, whatever the group, whatever the destination—the standard never changes.
My job is to take everything off your plate, so all you have to do is show up and enjoy. Clients tell me I take the anxiety out of travel and replace it with anticipation. That’s exactly what I aim for.
Reviews (8)
Joseph L.
2 days ago
Joseph L.
2 days ago
Thomas B.
about 1 month ago
A truly first class experience! We will definitely use Dione’s services in the future.
Laura F.
3 months ago
Exceptional service from start to finish! Dione handled every detail with professionalism, quick communication, and thoughtful planning. The trip was seamless and stress-free thanks to her expertise and the Fora App. Dione listened to exactly what we wanted, offered amazing suggestions, and made the entire process easy and fun even when we continued to make changes to our dates and destinations. She was available all the time to listen to our preferences and made great suggestions. Every detail was taken care of — all we had to do was enjoy the trip. Planning was smooth, stress levels were zero, and the trip to the Florida Keys was absolutely incredible. Great communication, awesome recommendations, and everything went off without a hitch. Cannot wait to plan my next adventure with her! Truly above and beyond service! I highly recommend her to anyone looking for a well-organized and enjoyable travel experience.
Charles R.
3 months ago
All very positive! I'm MOST pleased and grateful for Dione Bailey's excellent and timely and thorough and professional communications and service.
Joseph L.
2 days ago
Joseph L.
2 days ago
Thomas B.
about 1 month ago
A truly first class experience! We will definitely use Dione’s services in the future.
Laura F.
3 months ago
Exceptional service from start to finish! Dione handled every detail with professionalism, quick communication, and thoughtful planning. The trip was seamless and stress-free thanks to her expertise and the Fora App. Dione listened to exactly what we wanted, offered amazing suggestions, and made the entire process easy and fun even when we continued to make changes to our dates and destinations. She was available all the time to listen to our preferences and made great suggestions. Every detail was taken care of — all we had to do was enjoy the trip. Planning was smooth, stress levels were zero, and the trip to the Florida Keys was absolutely incredible. Great communication, awesome recommendations, and everything went off without a hitch. Cannot wait to plan my next adventure with her! Truly above and beyond service! I highly recommend her to anyone looking for a well-organized and enjoyable travel experience.
Travel ideas (6)

Raffles: Where Bali Breathes Slowly
Raffles Bali is the kind of property that reminds you why you fell in love with travel in the first place. Perched above the gentle curve of Jimbaran Bay, spread across 23 hectares of untouched hillside, and comprising just 32 private villas, it manages something genuinely rare: the grandeur of a world-class resort matched by hospitality that feels personal, unhurried, and completely sincere. This isn’t a property that simply meets expectations—it consistently anticipates them. For clients who want Bali at its most refined without sacrificing soul, this is where I would send them first, every time.

Raffles: Where Bali Breathes Slowly
Raffles Bali is the kind of property that reminds you why you fell in love with travel in the first place. Perched above the gentle curve of Jimbaran Bay, spread across 23 hectares of untouched hillside, and comprising just 32 private villas, it manages something genuinely rare: the grandeur of a world-class resort matched by hospitality that feels personal, unhurried, and completely sincere. This isn’t a property that simply meets expectations—it consistently anticipates them. For clients who want Bali at its most refined without sacrificing soul, this is where I would send them first, every time.

Slovenia's Open Secret: 4 Days That Ruin You for Everywhere Else
Slovenia captured my heart with its intimate scale and outsized beauty—a country where you can have breakfast beside alpine lakes, lunch in vineyard-draped hills, and dinner in a medieval castle, all within a few hours' drive. This itinerary follows a carefully choreographed progression from the otherworldly turquoise waters of the Soča Valley through the fairytale setting of Lake Bled to Ljubljana's living-room warmth and finally to the sun-drenched wine country that rivals Tuscany. It's a destination that rewards those who look beyond the postcard views to discover a culinary scene punching far above its weight, where Michelin-starred chefs work with ingredients foraged that morning and winemakers pour their stories along with their wines.

Slovenia's Open Secret: 4 Days That Ruin You for Everywhere Else
Slovenia captured my heart with its intimate scale and outsized beauty—a country where you can have breakfast beside alpine lakes, lunch in vineyard-draped hills, and dinner in a medieval castle, all within a few hours' drive. This itinerary follows a carefully choreographed progression from the otherworldly turquoise waters of the Soča Valley through the fairytale setting of Lake Bled to Ljubljana's living-room warmth and finally to the sun-drenched wine country that rivals Tuscany. It's a destination that rewards those who look beyond the postcard views to discover a culinary scene punching far above its weight, where Michelin-starred chefs work with ingredients foraged that morning and winemakers pour their stories along with their wines.

A Journey Through Jordan & Israel: From Rose-Red Petra to the Lowest Point on Earth
Having lived in Tel Aviv for several incredible years, I was fortunate to have the natural wonders of Jordan and Israel just a drive away. This itinerary captures a very special trip that my husband, in-laws, and I took, connecting some of the region's most iconic and contrasting landscapes: the awe-inspiring, hand-carved history of Petra, the vast, cinematic desert wilderness of Wadi Rum, and the otherworldly experience of the Dead Sea—the lowest point on Earth. The journey created a profound travel experience that offered historical immersion, deep connection to nature, and moments of pure wonder.

A Journey Through Jordan & Israel: From Rose-Red Petra to the Lowest Point on Earth
Having lived in Tel Aviv for several incredible years, I was fortunate to have the natural wonders of Jordan and Israel just a drive away. This itinerary captures a very special trip that my husband, in-laws, and I took, connecting some of the region's most iconic and contrasting landscapes: the awe-inspiring, hand-carved history of Petra, the vast, cinematic desert wilderness of Wadi Rum, and the otherworldly experience of the Dead Sea—the lowest point on Earth. The journey created a profound travel experience that offered historical immersion, deep connection to nature, and moments of pure wonder.

Discovering Riga: A City of History and Heart
Riga, Latvia’s capital on the Baltic Sea at the mouth of the River Daugava, is a cultural hub where history and modernity coexist. As my mother’s birthplace, walking its cobblestone streets makes me feel deeply connected to my family’s past. The city is renowned for its wooden buildings, Art Nouveau architecture, and medieval Old Town. Affordable and welcoming, Riga offers surprises like hidden courtyards, local treats like pīrāgi, and fascinating stories behind its grand facades.

Discovering Riga: A City of History and Heart
Riga, Latvia’s capital on the Baltic Sea at the mouth of the River Daugava, is a cultural hub where history and modernity coexist. As my mother’s birthplace, walking its cobblestone streets makes me feel deeply connected to my family’s past. The city is renowned for its wooden buildings, Art Nouveau architecture, and medieval Old Town. Affordable and welcoming, Riga offers surprises like hidden courtyards, local treats like pīrāgi, and fascinating stories behind its grand facades.

Savoring Healdsburg: A Food & Wine Lover’s Guide to Sonoma’s Heart
I had a second home in Healdsburg for over five years, using it as my weekend escape from city life. Over that time, I hosted countless friends and family, exploring every corner of the town and far beyond. My favorite part was being able to stroll to the square for a wine tasting followed by dinner at one of the many available options. I’ve sipped and swirled my way through Healdsburg’s many festivals, but two stand out: Pigs & Pinot in March—hosted by Charlie Palmer at Hotel Healdsburg—and Pinot on the River, a celebration of my favorite grape. If you can’t tell, I’m a pinot noir devotee.

Savoring Healdsburg: A Food & Wine Lover’s Guide to Sonoma’s Heart
I had a second home in Healdsburg for over five years, using it as my weekend escape from city life. Over that time, I hosted countless friends and family, exploring every corner of the town and far beyond. My favorite part was being able to stroll to the square for a wine tasting followed by dinner at one of the many available options. I’ve sipped and swirled my way through Healdsburg’s many festivals, but two stand out: Pigs & Pinot in March—hosted by Charlie Palmer at Hotel Healdsburg—and Pinot on the River, a celebration of my favorite grape. If you can’t tell, I’m a pinot noir devotee.

Penang Perfected: Culture, Cuisine & Charm
Penang is a vibrant blend of cultures, flavors, and history that comes alive on every street corner. From its UNESCO-listed George Town, bursting with colorful shophouses and street art, to its legendary food scene where Chinese, Malay, and Indian influences collide, the island is a feast for the senses. I love the way the pace slows just enough to savor an afternoon tea in a grand hotel, followed by evenings filled with rich flavors and local charm. Penang offers that rare combination of world-class dining, fascinating heritage, and warm hospitality.

Penang Perfected: Culture, Cuisine & Charm
Penang is a vibrant blend of cultures, flavors, and history that comes alive on every street corner. From its UNESCO-listed George Town, bursting with colorful shophouses and street art, to its legendary food scene where Chinese, Malay, and Indian influences collide, the island is a feast for the senses. I love the way the pace slows just enough to savor an afternoon tea in a grand hotel, followed by evenings filled with rich flavors and local charm. Penang offers that rare combination of world-class dining, fascinating heritage, and warm hospitality.

Raffles: Where Bali Breathes Slowly
Raffles Bali is the kind of property that reminds you why you fell in love with travel in the first place. Perched above the gentle curve of Jimbaran Bay, spread across 23 hectares of untouched hillside, and comprising just 32 private villas, it manages something genuinely rare: the grandeur of a world-class resort matched by hospitality that feels personal, unhurried, and completely sincere. This isn’t a property that simply meets expectations—it consistently anticipates them. For clients who want Bali at its most refined without sacrificing soul, this is where I would send them first, every time.

Raffles: Where Bali Breathes Slowly
Raffles Bali is the kind of property that reminds you why you fell in love with travel in the first place. Perched above the gentle curve of Jimbaran Bay, spread across 23 hectares of untouched hillside, and comprising just 32 private villas, it manages something genuinely rare: the grandeur of a world-class resort matched by hospitality that feels personal, unhurried, and completely sincere. This isn’t a property that simply meets expectations—it consistently anticipates them. For clients who want Bali at its most refined without sacrificing soul, this is where I would send them first, every time.

Slovenia's Open Secret: 4 Days That Ruin You for Everywhere Else
Slovenia captured my heart with its intimate scale and outsized beauty—a country where you can have breakfast beside alpine lakes, lunch in vineyard-draped hills, and dinner in a medieval castle, all within a few hours' drive. This itinerary follows a carefully choreographed progression from the otherworldly turquoise waters of the Soča Valley through the fairytale setting of Lake Bled to Ljubljana's living-room warmth and finally to the sun-drenched wine country that rivals Tuscany. It's a destination that rewards those who look beyond the postcard views to discover a culinary scene punching far above its weight, where Michelin-starred chefs work with ingredients foraged that morning and winemakers pour their stories along with their wines.

Slovenia's Open Secret: 4 Days That Ruin You for Everywhere Else
Slovenia captured my heart with its intimate scale and outsized beauty—a country where you can have breakfast beside alpine lakes, lunch in vineyard-draped hills, and dinner in a medieval castle, all within a few hours' drive. This itinerary follows a carefully choreographed progression from the otherworldly turquoise waters of the Soča Valley through the fairytale setting of Lake Bled to Ljubljana's living-room warmth and finally to the sun-drenched wine country that rivals Tuscany. It's a destination that rewards those who look beyond the postcard views to discover a culinary scene punching far above its weight, where Michelin-starred chefs work with ingredients foraged that morning and winemakers pour their stories along with their wines.

A Journey Through Jordan & Israel: From Rose-Red Petra to the Lowest Point on Earth
Having lived in Tel Aviv for several incredible years, I was fortunate to have the natural wonders of Jordan and Israel just a drive away. This itinerary captures a very special trip that my husband, in-laws, and I took, connecting some of the region's most iconic and contrasting landscapes: the awe-inspiring, hand-carved history of Petra, the vast, cinematic desert wilderness of Wadi Rum, and the otherworldly experience of the Dead Sea—the lowest point on Earth. The journey created a profound travel experience that offered historical immersion, deep connection to nature, and moments of pure wonder.

A Journey Through Jordan & Israel: From Rose-Red Petra to the Lowest Point on Earth
Having lived in Tel Aviv for several incredible years, I was fortunate to have the natural wonders of Jordan and Israel just a drive away. This itinerary captures a very special trip that my husband, in-laws, and I took, connecting some of the region's most iconic and contrasting landscapes: the awe-inspiring, hand-carved history of Petra, the vast, cinematic desert wilderness of Wadi Rum, and the otherworldly experience of the Dead Sea—the lowest point on Earth. The journey created a profound travel experience that offered historical immersion, deep connection to nature, and moments of pure wonder.
Travel photos





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