Jessica Osaki
She/Her
Based in California
Speaks English
Jessica Osaki
Ask me about
My Story
A California-based globetrotting lover of food, art, and culture. Passionate about crafting unforgettable journeys. From hidden gems to luxury escapes, let me plan your next dream adventure.
My Travel Style
Some kids grow up playing house. I played airplane and filled my childhood games with exotic and fanciful locations. Not surprising that I have spent much of my career working in global business and taking my off-work hours to bask in the culture of whatever town I find myself in. Over the years, I have traveled to Hong Kong to New Orleans and most recently Grasse, France. Sometimes for work and sometimes with my family. Always curating along the way lists of favorite places to feast, wander, and celebrate what makes each destination special. I am so excited to share what I have learned on my journeys and help you get ready for your own adventure. Pret a voyager!
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My reviews (7)
Kalai T.
a month ago
Jessica is great travel planner! She listened to our needs and wants and came up with some great ideas. Would definitely work with her again!
Jennifer O.
2 months ago
Booking with Jessica was a dream! It truly helps to work with someone who genuinely loves to travel and considers everything; very detail-oriented, she brought up ideas I didn’t consider!
I gave her my preferences and goals for my Japan honeymoon trip and she delivered by giving me a selection of places to choose from. As a result, my husband and I got to stay in a delicious variety of hotels including a spectacular boutique hotel in Kyoto and an Osaka hotel off a major train hub, steps away from famous Dotonbori. We also loved the detailed itinerary, which included all the confirmation numbers and details we booked during our 2.5 week trip. Everything about her was five star, just like the stays we got to enjoy! Thank you so much, Jessica — we look forward to working with her again in the future.
Sarah F.
4 months ago
Each of the options was fantastic, and Jessica did a great job of walking through the advantages and disadvantages of each, coming up with the perfect place for us.
Andrew O.
7 months ago
Jessica was great. We planned a last-minute trip and we were struggling to plan the trip ourselves. We starting planning the vacation with Jessica and she worked with us each step of the way to make our trip planning a breeze. She was able to help us get hotels, hotel transfers and helped us book some tours during our vacation. The vacation was a truly unforgettable experience for us and we would love to have Jessica help plan our next trip.
Christina H.
8 months ago
I cannot recommend Jessica enough for helping us plan our multi-generational family trip to Hong Kong and Taiwan. She was absolutely amazing throughout the entire process, negotiating with hotels on our behalf and ensuring that everything went smoothly. Our family of six had such a seamless experience thanks to her attention to detail and thoughtful planning. The hotels she selected were perfect for our needs — comfort, convenience, fun and luxury all rolled into one. Working with Jessica was a breeze, and I’d happily book another trip with her in the future. She truly made our travel experience memorable!
Kalai T.
a month ago
Jessica is great travel planner! She listened to our needs and wants and came up with some great ideas. Would definitely work with her again!
Jennifer O.
2 months ago
Booking with Jessica was a dream! It truly helps to work with someone who genuinely loves to travel and considers everything; very detail-oriented, she brought up ideas I didn’t consider!
I gave her my preferences and goals for my Japan honeymoon trip and she delivered by giving me a selection of places to choose from. As a result, my husband and I got to stay in a delicious variety of hotels including a spectacular boutique hotel in Kyoto and an Osaka hotel off a major train hub, steps away from famous Dotonbori. We also loved the detailed itinerary, which included all the confirmation numbers and details we booked during our 2.5 week trip. Everything about her was five star, just like the stays we got to enjoy! Thank you so much, Jessica — we look forward to working with her again in the future.
Sarah F.
4 months ago
Each of the options was fantastic, and Jessica did a great job of walking through the advantages and disadvantages of each, coming up with the perfect place for us.
Andrew O.
7 months ago
Jessica was great. We planned a last-minute trip and we were struggling to plan the trip ourselves. We starting planning the vacation with Jessica and she worked with us each step of the way to make our trip planning a breeze. She was able to help us get hotels, hotel transfers and helped us book some tours during our vacation. The vacation was a truly unforgettable experience for us and we would love to have Jessica help plan our next trip.
My travel ideas (1)
All The World’s a Stage - A Theater Kid’s Dream Mother-Daughter Trip to London
Though Shakespeare said all the world’s a stage, he clearly meant that London was the center of it. So, it is impossible to imagine a more perfect stop for a mother-daughter theater vacation, especially when your teen (or tween) is a theater kid. From the vocal arrangements of musical theater to the graceful ballet, there are an endless number of London stages to enjoy. Take a look at these options for a performing arts-focused school break.
All The World’s a Stage - A Theater Kid’s Dream Mother-Daughter Trip to London
Though Shakespeare said all the world’s a stage, he clearly meant that London was the center of it. So, it is impossible to imagine a more perfect stop for a mother-daughter theater vacation, especially when your teen (or tween) is a theater kid. From the vocal arrangements of musical theater to the graceful ballet, there are an endless number of London stages to enjoy. Take a look at these options for a performing arts-focused school break.
All The World’s a Stage - A Theater Kid’s Dream Mother-Daughter Trip to London
Though Shakespeare said all the world’s a stage, he clearly meant that London was the center of it. So, it is impossible to imagine a more perfect stop for a mother-daughter theater vacation, especially when your teen (or tween) is a theater kid. From the vocal arrangements of musical theater to the graceful ballet, there are an endless number of London stages to enjoy. Take a look at these options for a performing arts-focused school break.
All The World’s a Stage - A Theater Kid’s Dream Mother-Daughter Trip to London
Though Shakespeare said all the world’s a stage, he clearly meant that London was the center of it. So, it is impossible to imagine a more perfect stop for a mother-daughter theater vacation, especially when your teen (or tween) is a theater kid. From the vocal arrangements of musical theater to the graceful ballet, there are an endless number of London stages to enjoy. Take a look at these options for a performing arts-focused school break.
My travel photos
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