Olivia Garwood
Based in San Francisco, CA
Olivia Garwood
Ask me about
My Story
From collecting hotel room keys as a kid to shaping travel programs for global brands, I’ve turned a love for beautiful places into a career in hospitality — currently based in San Francisco.
Travel Style
After studying hospitality in Switzerland and at Cornell, my love for hotels and travel only grew stronger. I’ve always found joy in flipping through travel magazines and building vision boards of must-visit places. Over the years, I naturally became the go-to person for planning friends’, couples’ and family trips — it never felt like work, just something I genuinely loved. I’m a firm believer that there’s a time and place for every kind of trip — whether you’re craving adventure, a spa day, a standout restaurant or just a weekend on Do Not Disturb. Now, I’m so excited to help others plan unforgettable getaways, from bachelorette and bachelor parties to solo escapes and everything in between!
Reviews (16)
Olivia S.
travel to New York City
20 days ago
Jeanine V.
travel to Auckland
3 months ago
Olivia is everyone’s dream travel agent. She listens to all your crazy ideas, thoughts, and concerns and works her magic to create a trip that will beyond your expectations. The wonderful trip Olivia planned for my family had the added complexities of finding activities for three generations with varied interests. Olivia was organized, professional, and a huge support before and during our trip. Anyone that has the pleasure to work with her is very lucky!
Sarah S.
travel to Mendoza
4 months ago
There truly aren’t enough words to describe how incredible Olivia is. As someone who works as a Director of Business Development and also plans weddings on the side, I know firsthand how much time, detail, and pressure goes into planning a seamless experience. And honestly—Olivia took all of that off my plate.
Yes, you can use Google or AI to plan a trip, but having someone who genuinely understands travel, enjoys the details, and knows how to bring everything together into a thoughtful, well-executed itinerary is on another level.
Olivia planned both my 40th birthday trip to Argentina and my Park City family trip—and for both, I didn’t have to lift a finger. From coordinating sitters, to dinner reservations, to being available for every question or last-minute need, she handled everything effortlessly.
What stood out the most was how easy she made it for not just me, but for my entire group. My friends had an amazing time, there was zero stress, and everything flowed perfectly. I simply showed up and followed an itinerary that was incredibly well thought out.
There were maybe one or two minor tweaks I made along the way (just personal preference on a couple restaurants), but overall—everything was spot on.
I can honestly say this: Olivia has made me want to travel more, simply because I know I can trust her to take the lead and handle it all.
I’m beyond grateful for her and everything she put into these trips. She is truly exceptional at what she does.
Kim A.
travel to Osaka
8 months ago
Olivia is the best travel advisor I have ever worked with! She listened to and considered all of my requests, suggestions, goals, and needs in planning my trip to Japan, and created the trip I had dreamed of for so many years. Her suggestions for hotels, restaurants, and activities, were spot on. She was timely with all communications and was always available to discuss various details, large or small. Destination Asia did an incredible job helping us with planning the itinerary, with English speaking guides. Olivia and Destination Asia were successful in delivering EXACTLY what I asked for during my 24 days in Japan. It was such a pleasure planning this trip with her as I felt she truly enjoyed arranging and providing the perfect trip for me. I can’t wait to plan my next trip to Paris with her!
Leanne Y.
travel to Hawaii
8 months ago
Olivia was amazing in helping us plan a relaxing, magical honeymoon just weeks before our trip and we are so grateful for all of her help. She was so responsive with this trip on such short notice. We were overwhelmed about how many options of places to stay on the Big Island, but she narrowed it down for us so quickly and took care of the rest. Every property she recommended looked wonderful, and we are so happy with the itinerary she helped us choose. We can't wait to return to Hawaii. Thank you Olivia!
Olivia S.
travel to New York City
20 days ago
Jeanine V.
travel to Auckland
3 months ago
Olivia is everyone’s dream travel agent. She listens to all your crazy ideas, thoughts, and concerns and works her magic to create a trip that will beyond your expectations. The wonderful trip Olivia planned for my family had the added complexities of finding activities for three generations with varied interests. Olivia was organized, professional, and a huge support before and during our trip. Anyone that has the pleasure to work with her is very lucky!
Sarah S.
travel to Mendoza
4 months ago
There truly aren’t enough words to describe how incredible Olivia is. As someone who works as a Director of Business Development and also plans weddings on the side, I know firsthand how much time, detail, and pressure goes into planning a seamless experience. And honestly—Olivia took all of that off my plate.
Yes, you can use Google or AI to plan a trip, but having someone who genuinely understands travel, enjoys the details, and knows how to bring everything together into a thoughtful, well-executed itinerary is on another level.
Olivia planned both my 40th birthday trip to Argentina and my Park City family trip—and for both, I didn’t have to lift a finger. From coordinating sitters, to dinner reservations, to being available for every question or last-minute need, she handled everything effortlessly.
What stood out the most was how easy she made it for not just me, but for my entire group. My friends had an amazing time, there was zero stress, and everything flowed perfectly. I simply showed up and followed an itinerary that was incredibly well thought out.
There were maybe one or two minor tweaks I made along the way (just personal preference on a couple restaurants), but overall—everything was spot on.
I can honestly say this: Olivia has made me want to travel more, simply because I know I can trust her to take the lead and handle it all.
I’m beyond grateful for her and everything she put into these trips. She is truly exceptional at what she does.
Kim A.
travel to Osaka
8 months ago
Olivia is the best travel advisor I have ever worked with! She listened to and considered all of my requests, suggestions, goals, and needs in planning my trip to Japan, and created the trip I had dreamed of for so many years. Her suggestions for hotels, restaurants, and activities, were spot on. She was timely with all communications and was always available to discuss various details, large or small. Destination Asia did an incredible job helping us with planning the itinerary, with English speaking guides. Olivia and Destination Asia were successful in delivering EXACTLY what I asked for during my 24 days in Japan. It was such a pleasure planning this trip with her as I felt she truly enjoyed arranging and providing the perfect trip for me. I can’t wait to plan my next trip to Paris with her!
