Jamie Stapleton
Based in Bay Area, California
Jamie Stapleton
Ask me about
My Story
I tend to approach travel the same way I approach most things in life: thoughtfully, a little analytically, and with a quiet obsession for making things work better. Before starting Staple Trips, I spent years working in operations and supply chain, where details matter and small decisions can ripple through an entire system. That mindset naturally carried over into travel planning. While many people see a trip as a list of bookings, I see it as a sequence of moments. I don’t consider myself a “creative” in the classic sense of the word, but I bring immense operational creativity into a trip. Quality time is my love language, and I bring that to each and every trip I plan.
Travel Style
My travel style is relaxed on the surface but backed by serious strategy. I love efficient park days at Disney, slow mornings with good coffee, and itineraries that leave space for the unexpected without feeling sloppy.
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Reviews (3)
Patricia S.
4 days ago
We had a trip to California and we had some trouble (and nerves) travelling by plane. Jamie helped us pick the right flights and texted us when things changed. She also recommended tours while in California. Overall we had less stress working with her.
Ashley G.
5 days ago
Jamie helped us with our trip to wine country. We had done most of the planning up front before she stepped in. She recommended some amazing wineries. She also helped smooth our transitions and offered advice for tweaks in our itinerary. I didn't realize what working with a travel advisor meant until I worked with her. I'll be booking with her for trips moving forward!
Doug T.
a month ago
Working with Jamie made our trip much easier than we expected. The biggest help was with the flights and airport logistics. I originally thought I didn’t need wheelchair assistance, but standing for long periods would have been difficult. Jamie encouraged us to arrange it, and it completely saved us. We moved through the airport and customs in Cancun incredibly fast and avoided what would have been a stressful wait.
She also checked us in for our return flight and texted our boarding passes, which meant we could relax and enjoy our final day instead of worrying about airport details. When we landed back in the U.S., she reminded us to complete Mobile Passport Control while we were taxiing. That alone probably saved us at least 30 minutes in the customs line.
The resort she recommended fit us very well. It was smaller, modern, and exactly the kind of place we were looking for. When the hotel initially didn’t provide the level of service included with our club reservation, Jamie stepped in and contacted them directly. After that, the service noticeably improved. It was reassuring to have someone advocating for us while we were traveling.
She also arranged our transfers, which made every arrival and departure smooth and clear. Overall, having Jamie handle the details let us focus on actually enjoying the vacation.
Patricia S.
4 days ago
We had a trip to California and we had some trouble (and nerves) travelling by plane. Jamie helped us pick the right flights and texted us when things changed. She also recommended tours while in California. Overall we had less stress working with her.
Ashley G.
5 days ago
Jamie helped us with our trip to wine country. We had done most of the planning up front before she stepped in. She recommended some amazing wineries. She also helped smooth our transitions and offered advice for tweaks in our itinerary. I didn't realize what working with a travel advisor meant until I worked with her. I'll be booking with her for trips moving forward!
Doug T.
a month ago
Working with Jamie made our trip much easier than we expected. The biggest help was with the flights and airport logistics. I originally thought I didn’t need wheelchair assistance, but standing for long periods would have been difficult. Jamie encouraged us to arrange it, and it completely saved us. We moved through the airport and customs in Cancun incredibly fast and avoided what would have been a stressful wait.
She also checked us in for our return flight and texted our boarding passes, which meant we could relax and enjoy our final day instead of worrying about airport details. When we landed back in the U.S., she reminded us to complete Mobile Passport Control while we were taxiing. That alone probably saved us at least 30 minutes in the customs line.
The resort she recommended fit us very well. It was smaller, modern, and exactly the kind of place we were looking for. When the hotel initially didn’t provide the level of service included with our club reservation, Jamie stepped in and contacted them directly. After that, the service noticeably improved. It was reassuring to have someone advocating for us while we were traveling.
She also arranged our transfers, which made every arrival and departure smooth and clear. Overall, having Jamie handle the details let us focus on actually enjoying the vacation.
Travel photos
