Schuyler Bailey
She/Her
Based in Boulder, CO
English
Trips starting at $500/night
The Masthead
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Our Story
The Masthead was built on a simple premise: travel deserves an editor. Before founding this collective, I was an editor-in-chief of a lifestyle magazine—deciding what was worth readers' attention, what wasn't, and why it mattered. I bring that same ruthless curation to every trip we plan. We don't overwhelm you with options. We edit them down to the ones worth taking.
Travel Style
I'm a former food editor, which means every itinerary starts with where we're eating. Destinations are chosen, hotels are vetted, and tables are reserved—all before the flight is booked. Traveling with three kids has made me a smarter planner: I know how to build in breathing room, find the off-the-beaten-path gem that still works for a ten-year-old, and balance the luxe with the livable. The research is deep. The schedule is not.
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Reviews (17)
Caleb Z.
travel to Denver
5 months ago
Schuyler was such a treat to work with. She was in touch with us, helpful about thinking how we might approach the trip, patient as we made decisions and kind throughout.
Catherine W.
travel to Orlando
5 months ago
Schuyler was easy to work with. Made planning seamless, and we had a great time at Disney.
Marjorie B.
travel to Barcelona
7 months ago
Great advice, super smooth experience and appreciated the perks as well
Thomas H.
travel to Barcelona
8 months ago
Jennifer Q.
travel to Barcelona
8 months ago
Great experience and helpful to have map of restaurants around the hotel though the one restaurant we went to was fun and unique but the food was not great and definitely not for teenagers. A little miss but still an adventure. We loved all the tours we booked however and enjoyed seeing Barcelona.
Caleb Z.
travel to Denver
5 months ago
Schuyler was such a treat to work with. She was in touch with us, helpful about thinking how we might approach the trip, patient as we made decisions and kind throughout.
Catherine W.
travel to Orlando
5 months ago
Schuyler was easy to work with. Made planning seamless, and we had a great time at Disney.
Marjorie B.
travel to Barcelona
7 months ago
Great advice, super smooth experience and appreciated the perks as well
Thomas H.
travel to Barcelona
8 months ago
Travel ideas (1)
A Guide to Greek Island Hopping
The Greek islands have captured our fascination for centuries and it's no wonder, they're as diverse as they are beautiful and open a new world at every port. For a once-in-a-lifetime itinerary, the Cyclades offer both famed destinations (Mykonos, and Santorini) and lesser-known gems. And while you could spend days (or weeks) at each of these isles, you can get a good taste with a well-planned 7- to 10-day itinerary.
A Guide to Greek Island Hopping
The Greek islands have captured our fascination for centuries and it's no wonder, they're as diverse as they are beautiful and open a new world at every port. For a once-in-a-lifetime itinerary, the Cyclades offer both famed destinations (Mykonos, and Santorini) and lesser-known gems. And while you could spend days (or weeks) at each of these isles, you can get a good taste with a well-planned 7- to 10-day itinerary.
A Guide to Greek Island Hopping
The Greek islands have captured our fascination for centuries and it's no wonder, they're as diverse as they are beautiful and open a new world at every port. For a once-in-a-lifetime itinerary, the Cyclades offer both famed destinations (Mykonos, and Santorini) and lesser-known gems. And while you could spend days (or weeks) at each of these isles, you can get a good taste with a well-planned 7- to 10-day itinerary.
A Guide to Greek Island Hopping
The Greek islands have captured our fascination for centuries and it's no wonder, they're as diverse as they are beautiful and open a new world at every port. For a once-in-a-lifetime itinerary, the Cyclades offer both famed destinations (Mykonos, and Santorini) and lesser-known gems. And while you could spend days (or weeks) at each of these isles, you can get a good taste with a well-planned 7- to 10-day itinerary.
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