Room for the whole day
The room needs to work after bedtime as well as before breakfast. Layout and usable space matter as much as the room category.
The travel edition / Work in progress
Travel, considered.
I’m interested in what makes a trip feel right: the place, the pace, the people, and the small decisions that shape a day. I’ve been using AI to turn those questions into a more thoughtful way to plan.
Start with the index01 / A framework for choosing
Family Value Travel Index.
A framework I’m developing to compare family trips by more than the nightly rate. Space, daily rhythm, enjoyment, and confidence all shape what a vacation is actually worth.
An easy daily rhythm
How naturally do the room, food, pool, beach, and downtime fit together? A good day should not take constant coordination.
Something for everyone
Children having a good time and adults enjoying themselves belong in the same decision.
The full picture of value
Compare the exact room, total cost, travel effort, and the strongest available alternative—not just a headline rate.
Confidence in the choice
Separate what is known from what still needs checking. The quality of the evidence matters alongside the appeal of the place.
The day-five question
Will it still feel good when the novelty wears off? Could this become a place worth returning to?
This work began as the Sigler Vacation Index. The next step separates the character of a place from the price and conditions of a particular booking.
02 / Four travel profiles
Same person. Different trips.
A work trip and a family holiday should not share the same brief. These four profiles help me begin with the right questions, then adjust for the actual trip.
Profile / 01
Personal
An interesting base, neighborhood wandering, good casual food, and room for whatever catches my attention.
Profile / 02
Work
A comfortable room, an easy commute, and places to work or unwind between commitments.
Profile / 03
Couples
Time together, good food, a relaxed pace, and fewer transfers. Leave room to stay somewhere longer.
Profile / 04
Family
Space, simple logistics, and a daily rhythm that gives everyone something to enjoy.
03 / Favorite hotels
Places I’d go back to.
A few of my favorite hotels, from city bases to places where the whole day slows down. A personal collection, in no particular order.
London, England
Bankside Hotel
Bordeaux, France
Les Sources de Caudalie
Slow days, comfortable classic rooms, spa time, and a wine bar made for lingering.
Amelia Island, Florida
The Ritz-Carlton, Amelia Island
Premium comfort, a great beach, and a daily rhythm that made family travel easy.
Key Biscayne, Florida
The Ritz-Carlton Key Biscayne
San Francisco, California
The Jay
Findlay, Ohio
Hancock Hotel
County Kilkenny, Ireland
Mount Juliet Estate
Scottsdale, Arizona
The Phoenician
New York, New York
Virgin Hotels New York City
A large room, a great shower, and two bars I enjoyed working from. An easy New York work-trip base.
Toronto, Canada
Union Hotel
A comfortable, boutique-feeling base in Toronto. I’d pay attention to the room category next time.
04 / Building with AI
Context that travels with you.
The most interesting part is the continuity: a planning conversation can become a useful guide during the trip, then better judgment for the next one.
Before
Start with the people and purpose. Compare a short list, check the details, and make the trade-offs explicit.
During
Bring the plan into the moment: where I am, what comes next, and what fits the time in between. A small trip guide keeps useful options close.
After
Remember what worked and why. Let actual experiences improve the profile instead of starting every trip from scratch.
These are working ideas, built around the way I travel and refined through experience. I’ll share more as they take shape.
Back to the personal edition