Westport, Connecticut
A travel advisor for Westport.
Well travelled, design-conscious, and generally after something with a bit more character than a package.
Westport clients tend to have opinions, which makes them my favourite kind to plan for. The brief is rarely "somewhere warm" — it's usually a specific idea that needs testing against reality, and occasionally talking gently out of.
What Westport clients usually need
Europe, done properly. Italy above all — and usually the version with fewer places and longer stays than the original plan.
Villas and private homes, particularly for summer, which need booking nine to twelve months ahead for anything good.
Character over chain. The small hotel with twelve rooms rather than the resort with four hundred, which requires knowing which small hotels actually deliver.
Family trips that aren't theme parks — though plenty of those too, and no judgement either way.
On Italy, since it comes up most
The itinerary most people arrive with — Rome, Florence, Venice and the Amalfi Coast in ten days — is four travel days and three hotel check-ins, and it's the single most common thing I redesign. Two bases with day trips will show you more and cost less, and you'll unpack once.
Book the constrained things first: the Borghese, the Last Supper, the Uffizi. They sell out months ahead and the rest of the trip should be built around them, not the other way round.
Getting out of Westport
LaGuardia is around an hour without traffic, JFK a little more, and both open up the European nonstops that make a one-flight trip possible. Bradley is roughly an hour and a half and is the easier experience if the schedule works. Westchester is close and worth checking first for domestic routes.
Westport and Greens Farms stations are both on the New Haven Line, which puts the Manhattan cruise terminals within easy reach — and makes a transatlantic crossing a rather civilised way to start a European summer.
School calendars
Westport's February and April breaks concentrate family travel into two fixed weeks, the same as most of the county. If you're tied to them, book early — nine to twelve months is not excessive for those dates. If you have flexibility, moving even one week off-peak changes both the price and the experience considerably.
How we'd work together
Most of my Westport clients and I never meet in person, and that's fine — phone, email and video cover it. If you'd rather sit down somewhere local and talk it through, I'm happy to do that too.
There's no fee either way. I'm paid by the resorts, cruise lines and tour operators, so you pay the same as booking direct.
Tell me where you want to go.
No fee, no obligation. Most first conversations take twenty minutes and end with a couple of ideas worth thinking about.
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