Hello friends,
September feels like the start of the "real" planning season around here: grad trips for next spring's seniors and Europe itineraries for families eyeing next summer. I'm knee-deep in some of these myself right now, so this month's issue offers a peek into what I'm getting requests for.
Cap, Gown, Passport
For high school seniors: the "senior trip" has quietly become a milestone trip in its own right. Think a friend-group adventure to Panama, or a family trip that treats celebrating the diploma as the occasion to visit Spain and Portugal.
For college grads: this is the one true "no responsibilities yet" trip - longer, more independent, and willing to rail-hop through a region rather than stick to one city. A two-week Railbookers train trip, or a Greek Isles cruise before the first day of a new job are wonderful options.
I'm currently building both types of trips: an Alaskan cruise for a client's graduating high school senior, and my own family's grad trip for summer 2028. It's never too early to start, especially for cruises; locking in your rate as early as possible usually saves a lot on price.
Europe, With Kids
Europe with kids works best when you go deep, not wide - one region, unhurried, with room for playground time between the museums. A few cities are simply easier with a stroller or a tired six-year-old in tow: Copenhagen, Berlin, Barcelona, Florence, and Amsterdam consistently top the "easiest family city" lists, thanks to walkability, parks, and food kids actually recognize.
If budget is the hesitation, it shouldn't rule Europe out - Portugal, Spain, and Hungary all stretch a family budget noticeably further than the usual Paris-London-Rome trio, without sacrificing the "we're really in Europe" feeling.
Good rates on Summer 2027 flights and family suites go early - let's start now.
Also a live project on my desk right now: I'm mapping out a first-time Europe itinerary for a family. I'm knee-deep in itinerary research for countries such as England, Scotland, Wales and Portugal. If you're thinking of going with younger kids, here's my rule of thumb: pick one country, maybe two cities, and build in real downtime.
A Sweet Tip
Pack one brand-new small toy or activity per kid. Wrap it and save it for takeoff - the novelty buys you the quietest hour of the whole flight.
ON THE RADAR
Popular for 2027 - This Side of the World
A quick look at where people want to go next year, in case you're not ready to think about long-haul flights yet.
Grenada The beautiful "Spice Isle" is having a moment - nutmeg farms, waterfalls, and quiet beaches for travelers ready to skip the crowded Caribbean stops. Grenada has some amazing hotels and even a few luxury all-inclusive resorts. Fun fact: my beloved grandmother was from this island, so I'm part Grenadian.
Alaska Nearly every major cruise line is adding ships and cruisetours for 2027, pairing glaciers and wildlife at sea with Denali and the Yukon on land. Interested in sailing Alaska? Send me a message. My family went to Alaska last year and it's still our BEST trip to date!
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