My favorite combos:

Holiday
iPhone XS - almost don't need the iPad with this; it's also my main (only) camera these days.
iPad Mini 5 - better than the phone for watching video and for NYT crossword
Kindle Oasis - I like having a non-phone, non-tablet reader. I also like the leather-like cover with battery, although if I were to replace it I'd get the waterproof one (or the new paperwhite which is also waterproof).
Garmin Vivoactive 3 - I use this to track hikes and bike rides, and surprisingly often for contact-less payments. Don't really want an Apple Watch - I'd rather keep all that stuff separate particularly on holiday.
Zen tofu and/or Mogics Bagel adapters. TOFU (also the new Maru and masa combo!!)

Work trip
As above, perhaps adding a Google Pixelbook (Chromebook) or Dell XPS 13.
Pixelbook does everything I need except Quicken and MS Office (android versions work but are hobbled). It's a beautiful (if pricey) device and runs full Linux in a container which works well for much of my work.
The Pixelbook display is way too glossy for my taste so I add a glare-reducing screen: Dell has the finest laptop screen and form factor in any PC I've ever owned, EXCEPT the 'up the nostril' bottom of screen webcam location.

I also like to add webcam covers to the laptops:
The Chromebook / iPad Mini combo really works great for teleconferencing with video plus a separate screen. Thin and light.