Help us decide for May 2027
Hi all,
We‘re a family of three with a young child that will start school in 2027. We‘re based in Western Europe.
Before being bound to school holidays for the foreseeable future, we want to take a 3-4 week trip in May 2027. Unfortunately we only have May available due to other commitments and planned trips - can‘t leave earlier, can‘t return any later than first week of June.
We are torn between a couple of destinations / trips but unsure what to choose for best weather, value for money and a good mix of cities (living in a big city and our kid enjoys the hustle and bustle of cities as much as we do), culture and nature. Ideally with a warmer stop that allows us to relax/swim for a few days.
Currently our top contender is Toronto - Vancouver - Vancouver Island - Hawaii (preferrably Oahu, or else Maui). We feel like it would hit our sweet spot, especially since we‘d be able to visit our friends in Canada whom we really miss. But all my research points to West Coast Canada being better in the summer (so far we‘ve only been to the East Coast) and despite it being shoulder season, Hawaii is quite expensive (we enjoy good hotels and wouldn‘t want to downgrade much). Wondering if it‘s really worth the money, and hoping some if you could share your experience of West Canada and/or Hawaii in May.
Other contenders are
- Japan, maybe combined with Singapur and/or Thailand (we‘ve been before and are also worried about flying east due to the Middle East situation but seems to be ideal weather- and money-wise right now)
- Australia (travel time and cost of flights are a bit off-putting with a 5yo in tow)
- Toronto (to visit our friends) + then fly out to a Caribbean island e.g. Barbados or Turks and Caicos just for the beach vibes, or do a road trip through Costa Rica (honestly this is my second favorite option)
Excited to hear what you think and get some advice on what to do!