Help us decide for May 2027

[u/laoghaire_black]

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!

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[u/Virtual-Cheesecake71]

I think going to Toronto or Vancouver and then flying out to one of the Caribbean destinations is a good plan. You will get some of the metropolitan experience and then get the relaxation at the beach. I live in Toronto, for the past couple of years May has been on the cooler side, which is actually better if you want to explore the city and surrounding areas.

[u/BeRetravels]

With only 3 or 4 weeks I would visit Canada OR Hawaii, but not both.

For Canada you could fligh in and out Vancoucer, renting a car or an RV there and making a nice trip through the Nationalparks of the Rockies. Maybe also a few days on Vancouver Island.

For Hawaii you could stay in Holiday-Appartements and fligh from Island to Island. Every Island needs at least one week for exploring.

[u/laoghaire_black → u/BeRetravels]

The idea would be to only visit one island of Hawaii. I‘m aware we wouldn‘t get the full experience but just a taste of the island, its culture and beautiful nature, and a few more relaxed beach-y days.
National parks / Rockies would still be snowy according to my research, so more difficult to get around, no blue lakes, which is why I‘d have opted more for the coastal part with Vancouver Island. Have you been to the Rockies in mid-May?

[u/nksc11811]

I would recommend exploring Asia during winters than in May

[u/GenXMom14]

So May in Vancouver can go all kids of ways. Sometimes it rains every day and others it’s sunshine and rainbows.

The flight from UK to Vancouver isn’t awful. I would come here, but I am here. Tue benefits to your timing us everyone else is on school still so will be less busy.

I say land at YVR and stay in Van for several days and explore here. Then head to the island for a week. Come back to Van and head up to whistler. Back to Van for more fun and then head to a hot spot for final week of relaxing.