+1 for Majorca - been there many times and it never gets old
Gran Canaria was awesome (and cheap)
The Lake District in England is also spectacular although majority of the climbs are shorter (and often steeper) than those longer steadier ones found in places like the Canaries / Mediterranean islands or the French / Swiss Alps.
Enjoy your trip wherever you select 
Early June is still very much spring. Pick something where you don’t have to pack a thousand ‘maybe’ clothes, and maybe just need a lightweight wind jacket. "just in case’ stuff means over packing and carrying a lot of stuff with you.
I’d recommend some place it’s easy to find food/water as you’re riding. If you get too adventurous, you’re 30mi from a town and out of water. Also pick a place where you know you’ll be exploring and when you’re not exploring. Hiring a guide (guide or kid from a local bike shop) isn’t a bad idea even if the location is pretty approachable. Also, keep in mind that you’re only biking x hours /day, you’re chilling the rest. It’s better to dip your toe into adventuring with a group then it is to go full Laos.
Recommendations… remember you don’t travel to France, you don’t travel to Paris, you travel to a particular part of Paris - you can go to that spot in Paris and never see “France”. I never biked there, but northern Italy based out of Florence. Have someone drive you out (or train) to somewhere everyday and ride back to the hub. You can hit the Cinque Terra, Sienna/"Tuscany, a finger lakes day (keep the main room in Florence and an overnight room at the daytrip for showers), etc. That gives you ocean, hills, weather, flats, and some convenience - more variety is better than less variety. Maybe pick another and you’ve got a full trip.
Ignoring the cycling portion of the question, if its your first time in Europe try and visit Rome and Paris.
Really? Rome is one my all time travel let downs. Been there twice, checked out of my hotel two days early both times. You see the Vatican, the forum,… and pretty quickly you’re looking at yet another church and god statue. The eateries aren’t plentiful, the neighborhoods aren’t fun to explore…there are better places to be. For urban Western Europe - Berlin, Paris, London, Amsterdam, and Barcelona are legit. Rome is up there with Brussels, Frankfurt, and some airport corridors.
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Actually, that would be a GREAT trip… get a Europass, explore the city one day by bike, go for a big ride the next, train ride to the next town, and repeat.
Weather in Ireland. Like the UK, is pretty unpredictable.
One of the reasons I think the wicklow mountains is great for cycling is simply because it’s quiet of cars and people and 10-15km from a capital city! There is even great mountain bike trails all over. Other places in the south of Ireland (dingle/kilarney) may be more interesting as a cycle holiday.
Although I must say when bikepacking across Wales though the most rural paved route I could weave together, I had a similar connection for cycling there too! Scotland, also not far off in terrain, is hooching with midges in the fairer months.
Definately give it a look into!
Yeah I agree the Europass idea sounds great! Only thing I’d be worried about is housing. I was thinking hostels but that wouldn’t be safe with bikes right? Other than that just hotels and Airbnb’s?
Hostel wouldn’t have enough space to unbox your bike and store the case. Airbnb / VRBO here. Sample $74/night with washer/dryer https://www.airbnb.com/rooms/32764347?adults=4&location=Florence%2C%20Italy&check_in=2022-03-27&check_out=2022-04-03&translate_ugc=false&source_impression_id=p3_1634478473_l6PlwyODk81yiUBp&guests=1
I’d skip Tenerife because it looks like Zwift island
+1 for Tenerife
YouTuber PeakTorque has high praise for Greece, I personally haven’t been there, but may be worth checking out. Check his YouTube channel for details.
I’ve been to Greece a few times. Both to the mainland and the many islands. I wouldn’t cycle there.
Slovenia. Check out the Tour of Slovenia. A beautiful cycling country.
Same here. Many roads are terrible, traffic is wild, and there isn’t much of a cycling culture.
Many many Mediterranean countries I‘d prefer to Greece.
I go to Greece regularly for cycling.
Highly recommend the Peloponnese for cycling. Great roads, wonderful terrain, amazing food and people. I’ve never had a sketchy moment with a driver passing too close or doing some asshole maneuver - and I’ve been quite a few times. I’d definitely avoid the big cities and would absolutely recommend you check out the areas around Kalamata.
Whistler.
That time of year, southern Spain or Southern France. Hands down. Great good. Excellent riding. Superb riding.
A few cycling destinations that have been recommended to, but I have never been there:
Most hostels in Europe have bike sheds.
Regarding bike box, you could use a cardboard box, get rid of it at your destination, and geta new one before you fly back.
To be honest, I’d go on youtube and watch where other people are riding, and then go whereever looks good to you. Other than that, you might need to think about what you want out of the trip - experience (road) cycling culture? See something new with some cycling thrown in? Amazing scenery? Somewhere remote, where others don’t go?
Has anyone been to Mallorja / Tenerife in December or over Christmas? I’m considering a 4 day break and would love to hear about experiences and opinions.
Yes I’ve been to Tenerife in December. We went for a 3 week cycling holiday. The first day we went out Teide was closed near the top with snow but it was cleared and open the next day. The locals were all up at the top of teide snowboarding.
Weather was pretty good all 3 weeks.
If you have any questions ask away.
A lot of pros in the off season head to the Costa Blanca in Spain (first time I went it was the Denia area). I’ve only been once but I can see why. I was supposed to go back with my club mates from up north when this wee c thing hit; they are talking about reorganising there (Calpe) or Mallorca; I hope the majority votes for Calpe in the Costa Blanca. I’ve done Mallorca a few times and my memory still prefers the Costa Blanca. In the meantime Tenerife is probably my next destination.
My mates round here tend to go to Oudenarde, Belgium probably as its easy for us to get to, if you like Flandrian stuff its good, but less off season weather reliability. Ive done the Alps once with them too, but it not so easy for us to get too and its also weather dependant but if you are a climber its ace.
Any of the European classics except for France - Accommodation, food and drink are far better quality for the same cost everywhere else.
Pardon?
Food and drinks are better elsewhere than in France? Difficult to argue taste, as it’s so individual, but for me, France is No1 in terms of food and drinks.
My wife and I just spend a few weeks in and around Savoien region, Region Isere, and Haute Provence. Besides having arguably the best climbs in the world, the food was fantastic, all local ingredients and locally sourced wine. 11/10 for me.