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Maybe it's just me, but this sounds so backward. When my toddler was two, we went on our first trip without him. Take the kid to Disney World. He deserves vacations too.
You should definitely do some trips without the kiddo too! But that’s not the OP’s objective here.
You can travel wherever you like with kids. We have been abroad a few times with our kids, now 3.5 and 1. We like booking Airbnbs to have a full kitchen, a washer / dryer, and a dining table but suites can also work. We try to avoid places with stairs or a personal pool due to the lack of child proofing. The hardest part for us is navigating from the airport to the rental car / uber with two travel cribs, two car seats, and the stroller. After that, remember to not plan too much per day and enjoy the things you do choose. We also like to hire babysitters after bedtime or bring the grandparents so we can go out as a couple.
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Any advice on car seats ?
We did our first longer trip with our toddler around 1.5 and did a cruise, which was very simple and easy (didn’t have a suite though, which was a bit tricky). Second trip at 2.5 to the Netherlands and Belgium, which ended up being great - particularly the Netherlands. Things are SO family friendly there! Very accommodating and welcoming to small children, and lots to do. We did the Amsterdam Zoo, Science Center, Maritime Museum, Canal Boat Ride, and Windmill historic town. My daughter loved it, and so did I. So fun to show show her the world and see it through her eyes. This year we did Scotland and London at 3.5, and we are going to Atlantis Bahamas soon.
Biggest piece of advice is limit the # of times you move hotels/locations with all the stuff. That’s the hardest part. When traveling with your partner, you may jump around to lots of different cities, with a new hotel every 2-3 nights. I highly recommend against this with a toddler. Stick to 1-2 locations and at least 3-4 nights in each. Moving hotels is the hardest part.
We did Great Wolf Lodge twice within our twins’ first year, including for their first birthday. They love it and have returned again after their second birthdays. We did a 2br suite and had them in pack n plays separate from us. We conceived our third during that first birthday vacation so fun was had by all.
Nothing wrong with a childless trip when they’re this young, but vacations with them are also fun. We took our then 2.5 year old and 1 year old to a Marriott in Aruba and it was awesome.
Where do you live?
Go to Rose Hall in Jamaica
How’s Jamaica after the hurricane?
Leave him with grandparents
I don’t have any all inclusive recommendations, but echo that you can travel anywhere you want! We’ve traveled a lot with our 2 toddlers starting from birth. We’ve done Europe and several US destinations. Almost every city has kid friendly stuff you can find - children’s museums, aquarium, zoo, playgrounds, etc.
1 or 2 bedroom suite is ideal. You want to be able to put your kid to bed and stay up in another room. Depending where we go an Airbnb is a good option or hotel rooms with balcony/outdoor access we can enjoy in the evenings.
We took our first family vacation when my youngest was 3.5. But some tips that worked well for us was
1) a short trip (3 or 4 nights)
2) a short flight (2.5 hrs)
3) a place we’d been to before (we went to cape cod; which I hadn’t been per se but we had lived in Boston so the area and airport were very familiar)
4) Airbnb so we could cook, spread out a little, there was a small yard to play in; just keep up more of the “home” routine
I believe that winter we took another short trip to Mexico - all stayed in one room with 2 beds; we took one, gave older child the other, made a bed with a small air mattress we brought for the little one. It was fine mostly because there was an enormous bathroom so husband and I went in there after bedtime to watch shows on iPad.
Now the kids are bigger we usually get two connecting rooms but for one small child I’d just get one room especially if there’s a bathroom or balcony you can hang out in after they sleep.
I think the earlier you start traveling with him, the better so he gets more used to it and more comfortable on planes.
My son’s first flight was at 3 months and he’s been with us on almost every vacation since. We leave for DR in a few days and there are several child friendly resorts there, we’ll be at Punta Cana Macao Dreams resort which has a kids club, a kids “water park”, and a lazy river.
You refer to your toddler as “them”? Genuinely curious why is it the case.
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