Multi-destination once in a lifetime trip - recs please

[FussInBoots]

Apologies if this is in the wrong Topic group, please move if needed.

Looking for recommendations of areas to stay and things to see/do on our once in a lifetime trip, hopefully being planned for Autumn 2027 - which gives us plenty of time to save, save, save!!

2 adults and 3 children (17,14,9 by this time)

1. OH wants to do New York - so was thinking 2-3 days
2. We all want Disney World Florida, so was thinking 7 days
3. We want to round off the trip with a 7 night all inclusive in either Mexico or the Caribbean.

With travel we're expecting to be out of the UK for around 3 weeks.

Has anyone done a similar multi-destination trip and have any hints, tips and tricks for the trip?

Is there somewhere you would/wouldn't travel to again?

Is there a middle stop somewhere between the above 3 I'm missing that we could swing by and do as well?

I've reached out to a travel agent, and they've already said we would need to book with a specialist company from October and a very rough cost per person.

Look forward to hearing any advice or experiences you've had

Thanks ☺️

I would consider dropping the 1 week all inclusive at the end (just personal preference) and replacing it with a one week transatlantic crossing from Southampton to New York (never done it - just on my list).

Unless your DC are Disney fanatics I would steer you toward Universal Studios instead and all that Harry Potter business. If you're at the end of Aug then you should be in time for the first Halloween Nights. They're really big at USO. If you have the budget (big!) then try to get one of the three USO hotels that offer all day skip the line privileges. Just do a one day side trip to WDW. You can Uber it in 30 mins from USO.

I'd add a one day trip to Discovery Cove if you want to swim with dolphins.

Bone up on all the YT videos to learn all the latest news about skip the line and attraction closures.

Universal Halloween horror nights is not recommended for children as it’s horror oriented.

i would consider 3 or 4 days in NY before flying into Orlando. You also have the new Universal Epic park too.

My personal view is that it’s too many things and you’re not getting best use of your time.

I disagree with PP about doing Universal only. Disney world is 4 massive parks, very little of which is exclusively for young kids or princess themed.

personally I’d do a few days NYC, 11 days Orlando - 2 days per Disney park and then one day each of the 3 universal parks.

you could also expand your time in Orlando and have some water park days or finish with 4 days on the Florida coast enjoying beaches, or do a short Caribbean cruise from one of the Florida ports.

I haven't done all of these destinations in one trip but I have done NYC 3 nights followed by a week in the Carribbean.

Also done Orlando followed by a week in The Bahamas (not too far away via Miami) and also Orlando followed by Key West which is beautiful. Universal is a must like others have said.

A Carribbean cruise from Florida will also let you see a few islands. I realise not everyone enjoys a cruise but I personally love it. I've always booked multi stop flights directly with Expedia etc and booked accommodation separately to save £££ rather than using a travel agent but again I realise not everyone is confident to do that. We are a family of 6. Good luck. Sounds awesome 😎

I would do more time in New York and don’t go all inclusive in the Caribbean! See the place! Do a beach holiday sure but I’d do a villa or hotel by the water where you can get out and about. Barbados is great, and felt very safe. You can hire a car and explore all of the island as it’s not huge.

This just feels like 3 different holidays shoved together. It will be exhausting and hard to pack for. Orlando is a 3 week holiday, or 2.5 weeks at least.

You can simply fly to Orlando. Zero need to go via NYC. And for the beach relaxation look at clearwater and other gulf coast resorts. Perfectly possible to have beachy relaxation tacked on to theme park.

The parks are tiring and you need downtime between full on days in the parks so my itinerary was something like

Flight day
Day 1 universal vip tour
Day 2 volcano bay
Day 3 universal water rides morning and pool time afternoon
Day 4 redo universal rides or older rides missed in the morning and travel to kissimee villa pm
Day 5 resort pool chill day
Day 6 DMK 8am til midnight
Day 7 absolutely knackered just stayed at resort pool
Day 8 epcot tomorrow land 8am til midnight
Day 9 pool at resort as can barely walk
Day 10 typhoon lagoon
Day 11 DHS on labour day weekend, mental
Day 12 resort pool
Day 13 typhoon lagoon
Day 14 DAK
Day 15 resort chill
Day 16 epcot world showcase
Day 17 resort chill
Day 18 fly home

Except I know we did 19 days so we must have done more chill time because thats the parks we did.

It costs a fortune for the tickets so its a shame not to see each park. Epcot we went twice because its 2 parks in one. Universal we did 4 nights but next time I will do 5 to do volcano bay twice (it's massive so I didn't get to do everything) and do epic universe. A VIP tour is worth it but £££.

If you want a city break add in miami. Save NYC for another time.

When my kids were teens we did the following trips. Would have been 15 years ago for the first one. All booked myself as a mix of Expedia and direct bookings

Flew to LA
4 nights Hollywood
Train to Anaheim
2 nights Disneyland California
Train to San Diego
3 nights in San Diego, including a day we walked across the Mexican border to Tiajauna (not for the faint hearted)
Re eye flight to New York
3 nights in NY although we stayed in New Jersey
Flight home

We've also done
Flew to Orlando (via Dublin, much cheaper and clear US customs in Ireland)
3 nights in Orlando, including two days at Universal studios
Coach to Miami
1 night in Miami
5 night Carribbean cruise
2 nights in Miami
Flew home

Both great trips 2 years apart. Agree with other posters that you can make Orlando your whole trip but you don't have to. Doing all the parks would've tipped this into an unaffordable trip for me.

I would do the AI at the end as I like chilling out but do think about what your flights home look like. I find connecting flights are fine on the way out when everyone excited but you want direct on the way home.

Have fun!

We pretty much did this trip this April - It was amazing and absolutely a trip of a lifetime. Loved every second of it and it took me about 2 months to get over the holiday blues. It was a perfectly balanced holiday (for us). The excitement and exhaustion of Disney, then a relaxing beach trip and then a city break.

We did 9 nights in Disney - we could have EASILY done more (particularly as we didn't do Universal)

We then did an hours flight to Cayman Islands for 5 nights - which was lovely and chilled. If you want all inclusive then you'd probably need to do a different island for more choice.

Finished off with 3 nights in New York and then home.

Happy to answer any q's!

I would think you might want a day or two longer in New York. Apart from that, would you consider a Caribbean cruise out of Florida? That way you get to see a few different places, you still get all your food included, and you don't have to take another flight.

Edit to say, I don't know how old your kids are, but Disney cruises are amazing for children! And pretty great for grown ups too.

I’d do a road trip; have done various in this area. New York/ DC / Outer Banks/ Charleston/ Hilton Head (or similar)/ Savannah/ Orlando. Chat GPT or similar AI will help you craft a fantastic itinerary. I prefer to book direct. Leave your car when you reach Florida and just uber around as the parks area is actually relatively small.
with kids that age I’d lean to universal (it’s also a lot easier to plan and manage). On site and free express passes are well worth it. (Epic you have to pay separately). Disney is much pricier and having just steered two teens around they couldn’t wait to get to Universal. If you do both you must do Disney first as the thrills get bigger at universal!
been here a while and mine have zero interest in HHN - it’s fairly scary stuff but depends what they are into. Strictly 13+. Disney you could do one evening Halloween party at magic kingdom - it is tame by comparison and people seem to go for the bags of snickers and M&Ms they hand out but you get some cool parades with villains and short lines for a handful of rides.

*other alternative is a day at Hollywood studios the best park for teens especially if you have Star Wars fans!

Sorry I know this is old but having done many multi destination trips my biggest tip is not to rush things just to fit more in. You dont get time to actually enjoy/make the most of where you are and it just becomes a tick box exercise and you are exhausted. I would recommend if you can that you either add another week (highly recommend for once in a lifetime trip) and do 5 nights NY, 14 nights Orlando, 7 nights in all inclusive or else maybe consider dropping 1 part of your trip and fully enjoy 2 destinations as Florida in itself would be easy spend 14+ nights in to visit all parks and do many of the other activities, visit beaches etc.
If you have 3 weeks only and really want to visit all I would suggest finish up work etc on Friday, fly out on a Saturday earliest flight and do 4 nights in New York, then 13 nights in Florida, then 5 nights all inclusive somewhere with a short flight from Florida or what about a carribean cruise from Florida? (5 nights may not be enough for cruise & flight home etc) Assuming you fly out on a Saturday you would take 3 weeks holiday from work and then you will absolutely need to take the Monday of the 4th week off at the very least (keeping a close eye on flight times as you may not arrive home until the Monday evening/night)
The first week back to work will be tiring but you will get through it and you will have had the very best time!!!
Multi destination extended holidays are always my absolute favourite and have done many throughout the years worldwide so I highly highly recommend making it work somehow but I just always regret our first couple that we rushed just to see more, you will likely have a bit of jetlag/travel tiredness so need to account for this.
Keep us updated 😊

Also think maybe speak to DC in regard to what their wishes are in Orlando, for my family & I all Disney parks, all universal parks, some water parks, shopping days, days to relax at some of Florida's beaches, time to wander around international drive, do airboat tour, visit the Kennedy space center etc all come high importance to us so 14+ days in necessary. I can't imagine a trip to Florida with anyone who doesnt want to do the parks but maybe your DC hate the attractions/rides, dont like Disney etc and in this case then maybe you dont need as much time in Florida? My previous post was from the eyes of someone who absolutely Loves all of the fun and excitement of the parks, but maybe your family have no interest in this side of things