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Which Disney Halloween Cruise for Multi Generation Family Dream Vacation?


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Hello, I'm in the initial planning stages of a Once-in-a-Lifetime? memorable Cruise Event that will hopefully include 13 grandchildren, and their families. The grandkids ages will range from 4 years old to a Senior in High School. (This trip is intended to happen before the oldest graduates High School.)  

 

My thought is to do a Disney 7-day Cruise over Halloween. The choices for me are between the Port Canaveral Cruise that goes to Tortola and Castaway Cay, or the San Juan Cruise that includes Antigua, St. Kitts, Barbados, etc. I am leaning toward the San Juan Cruise so the kids experience the islands and communities of the Caribbean, even though that many shore visits with that many people may be a huge amount of work that can suck the happiness out of the trip. The work of the trip can't be allowed to overwhelm the enjoyment of the trip. Port Canaveral has more sea days and isolated Castaway Cay. So I can see it being a lot less work.

 

Any thoughts and insight would be appreciated!  

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Will the grandkids be out of school already, or are you planning to pull them? My only input would be that at the point of senior in high school, that is the wrong time of year to be pulled out of school for a vacation. 

Also, will the senior still be under 18?

 

I would probably pick the cruise out of San Juan, but it's easier to get to Port Canaveral than it is to San Juan.

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Yes, they'd all have to skip a week of school. If you want Halloween, you have to skip school! 

 

Very good point about getting to the Port. You can drive to Port Canaveral. Flying 20+ People to and from San Juan would add a huge cost to the trip.   

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2 hours ago, MikeinNebraska said:

Yes, they'd all have to skip a week of school. If you want Halloween, you have to skip school! 

You don't have to cruise over actual "Halloween" to get Halloween on DCL.  Halloween on the High Seas cruises usually start mid September through end of October.

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Please check with the grands (and their parents) if being pulled out of school is an option. I can tell you that for me personally, if I was told I was getting pulled out of school during that time, between college applications, extra curriculars, etc, I'd ask to stay home while everyone else went and had a good time. 

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As others have suggested, I'd consider a different time of year. See when the kids have breaks and try to schedule around that (+- a few days). I'd also suggest the itinerary that doesn't require you to figure out excursions for 13+ people because that will be a legitimate nightmare, nor will you find a happy place between everyone involved. At least with Castaway Cay, y'all are going to the same place and can find things to do that each likes.

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On 7/15/2024 at 1:20 PM, 1025cruise said:

Please check with the grands (and their parents) if being pulled out of school is an option. I can tell you that for me personally, if I was told I was getting pulled out of school during that time, between college applications, extra curriculars, etc, I'd ask to stay home while everyone else went and had a good time. 

Agree.  We scheduled a short trip to WDW last year over a day off of school for my 9th grader and she still missed a rehearsal for an activity. Not the end of the world, but missing a week in high school is a lot.  We pulled her out for a week in lower elementary and it was fine.

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Given your likely dealing with a large range of ages and abilities, the Port Canaveral Cruise that goes to Tortola and Castaway Cay would be a lot easier and airfare if need is a lot cheaper for a large family.

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Hi Mike, if the family is all coming from the midwest and possibly flying from KCI, the airfare to Orlando is very reasonable, and you can charter a van taxi that can take you from the airport to the port, or if you stay on disney property the day before they have affordable shuttles. 

 

My concern like everyone else is the senior's missing school. I have a 18 yr old who just graduated HS and her schedule was packed with SAT testing, college tours, etc in the Fall. Also, I don't know when their 18th birthday is, but once they turn 18 they can't go to the Teen Kid's club. Mine was 18 and was bored on the Wish. Everything was geared towards 21+. 

 

If you do book on a Disney Cruise, book those kid's activities ASAP. Olaf's Lunch and the Bibbity Bobbity Boutique sell out super fast!

 

With that large a group, I might suggest letting the parents decide on the shore excursions and the option of splitting up. There are a lot of fun options for older kids and some designed specifically for younger ones. If you're looking for entire family recommendations we all loved the glass bottom boat.

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