Need help deciding which destinations for Disney Cruise.

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This is my very first cruise I am planning for my family. We will be booking the Disney Wonder out of Galveston but I am having a hard time deciding which places to stop, as I have not ever been to any of the listed destinations. Falmouth, Jamaica, San Juan, Puerto Rico, Cozumel, Mexico, Georgetown Grand Cayman, Nassau, Bahamas, and Disneys Castaway Cay. What are the advantages and disadvantages of the destinations? I am leaning toward a 2 stop trip at Castaway Key because we love the beach. Any help would be greatly appreciated.
 
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Thank you. My wife has been to the Gran Cayman but it was a long time ago and she said it was just beautiful. I am now looking at either 2 stops at Castaway Cay or the trip that goes to Grand Cayman and Cozumel. Can somneone elaborate on the differences between the Gran Cayman and Castaway Cay? Thank you for your responses and your time.
 
If you like going to beaches, then I would pick a cruise that goes to CC (Castaway Cay) twice. CC is very nice, has tons to do there and you don't have to pay an extra fee to go there. Some excursions do cost extra, but they aren't too expensive and you can do a lot there without spending any extra .We haven't been to Nassau, but I haven't read many positive things about it. Falmouth was OK, but had longer travel time to get to excursion. In San Juan we went to a beach, wasn't as nice as CC and cost over $100 per person(booked through Disney). We did dolphin excursion in Cozumel and really enjoyed it. Our excursion in Grand Cayman was cancelled because of rough seas. You have to tender in GC, so you are more likely to have things cancelled there than anywhere else if they can't tender. We were on the Wonder last March and went to San Juan. We were also suppose to go to St Maarten but there was a tropical storm that was in the area so St Maarten was cancelled and we went to CC instead. We went to CC twice on that cruise and I LOVED it!! If all you care about is going to to beaches, than you won't find any as nice as CC (unless you go to some fancy resort and spend thousands of $$$)
 

Grand Cayman you will go to a public beach and get a chair and umbrella, may or may not get food included if booked through Disney. CC get chair with umbrella, all the food/drink/ ice cream you want for no extra cost(alcohol does cost extra). Fun areas like splash area, kids club on island, slides, area to snorkel(can rent equipment or bring your own), bikes to rent, volleyball court, floats/tube(I think $13 for the day), they have a 5k you can run/walk in the morning, parasailing, his is just some of what is on CC. If you look at the port excursions for CC it will show what all there is to do.
 
CC is awesome! Include it at least once in any cruise you chose. Be sure to snorkel there, take a camera and look for the hidden (sunken) Mickey & Minnie.
 
I would 100% book the Castaway Cay "double dip" cruise from Galveston. As long as it was at least 5 nights, since I prefer longer cruises.
 
Your family may like certain ports or tours, since you know them best you can review the port adventures for specifics that might appeal to them.

That said, we feel that there is a lot of similarity between many of the ports. Since we have been to all the ports you mentioned, San Juan is the one place we would choose to go back too. (They are still rebuilding but things are coming along, especially in that San Juan area.) The double CC stop is always a popular itinerary. If you are a beach family that would probably be at the top of my list.
 
Falmouth we didn’t care for, in the port it is just shopping. Jamaica was our least favorite port. Grand Cayman the water is beautiful and the snorlking was great! My brother did 7 mile beach and they didn’t think it was great. Cozumel was a fun port, we felt safe. We love Castaway Cay but one day was enough for my teen girls and I. San Juan I thought was run down prior to the hurricane and excursions were expensive. St Thomas is a nice port too, we have always had fun here. You will have fun either way
 
Thank you for all the responses. I just noticed that Nov 29, 2019 is the day after thanksgiving and that date may not be feasible. My other option is to fly to Mco and take a cruise from Port Canaveral. Looks like a lot more options date wise. I know nothing about the following destinations Tortola, British Virgin, St. Thomas, U.S.Virgin Islands, Basseterre, St. Kitts and St. John's, Antigua. I am looking at either the Halloween or Christmas cruises. Any insight on the above destination would be much appreciated.
 
Thank you for all the responses. I just noticed that Nov 29, 2019 is the day after thanksgiving and that date may not be feasible. My other option is to fly to Mco and take a cruise from Port Canaveral. Looks like a lot more options date wise. I know nothing about the following destinations Tortola, British Virgin, St. Thomas, U.S.Virgin Islands, Basseterre, St. Kitts and St. John's, Antigua. I am looking at either the Halloween or Christmas cruises. Any insight on the above destination would be much appreciated.

For starters, the Christmas cruises are in high demand, and you'll pay through the nose. When we were in St. Thomas several years ago, we were one of seven ships in port. The little shops were overwhelmed with tourists. Tortola is still recovering from the latest hurricane there.

Meanwhile, San Juan has a huge fort with cannons, which looks like something out of "Pirates of the Caribbean." Grand Cayman is more upscale than most Caribbean islands, because of the off-shore bank accounts hidden there. We liked Jamaica's "climb the falls" excursion, but that port has way too many pushy sales people.

Most of the islands have beautiful beaches, but a lot of poverty.
 
Thank you for all the responses. I just noticed that Nov 29, 2019 is the day after thanksgiving and that date may not be feasible. My other option is to fly to Mco and take a cruise from Port Canaveral. Looks like a lot more options date wise. I know nothing about the following destinations Tortola, British Virgin, St. Thomas, U.S.Virgin Islands, Basseterre, St. Kitts and St. John's, Antigua. I am looking at either the Halloween or Christmas cruises. Any insight on the above destination would be much appreciated.

In response to all of the ports you mentioned, I would choose an Eastern Caribbean itinerary over a Western Caribbean itinerary. Cozumel and Falmouth are not great ports, IMHO. We did a western in March and they had to cancel a few excursions because of bomb scares on the ferry in Cozumel and Jamaica has a ton of travel warnings in areas due to violence.

Grand Cayman is a lovely port with beautiful beaches on Seven Mile beach very close to the pier and a ton of sailing activity opportunities.

In terms of beaches, you will find many more beautiful beaches on an Eastern itinerary, IMHO.

Castaway Cay is fantastic - if you can do a double dip, go for it!
 
This is my very first cruise I am planning for my family. We will be booking the Disney Wonder out of Galveston but I am having a hard time deciding which places to stop, as I have not ever been to any of the listed destinations. Falmouth, Jamaica, San Juan, Puerto Rico, Cozumel, Mexico, Georgetown Grand Cayman, Nassau, Bahamas, and Disneys Castaway Cay. What are the advantages and disadvantages of the destinations? I am leaning toward a 2 stop trip at Castaway Key because we love the beach. Any help would be greatly appreciated.

George Town Grand Cayman is awesome. Cozumel has a lot of fun activities to do.
 
I have cruised the Caribbean a few times and I have to admit that the ports sort of blend together in my mind. Tropical, hot destinations with beachy locales.... that's sort of what I have taken from my trips there. I am of the opinion that you can make any itinerary fun and you can find something to do in any port. I honestly only chose W. Caribbean with Disney because it worked out price- and time-wise.
 
In general Eastern are for beaches/shopping and Western are for more activity. Since you're beach people, I suggest checking out CC. We're not really beach people and to us...well, it's just a crowded beach.

We've done various excursions on St Thomas but the best was getting away from St Thomas and heading to Trunk Bay Beach on St John for beaches/snorkeling.
In Falmouth we did a great walking tour and tubing down the Rio Bueno (which was a blast - we're doing it again in Nov).
Haven't been to Grand Cayman in a while but have done island tours, visit to the Turtle Farm, and best was time at the beach. If I were to go back, I'd do the stingray excursion, which is supposed to be great there. (Don't waste your money on Disney's stingray excursion on CC!)
San Juan is one of my favorite ports for exploring - 2 interesting forts, colorful buildings, beautiful churches and parks, and great food!
We've always had a great time in Cozumel - have gone to Paradise Beach (best pool on the island!), did a dolphin excursion at Chankanaab and spent time there on the beach and by the pool, and did an amazing Sea Turtle Release excursion.
We've been to Nassau a ton of times - have done the dolphin excursion at Blue Lagoon, Frommer's Walking Tour, and a few times got day passes at the British Colonial Hilton.

The Very Merrytime cruises are a blast, more so if you love Christmas. I wasn't sure if you meant of one those or actually cruising on Christmas Day.
 

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