We will be going on our first every cruise end of March on the Dream & after submitting the final payment there’s this actual real-life hope & excitement that we will really make it to our our first cruise! 
Which is huge because ever since the start of a certain global event when we canceled the many travel plans we had for 2020, I’ve had this giant big emotional block around any big trip planning (a defensive mechanism for sure due to all the re-booking & still mourning some really fun things we had booked & planned for 2020 that I don’t know if we’ll ever truly get to make up but those aren’t this trip so we won’t dwell on them). So what better way to celebrate the fog lifting than a thought dump all the things about this most exciting trip on the forum with all the best Disney people on the internet.
Some Background to Explain HOW Really, Realy F’ingLONG We’ve Waited for this Moment
We first stumbled onto the idea of a cruise when fellow Disney fanatic DSIL was over with her kids to play with our kids & threw out the statement (in Dec 2018) “We should do one of Disney’s Halloween cruises to make up for not going to WDW this year” (At the end end of 2017 we’d penciled in WDW for Aug 2018 & then decided halfway through planning it that it was just financially not in cards for any us). Well, that night I began looking into cruising for the 1st time ever and a week later had spreadsheets of Halloween sailings that fit our 2019 Fall Break dates, the pro’s & con’s of each ship & itinerary for said dates, pricing for different levels of staterooms and a log of the best staterooms available in the categories I thought we’d want to book. So basically I had gone into obsessive planning, I mean ahem, full Liner mode. One hiccup though, I knew (but DSIL didn’t) that DH & I had just greenlighted Operation: Caboose Baby with a tentative Launch Date Sept. 2019. Luckily my bacon was saved by realizing we were already within a year so prices were already so much higher than if we’d planned to book 1yr+ out. So, phew, using the price argument alone (and not having to talk about the goings on in the bedroom I share with DSIL’s baby brother), I convinced DSIL we should try for the Halloween Cruises in 2020. (spoiler: our attempt to book a sailing for 2020 didn’t even take flight, because as we were getting ready to submit our bookings on the day they opened for the ship & dates we had sat down & planned for, DSIL double checked the school schedule & found out they had completely eliminated fall break in a recent redo of the future school calendar and as an educator she couldn’t just be gone for a whole week during the school year to pull off a Halloween cruise & WDW).
We did our first real booking (and at the time it felt like oh finally! we’ll get to go! Ha! How little we knew then) for April 2021 when those sailings opened up late 2019. It was going to be perfect. 4 night Caribbean on the Dream. Stop in Nassau (which I was actually excited about the total lack of pressure to go see anything & my only goal for that day was to wander, find somewhere to eat a conch and maybe walk to a fort), one sea day, then Easter Sunday on Castaway Cay. I don’t have to rehash what happened that killed that plan, but eventually, after a few more re-schedulings, we’ve landed with what we have now.
The Actual Real-Live Plan!
Please don’t scare it, we want it to stay this time
5 night Western Caribbean on the Dream from Miami March 2023
Stops: Castaway Cay (Day 2) & Cozumel (Day 4)
2 sea days (Days 3 & 5)
Staterooms: Because I have a bushel (4 is about a bushel, right?) of kids, we’ll be in 2 connecting staterooms, Deck 6 midship (I think it’s category 4D?) Deluxe Family Oceanview with Verandah’s. DSIL, DBIL and their 2 kids will be in the same category of stateroom next door and their room will connect to another stateroom of the same category that will be occupied by a relative that we are so excited will be coming too! DH’s & DSIL’s 2nd cousin, his wife & their two kids. DH & I did WDW with the cousins back in 2016 because they are basically our East coast equivalents & go to WDW about as often as we do DLR and we both have similar drives from our homes to h 
me.
That trip with them was the first time we met them in person (well DH & his 2nd cousin had seen each other growing up a time or two, but hadn’t hung out on account of living on opposite coasts & it was my first time meeting them and they me) and it was our 2 older kids first time to WDW & was nothing short of amazing, over far too soon! The cousins then came out west to DLR in 2017 (and DSIL at the last minute jumped on the trip with 1 of her kids as a surprise to them) and we had another amazing trip with the cousins of all generations that ended up there. The cousins pulled of a giant cross-country road trip summer 2019 and made a stop in our hometown between other great sites and so all the kids got to hang out (not in a Disney park but at least all together) for another awesomely fun, but not nearly long enough amount of time. We are SO excited to get all the kids together. In a Disney park. And on a Disney ship. For our DD3 (Operation Caboose Baby was successfully launched Dec 2019) it will be her first time seeing these wonderful cousins. Also, DS5 doesn’t really remember that 2019 trip on account of him being 2 then so it’ll be the first time he will remember hanging out with them.
Some of us will also do 4 days at WDW before (Thur-Sun). The ones that are not doing the 4 days may come down to do just Sun in the parks. Then all of us will drive down to Miami where we embark on Monday. TBD if we start driving Sunday night (“just in case the 3 hour drive takes 6 hours” that’s a direct quote from DW of DCuz who lived in Florida for a time, has a sister that still does & whose wisdom we probably should heed). But alternatively, we could leave in the wee hours of Monday to arrive closer to when we could actually be let on the ship.
Finally after the cruise, we’ve earmarked debarkation day on Saturday to hang out with everyone as one big group before going all our own separate ways. Mine & DH’s crazy but not yet fully formed plan is to drive back to Orlando that evening with the goal doing Universal Sunday (maybe?), Monday (definitely but can we even do all the HP things let alone the other great things in just 1 single solitary day so we’ll be better off doing both?) before flying home Tuesday.
We feel really good about sticking with the Dream (maybe a little nervous about the change to Miami instead of Port Canaveral but we think it’s manageable). I am more nervous that one of us (mostly all first time cruisers) will end up not loving a cruise. We had originally thought 4 nights was a good plan to have enough time actually get to enjoy the ship if we were loving it but also short enough that if we weren’t feeling it, we wouldn’t be stuck. One day extra seems to tempt that fate. On the other side of the coin, all the kids are insanely bonkers excited about every detail we share with them and DH & I keep finding more reasons to ask ourselves “Why haven’t we done this yet?” So I think we’ll be ok. Just hopefully DSIL & BIL end up not totally regretting a cruise (DSIL is prone to motion sickness that’s probably my very biggest worry but lately she’s mentioned that DBIL is having a hard time getting excited to go on such a big trip and has asked her if they just can’t get their Disney fix on a 3-4 quick trip to the much closer, much more familiar DLR).
And I think that’s a good place to wrap it up for now, but up next I plan to grapple with the question “What in the world do we want to do in Cozumel?” and how do I shift from the no-stress-no-pressure-no visions I’d had of wandering Nassau to the stakes of planning something with a little (but feels like a lot) more pressure in Cozumel?
You’re welcome!
That’s true! 
