Planning Flights, Hotel, and Travel Insurance
Brace yourself - this chapter is going to be LOOOOONG and involved! Maybe go pour yourself a glass of wine or mug of coffee, grab a snack, and settle in.
I'll categorize, rather than going completely chronologically.
Hotel & Transportation
As you may have read, we were watching for space available rates and weren't super committed to cruising unless something popped up in our budget. This means that I started a gigantic Google Document planning for about five different cruise eventualities. I wanted to be knowledgeable and prepared whenever those Very MerryTime rates started appearing! I started planning for the following potential cruises:
- December 8, 15, or 22, 7-night Bahamian itineraries from Galveston on the Wonder
- December 16 or 23, 7-night Caribbean itineraries from Port Canaveral on the Fantasy
- December 24, 5-night Western Caribbean itinerary from Miami on the Magic
Galveston became a top choice because it had come up in space available rates in the past and flying to Houston around Christmas would be cheaper than flying to Orlando. The PC cruises came in second because they were still 7-night cruises, and we wanted a nice long trip for our first cruise. The 5-night from Miami was reluctantly tacked on as a last choice even though it was just too short for us.
So, I started looking at hotel options for three different cruise ports: Galveston, PC, and Miami. Within my planning document, I dedicated a page to pre-cruise hotel options for each night. Here are some random notes on our hotel possibilities:
- I have lots of Hilton HHonors points from my day job, which involves quite a bit of travel.
- I can also get good TA rates at some hotel chains, but we really preferred to book a Hilton property for basically free
- If staying in Galveston, we'd need a hotel with a cruise shuttle.
- If cruising from PC, we'd need to decided whether to stay the night near MCO and take the DCL bus, or get ourselves to PC and stay the night there.
- I barely even looked into Miami, but I know there are Hilton properties near the cruise port and we are prolific Uber users
After doing some Galveston cruise research, I decided that
if one of our top choice Galveston cruises became available, we'd stay at the Hilton Galveston Island. I chose this hotel for several reasons. First, we could book it for a very reasonable number of HHonors points (21,000). Second, it has a cruise port shuttle that will get us to the port, if somewhat inconveniently (I have read some mixed reviews of the service). Third, it is right next door to the Rainforest Cafe, and DD has harbored a deep desire to visit a Rainforest Cafe since we visited Disneyland last year. (We had to walk past their RFC every day between DLH and the parks, and she was always asking to eat there!)
So, the day I booked our cruise, I set up a pre-cruise stay at the Hilton Galveston Island. Cross your fingers the shuttle works out for us!
I'll add a bit about transportation here: I am a fan of Uber, and the service is back in Galveston as of earlier this year. Right now, we plan to Uber from HOU to our hotel, and then after the cruise from the port to HOU.
Flights
Once the cruise and hotel stay were booked, it was time to tackle flights. This was another points situation: we have some credit card travel points from doing the Chase Gauntlet, and we wanted to use said points for this trip. The question remained: fly from our home airport (GRR in Grand Rapids, Michigan) to HOU, or drive to Chicago and then fly to HOU? Grand Rapids is 30 minutes away and undoubtedly more convenient, but can often be more expensive.
Well, it was about the same number of points to fly from GRR as it was to fly from MDW on Southwest. Great! Let's fly from close to home, get a ride from somebody, and save on parking. Sweet.
But upon closer inspection, I did not like the flight itineraries at all. Too many stops, and we'd get back at 1:00 AM after the cruise. Our friends and family like us a lot, but not enough to get us from an airport at that time of night two days before Christmas! So the GRR flights were nixed and we decided to fly from Chicago Midway, where we could get nonstop flights to HOU at a variety of convenient times. We'll deal with the 2.5 hour drive and happily pay for parking to avoid multi-stop late-night flights!
Here's the next complication: when to fly? We cruise on December 15 and want to fly on December 14. DD has a full day of school on December 14 and a half day on the 15th. In an ideal world, she would have been able to attend part of the day on December 14. (I feel bad that she will likely miss her first school Christmas party, but she will be on a
Disney cruise, which seems like a fair trade.) I began looking at flights late enough to leave her in school until noon or so. Unfortunately, that would have put us into Houston late at night, and I want to be in Galveston for dinner and in time to hit the grocery store. Thus, we booked mid-morning flights out of Chicago Midway that arrive in Houston around 3:30 in the afternoon.
Then there was the matter of a return flight. I know that fog is a common challenge with Galveston disembarkations in December; that is, cruises are often delayed in returning to the port due to fog. So I wasn't about to book a flight around noon, but I also didn't want to get home too late. So we chose a flight that departs HOU at 4:00. This puts us in Chicago at 6:30 PM, so if we can be out of that airport by 7:00 PM, we can snag dinner and be home before midnight. (We are in the Eastern time zone, so we jump forward an hour driving back from Chicago.)
Because it's Christmas, flights certainly weren't cheap, but they weren't terrible, either.
Travel Insurance
In general, I'm not jazzed about the price, level of coverage, or administration of DCL's travel insurance. Our agency works regularly with Travelex, and I had said I'd buy one of their policies if we ever cruised. As we've gotten older, added our daughter to our family, and begun spending more on travel, I'm eager to make sure all our trips are covered by insurance. Especially now that see many clients needing to postpone, interrupt, or cancel their travel plans, I recognize the need for insurance. So right after we nailed down flights and hotel and had a ballpark total cost for our cruise vacation, I popped over to the Travelex website and purchased a Select plan. I feel good about the coverage, especially in the event of some midwestern weather or Galveston fog that might interfere with our trip!
Conclusion (of this post, that is!)
So that's how the rest of the technical details for this cruise fell into place! I enjoy navigating logistics, so planning multiple hotel possibilities and digging into a number of flight options was super fun for me, actually. And having the travel insurance makes me feel more calm about traveling in December, which we normally don't do. Now we just have to plan the fun stuff!
