Generally speaking, you will only provide tips one time once on board – at the end of your cruise. Disney will provide you with a perforated sheet of paper that breaks into slips of paper with recommended tip amounts for your: Stateroom Steward, Head Waiter, Waiter, and Assistant Waiter. Regardless what you might think about the provenance of tipping the Head Waiter (who really just comes around to your table to say hello), remember that these folks’ pay takes tipping into account. The recommended amount is usually reasonable (currently $12/person/night). In fact, if you don’t tell them otherwise, the tips will be included in your stateroom folio bill and the slips of paper are merely confirmation that you’re giving the “usual” amount.
However, this tipping DOESN’T include people who help you on your way to/from your stateroom, including any porters you might use to help with your bags. Use your discretion.
Dining is, stereotypically, a big deal on cruises, and it’s no different on a Disney Cruise. Even knowing that food is almost entirely included, it still seems to cause some people stress (maybe it’s because you feel like you’re trapped with no other choices). But just look at the options. I think you’ll agree that there’s something for everyone.
There are two dinner seatings every night. You can select your seating, but once chosen, you usually can’t switch. And, in fact, you probably won’t want to once you form a relationship with your waitstaff. They follow you from restaurant to restaurant each night and actually do learn your preferences. But there are a lot of other dining options on board, from the traditional buffets expected on a cruise all the way to included room service. Your bonus secret is that the Mickey Premium ice cream bars (vanilla ice cream shaped like a Mickey head, dipped in chocolate) are available on board at no charge. Yes, free! You can get them as desert, or call room service to bring you a few.
If you enjoy the dining experience, you will have at least one, and possibly two, additional restaurant options available to you for a nominal additional charge ($20/person at last check). On the Dream and Fantasy, it’s Palo and Remy’s. On the Wonder and Magic, it’s Palo. These are adult-only restaurants (must be 18+ to dine there), as well, but from what I hear, totally worth the cost. Make sure you book early if you want to be sure you get to have the experience.
I mentioned excursions in more detail on the On Board section of the guide. Depending on your specific cruise, you’ll have your choice of more than a dozen shore excursions at each port. From tours of the local area, to things highly-specialized for the region you’re in (dog sledding in Alaska, scuba diving in the Caribbean, etc), you will have ample opportunity to do fun things at each stop.
But these excursions can be incredibly pricey. And if you’re familiar with the area you’re going to, it’s true that you’d be able to find cheaper versions of the exact same thing. But here’s the catch. If you’re late getting back to the boat and you’re not on a Disney-arranged excursion, the boat probably isn’t waiting for you. Yup, things work on a pretty tight time schedule and the ONLY reason the boat might wait for someone is if Disney is to blame in some way. So for that reason alone, it’s worth the extra money to book the excursion via Disney.
Booking is simple – you can do it via the DCL website once you’ve booked your trip – or, if you’re more daring, you can wait until you board (or the night before a particular port). But don’t be surprised to find out that a particular trip isn’t available. They tend to fill up – even at their inflated cost. On the flip side, don’t feel like you have to go on one (or any). There are plenty of things to do on the boat while docked at port, not to mention simply wandering around whatever port of call you’re in.
After you sail once with DCL, you are automatically a member of the Castaway Club. Your first sail gives you “Silver” status, 5 sails is “Gold” and 10 sails is “Platinum”. Each level has some perks associated with said level, from welcome gifts to exclusive on-board experiences. After that first sail, you can get your Castaway Club ID and see all of the details for yourself. I only wish they had something like this for WDW or DL.