Heigh-Ho Jamie,
It sounds like you have a Very Merry Magical Day planned and I am happy to map out the best route for a seamless turn-by-turn experience. To confirm, you are beginning your day at Disney's Hollywood Studios, continuing on to take a
Holiday Sleigh ride at The Cabins at Disney's Fort Wilderness and finally ending your day at Disney Wilderness Lodge for a western-style feast at
Whispering Canyon Cafe. Now let's talk transportation.
The first part of your day is filled with choosing sides between The First Order or The Resistance, going to Infinity and Beyond, plummeting down elevator shafts and speeding through a cityscape. And once that's over it is time to Deck the Halls with a sleigh ride for the holidays. From Disney's Hollywood Studios make your way to the bus depot and board a bus to The Cabins at Fort Wilderness. Once you arrive, at the Resort, your family will board the internal resort bus to The Settlement Bus Depot and walk over to The Tri-Circle-D Ranch where your carriage ride awaits. Give yourself 1.5 hours of travel time from the exit of Disney's Hollywood Studio, taking into account waiting for buses at both the park and resort, walking and checking-in for your ride.
After Jingling All the Way and taking in the sites I am sure that rumbly in your tumbly will be calling out loudly. Because I do not know how much time you have between your sleigh-ride and dining reservation I am going to suggest a quick and direct route. Your family will once again board the bus and make your way back to the front of the resort, from here I highly recommend utilizing a ride share to transport you to Disney's Wilderness Lodge. Anticipate approximately 30 minutes of transportation time from the moment you are at The Settlement Bus Depot until your arrival at Disney's Wilderness Lodge. While it will cost extra, it is worth budgeting for. The reason is, if you used Disney's Complimentary Transportation, you would have to take a ferry or bus to Magic Kingdom Park and then board a bus or ferry to Disney's Wildnerness Lodge making your transportation time considerably longer. I prefer using ride share or taxis to travel to many of the Walt Disney World Resorts, especially when there is not a clear and direct route.
I hope I have helped, in mapping out your Practically Perfect Day, and continue to ask us any further curiouser and curiouser questions you may have, we are always ready to help our Fellow Guests.
Amy M.