Caribbean Beach to Trails End

Yes and no. You can take Uber to the Fort Wilderness Outpost, not to Trail's End which is at the opposite end of the campground. Then you would have to take an internal bus to the restaurant. A private vehicle - car, Uber or taxi - can not go there.
The easiest way would be to take a bus to the MK then the boat to Fort Wilderness.
 
We just did this on August 15th! We went from CBR to Trail's End....but we took a bus to MK and then the boat ride over to Fort Wilderness.
 
The boat dock at FW is not too far from Trails End, a short walk. Boat from MK is the way we go too, it's the easiest way. We were there late, so they had bus service back to MK at the end of the last Hoop de Doo, or you can take the boat back to MK. From MK can get the bus back to your resort.
 

There are 3 Disney Transportation options from CBR to FW-Trails End (some have been covered):

1. Travel to MK and travel by boat or bus to the Fort. There are 2 boats that serve the Fort: the "big boat" which runs from about 30 minutes before Rope Drop until about an hour after official close. Pick it up at the FW dock on the beach or the MK dock directly straight ahead from the bag/security check; or walk from the MK entrance to the Contemporary boat dock and take the "little boat" (think Jungle Cruise size) that runs between 3 stops - Contemporary Resort-Wilderness Lodge-Fort Wilderness. It's there primarily to provide access to food choices between the 3 resorts. In the evenings (only) there is one-way bus transportation from MK to FW (Settlement Depot) for access to Trails End and the dinner show Hoop Dee Doo Review.
2. Disney Transportation (or Uber) to Wilderness Lodge. At Wilderness Lodge a bus runs up to one end of Fort Wilderness (The Settlement Depot) which is nearest to Trails End.
3. Disney Transportation (or Uber) to Fort Wilderness. At the main FW entrance across the parking lot, there is a large bus stop (The Outpost Depot). Choose any of the 3 internal FW bus lines (Orange, Yellow, Purple) which take different routes but all terminate at either the Settlement Depot or the Outpost Depot. It doesn't matter which one you choose since you are travelling between both end points.

I'm a Fort Wilderness guy and admittedly it's not easy to get to Trails End but it has a great buffet for dinner/breakfast and relative to other buffets on property, it's one of the better values on property.

Have fun and enjoy your meal at Trails End. Make the journey into an adventure. All these directions work in reverse, as in your case, go to TE first for breakfast then on to MK for the day.

Bama Ed

PS - here is a map of Fort Wilderness (see post #9): http://www.disboards.com/threads/fort-wilderness-resort-information-a-work-in-progress.3502095/

Your destination is #11 (Pioneer Hall) up near the beach which is where Trails End restaurant is

PPS - there are other possible connections via Disney Springs or the other Disney Parks but these are the most direct routes (such as they are).
 
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