I would be happy to offer my assistance organizing such an event to assist you as lead of the event. After living in Alaska for 25 years and traveling the Alaska Hwy many times and organizing a group tour of the interior of AK and back down the Hwy to the Lower 48 for a group of 7 friends on motorcycles it takes an enormous amount of advance planning by the event organizers. For me I planned out each nights stops, lodging and in some instances where we ate that evening as I knew of a great place to get grub for the group. All the riders had to do is show up and off we went. Riders from around the US caught the AK Marine Hwy Ferry in Bellingham and rode to JNU where I jumped on for our final ferry leg to Haines, AK. One close friend from Whitehorse Y.T. met us in Haines Jct. Another from NV had a daughter getting married in SEA so he caught a ferry a day later out of Prince Rupert and sailed to Skagway and then rode most of the night to join us in Haines Jct. at around 0300 hrs. We were up early the next day and headed north back up into AK later that day.
There will be a couple major decisions to be made by those who opt to travel to Alaska. It's a very long drive one way to access the interior of AK to begin your adventure of the 49th state. Southeast AK is very different from the interior of AK. So driving both ways is cheaper then taking the ferry but taking the ferry permits you to see the inside passage one city and town at a time. People don't realize how long it takes to drive to AK at a relaxed and reasonable pace. A 300 mile day is a LONG DAY on the roads up there. Taking fuel costs in Canada and Alaska into account vs. ferry fare for vehicle, driver, passenger and a cabin for the 3.5 day trip if you don't disembark along the way to visit communities along the inside passage adds up fast.
Just to toss some numbers out our truck and Lance 1190 camper with NO TRAILER would cost $3,894.00 one way from Skagway to Bellingham, plus meals on board. The only time you can access your vehicle is while in port. So pets are a bit of a pain, especially dogs who don't take to a litter box very well. Pets are not allowed off the car deck of the ships.
I just picked up a copy of the 2015 Alaska Milepost and Travelers Guide to Alaskan Camping 6th edition for us to use to plan our trip summer of 2016.
Since Sally and I are going next summer we can keep in mind a caravan and take notes on good places along the way to boondock along the Alaska Hwy. We will plan to spend a couple days with friends in Whitehorse Y.T. visit Valdez, Seward, Homer, Denali National Park, Fairbanks, Dawson City (depending on road conditions up over the Top of the World Hwy) We can stop in Tok on the way through and check with the AST Detachment there to get a road report on what to expect on the way south once we circle the interior of AK and head back down into the Yukon. I've done it in a truck and seen people shred a tire on shot rock road base and done it on a MC and it was slicker then snot with slimy mud. Dawson City is fun as they have a casino with cancan girls and I always enjoy checking out the old abandoned Gold Dredges from back in the day south of town. Plus the Govt. run ferry across the Yukon River is FREE.
For our 2016 trip next summer I'm thinking we may leave the 5th wheel at a friends place in Whitehorse, drive down to Skagway, check it out, take the White Pass & Yukon Route Railway up to the pass where the miners trekked during the gold rush and then charter a float plane and fly to JNU where I lived for 21 years. Get a motel room, rent a car and spend a couple days seeing the sights. Then fly back to Skagway and drive back up to WH and fetch the 5'er.
Also need to stop at the Liard River Hot Springs Provincial Park and spend a night there and visit the hot springs. Another cool place I enjoy staying at is just north of Whitehorse at the Takhini Hot Springs & campground.
Oh well, time to publish this book.
PS: Most of you probably know this but a passport is required to exit and re-enter the US to Canada and I highly recommend you obtain a credit card that does not charge a fee for foreign transactions as you will be buying fuel and supplies in Canada and the charges do add up.