First off....I like your style....you seem as crazy as me when I look at your drive times and although some will say you have to much driving I think your doing it right and hitting the "big courses". My advice might draw some criticism which is fair but I am also a guy who usually drives 6 hours (one way) to sand Valley each year and play 53 holes and drive 6 hours home right after to keep my wife happy. I usally make a number of 3-5 hour drives (one way) to play Whistling Straits, Forest Dunes, Arcadia and then drive the same time home to keep my wife happy. Understand that I dont mind driving and I enjoy playing the best of the best courses and I dont need alot of relaxation time as others do. My buddies think I am crazy but I am just a golf nut....Recently played 16 rounds of golf at Bandon Dunes in 7 days.
You have an amazing trip planned and I am lucky enough to have played all the courses you have listed Your Monday is a pretty busy day and you are looking at about a 3.5 hour drive from the Dunes Club to Arcadia. I am guessing that is the only tee time you could get at Arcadia since the place is basically booked a year out so that might be why you have your trip set up that way. In the event that you could change your Tuesday to a 36 hole day to Arcadia Bluffs and the South Course then I would do it. I will assume that is not an option but if it were then it would be worth trying to play Lost Dunes after you play Dunes Club on Monday. Lost Dunes is a Tom Doak Private course that is 15 minutes from the Dunes Club and is an amazing track if you can get on. Its not as good as the Dunes Club in my opinion but its still pretty sweet and would make your 36 hole day easier.
Back you your original Agenda .....I have actually played Arcadia Bluffs and Forest Dunes in the same day and have made that drive. Its not a bad drive and will prob take ya 2 hours so its not terrible. The bootlegger is a great little course but its really short and you will be able to play it in around a hour if you are by yourself. Forest Dunes has a great scene and has a great bar outside and fire pits with a sweet practice area and putting green....dont hesitate to try and play 18 at Forest Dunes as well. A quick suggestion for Forest Dunes and the Loop is to wear pants and a hat. There are some black flies that will get ya if you wear shorts so plan on wearing pants as it will save ya alot of swatting at flies. I have wore shorts plenty of times but each time I swear on pants. Buy the bug spray they have in the shop (special stuff) as it will be a game changer. One last crazy idea...you are already driving a ton so I am guessing you are crazy like me. This advice will probably get slammed but again as I posted above I drive alot for golf and usually do it all in one day. Forest Dunes and the Loop are outstanding but if your goal is to play the best of the best in Michigan maybe consider Drive from Arcadia bluffs to Bay Harbor (play links quarry) and you will see some of the best scenery that Northern Michigan has to offer. I would also suggest if you did that to play Black Lake Golf Club in Onaway Michigan. Its a lot of driving but if you did not want to play FD and the Loop twice then you would be adding two legendary courses in Michigan and both are far different than the others you played. You would have the trip of a lifetime. I actully did a trip in two days where we played Arcadia Bluffs, Forest Dunes, The loop, Black Lake and Bay Harbor and it was an unrealy trip so seriously consider that if you are up for driving and seeing the best Michigan has to offer. It would be alot of driving but its really not that bad...if you are on a mission
Is Forest Dunes and the Loop worth 2 rounds each???.....absolutely as you dont want to be driving all over the place and that will allow you to relax and enjoy your trip. Arcadia Bluffs Should be a priority to play twice as its the best of all your courses but assumuing that is not an option I would play both Forest Dunes and the Loop twice. The courses are unique and Forest Dunes is the better of the two courses but the Loop is plays as firm and fast as Bandon Dunes and Sand Valley. Some guys dont like it but it plays as a true links course in terms of firmness and the greens on both courses will be smoking fast.
Kingsley is a must if you can get on and I would at least try and play it. Give them a call and hopefully they will let you but plan on spending around $300 (includes caddie) if they let you. I would skip bootlegger and play Kingsley the same day as Arcadia as its not that far from Arcadia...prob a 45 minute drive from Arcadia to Kingsley. If you need a friend to join you at Kingsley PM me I have played it twice and it also plays fast and firm.
Lastly, I think Pilgrims Run is worth a play if you are flying out of GR. It is far superior to Tullymore and Stoatin Brae so if its between those three then Pilgrims Run is an easy choice. The great thing about Pilgrims run is its cheap compared to the other courses
Lastly, The courses we mentioned on here are as follows:
The Dunes Club
These are the best of the best in Michigan and you really cannot go wrong with playing any of them.
If you need a sidekick hit me up
There are alot of great guys on this forum like Knickerbocker and others who will chime in and all of them know the golf scene in Michigan and although we may disagree on some courses they all have good info and suggestions that you should listen to