In order to get this achievement you have to do 5 things:
On day 8 when you deliver the letter to June and mickey choose option one until you get invited to the campfire – then choose option 2 "oh cool yeah why not "
On day 10 In the woods with June and mickey chose option 1 all the way – the key point is when they offer the tv, say "really guys that’s awesome"
On day 11 when talking to Lori don’t give her the RV
On day 14 at the event when talking to Angie don’t give her the RV
On day 15 you will have one last talk with frank.
Tell him:
"but no I’m talking it off and will leave town"
and then
"I'm going on a road trip"
You will get the achievement before the credits
For a Fast Achievement Guide check the link below:
Timestamps:
00:00 Intro + Day1
01:39 Day2 Intro
01:55 Day2: Higher Ground Achievement
02:22 Day2: Deliver Mail
04:39 Day3: Deliver Mail
05:24 Day3: Cat Lover Part 1 of 2
06:26 Day3: Deliver Mail
07:01 Day3: Workoholic Part 1 pf 4
07:19 Day4: Tower Watcher Achievement
07:57 Day4: Cat Lover Achievement
09:12 Day4: Movie Carrier Part 1 of 5
09:44 Day4: Deliver Mail
11:20 Day4: Movie Carrier Part 2 of 5
11:35 Day4: Workaholic Part2 of 4
11:46 Day5: Shutter Bug Part 1 of 3
12:19 Day5: Movie Carrier Part 3 of 5
12:51 Day5: Metal Detector Achievement
13:59 Day5: Deliver Mail
15:21 Day6: Shutter Bug Part 2 of 3
15:42 Day6: Movie Carrier Part 4 of 5
16:51 Day6: Deliver Mail
19:09 Day7: Workaholic Part 3 of 4
19:35 Day8: Interrogation
19:56 Day8: Shutter Bug Achievement
20:51 Day8: Movie Carrier Achievement
23:31 Day8: Deliver Mail
25:01 Day8: Free Spirit Part 1 of 5
25:46 Day9: Deliver Mail
29:03 Day9: workaholic Achievement
29:48 Day10: Deliver Mail
32:11 Day10: Free Spirit Part 2 of 5
32:25 Day11: Deliver Mail
33:54 Day11: Free Spirit Part 3 of 5
35:20 Day12: Deliver Mail
37:40 Day13: Deliver Mail
40:35 Day14 – Repeated 3 times
40:57 Day14: Free Spirit 4 of 5
41:10 Free Spirit Achievement (Ending 1)
42:31 Life in a Fast Lane Achievement (Ending 2)
43:29 Hometowner Achievement (Ending 3)