I have always prepared a separate playlist when coming down and find if you get a good mix of different genres of music it will appeal to everyone. I also try to keep the music relative to the trip and vibe. Here are a few less well known tunes people seem to enjoy.
Anegada - Rick Glaze
Aurora Borealis - John H Clarke
Bon Jur - The Mussington Brothers
Can You Feel It - Inner Visions
Caribbean - Barefoot Man
French Shore - Great Big Sea
Fun In The Sun - Steve Oliver
Island Life - Ken Navarro
The Last Saskatchewan Pirate - Arrogant Worms
Just Another Dream - Stick Figure
Moondance - Liz Longley
Nickel Beer - Rick Glaze
Pump Me Up - Edwin Yearwood & Krosfyah
Swaying Palms - Govi
Virgin Gorda - Warren Hill
Sloop John B - Relient K
St. John Shuffle - Jimmy Junkins & the Soulcats
Sunny & 75 - Joe Nichols
Closer to Home/I'm your Cptn - Mark Farner
Stronger Beer - Tim Hicks
I Like to Move It - Reel 2 Real
Change the Tides - The Northwest Sons
Wonderful World - Third World
Samba Pa Ti - Ottmar Liebert
Don't Want to be a Conch - Barefoot Man
Heave Away - The Fables
The Crawl - Spirit of the West
Captain Kid - Great Big Sea
Sinnerman - Nina Simone & Felix da Housecat
Home for a Rest - Spirit of the West
X-Rated - Dennis de Mennis
Wotless - KES the Band
1865 (96 in the shade) - Third World

These are just a few, and some fun Canadian content in there.
Of course you mix lots of JB, Kenny C, Zac Brown and classics from CS&N, Van Morrison, Bob Marley etc.