Last summer, before I had Gracie, I brought Lady on the airplane to Newfoundland with me to spend time with family. This past summer my sister came along and we brought both dogs in the cabin. Lady is very used to her carrier and has no issues at all going inside (she was so excited when I took them out a couple weeks before our trip!). Gracie is not as impressed with the carrier, but she was fine. They've also gone on longer road trips with me to New Brunswick - I just get a pet-friendly hotel.
If I am going somewhere non dog-friendly (like last winter when I went to Dominican) I leave them with my mom and her husband, where they are completely spoiled .
Ready to go!: http://instagram.com/p/b3hRhwpu7v/
Enjoying the ocean views: http://instagram.com/p/cKQWHApu7C/
Lady (1.5 year old tricolour) & Gracie (4 year old blenheim)
"Happiness is a warm puppy" - Charles M. Schulz