My company allows a 5 week paid sabbatical every 5 years. The issue always is where to go. Right now I have two options (three I guess if I make it a staybatical): Option 1 - January The wife and I are already booked for a 7-day Caribbean cruise and a few extra days in San Juan that bring it up to 13 days including travel days. That leaves me 3 more weeks to plan something else. Option 2 - July/August We have planned 2-3weeks to travel to St John's, Newfoundland, St Pierre and Miquellon, Halifax, Moncton, and PEI. So my question is first (obviously) when would you take your sabbatical? Second, if you took January, where else would you go? I would want a few days of home time before going back to work, but other than that it doesn't matter too much. I don't know if I would go back to Paris, Amsterdam, Brussels, or Luxembourg and no Canada. Taking option 1 would also mean any subsequent travel would be solo as the wife has to be back to the SBUX monster.