I have been feeling a bit overworked lately and I think a longer vacation would be beneficial for me. I only had short vacations in the recent years. The problem is I feel a bit uncertain about how to even approach it. One problem is that I don’t feel very inspired in visiting any particular place or doing any specific activity. I guess I could choose something kinda randomly but the bigger problem is I don’t know who to go with. I am a divorced single dad with a 6y daughter but I would prefer to have a vacation without her as taking her seems like too much worry that would easily prevent me from being able to really relax unless there is someone to babysit her at least half of the time. In the past I used to have vacation with family (ex wife, parents, brothers, etc) but I don’t feel comfortable going on a long vacation with them anymore and they probably wouldn’t be available anyway. I have a wide circle of friends, but I feel like I suck at organizing people and getting to organize just a single friend (not even being sure who it should be and what we would do) to go with me seems like a massive struggle and I don’t really have any experience with that – besides the family, I mostly travelled on my own in adult life, which used to feel pretty cool, but recently I have been feeling very lonely and I fear going on a vacation on my own could easily reinforce that and thus prevent me from having a good time. Advice?
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First. Breathe.
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Second, I would suggest Europe with a rail pass. Leaves a lot of options with one expense. Don’t organize everyone. Make an itinerary based on certain cities around certain dates and let people know they are invited and if they want to come for some or all of the trip they can HELP you organize.
Seems like it would be fun to have various groups of friends come and go throughout the experience maybe all being in one place for a short time.
Go camping. Stare at a fire. Something will come to you.
I like to browse through Atlas Obscura’s planned vacations. They do a full itinerary.
If you’re in the US, many national parks have a vacation planner.
Also, don’t knock a staycation. Being a tourist in your own city/state would probably make things a lot easier for you.
All inclusive resort in Cancun is where I go to recharge. Can be fun with friends or alone (I like poolside reading). Not much to
Plan except getting there. If you don’t want to sit all day you can book full or half day excursions usually right at the hotel.