Holidays alone

A cruise would be interesting as you would be visiting fifferent places, or a tour maybe with lots of stops in hotels which means you would probably meet lots if people but they coukd be a ( good) bit older than you.
But if you want a break to totally relax then its probably going to be a hotel. a smaller one might be more friendly. Somewhere there are places to get too to visit. Perhaps a week or 10 days might be an idea. Enjoy yourself

Cruises are ideal for sheepish single travellers. Most lines are very helpful in this regard.

Yes - HF are good - they also do holidays for particular interests - e.g. a music festival. All tickets booked, coach travel to venue, full board etc. Lots of other interests catered for.

Click on this link for more about HF.
www.hfholidays.co.uk/

I used to holiday alone several times a year, often in the Canaries. I am a bit of a loner anyway, so always booked a self-catering apartment. I would have felt uncomfortable on my own in a dining room at a hotel, didn't want anyone feeling sorry for me and latching on!
I would hire a bike and explore during the day and in the evening cook myself a meal. On some holidays I would speak to nobody except shop assistants, but that didn't worry me.
If you like company check out HF holidays who do walking and special interest holiday in the UK and abroad. There are always several single people in the group, mainly middle-aged women. I really enjoyed the UK walking ones that I did. Not cheap but you don't have to spend any money at all while you are there. The meals, especially the packed lunches, are amazing!
I hope you will pluck up the courage to go away, it sounds like you really deserve a break!

Sounds like you really need the break , so as our American friends say- put your big girl panties on.... you can do this.

I have travelled alone extensively , although mostly for business but I think the same things apply.

Why not book yourself the perfect holiday. First off find a hotel you like the look of - what MUST you have ...beach? pool? culture? Then book flights with a low cost carrier. Take your kindle ,stacked with books and an open mind and head off.

People on holiday are likely to welcome you, everyone seems friendlier somehow so you are unlikely to speak to no one. You can suit yourself and really relax.

Enjoy!! You deserve it x