Hi Ellen,
Welcome to the world of Just You, personally I have thoroughly enjoyed all of my Just You holidays but don't just take my word for it - I would recommend that you take a look around the boards and see what some of our travellers have said about travelling with us - hopefully their comments will help calm some of that apprehension.
Our Flavours of Tuscany tour launched last year and Janib (a community regular) travelled on the October departure. You can read her review here: forum.justyou.co.uk/thread-81981.html
We don't include Travel Insurance in the price of the holiday as different travellers have different requirements. I'm sure some of our community members will share with you who they use. We recommend Holiday Extras, a company we have partnered with for a number of years. You can find out more about their cover by calling 0800 042 0201 and quoting ALJUS.
If you have any further questions or queries please don't hesitate to ask.
Kindest regards,
Julia