A little anxiety ahead I think is normal. What will it be like traveling with this group of strangers for 3 weeks? Will the food be good? Will I figure out what I want to do in my free time? How strenuous is this tour? Will I be able to find my way around in my free time? etc!!
Group travel - After your first couple of days you will know everyone's name and you will not be strangers. Be sure to print out your roster which will come about a month ahead with the list of the hotels other than the first and last which you will already have. Take that with you to the first meet-up as there will be introductions then. I usually try to make a few notes...where people are from, who is with whom, etc. I also try to talk to everyone and try to sit with different people for each meal. There are some really interesting and entertaining folks on these tours!
Food - I think the group meals are very good. I am a vegan so my expectations are probably lower than others but I've had some delicious meals. Right now, wishing for cooler weather, and remembering the vegan pumpkin soup the hotel in Reutte served me as a starter. Oh My Word. If you need restaurant recommendations for your free time the guide will be excellent about that!
Free time - In the cities you will usually start with a city walk and you can often decide what you want to come back and see. Take your guide book (tear out the sections for the areas you are visiting!) and flip thru it on the bus before you arrive at your next destination. Your guide will also have excellent suggestions on what to do if you are stuck.
Activity level - Believe Rick when he says a day is strenuous. I usually am very good about increasing my walking ahead of a tour and for this tour I was up to walking 10 miles 1 day a week and doing 4 miles 2 or 3 other days. That was probably overkill but I did not run out of energy! I would say you need to be able to walk 4 or 5 miles several days a week. I am leaving next week on a RS tour and it is so smoky here I have not been able to get my walking in. Even inside it is smoky. I will just make the best of it and it will all be fine!
Finding your way around - In each city your guide will do an orientation to the city and to transportation. At each hotel, as you get your key, pick up a business card from the desk and put it in your purse/pocket. You will also have a list from Rick that he encourages you to keep in your money belt. The hotels in the big cities like Venice, Florence, Rome and Paris all have big pads of maps at the front desk they will give you and they will mark the location of the hotel on it if you ask. I had them do this in Venice because that city confuses me!
Luggage - You do need to manage your own so it is good to pack light. In both Venice and Monterosso you leave the bus and take public transport to your hotel. In Venice, of course, it is vaporetto. In Monterosso you leave the bus in Levanto and take a train in to Monterosso. Both times I just packed a change of clothes and toiletries in my tote bag and left my suitcase on the bus so I didn't have to manage it off and on the boat/train.
Wow, went over the character limit so have to do another post!