A father and son trip (previously posted other questions).
Itinerary- thought/suggestions welcome as to all. Winery visiting planned for all locations

Day 1. Fly into Santa Rosa, Drive to Bodega Bay- considering Bodega Bay Lodge

Day 2. Spend and stay in Headlsburg Area- issue: booked up, considering staying in Windsor- any thoughts/comments on this concept?
Considering Peddle and Paddle trip here. any experience with this?
Day 3. Spend/stay in Calistoga area. Maybe a bike tour here. Any view on whether it would be nicer here or on Day 2 around Headlsburg?

Day 4 Spend/stay in Yountville Area OR Sonoma Area- opinions?

Day 5 Leave from Santa Rosa

Still looking for hotels in most areas, and I realize things are getting booked up. But, if you have some gems or personal suggestions, we'd love to hear them. I'm working through tripadvisor, etc., but I trust fodorites the most. Goal is to stay under $200/night -but less is ok too!

Thoughts for must see wineries or other 'things' at any of these locations also appreciated.

Thanks in advance as always!

Healdsburg, Calistoga and Yountville are not very far apart. You could leave Bodega Bay and be in Healdsburg in an hour or hour and a half and spend a full day exploring Healdsburg; then drive to Calistoga for the night. It is only a half hour from Healdsburg. And Yountville is only about an hour from Healdsburg. So you can stay in one place for 2 or 3 nights if you wish. I don't know much about Windsor but it is pretty close to Healdsburg and that would work fine for a night's stay. I think spending a night or 2 in Napa Valley would be nice also. The relatively inexpensive hotels I know of are Washington Street Lodging in Calistoga (pleasantly rustic cottages), Napa River Inn in the city of Napa (very nice) and the new Avia Hotel in Napa. The city of Napa is a half hour from Calistoga and 45 min. to 1 hr. from Santa Rosa.

We recently stayed in Windsor for 6 days and loved it. The town is adorable and has a small-town charm to it. It was an excellent base for making day trips to Sonoma, Calistoga, etc. I'd definitely recommend Sonoma over Yountville, the wineries in Sonoma were some of our favorites. I can't help you w/accommodation since we stayed in the Worldmark timeshare and also rented a house for a family reuinion. Also, we ate at Bistro M in downtown Windsor which had great food and moderately priced.

I wouldn't recommend staying in Bodega Bay, we went thru here on the way down to Point Reyes and the road is very wind-y and it took much longer to get there than we thought it would. With only 4 nights, I would just pick a place and stay there the entire time.

Also if you want to do a kayak trip, make sure you plan ahead! We showed up at a place along the Russian River at about noon and they said they only take people out once a day at 10-ish.

Thank you both for your thoughts- it does makes sense if they can avoid the checking in and checking out of places every single day. As soon as the airline tix are set, we'll book the 'outings'.

Hi; This is an all day wine tour that includes a very nice lunch. They go to smaller wineries where it isn't overrun with people. We had a lovely with these folks. They use a small van and we only had ten people with us that day. Richard www.platypustours.com