I wanted to post a message about our time in Westport since I relied heavily on these forums for the planning.
We were there from March 1 - 3, stayed 2 nights in the Boulevard Guest House.
We drove from Dublin on the M4 / N4 and it was super easy. We are Americans that had never driven on that side of the road. If you are careful, and especially if you have another person in the passenger seat to help, it was no problem. We spent the extra money on the Garmin GPS ($13/day at Avis), and it was definitely worth it.
Matt Molloy's is worth it, but you don't really have to plan an evening around it. You just sort of pop in after dinner and get a drink. We heard some fun live music. I enjoyed a pint of Guinness and my wife had a Baileys and coffee. Cost us 11 Euros I believe.
The Boulevard Guest House was not as fancy as I imagined. I think I was forgetting what standard to have in mind for a B&B. We had a simple, but pretty room (the blue room), and it was very nice. It's hard to say if it was worth 80 euros ($105), because I don't know about the other places. We loved the owners and inn keepers. There is no question it is incredibly convenient. If you have the money, spend it at Boulevard.
We ate dinner at 2 Italian Restaurants. One is called Sol Rio, the other was just up the street called (Mediterranean?) I think. It's in a little alley up from Sol Rio. Both were nice. Spanish house wine at the Med. Italian Place was best house wine I have tasted, even better than Italy.
Marlene's Chocolate Haven was worth it for us. My wife got a hot chocolate which she loved, and we got some little chocolate treats and used it as our Starbucks-type place to hang out and journal about our trip. They were pretty ok with us camping out there for a few hours since we bought stuff.
Lunch we got some food from Gavin's Cafe. I think it's better than the stuffed sandwiches next store. My wife loved her soup and the Irish brown soda bread.
We didn't climb Croagh Patrick, but we went up the ten minute walk to where the statue of St. Patrick is the overlooks Clew Bay. If you don't want to hike, it is worth it to walk up there. You get a nice view, and it would only take 45 minute roundtrip from your B&B in Westport.
I'd be happy to answer any questions anyone has about anything else. I tried to be as detailed as possible. Westport is very very walkable. We were there in early March and it was chilly, but we were blessed with sunny weather.
Euro is strong right now.
From Westport we drove to Louisbourgh, Leenane, down through Ma'am s Cross, toward Galway. We spent the night in the Waterfall Lodge in Oughterard. This was our favorite B&B in our 2 week trip. VERY WORTH IT!