I have purchased 2 of the boat totes, 1 med and 1 small. I use the med on a daily basis and it's great. I bought the small one for days that I don't need to carry quite as much. While I love the med one I'm a little disappointed with the small one - it sits lopsided. I should have returned it, but didn't want to bother with it. Overall I really love these totes.
My new bag is very nice. I opted for monogramming as well. Looks great. Very durable fabric. My only complaint is that the handles are too wide at the top (where you hold the bag). I am a woman with average size hands, but the handles are the whole width of my hand and it hurts after a while (I get marks on my hand). The fabric being heavy, it does not bend. I wear the bag on my shoulder to avoid this problem, but sometimes, when my bag is heavy, I would prefer to carry it in my hand.
I received a Boat and Tote bag as a gift about 12 years ago. I'm a teacher, and I've used the bag every day to lug lots of stuff to and from school. It has finally just gotten grungy and worn looking enough (although still certainly usable) that I wanted to replace it. Not knowing the size, I guessed I had an x-large (I carry my school stuff, laptop, lunch, purse in it), so I ordered an x-large. OMG. The xtra-large is HUGE. The kitchen sink would LITERALLY fit in it! After talking to a customer service representative, I figured out that the size I owned was a medium and, if I wanted the same size, that's what I needed. So, I'm sending back the x-tra large and ordering a medium!