averaged 90 days a year on the water for several decades. Can't recall ever seeing anyone landing a dink in surf. I had a RIB for the last 6 years, and that's about as seaworthy a boat as you'd find, and even that didn't go in breaking surf. Inflatables are way more stable, but will get chewed up by the shore, and they're expensive. A rigid dinghy lacks the handling ability to land in surf, though as a kid I had a plastic double hulled dinghy that did alright. Can't remember the brand, long defunct I believe.
Not sure how big your sailboat is, but personally, I'd go with a dory as a good "recreation/transportational" combo. Way easier backing into the beach with a pair of oars and a double ended hull or wineglass transom.
I packed a 15' canoe on my cabin top and surfed that several times, but not out of neccesity or any desire to stay dry. It also made a good "anchorage recreational vehicle", carried groceries easily.
Historical Note On the Pacific Coast during the age of sail, several ports had hired Hawaiians, who would row the tender boats in through the surf, especially for the Brits who did not know how to swim. San Diego had a famous crew of Hawaiians who were excellent at surf landings. Look at Two Years Before the Mast for a description of life on a sailing vessel off the California coast.
Personally I would go with a Sit on Top like an old Ocean Kayak Malibu II, heavy and slow, but very seaworthy. Most boats on sailboats on the West Coast all the way up into Canada are sit on tops.
no longer confused Well to everyone that suggested I try them out (a few here and a few of my close friends that are also kayakers) THANK YOU!
So here is what I did.
There isn’t too many places around here other than some REI or EMS type places and some other Outfiters that are nowhere near water, but my friend in Rochester mentioned there are a bunch up there. So up to Rochester, NY I went.
Day 1: Bay Creek Paddling Center.
I Rented 2 Sit In kayaks Bay Creek Paddling Center with my friend and we went out into the bay and tried it. I loved it! We were out for 4 hours. In that short time, I learned what you mean by tracking, I felt the effects of Weather Helm in this kayak big time. It was bear to paddle. These guys were so nice, but they didn’t have any of the Sit On Tops I wanted to try.
I found another place Oak Orchard Canoe and Kayak (http://oakorchardcanoe.com/) across the street. They had a much bigger selection and also carried sit on tops as well as sinks.
Well I have to tell you, the Manager there - Michael. Two seconds with this guy and I never wanted to go back in there, but luckily I got to meet Patrick (another manager there) and Patrick is the reason I returned the next day.
Day 2: Oak Orchard Canoe and Kayak - Rochester
To my horror, Patrick was off, Rude Michael was still there and I was ready to leave when I met Lou…Lou would spend the next two days and over 12 hours with me.
Lou was as patient and knowledgeable as Patrick. I told him what I wanted to do and one by one, we went through each kayak. Anything that seemed like it would work, he carried down to the bay and let me launch it. That day I sat in over a half dozen kayaks and took out 4 for extensive test paddling. All the time, he was educating me as I was providing him feedback as to what I liked and what I didn’t about each kayak. (Note, I later heard Michale laced into Lou for providing me with exceptional service)
Day 3: I returned to Oak Orchard with plans to try extensively, two kayaks I was most interested in. One being a Sit in and the other a Sit on Top. But when I got there I started to discuss some questions I thought of overnight which some of you mentioned here…Roll Over.
While I can learn and understand what is happening, my dog could not. I began to think that I may be better off sacrificing speed and dryness for stability and ease of re boarding a knock off in the ocean. Lou confirmed my fear as before this I had no idea the process of either bailing out a sit in or how dangerous it could be for her.
That led Lou to have me reconsider length. We had previously confirmed that 14’ was the right length for me, but now he asked if I could manage with bigger. In agreeing to explore this, Lou had three suggestions. The Wilderness Tarpon 140 (the only boat he did not have on site, but I tried a 120) , An Ocean Kayak Trident 13 and in an attempt to replicate the weight and length of the Tarpon 140 to save me a 1 hour drive to the other shop, a Trident Ultra 4.7 w/Rudder
The bay I was kayaking in was perfect. This day was even better. Water was ROUGH, big boats causing nice rollers and if I got close enough to them, breakers! Wind was strong and gusting. Perhaps a crappy day to be enjoying the bay, but for me - Test Paddling in these conditions…PERFECT!
10 minutes in this kayak and I was loving it. The rudder assisted in compensating any weather helm I encountered due to strong gusts, but even with the rudder up, I found she tracked real nice. She was fast (fast enough for me, my GPS had us at 3-5 mph and 7-8 when not going against the wind and tide) She handled the swells very nicely due to the up-swept bow and when I got her into breakers, only with the biggest and timed right, could I get a boat full of water which quickly drained.
While paddling it, I saw many options for a place to mount a seat for my dog, but also places to securely store food, camping gear and still have plenty of room.
I returned after an hour out on her and said to Lou, I think we found the right boat, but to be sure, I wanted to test her out in the creek. He sent me back on my way and Up the Creek - with a paddle, I went It handled the bends very nicely with or without the rudder and I was paddling against the current and wind. Only when I was entering the creek, did I ever become stalled, but once the gust stopped, she got right up to speed.
When I came back I was able to steer the kayak with the rudder alone as I rode the current back to the bay. When I did Paddle, we were doing 6-8 mph with little effort.
Now for the funny part.
I put the kayak up on the dock and went inside. It was actually closing time (I was embarrassed for getting back so late) and Lou began educating me on PDF’s and Paddles. He told me I should try the PDF’s on when int he kayak. We both went to go get it off the dock and it was gone! His first though was that the other employees put it away when I spotted something yellow out in the bay…MY KAYAK!
Lou quickly grabbed a Tandem Kayak (I began my search thinking I wanted a Tandem ) and he and I raced out there together to recover it and tow it back.
He was right, you do need to try those PDF’s on in the kayak.
At the end of Day three…I was the new and proud owner of the Trident Ultra 4.7 Here she is on the dock before blowing away (yes, the wind gusts blew a 77lb boat off the dock! - Told ya it was strong)
It handled the bends very nicely with or without the rudder and I was paddling against the current and wind. Only when I was entering the creek, did I ever become stalled, but once the gust stopped, she got right up to speed. 
