I haven't been on one, but I have been on cruises which is a lot of fun, as long as you don't mind dressing for dinner. IMHO adding great music to the mix could only be a good thing.
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My wife and I went on "Art Goods Jazztracs" cruise about 10 years ago. It was a short 3 day trip that left from San Diego, stopped at Catalina Island, and then down to Ensanada Mexico. It was relatively cheap to do, except for the alcohol, which really gets crazy expensive on a cruise ship. It's not like my wife and I are BIG drinkers or anything, just that people on a cruise are a "captive" market,so they gouge you big time on beers and cocktails. At the end of the cruise we ended up spending more on liquor than the cruise cost. Crazy huh? The room we got was reasonably sized, but upgrades are always possible if you want to pay the upcharge. I would reccommend doing that so you can get a room with a view of the ocean. I think rooms on the interior of the ship,(no view), are closterfobic. The food on our "jazz" cruise was excellent and plentiful as most cruise ship cuisine is. Definately can eat non-stop till you pop! As for the bands/performers we saw- Our lineup was varied with artists like Richard Elliott, Norman Brown, and Warren Hill. We also had David Arkenstone(new age guitarist), and Richard Smith(another Guitarist), and Jeff Kashiwa(Saxaphonist for the Rippingtons). I thought the line up was cool and they spread the shows out over the ship at different times of day and night at different venues, which I thought was a good thing to do(so you can go do other non-jazz stuff around the ship).We saw different performances out side on a big deck by the pool one day, inside a small cocktail lounge one afternoon, and also inside one of the big showroom/theaters(usually all the acts end up doing a set at night in the big showroom).
One of the coolest things that happened was on Saturday when the ship was docked in Ensenada for the day, all the artists and their band members were out and about the little mexican party town with all of us, so we hung out with the likes of Richard Smith, and his drummer, and keyboardist from his band. We had lunch with them at Hussongs Cantina in fact. Drank margaritas with them. Because the band members of all the acts were on the ship for the whole weekend with us, we saw them hanging out, had drinks with them in the bars on the ship, and caught rays with them out by the pool. 2 members of Richard Elliots band ,(guitarist Richard Smith and the drummer, whose name I can't recall)sat at our "assigned" table in the main dining room...for breakfast, lunch, and dinner,(ALL WEEKEND LONG),we got to b.s. about everything under the sun, got to know them as "people", saw pictures of their kids, talked music, politics, and just about everything else you could think of. My wife and I really thought that was rightous experience. On Saturday,the day we were roaming around Ensenada "half-lit" on
Coronas and shots of tequila, buying all kinds of "tourist" junk and other stuff you don't ever need, we walked into this little gift shop, and right there in the middle of the place, Richard Smith was jamming on some little guitar that was for sale by the locals. His wife who is an awesome singer was doing some scatting' and singing, while some other guy was playing on some congo drums(also items that were for sale in this gift shop). How cool is that? Our very own impromptu performance unfolding in a mexican gift shop! It drew quite a crowd as the little jam session went on for about 10 minutes!
So I think jazz cruises are cool. But buy your own bottle of liquor and mix-up drinks in your room unless you want to dump a grand on cocktails and beer, (which we did). So go for it Slowhand because it's a BLAST! lots of great music lies ahead, and you might even make friends with one of your favorite artists!