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I'm booking a mini-tour for a folk-pop acoustic duo this June 4th-26th. We're hoping to head from San Francisco (staying for a week) to Seattle, to British Columbia, Canada. We've been sending out messages to venues, bands, community pages, craigslist, and so far, people say they'll help or direct us to someone else, but nothing has actually pulled through. Do you have any suggestions about who to message, potentially hitting up different cities along the way, or what we should do in general? Any advice would be extremely appreciated.
Your initially wrote a couple-few weeks ago, and so I am not surprised that perhaps you were not getting a response from folks -- being an unknown band trying to book dates three and half months out is tricky. It's probably a little too far out. I understand wanting to plan, but the small clubs and cafes and house venues you may be hitting up are not likely booking openers that far ahead.
Since I don't know what kind of messages you are sending or who you are asking for help, it's hard to exactly diagnose what could be hindering you, so I just have to instruct in what you should do. Check with friends who go to shows or are musicians in other cities you would like to play and ask where you should play. If you do not know someone there, try your best Google-fu -- look at the weekly listings online for the Portland Mercury and see what is the best acoustic folk spot there, look at the tour routings of bands you know that are like yours -- even if they are a little bigger. Where do they play in Eugene or Oxnard? You might have to book some fill-in dates in secondary markets or smaller college towns. That might be an easier nut to crack than, say, Seattle on a Saturday night.
Approach clubs and promoters directly unless you have a good connection through another band. Some of these bands -- hopefully folks you have played with before who are interested in reciprocating in their town -- might be too busy/lazy to proactively help you. Can you drop their name? How about just asking them if they will get on the bill directly? It's important to ask for exactly what you want. When you are a band that promoters do not know, it is sometimes a better bet to come with the outlines of a bill. Say, "Oh, we are friends with 3-D Cosbys, we are checking to see if they can play." Something that at least hints that you have initiative and a connection or two, which separates you from every other teeny tiny touring band with no draw that dials them with hands outstretched, hoping for a favor. June is busy. They may not have favors for you because the have national tours through most every night.
If someone says no, ask them if they have another suggestion for who you should try. You might just be knocking on the wrong door. Some clubs or promoters might have an FAQ about booking shows -- they might have a specific protocol about how to try to get a booking. Make sure you check that. No answer at all? Try them on Twitter. Maybe the club intern or publicist who (wo)mans that ish is crazy helpful in a way that the booker is not and can tell you, "Try Jenny at Taco Yurt, they do folk house shows." When in doubt, call the independent record store and ask where the spot is. There are lots of them all along the West coast. While you have them on the phone, ask about an in-store. Work all angles at all times. You can also try the punk standby Book Your Own Fucking Life site.
Wherever is your best connection, try and see if you can lock down a hold on a date with them and make that be your anchor date which you book the rest of your dates around. Then you can call these other venues, email these other cities promoters and say, with specificity, that you are looking for Tuesday the 14th, ideally, but could swing Wednesday if you had to. Telling them exactly what you are needing is going to yield results that saying "Any night between June 14th and 19th, or maybe the 22nd?" might not.
Also, the sad truth about booking is that you have to hound people. First email is all the basic info they might need -- what date you are looking for, and TOPS two sentences about the band: including if you have another band locked down to play with you, if you have a new album, a publicist or label promoting your tour, if your friend who does the listings at the cool blog is going to preview your show -- anything that would be beneficial. Make sure there is a link included where they can hear your music easily. I'm a big fan of Bandcamp for that (lest someone get lost in the netherworld of the Myspace reboot). Your description of your band's music should not exceed five words: "female-fronted acoustic folk band" or "queer-positive Mumford-influenced folk," "French ye-ye meets a stoned Zombies," or whatever. No one needs a long description of your band or a full bio. Link the bio, link the music, make it sound like you have your shit together and are just anxiously waiting to send out a bunch of nice looking flyers and promote the shit out of your show.
Not sure what sort of community forums for flakes or Craigslist postings you are sourcing info from, but if you are looking to keep things at a DIY level, ferret out the house show folks in the city. Any scene worth its salt should have at least one good warehouse, a feminist collective space and one nasty art school drop out-run basement venue. You are a folk act on the road in June -- work that Farmer's Market circuit, starting now. You might have to dig a bit, but is there some Concert In The Park series you can get in on through the city? Could you book yourselves into a pergola/gazebo at dusk at some park on a Friday night? Maybe you need a $22 permit, or maybe you just need permission, or perhaps you just need the punk mettle to bum rush that Quonset hut or pop open the van and play outside someone else's show. That is the true advantage of being acoustic -- people don't call the cops on you to complain about the noise. (I have an entire chapter in my book about super DIY touring, if you want more ideas).
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Given that you probably are not going to make much (or any) money on this tour, focus on what is going to be fun and memorable. Does you college roommate have access to her parents' house on Mercer Island -- maybe she wants to throw a party and have you guys play! I think the birthday party/on-campus Chinese resturant/ troubadouring at the dog park on a Sunday morning circuit is way more enticing than clubs, but really, you can do both. You are in a position to build whatever the heck you want, and your dream needn't die because some hoser off Craigslist didn't email you back with the number of the bar where his cousin is a DJ. Go nuts, say yes to weird ideas, get up in the pagoda and busk. You are going to figure this out, just be tenacious and ask for what you want and don't wait around for other people to do for you what you can do yourselves.
Good luck and have a safe tour!