You don't just pack up the van and head out on the road. These days, they start planning their tours at least 4 months in advance. Ideally they'd be looking even further ahead, but they can put together a tour in 4 months now. "Our first tour was very difficult to pull together. It could only get better."
They start with a particular show that they want to play, and then figure out the logistics around that. One of their favorite examples is Moonlight on the Mountain in Alabama. A non-profit performing artist series, this isn't your standard bar gig. It's more of a concert series. That fits their folk style and allows them to really connect with their audience.
Once you have your keystone show booked, the real planning begins. Look for other gigs to play on the route there and back. They like using Sonicbids to find gigs because "its easier than trying to find gigs using google, and it's simple to apply." Look all throughout the region you're touring through to find other opportunities to play.
Another reason they like the keystone gig approach is they start to build a list of places they can go back to. "Pick one spot you know you can draw, and build a reputation." Build a local audience in different parts of the country you can re-visit in the future. Remember to connect with those fans on social media or get them to sign up on a fan email list. Having fans is only half the game, you need to be able to reach them to let them know when you're coming back to town.
Hillary Reynolds Band played JD's bar in Greenbay, which is a biker bar. Despite the style mismatch, the gig went really well. The booking agent at JD's bar knew one of the producers for the morning show on the local Fox affiliate, and arranged an introduction. The band ended up performing on TV as well, and now always give that station a call when they go through that area. As you perform in various parts of the country, keep a list of your contacts so you can revisit them in the future.
Hillary Reynolds Band learned early on that they can't just rely on the venue to promote their shows. You need a plan. Look for press opportunities, local news and radio shows. They'll take press opportunities over another show in the same town. It's better to play one sold out show than two half filled shows in the same city.
When they book a show, they always ask the venue for their press list. There are two advantages for you here. First, you get a head start on who to contact in a town you may not know. Second, if the venue doesn't have a press list ready, it's an indication of their professionalism. Once you've got that press list you can start doing the leg work. It's much easier to reach out to someone when you can say "I got your contact info from so-and-so from this venue where we're playing." By giving them some context, they're already more at ease and receptive to working with you. Also, because you're calling about a specific gig you've already booked, that gives you more legitimacy.
You're ready to reach out to a radio or TV station. What do you want from them? Do your research on the station and pick your goal. Figure out which show you want to get on, or which anchor you want to talk to. Calling with a plan shows that you have prepared. Look into what bands or events they have covered in the past. It's easier to start a conversation with "I saw you covered X band two weeks ago, you may be interested in what we're doing next week." The more context you can put around your proposal, the more successful you are likely to be.
Paying for hotel rooms can quickly eat into your touring budget. Look for cheaper alternative places to stay. Try reaching out to people you know to see if someone can put you up. Its not particularly safe to ask openly on social media if someone can host you, so try asking individuals through a private message instead. As Jeff said, "I prefer a couch to a floor." Fans are happy to help out the bands they love.
Some performing arts series, or other concert series, will offer lodging to their performers. That's a very nice perk.
Be realistic about your expectations. Are you really going to be happy if you're camping through your tour? Hillary Reynolds Band realized this is not something they'd be comfortable doing. Maybe your band is more comfortable roughing it. Bringing an air mattress opens a lot more possibilities and they can be pretty comfortable.
"Check into the motel with fewer people than will actually be staying in the room." If you show up in the lobby of a motel with 4-5 people, they'll know something is up. If just one or two of you go in then it looks more like a "normal" rental instead of a group trying to squeeze in as many people as possible.
Touring bands have gotten a bad reputation in the past with hotels. Blame Keith Moon for that. While celebrating his 21st birthday, he famously hurled a five layer tiered cake, kicked off a food fight that ruined the carpet and stripped to his underwear and backed a car into the swimming pool. That's probably not the best example to follow.
What have you learned from your tours? What are your favorite survival tips for the road?