All The Best Festival 2020

A record of our preparations for the music festival and vacation originally scheduled for November 2020 in Punta Cana.


Getting Started

For a number of years, I toyed with the idea of going on the Cayamo Cruise which annually gathered a bunch of my favorite musicians for a week in the Caribbean. The cruise was more or less “hosted” by Buddy Miller and Jim Lauderdale, whom I listened to regularly on Sirius/XM. I’d never acted on the notion because I couldn’t imagine Barb would be interested and I couldn’t figure out how to justify a potential trip for me and Joe, who shared a lot of the same musical tastes. I also honestly wasn’t that interested in being cooped up on a ship with a bunch of old farts like me, jockeying for seats at various shows. Some of it sounded fun, a lot of it seemed like an ordeal.

In early February, 2020, it was around the time of the cruise and I was wondering when the Buddy and Jim Show would feature it on the radio. I searched for the cruise and stumbled upon the All The Best Festival being offered by the same company, Sixthman. This festival was land-based at a pair of adjacent all-inclusive Punta Cana resorts and also featured a bunch of my favorite musicians.

The inaugural All The Best Festival had been held in November, 2019 and had an impressive line up (though it would have been even more impressive if Jason Isbell and Amanda Shires were included as originally announced; Kacey Musgraves was also on the bill for awhile, an indication that these things have a way of changing). The 2020 acts announced at that point included John Prine, Bonnie Raitt, John Hiatt, Steve Earle, Todd Snyder, The Jerry Douglas Band and Ana Egge — plenty enough to get me interested. I checked out the resorts, Breathless Punta Cana and Now Onyx, and they both looked decent.

I toyed once again with the idea of going with Joe since I figured the musicians were right up his alley as well as mine. Then I also thought of asking Allie and potentially Dan, her boyfriend. Then I thought of maybe blowing things out to extend the invitation to Betsy, Sara (and maybe Tyler) and Kristen. It all got too complicated and I figured it would never actually work out. The last thing I thought was that Barb might actually be interested in coming.

I mentioned the festival to Barb as casually as I could manage at dinner one night and was shocked to find that she was potentially interested in going for a November getaway in the sun, as long as she didn’t have to deal with the music. I broached the idea of maybe inviting Allie and Dan (I figured I wouldn’t be able to get away with the whole Embrey crew) and Barb seemed open to that as well.

I texted Allie the next day, February 10, with the idea and she was at least somewhat interested. She didn’t know the musicians very well, but it was tempting to have a vacation in the sun. She checked with Dan and again, there was interest but also concern over having enough vacation time and the cost. The festival was in pre-sale mode so within a couple of days we put our names on the pre-sale list and waited for more information. No one was ready to make a final decision yet.

The following week, February 17, I got an email saying my booking window would start the next day at 11:15am and would last about 36 hours. Time to make decisions, ready or not. After a bunch more texting back and forth, we got a green light from everyone. I took a deep breath and booked two rooms for us. I got travel insurance so at least we’d get something back in case people changed their minds or something else happened.

The day after we booked, February 19, they announced additional acts including, I’m With Her, Margo Price, Iris Dement, Paul Thorne, Watkins Family Hour, Ian Noe and Jeremy Ivey. I was very excited by the additions and spent hours listening to the various acts to start getting acquainted.

Today is February 20 as I write this and I must say I’m quite excited and pleased with the prospect of this festival. I’m cautiously optimistic that it will all turn out well for everyone. I like the anticipation aspect of a big event, plus it helps lock in our calendars for the year. In a couple of weeks we’re heading to Aruba with Allie, then Barb and I will be going to London in May. Laurie is coming here in a few days and I hope to nail down a trip to Spain in July/August. I also want to figure out a time to go see Allie in Boston later in the year, which I hope we can figure out in Aruba. That makes for a nicely busy year, I think.


March 30, 2020

What a difference a month can make. The Covid-19 coronavirus has become a global pandemic and the world is in various stages of lockdown. We haven’t heard anything specific regarding the festival, but I see there is a Coronavirus Travel Alert dated March 3 on their website (funny how they didn’t push that out to us). Basically, it says that the resorts will do everything they can to stay clean and that the festival organizers are closely monitoring the situation. I know at this point, with many payments (including ours) in hand, they don’t want to cancel or postpone the event. There will be a lot of ground to cover between now and that point.

For the moment, I retain a small hope that the festival will go forward in November. That would mean the virus has abated enough worldwide to allow travel and gatherings. I admit, though, that’s probably wishful thinking even now, nearly eight months out. My secondary hope is that my “cancel for any reason” travel insurance doesn’t have a clause that excludes the virus.


May 23, 2020

Within days of writing my previous entry, it was announced that John Prine was in the hospital with Covid-19 symptoms. I started working on an appreciation of his music as a way to celebrate and remember him. A week later, on April 7, 2020, John passed away.

The Festival organizers, including John’s family, took some time to mourn and reassess. In May, they announced that the Festival would go on but rescheduled for May 19-23, 2021. They also announced several lineup changes: Bonnie Raitt was unable to reschedule but all the others were still on the bill; added were Jason Isbell and the 400 Unit, The War and Treaty, Tre Burt, and the John Prine Band. We were given the option of a refund or credit toward other events, but we decided to stick with the Festival and now look forward to next May, with fingers crossed. If the festival happens, it will be an extra special celebration of John Prine’s life and songs as well as everyone surviving in a post-pandemic world. I hope to be there.


November 6, 2020

The All the Best Festival sent an email yesterday that they are postponing the event indefinitely and issuing refunds. Sigh. I was holding out the faintest hope of the festival going forward in Punta Cana in May 2021, but no more. It may eventually be rescheduled. Or maybe not. It was nice while it lasted.

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