My DIY Italian Art Show Experience

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I took a leap of faith this past summer and went to the Amalfi coast in Southern Italy.  My goal was to paint a series of paintings and to sell them in the heavily-tourist area of Positano.  This area is special because of the old hillside homes, amazing landscape and the Positano painters, a group of older (elderly) painters who make a living painting the natural scenery around them.

So I took my half-size french easel, supplies and small paintings with me, went on a bus from my hostel in San'Agnello to Positano about 3 times.  Mind you that being on a crowded bus with all my gear wasn't the hardest part.  It was carrying everything to the beach and back.  Painting when I got there?  That was a lot easier, and more fun.  I designed my easel that it would be a smaller version of an art booth at some art fair, except that I would have much smaller work and use my easel as my workstation and booth.  I kept my paintings in a small basket and a price on the outside.  I also had a big chalkboard sign saying "Art for Sale" hanging from my easel.  People may have noticed I wasn't Italian considering I wrote in English.  And I wanted to see if people would really go for my work or not.  

As for marketing materials, I had postcards made up with a few of my best works.  I also had a guest book to get their email addresses.  Always be upfront and tell them what it's for so they will understand and trust you.  I usually go back home later and put them into my email list.  I mention on my postcards that I am on Facebook, Instagram and YouTube.  Give the people something to remember you by.  Postcards are valued because they are more special than business cards.  People tend to keep postcards and the images are larger.

I painted a different work each time I went out, and I got more comfortable with the set-up.  Several of the Positano painters were curious about my work, they were nodding like they approved.  

I painted for a few hours of the cliffs and a castle ahead of me, I was several feet from the sand with the water also glimmering nearby.  I did get to mingle with a few Italian tourists.  I was painting and being as polite as I can be.  

Though some tourists did look at my work, none of them bought my little paintings.  At one point, it was exhilerating painting in that location.  Another point, I was crushed that I didn't sell any work.  But whether you sell or not, there are some rules to apply so you at least play the successful artist until your ambitions meet your reality.


  • Make sure you have all your gear ready.  Use the best equipment money can buy.  Easel, paints, credit card swipers, whatever it takes.  You have to set your highest standards.
  • Get some good night sleep.  I went to bed a little late, maybe 12:30am every night.  I wanted to relax the night before and just bought the original Karate Kid movie and watched it.  Had several burgers and chocolate wine too.  It’s ok to relax and let loose, but try to go to bed early if you have to get up at 5:30am.  I wasn’t too tired, but I could’ve had more sleep.
  • Love your neighbor. All of the vendor’s tents were very close, every inch counts, so get along with your neighbors and don’t have tent wars.  It will create bad vibes that could haunt you during the day.  I was in a good mood and had patience.  It’s pressure enough selling your art, but don’t fight with other vendors if you can help it.
  • Experiment with your booth.  I was putting my umbrella and baskets in different positions, readjusting signs, learning how to be more efficent.  Nothing wrong with experimenting, I’m just trying to find the right setup that works well.  I felt good about this set-up once I got the hang of it.
  • Speaking of Bungee cords, grab a few.  They are valuable for connecting your weights to the tent so your tent won’t go airborne.  They have become like gold to create my walls with my grids.
  • Bring guestbook to collect new fans.  I didn’t have my business cards with me, but I did ask some people who appeared to be true fans that they can sign my guestbook and I’ll shoot them a link to my website.  Plus, they can also receive my free monthly newsletter.  I like this approach, because building trust is essential in maintaining long relationships, and it get the people involved.  It also helps to assure them that you don’t believe in spam.  And I hate getting spam too.
  • Start a conversation or at least smile.  Who wants to stop at a booth with the artist looking so grumpy?  I know I wouldn’t.  I sometimes struggle because some days I’m in a bad mood and it’s hard to wear a fake smile on my face.  I try to greet many people as possible to my booth, start asking them, “Where are you from?”, “What kind of art do you collect?” and so on.  I just want to get to know them better and see if I can help them.  Last thing I want to do is come across like a salesman.  I hate salesmen as much as wind.  I’m down to earth and want to express my true self.  Good presentation keeps you on your toes and makes you look good.   You want to sell art, but just be a bit subtle about it and don’t act like a shark.
  • If the wind does suck, make the best of it.  Hey, weather happens and you have to adjust to the elements.  Do your best to paint the best you can outdoors.  There's always tomorrow. 

I hope these steps are helpful to anyone painting and selling art outdoors.  Yes, it would have been a better story if I would have sold a lot of work, but then again it was just one chapter.  Many more to go in my book of life.  And I may be back one day.  I'm currently in Portugal now and continuing my journey.

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