How to Start With Milan Art: Free First, Then $99, Then Decide
You don't have to decide about a $3,999 program today. Here's the order we'd actually recommend.
Start free, spend $99 when you want somebody to look at your paintings, and only think about the big program after that. That’s the order, and it’s the one I’d give a friend.
What can I try for free?
A 13-minute drawing lesson. It’s the real first lesson of the Two-Week Challenge, taught by Elli Milan, and all you need is a pencil. It costs an email address. If you want to know whether her teaching makes sense to you, this answers it in a quarter of an hour.
A free painting workshop with Dimitra Milan. It’s called Use This Mixed Media Technique to Sell More Art, and it’s a recording of a real session, two hours and twenty-four minutes with nothing sped up. Dimitra underpaints in acrylic and finishes in oil, and she takes about half the canvas into oil so you can see both stages side by side. Bring your paints and work along, or watch and take notes. It also costs an email address, and you can watch whenever you like.
The blog’s free library. No email wall at all. Every topic has an in-depth guide and a set of focused lessons underneath it.
YouTube. Hundreds of videos on the Milan Art Institute channel, no sign-up.
The prep course. Free, covering studio setup, managing your time around a life, and building an easel for under $100.
What’s the $99 Two-Week Challenge?
The Two-Week Challenge is where most people should go next.
$99, once, no subscription. Five step-by-step lessons producing five finished pieces: two drawings and three paintings. A coach responds personally to every piece you submit. You get assignment briefs, materials lists, live group calls, and 30 days of access from your cohort start date.
The feedback is the point. Watching a video teaches you what to do; someone telling you why your values went muddy teaches you what you actually did. That’s the difference between free content and training, and $99 is the cheapest place we sell it.
One thing to know, because it changes who this suits. The five lessons come from across the Mastery Program and you take them out of order: five techniques, different mediums, different subjects. It’s a taster of how we teach rather than a small version of the program. If you’ve painted before, that variety is the appeal. If you’re starting from nothing, some of it will be harder than it would have been had you arrived at it in sequence, and that can be discouraging rather than motivating. The Mastery Program is the one that builds in order.
If you enroll in the Mastery Program within 30 days of your Challenge start date, the $99 counts toward your tuition. So it’s a two-week trial of how we teach, and it costs nothing extra if you continue.
Two things to know before you buy: it starts on a cohort date rather than whenever you feel like it, and two weeks means two weeks of real evenings.
What if I only want to learn one technique?
If what you want is to learn oil pastels, or portraits, buy a single masterclass rather than a program. Each one is a one-off purchase with lifetime access.
Watercolor Foundations is a bigger standalone course at $399. For teenagers, the Young Artist Program starts at $169 a month.
Can I learn in person?
One-day classes at the Milan Art Gallery in downtown Sarasota, most weeks, 11am to 3pm, at $90 to $100. Materials are included and everything is set up before you walk in, and all levels are welcome. This is the cheapest way to meet us in a room.
Multi-day workshops at the studio cost $995 to $2,300 and are capped at 15 or 16 artists.
All in-person bookings are final. No refunds, no credits, no transfers to another date. Book when you’re sure.
Retreats for 2026 are sold out. The next one is in Oaxaca and Puerto Escondido, Mexico, February 1 to 12, 2027, from $4,400, with a waitlist open.
When should I join the Mastery Program?
You can enroll whenever you’re ready. There’s no waitlist and no monthly registration window; we retired that in July 2026.
It’s $229 a month for twenty-four months, $399 a month for twelve months, or $3,999 paid once. Two years of group coaching, with feedback on every piece you make, is included on every plan, and lesson access is lifetime. The cost breakdown has every total and the refund terms, and the curriculum page walks through all three parts.
If you’re weighing it, there’s a free fit questionnaire and a free call with an enrollment advisor. Neither costs you anything and neither requires you to decide on the call.
How do I know which step I’m on?
Three questions settle it, and they take about a minute.
Have you painted at all in the last year? If the honest answer is no, do the 13-minute drawing lesson tonight before you buy anything, as a test of whether you actually want to sit down and do this. Plenty of people discover they wanted the idea of painting more than the hour it takes, and finding that out costs nothing. If it turns out you do want it, go to the Mastery Program rather than the Challenge, because a true beginner is better served learning in order than sampling five techniques out of sequence.
Do you know what’s wrong with your last painting? If you can name it, you need lessons, and you can go straight to a masterclass or the Mastery Program. If you look at it and just feel that something’s off without being able to say what, you need feedback more than instruction, and the Two-Week Challenge is the cheapest place to get it.
Are you trying to sell? Watch Dimitra’s free workshop first. It’s built around painting fast enough to have paintings to sell. The full business training, with pricing, galleries, commissions, prints and shipping, is Part 3 of the Mastery Program, and it isn’t sold separately.
What does each step ask of you?
The free lesson asks for thirteen minutes and a pencil. The free workshop asks for an evening.
The Two-Week Challenge asks for two weeks of real evenings and a trip for materials before you start. It’s a cohort, so it begins on a date rather than whenever you open the tab, and you get thirty days of access from that start.
An in-person class asks for a day and a drive. Everything’s set up when you arrive, so it’s the lowest-effort way to spend a day painting with other people in the room.
The Mastery Program is designed to take a year, and at your own pace most people land somewhere between twelve and twenty-four months. It’s self-paced, which sounds like the easy option and is the hard one.
Where would we start?
Watch the free drawing lesson tonight. If Elli’s teaching makes sense to you and you’ve painted before, do the Two-Week Challenge and get five finished pieces with feedback on each. If those two weeks leave you wanting the next thing rather than relieved it’s over, look at the Mastery Program with your $99 already counted toward it. And if you’re a true beginner, skip the sampler and start where the program starts, with a pencil.
And if at any point you just wanted to learn one technique and go back to painting on your own, buy the one masterclass and we’ve done our job.
Frequently asked questions
What can I get for free?
A 13-minute drawing lesson taught by Elli Milan, which is the same lesson that opens the $99 Two-Week Challenge and needs only a pencil. A free recorded workshop, Use This Mixed Media Technique to Sell More Art, where Dimitra Milan underpaints in acrylic and finishes in oil over two hours and twenty-four minutes. Both cost you an email address. The blog's free library has no email wall at all, and neither do the hundreds of videos on our YouTube channel.
What is the Two-Week Challenge and what does it cost?
It's $99, once, with no subscription. You get five step-by-step lessons producing five finished pieces, two drawings and three paintings, with personal coach feedback on every piece you submit. It includes assignment briefs, materials lists, live group calls, and 30 days of access from your cohort start date. If you enroll in the Mastery Program within 30 days of your Challenge start date, the $99 counts toward your tuition.
Do I have to do the Challenge before the Mastery Program?
No. You can enroll in the Mastery Program directly and immediately; there's no waitlist and no registration window. We suggest the Challenge first because $99 is a cheaper way to find out whether our teaching suits you than $3,999 is, and the money isn't wasted if you continue.
I only want to learn one technique. What should I buy?
A single masterclass. Each one teaches a single technique as a one-off purchase with lifetime access, and costs a small fraction of a program. Buying a full program to learn one thing is a waste of your money.
Can I learn in person?
Yes. One-day classes run at the Milan Art Gallery in downtown Sarasota most weeks, 11am to 3pm, at $90 to $100, with materials included and everything set up before you arrive. All levels are welcome. Multi-day workshops cost $995 to $2,300 and are capped at 15 or 16 artists. All in-person bookings are final, with no refunds, credits or transfers.
Are the retreats available?
The 2026 retreats are sold out. The next one is the Mexico Art Journaling Retreat in Oaxaca and Puerto Escondido, February 1 to 12, 2027, from $4,400, with 15 artist spots and a waitlist open. Past retreats have run in Greece, Italy, Mexico, South Africa and Florida.
Do I need to buy supplies before I start?
Not to start. The free drawing lesson needs a pencil. The Two-Week Challenge sends you materials lists. Supply kits are bought after enrolling in the Mastery Program, not before, and they're on the Milan Art Store.
