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I got a lot of questions about traveling with painting supplies, and I am going to try and explain my whole process here. 
#1 Rule of Traveling with Paint... Don't call it paint! Your paints are now 'Artist Colors' and they are allowed to travel with you. According to the FAA watercolors, acrylic and oils are all allowed, but solvents, brush cleaner, paint thinners are not. You can find more info here by searching paint. 
I always include paperwork stating on the FAA website that these 'Artist Colors' are allowed, with my name and phone number incase they need me to explain anything. 
1. PAINT I usually lay out all the paint I want to bring by color to make sure I am covering all my bases. Then they all go in ziplock bags and into my paint box. I have the medium in natural. 
2. BRUSHES I wrap my brushes in my apron and put them in a little leather case for protection.
3. EASEL I have an Italian MABEF travel easel, which you can buy at Blick and it comes with a sketch box incase I am not able tor bring my whole painting box. 
4. SURFACES I only bring flat small masonite board and paper to paint on while traveling. It is not worth it to me to worry about puckering canvases or the extra hassle of a cradled panel. I like to paint small while abroad and fill my idea book with sketches, shapes and colors. Once I get back to my studio I can explore the scenes in a larger size. 
5. JAR for water!
6. TAPE incase of wind!
7. PALETTE - I use disposable ones so I can just throw them away rather than worry about cleaning up all the leftover paint. 
8. Micron Pens
9. Neocolor Wax Pastels
10. Pencils 
I love the Calpak Trunk Luggage because it fit my art supplies plus clothes. Highly recommend it, just have to be a bit careful about the 50 lb weight limit as supplies add a lot of weight. (Shoes and jeans are heavy so put those in your carry on!) I also brought a small carry on rolling bag for more clothes. Once we arrived, I would only take my carry on for weekend trips and used a bungee cord to attached my easel to the top. 
You can see the whole process a bit better on the reel I made here
I hope this explains everything well and feel free to reach out with any questions!

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