How to tell apart despite and although?

After despite we use a noun, the noun form of a verb, or a pronoun.

We enjoyed our camping holiday despite the rain.
Despite the pain in his leg he completed the marathon.
Despite having all the necessary qualifications, they didn’t offer me the job.
Despite having a lot of money, they are not happy.

Remember that the gerund (‘-ing’ form) is the ‘noun’ form of a verb.

After although we use a subject and a verb.

We enjoyed our camping holiday although it rained every day.
Although he worked very hard, he didn’t manage to pass the exam.
he holiday was great although the hotel wasn’t very nice.
Although they have a lot of money, they are not happy.