For me to do it, it would need to be set up. The fourth words in Randy's last two sentences were and and and. Coupling the last three words in the last sentence with Miko's fifth word we have and and and and and.
First off ... Yer statement " which has 5 consecutives ' and's in it but is grammatically correct." That is so ungrammatical. No need for the use of " in it ". Instead of " but " a word like " however " or "nevertheless ". And no need to end with a ? { question mark }.
Failure.The word " gave " broke up any 5 consecutive. Plus misuse of the word " shandy ". It's like saying Barack Obama was a Great President. Misapplication of the word Great.
But forgetting the 2nd one. What's wrong with "I watched a band from on the sand, whilst handing a shandy to Mandy."
While practicing my calligraphy I wrote 'and' and 'and' and 'and' and, believe me, it helped my penmanship a lot. Here's another for 'that' That that 'that' that that boy wrote is smaller than the other word is an interesting fact.