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A person who opposes and rejects many of the conventional standards and customs of society, especially one who advocates extreme liberalism in sociopolitical attitudes and lifestyles.

Similar to the "hippie", but often with worse personal hygiene, less coherence, and a more extreme disposition to aloofness.

A person who eats, sleeps, and generally lives for Phish & The Grateful Dead, often following them on tour around the United States.
"Phish just reunited, and all the Gondolis are preparing to crawl out from under their rocks and reappear in society"

"It took 6 hours to drive from NYC to Albany NY for the Phish show because the roads were filled with Gondolis"

"It really smells in this arena because of all the Gondolis that haven't showered in weeks"
Gondoli by KMW231978 February 11, 2010

Fudge Gondola 

When you are having anal sex with someone you know has explosive diarrhea and you pull out your poopy dick to butter the taint and then blindly thrust between the woman’s legs and say “There's no earthly way of knowing , Which direction we are going

There's no knowing where we're rowing

Or which way the river's flowing”
Before Willy Wonka would agree to release Augustus from the chocolate tube he demanded that misses Gloop take a ride on his fudge gondola.
Fudge Gondola by Takearide90 July 8, 2019

Castle Gondola 

The motherfuckin spot
Surely meet me at Castle Gondola tonight

Let’s go to Gondola and get fuckin zoomed

gondolasoupin 

enjoying a nice bowl of hot soup in a gondola
kaitlyn: hey where have you been?
sophia: i was in venice gondolasoupin
gondolasoupin by sauceyum March 24, 2023
A light flat-bottomed boat used on Venetian canals, having a high point at each end and worked by one oar at the stern.
Another meaning is the seating compartment in a ski lift.
When I went to the Vatican city in Rome, I enjoyed a wonderful time on gondolas.
gondola by Oliviana123 April 4, 2015

Gondola Challenge 

When a man and a woman both try to reach an orgasm on a gondola while skiing or snowboarding before reaching the top of the mountain. This can sometimes be a very hard task if they do not devote themselves to the challenge at hand.
Man: "Hey, I just did the gondola challenge on the way up here"
Friend: "Damn! I've been trying for years to complete that."
Woman: "Ohhh yeah"