48 Travel Jokes: The 2000 “New Millennium & New Sim” Edition

Traveling in 2000 was a weird mix of survivalist relief and early tech frustration. You still had a pager in your pocket “just in case,” but you were also trying to load travel maps on a tiny monochrome phone screen while praying your 64MB USB drive didn’t corrupt your itinerary.

The 2000 Top 10: The “Surviving the Century” Classics

1. The Y2K Survivor: Why did the traveler keep a canned ham in his carry-on? Because it was Jan 2nd and he still didn’t trust that the airport’s automated sandwich machine wouldn’t start a revolution.
2. The Sims Addiction: Why did the tourist forget to visit the Eiffel Tower? Because he was back at the hotel trying to make sure his virtual Sim didn’t accidentally drown in a pool with no ladder.
3. The WAP Phone: Why was the traveler staring at his phone for 20 minutes? He was trying to check the weather in Rome using WAP, but he only managed to load a single pixel of a cloud.
4. The Nokia Snake 2: Why was the flight so quiet? Because Snake II just dropped on the Nokia 3310, and everyone was busy maneuvering a pixelated line through a maze instead of talking.
5. The USB Drive: Why did the businessman look like a hacker? He was carrying a 32MB USB “Pen Drive” that cost $100 and held exactly two Word documents and a very low-quality photo of his dog.
6. The GPS Navigation: Why did the family drive into a lake? Because they bought a first-generation GPS that told them to “Turn Left” into the Atlantic Ocean.
7. The Gladiator Vibe: Why did the tourist wear a toga to the Colosseum? Because Russell Crowe made it look cool, and the tourist didn’t realize that in 2000, “Roman Style” mostly just meant cargo shorts.
8. The Tripadvisor Start: Why was the hotel manager sweating? Because he heard a guest mention a “website” where people could post photos of the “hidden” mold in the shower.
9. The Euro-Wait: Why was the traveler confused in Germany? He was still using Deutsche Marks while everyone kept telling him that “Real Money” (the Euro) was just 12 months away.
10. The Britney Denim: Why did the couple get stuck in the airport doors? Because they were both wearing head-to-toe denim outfits inspired by the VMAs and they physically couldn’t move their joints.

The Full 2000 Travel Archive

11. The Digital Camera: Why did the tourist carry 10 SmartMedia cards? Because each one only held 8 photos, and he refused to delete the one where he accidentally took a picture of his own thumb.
12. The PlayStation 2: Why did the dad buy a PS2 for “the family vacation”? Because it played DVDs, and he spent the entire trip to Hawaii watching The Matrix in the hotel room.
13. The Linkin Park Fan: Why was the teenager so “edgy” at the gate? Because he was listening to Hybrid Theory on a Discman that actually had “G-Protection” so he could walk without skipping.
14. The Cast Away Fear: Why did the passenger hug a volleyball? He’d seen the Tom Hanks movie and wanted to make sure he had a friend ready just in case the flight went off course.
15. The Laptop Modem: Why was the traveler in the hotel lobby at 3 AM? It was the only place with a phone jack that didn’t have a “Hotel Surcharge” for dialing into EarthLink.
16. The Napster Shutdown: Why was the college student crying? He realized he couldn’t download music on the hotel’s 56k connection before Napster got sued out of existence.
17. The Airport Security: Why was it still a “Golden Age”? Because you could still bring a 12-inch sub, three sodas, and your grandma right up to the gate.
18. The PalmPilot m100: Why was the man tapping his wrist? He was trying to “Graffiti” a note into his new PalmPilot, but the device thought he was trying to draw a picture of a cat.
19. The X-Men Movie: Why were people wearing black leather in the desert? Because the first movie came out and everyone thought they looked like Wolverine instead of “heatstroke victims.”
20. The Seatback TV: Why was the child amazed? Because the plane had a screen that allowed him to play a version of Tetris that lagged so much it felt like a psychological test.
21. The Google Search: Why did the traveler find the best pizza? Because Google was finally better than Yahoo! at realizing “Best Pizza” didn’t mean “History of Pizza Technology.”
22. The Harry Potter Book: Why was the flight to London so quiet? Because The Goblet of Fire was 700 pages long and every kid on the plane was finally too busy reading to kick seats.
23. The Cargo Pants Peak: Why did the man have a limp? He had a Discman in one pocket, a Nokia in the second, and a “portable” DVD player strapped to his thigh.
24. The Wireless Mouse: Why was the businessman frustrated? He brought a “cordless” mouse but forgot the base station that was the size of a actual brick.
25. The Airline Food: Why did the passenger ask for the “Vegetarian Option”? Because he figured the “mystery pasta” was safer than the “mystery meat” in the new millennium.
26. The Payphone Hunt: Why was the tourist running? He had a calling card with 5 minutes left and he needed to tell his mom he’d landed before it “timed out” forever.
27. The Disposable Camera: Why did the woman wait 2 weeks for her photos? Because in 2000, “Instant Gratification” meant picking up your prints from CVS and hoping at least 4 of them weren’t blurry.
28. The Rollerblade Tour: Why did the guy have a broken arm? Because he tried to “Blade” through the cobblestones of Prague while wearing a 20lb backpack.
29. The Bye Bye Bye Dance: Why was the gate agent annoyed? Because a group of students was doing the NSYNC choreography every time their flight was called.
30. The Hotel Key: Why did it fail? Because the traveler put it next to his brand new “high-capacity” 1.44MB floppy disk and they destroyed each other.
31. The SkyMall Catalog: Why did the passenger buy a “Bird-Watching Hat with Built-in Radio”? Because 2000 was the year we officially lost our ability to say “No” to weird inventions.
32. The Baggage Carousel: Why did the man grab a black bag with a red ribbon? Because so did 400 other people on the same flight.
33. The iMac G3: Why did the student look so cool at the hostel? He had a “Bondi Blue” iMac that weighed as much as a small horse but looked like a piece of candy.
34. The “Who Wants to Be a Millionaire”: Why did the traveler ask for a “Lifeline”? Because he couldn’t find his hotel and his paper map was currently being eaten by a goat.
35. The Bug Spray: Why did the traveler look like a mummy? He was so afraid of the “West Nile Virus” that he wore long sleeves in 100-degree heat.
36. The Low-Rise Jeans: Why was the passenger freezing? Because she sat down in a leather airplane seat and the back of her jeans ended approximately 4 inches below her spine.
37. The Discman “Anti-Skip”: Why was the boy smiling? Because his “45-second G-Protection” meant he could finally drop his bag without the Backstreet Boys stuttering.
38. The Travel Agent’s Fax: Why was the room double-booked? Because the fax machine at the resort “survived Y2K” but died from a simple paper jam.
39. The Cast Away Volleyball: Why did the man bring a ball named “Wilson” to the beach? Because he wanted everyone to know he was “on trend” with his movie references.
40. The In-Flight Smoking: Why was it so strange? Because 2000 was the year we finally realized that “Smoking Row 20” didn’t stop the smoke from visiting Row 19.
41. The Passport Stamp: Why was the traveler worried? He heard the EU might start using “Digital Chips” and he was afraid he wouldn’t get any more cool ink in his book.
42. The Deus Ex Game: Why was the teen paranoid? He played the game on his laptop and was now convinced the airport security guard was a nanotech-enhanced cyborg.
43. The Travel Pillow: Why did it smell like plastic? Because it was the first year “Memory Foam” entered the travel market and it smelled like a chemical factory.
44. The Duty Free Toblerone: Why was it so heavy? Because the 2000 edition was basically a chocolate-filled construction beam.
45. The Seat Recline: Why did the passenger apologize? He didn’t. In 2000, reclining your seat was still considered a “God-given right” in Economy.
46. The Video Rental: Why was the traveler stressed? He realized he left The Phantom Menace in his VCR and the Blockbuster late fees were going to cost more than his trip.
47. The Tamagotchi: Why did the flight attendant help? Because a passenger’s digital pet was “sick” and in 2000, we were still soft-hearted about virtual suffering.
48. The New Year’s Resolution: Why did the traveler go to the gym at the hotel? Because it was Jan 5th and he still believed his “New Century, New Me” plan was going to work.