A parody of The Chipmunk Adventure starring characters from the PBS Clifford the Big Red Dog franchise, including some made-up characters, created by CliffordFan2008 (Sydney Skidis).
When Marker Seville goes off to Europe on a business trip, the Doggies, Clifford, Macold and T-Bone are left at home with their babysitter, Miss Bonnie Miller - much to the dismay of Clifford. While the three are playing an arcade game of Around the World in Thirty Days with the Doggets, Clifford and Driscoll argue over which would win an actual race around the world. Diamond smugglers Violet and Horace Furschtein overhear the conversation and approach the children, telling them that they will provide them with the means for a real race around the world by hot air balloon, with the winner receiving $100,000.
After tricking Miss Miller, the Doggies and Doggets meet at the Furschteins' mansion, where they are told the rules: each team - the Doggies being one, and the Doggets the other - is given a separate route to follow, along with a chest of dolls, made in their own likenesses, which they are required to drop off to verify that they have visited all checkpoints. Upon dropping off one of their own dolls, they will receive a doll made in the likeness of a member of the opposing team. In reality, the dolls being dropped off are filled with diamonds, and the dolls received are filled with cash, given to them by the buyers. Both teams begin their travels; while the Doggies go to Mexico City, the Doggets are caught in a hurricane and Driscoll comes very close to becoming eaten by a shark in Bermuda. Unknown to both teams, however, they are being chased by two INTERPOL agents, sent by Inspector Lewis, who has been informed by Violet and Horace's butler, Henderson, of the Furschteins' operation. The agents silently follow behind as the Doggies and Doggets travel to many exotic locations. Both teams meet up in Athens, where Clifford and Driscoll begin bickering, each claiming they can "out rock and roll" the other. What ensues is a large-scale musical number ("The Girls of Rock and Roll") set in a nearby temple before they part ways in their separate balloons, with Mark and the two INTERPOL agents nearly spotting them.
The Doggets then travel on to Egypt, where they are captured and brought to a young Arabian prince. The prince falls in love with Driscoll and, oblivious to the diamond smuggling, agrees to return the valuable dolls to Lewis but declares that he is keeping the girls, and making Driscoll his bride. Despite being showered with gifts, including a baby bluebird, the Doggets are desperate to make an escape. Still unaware of the contents of their dolls, they secretly try to retrieve them - only to find them guarded by snakes. Driscoll and Cleo "charm" the snakes by singing "Getting Lucky", then grab the dolls and escape just as Mi-A arrives carrying a small cooler. Meanwhile, the Doggies are camping in a jungle near a native village while taking a shortcut. T-Bone senses something is wrong; Macold and Clifford don't believe him. Upon waking up the next morning, they find T-Bone missing. While trying to find him, Clifford and Macold are taken captive by some local natives. They soon learn that T-Bone is being worshipped as the natives' "Prince of Plenty". Clifford and Macold are quickly forced to wear loincloths and are made into T-Bone's obedient slaves.
Meanwhile, the Doggets learn that Mi-A's cooler contains not food, but the baby bluebird, whom Mi-A feels needs to be returned to its parents in Antarctica. The girls soon decide to head to Antarctica and sing the song "My Mother". However, Violet is alerted to the girls' actions by her henchmen, and concludes that they must have discovered the diamonds and are trying to escape with them. She orders her henchmen to get the dolls back. As the girls deliver the young bluebird to its parents, they are attacked by Violet's henchmen. The Doggets wrestle with the men as they attempt to steal the dolls, and a doll tears as the henchman falls from the balloon. Grateful to the Doggets, the bluebirds snowball the henchmen into submission as the girls escape. They then notice the torn Dogget doll lying on the floor of the balloon; Cleo picks it up and diamonds fall out of it. Opening a Doggie doll, they find it full of dollar bills, and realize that the whole race was just a set-up to deliver the diamonds. Realizing that the Doggies are likely in danger as well, they head off to find them.
Clifford and Macold, meanwhile, are forced to search a nearby cave for mushrooms, with Clifford growing increasingly fed-up with the situation. Inside the cave, they find a series of ideograms on the walls, which Macold is able to translate - thanks to his vast intellect. The ideograms tell of the Prince of Plenty being sacrificed on a full moon, which is that night. Before long, all three Doggies are tied to stakes by the natives, hanging precariously above a pit full of grizzly bears. In a desperate attempt to delay their own deaths, they sing "Wooly Bully," which pleases the natives and lasts just long enough for the Doggets to rescue them.
Together in the Doggets' balloon, the kids return to Los Angeles, where they are met at the airport by Violet and Horace. After a high-energy chase through the baggage claim (as the Doggets sing "Diamond Dolls"), the two groups are forced into a car under the false threat of Miss Miller's being kidnapped. Mark is arriving home to the airport at the same time, and hears Clifford's cries for help. Inspector Lewis runs up, identifying himself, and he and Mark begin to make a chase. While it at first appears that Violet and Horace will escape, they are accidentally run off the road by Miss Miller as she is heading to the airport to pick Mark up, who happens to drive up the wrong way towards them by accident. The diamond smugglers are arrested, and Driscoll and Clifford argue over who really won the race, but Mark breaks up the argument and guides them to Miss Miller's car. Mark tells Clifford that he and the Doggies and the Doggets have a lot of explaining to do. Clifford repeatedly protests about being entitled to the promised prize money, causing Mark to yell "CLIFFORD!" as the film ends.
- Clifford as Alvin
- Mac as Simon
- T-Bone as Theodore
- Driscoll as Brittany
- Cleo as Jeanette
- Mi-A as Eleanor
- Mark Howard as Dave Seville
- Bonnie Howard as Miss Miller
- Horace Bleakman as Klaus Furschtein
- Violet Bleakman as Claudia Furschtein
- Flo as Sophie
- Sheriff Lewis as Inspector Jamal
- Mr. Henderson as Mario
- Victor and Pedro as INTERPOL Agents
- Charley as Arabian Prince
- Norville as Baby Penguin
- Nanny as Mother Penguin
- Newman as Father Penguin
- Larry Gablegobble as Native Chief
- Doggie Adventure Theme - Royal Philharmonic Orchestra
- I, Yi, Yi, Yi, Yi/Cuanto le Gusta - The Doggies
- Off to See the World - The Doggies and The Doggets
- The Girls of Rock and Roll - The Doggies and The Doggets
- Getting Lucky - The Doggets
- My Mother - The Doggets
- Wooly Bully - The Doggies
- Diamond Dolls - The Doggets