[A/N] - Greetings! This story takes place in sort of a modern-day AU of the 80's cartoon, so imagine the chipmunks as being essentially human. With that out of the way, enjoy the story!

Chapter 1 - The Plan

Sunday

"Are you sure you boys will be alright while I'm gone?"

"Dave, you shouldn't be worrying about us. We'll be fine."

It was a warm, sunny morning in Los Angeles, California. It was the middle of summer, so despite it being early in the morning the sun was out, the sky was blue and the temperature was hotter than it needed to be. Dave Seville was getting ready to drive out of town for a business trip, carefully putting his luggage into the trunk of his car. He would be gone for the week and was unsure if his three teenage boys would be okay on their own. He knew that his two sons, Simon and Theodore, would be fine but...Alvin? Even when he leaves Alvin home for five minutes, he's still afraid that he would somehow burn the house down.

Dave sighed anxiously. "Alright, alright. But just promise me you boys will behave." He focused on Alvin, his tone becoming more strict. "Especially you Alvin. I don't want to come back to a trashed house. You're almost 17. It's about time you start acting like it."

Alvin smirked at Dave. "Relax Dave, I didn't forget your invitation to my party."

"What Alvin means is-" Simon pushed up his glasses, interrupting in order to relieve the tension. "-we got this under control."

Dave closed the trunk door and let out another anxious sigh. "Well alright then." He turned around and gave a hug to his three sons.

"We'll miss you Dave," said Theodore.

"I'll miss you too," Dave smiled and pulled away from the hug. "Be good." He reiterated, looking at all three of them but mostly talking about Alvin. Once he got into his car, he waved to his boys as he pulled out of the driveway and drove on down the street.

The second Dave's car was out of their sight, Alvin let out a "Yes!" and ran back into the house. Simon and Theodore exchanged nervous glances and followed Alvin. Whatever Alvin had planned, they knew that it was gonna be something irresponsible.

"What are you planning on doing now Alvin?" asked Simon as they walked into Alvin's messy room.

"Let me tell ya Si," Alvin pulled out a duffel bag from under his bed. "How would you guys like to come with me to the beach house?"

The beach house was a little vacation home that the Sevilles would use during the summer or spring break. Sometimes, Dave would go there by himself to work on music in a more quiet, relaxing environment. It brought back many fond memories for the boys, especially Alvin. As much as a trouble he usually was, he would seem to be mostly well behaved on these simple little vacations. One of his favorite activities was surfing. Whenever he was at the beach house, he would surf all day until the sunset and was always devastated whenever it was time for him to go back home. While they were there, all of their troubles seemed to wash away in the ocean. It was always so peaceful and was seen as a relaxing treat for everyone staying there.

"The beach house? You mean without Dave?" asked Theodore.

"Well yeah," Alvin replied. "Think about it. Our summer has been sooo boring. We gotta go out and live a little, you know?"

"Alvin, that is a ridiculous idea!" Simon said. "We can't just drive to the beach house by ourselves without Dave. It would be insane! Besides, where would we get the money for gas and food?"

"Well, you know that jar for the 'rainy day fund' that Dave has in the study?"

"Oh Alvin...You wouldn't."

"I would. And I'm going no matter what you guys say. And you guys are coming with me."

Simon shook his head. "Nuh-uh. No way. We are not gonna be punished for your actions, Alvin. Right Theodore?"

Both Alvin and Simon stared at Theodore. He started to look nervous. "Um… Well it does sound kinda fun I have to admit." He sheepishly replied as he looked down at the floor.

"I don't believe this," Simon said, looking up at the ceiling and dropping his arms to his side dramatically. "What are you gonna do when Dave finds out you stole money from him? How are you going to pay him back? Last I remembered you didn't have a job."

"Easy!" Alvin replied, immediately pulling out his phone to show his brothers something. He scrolled until he found what he was looking for. "Boom!" He exclaimed, and turned his phone to face Simon and Theodore.

It was an advertisement for an amateur surfing competition. It was scheduled for the upcoming Friday, located at the beach not far from the beach house. The first place prize was a hefty amount of money, enough to put back in the rainy day fund jar and have some left over.

"You really think you can win that?" Simon asked with a raised eyebrow and his arms folded.

"You've seen me surf, Si. You know I'm the greatest at it."

Simon was silent for a moment, as if he was actually contemplating it. "Still no," he finally said.

Alvin dropped his hands. "Well alright then. It will just be me, Theo and The Millers then."

"Wait… The Millers will be coming with us?" asked Theodore.

"Of course. Brittany, Eleanor...Even Jeanette," Alvin smirked at Simon. "Are you sure you want to pass up this opportunity, Si? Think about it. Getting to spend a whole week with your nerdy girlfriend...With no parents around." Alvin moved his shoulders up and down and raised an eyebrow in a sly fashion.

"First off, she's not my girlfriend and second off-"

"You're blushing Simon," Alvin pointed out. Simon straightened his back. "Am not." Theodore giggled. "Alvin's right. You do have a huge crush on her!"

Simon stammered. "Well no matter. It still would be irresponsible."

"C'mon Si. Puh-leeeease?" Alvin whined. Simon stood there, silent. After no response, Alvin had no choice but to bring out the big guns. He pulled something from out of his pocket. "You could be the one that drives us there." Alvin held up the keys to the Volkswagen bus that Dave would use to haul around his musical instruments and equipment. While Simon did have his license, Dave wasn't super comfortable with Simon driving it. "You're a good driver Simon," Dave would say. "But I would feel more comfortable if you had just a little more driving experience." Simon understood where Dave was coming from, but still thought he was mature enough to drive a van.

All Simon could do was stare at the keys that were dangling right in front of him. Dear lord was that tempting. He always did want to drive the Volkswagen but he knew Dave would never let him, despite how responsible Simon thought he was. Simon was surprised that Alvin even got ahold the keys in the first place.

After a moment of staring, Simon grabbed the keys without saying anything, finally admitting defeat.

"Great! Now go pack your stuff. We're leaving in an hour and a half!"

"What? Why so soon? It's not that far of a drive."

"C'mon! The sooner we get there the better!"

Simon sighed and walked out of Alvin's room. Theodore followed him. Alvin returned his attention to his phone and started to text Brittany.

"britt. guess what."

"what?" She replied with a eye roll emoji.

"how would you and your sisters like to hang out with me and my brothers at our beach house? it will be just us. no dave. no miss miller."

"for real? how did you convince dave?"

"i have my ways."

"this isn't a prank or anything right?"

"i'm 100% serious. now go get your stuff and meet me at my house in an hour and a half."

"that soon? alvin, i need more time to pack!"

"an hour and a half. see you then!"

Alvin tossed his phone onto his bed and frantically started to pack, completely ignoring Brittany's texts cussing him out for not telling her sooner.

Vvvvrrrrrrrrrrrrr

Jeanette Miller looked up from her book to look at the fan creating the white noise across the room. Her sister, Eleanor, was sitting on the armchair, looking at her phone. Although she appreciated the quiet, Jeanette couldn't help but feel bored. The whole summer so far hadn't been particularly exciting. She knew that she wasn't exactly popular or the "party type" like her sister Brittany, but she wouldn't mind hanging out with some friends.

She let out an exhale through her nose and looked back down at her book. She continued reading until she heard her sister, Brittany, rush into the living room to break the silence. "Has anyone seen my sunglasses?

"Did you check the bathroom?" questioned Eleanor, not even looking up from her phone.

"Yes," answered Brittany, sounding slightly annoyed. "I've pretty much looked everywhere." She opened the drawer to the side table that was next to where Eleanor was sitting. She rummaged through the junk. "Found them!" she said in a sing-songy voice as she held them up in the air triumphantly.

"Are you going somewhere?" asked Jeanette.

Brittany closed the drawer. "Alvin invited me to his beach house for the week."

Both Eleanor and Jeanette looked up. "Woah, really? A beach house?" Eleanor was curious. The Sevilles had never mentioned anything about a beach house before.

"Yep. He said that you guys could come too."

"When are they leaving?"

"Today. They're leaving in about an hour and a half."

Jeanette closed her book. "What? That soon?"

"Yep. Better hurry up and get ready if you want to come."

"But what about Miss Miller?" asked Eleanor. "Did you tell her that we were gonna be gone for the week?"

Brittany paused. She didn't tell Miss Miller, her and her sisters' guardian. There was no way she would let her girls hang out with teenage boys for a week unsupervised. Brittany knew if she told Miss Miller her reaction would either be a "No" or "I'll come with you", neither of which Brittany wanted to hear. While Brittany wasn't the smartest sister, she probably was the craftiest one. She knew she could figure out a way to go and bring her sisters with her. "O-Of course I did! Why wouldn't I?" Brittany let out a nervous chuckle.

"Brittany…" Eleanor gave her a look.

"I did!" Brittany persisted. "It was supposed to be a surprise. Swear on my grave!" Brittany made a gesture to symbolize her honesty. "She said she was fine with it. Besides we're almost 17. We can take care of ourselves."

The two younger siblings exchanged glances. Jeanette finally stood up. "Well...I guess we better get ready."

"Great! I'm gonna go get ready as well!" Brittany trotted off back to her room. Eleanor grabbed Jeanette's arm. "You don't actually believe that she asked her do you? Shouldn't we wait until she comes back home to ask her."

Jeanette bit her lip. She wanted to believe that Brittany was telling the truth, but something didn't seem right. She knew it might not be a good idea for six teenagers to go on a vacation by themselves, yet deep down she did feel like she was missing out that summer.

"Well… I think we should give Britt the benefit of the doubt here. She might be actually telling the truth this time."

Eleanor shot her a concerned look. Could her sister really be serious?

"Besides Ellie, if anything goes wrong we can always just come back home," Jeanette gave Eleanor's hand a little pat. Eleanor sighed and let go of Jeanette's arm. "Yeah you're probably right."

"Also Ellie, Theo is gonna be there," Jeanette smiled sweetly at Eleanor. Eleanor couldn't help but smirk and giggle. "Oh stop it," Eleanor said, playfully swatting her sister's hand. "Now c'mon, let's go get ready."