Kick off the holiday weekend with rooftop revelry, frozen drinks, and a whole lot of heart.
If Labor Day Weekend had a pre-party, this would be it. Margaritaville Hotel San Diego is turning up the volume and turning back the clock with a rooftop bash that starts early, Friday, Aug. 29, to be exact. Dubbed “Jimmy Buffett Day,” this beachy blowout isn’t just about sipping margaritas and chasing sunsets (although those are on the agenda). It’s a feel-good celebration featuring live music, family-friendly energy and a mission to give back to the local music scene. Consider it a toast to summer that hits all the high notes. And with skyline view rooms just an elevator ride away, the vibes stay strong long after the music winds down. Consider this your invite to kick off the long weekend with purpose, palm trees and a whole lot of party. RSVP today!
1. The Jimmy Buffett Day Kickoff
San Diego might be on weekday time, but Margaritaville Hotel kicks off Labor Day early with a rooftop party and island vibes. From 4-8 pm on Friday evening, the 5 o’Clock Somewhere Bar will host a benefit concert to honor Jimmy Buffett’s legacy. And it’s all part of Margaritaville’s brand-wide Day of Service initiative!
“Margaritaville’s Day of Service was created for all Margaritaville properties, restaurants, communities, etc, to take a moment and honor Jimmy’s legacy and the way he lived his life in the support of others and the community – leaving the world a better place.”
You can expect live music from local musicians, tropical flair and a prime location in downtown minutes from San Diego’s bay. This isn’t just any hotel event; it’s a vibe. Steel-drum rhythms, breezy sing-alongs and themed fun will transform downtown San Diego into a scene straight out of Key West. It’s the kind of party that makes you forget your inbox exists and reminds you why we celebrate summer.
Taking the stage from 5 to 8 p.m., Mark Wood and the Parrot Head Band will bring Buffett’s greatest hits to life in a lively four-piece set. Known for channeling island rhythms with an authentic flair, the band has shared stages with members of Buffett’s Coral Reefer Band and continues to keep the Parrot Head spirit alive. Their mix of reggae, calypso, rock and country promises to turn the rooftop into a full-on beach escape, complete with sing-alongs to “Margaritaville,” “Cheeseburger in Paradise,” and more crowd favorites.
2. Frozen Cocktails + Food for a Cause
Let’s talk about priorities: sipping a frozen margarita while doing something good for your community? Now that’s the kind of multitasking we can get behind. During the benefit concert, 50% of 5 o’Clock Somewhere Bar’s food and drink proceeds will go to the San Diego Music Foundation. That means every frosty cocktail or tasty bite you order helps fund local music initiatives. The menu? Think tropical sips, seafood snacks and party-primed plates that pair perfectly with live tunes and rooftop views. So go ahead, and order another round. It’s happy hour with heart.
“This year we chose to honor Jimmy Buffet’s legacy by providing the community with a chance to give back in a ‘Margaritaville state of mind’ by enjoying our amazing rooftop, supporting local musicians and raising funds to support the next generation of students looking to embrace their love for music.”
3. Family-Friendly Fun for All Ages
No babysitter? No problem. This rooftop soirée was built for families, too. From ice cream carts to activity stations and photo booths, the hotel’s rooftop transforms into a playground for kids and kids-at-heart. Margaritaville Hotel San Diego knows that unforgettable weekends don’t come with age restrictions. While parents sip something cold, little ones can soak up the color, creativity and silliness that turns a party into a memory. And yes, the whole scene is selfie-ready.
4. Bid Big at the Silent Auction
Cheers to shopping for a cause! The rooftop will host a travel-themed silent auction packed with local experiences. Proceeds benefit the San Diego Music Foundation’s mission to expand access to music education. It’s the perfect way to score one-of-a-kind goodies while giving back to the creative community that makes this city sing. You’ll find everything from staycations to viral travel items, so bring your generous spirit (and maybe a little competitive edge). Every bid helps keep the music playing in San Diego schools, and that’s a reason to raise a glass.
“We love what San Diego Music Foundation is doing by supporting music education in public schools across San Diego County. The foundation’s biggest initiative is to bring guitars and an education program to schools, which we felt was a great way to connect with the locals here and give back the way Jimmy would have wanted. ”
5. Stay + Play at Margaritaville Hotel San Diego
Here’s the move: don’t just party; make it a staycation. Margaritaville’s Keep the Party Going package turns a Friday night into a full-blown Labor Day Weekend escape. With tropical-themed accommodations, poolside loungers and colorful drinks on repeat, this hotel is a one-stop vacation in flip-flops. Located steps from the Gaslamp Quarter and the Embarcadero, it’s close to all of San Diego’s end-of-summer happenings. But honestly, you may never want to leave the rooftop. Booking a room means no ride shares, no packing up early and absolutely no FOMO.
Reserve a room for two or more nights and get 20% off plus special edition commemorative cups. As a bonus, for each night you stay, a $5 donation goes toward supporting San Diego Music Foundation’s efforts. Check rates and snag your stay here.
No worries if you can’t make it on Aug. 29. Margaritaville Hotel San Diego is always bringing the island vibes to Gaslamp Quarter with a weekly Live Music Schedule. Browse the lineup and catch San Diego’s hottest acts turning up the heat on Margaritaville’s rooftop stage!
This article is brought to you by one of the many talented writers associated with Locale Magazine! We are a group of locals (whether born and raised or transplanted) who love this county we now call home!
