The rum is flowing again at Margaritaville Hotel San Diego, where Yo Ho Ho-liday Tavern has reopened inside LandShark Bar & Grill for a second holiday season of twinkling lights, nautical decor and treasure chests scattered around the Gaslamp Quarter restaurant. The pop-up transforms the usual beachy bar into what organizers call a holiday hideaway, complete with pirate-themed cocktails and seasonal bites, opening daily at 5 p.m.
A Bigger, Bolder Return
According to KPBS, the tavern is set to run from November 21 through December 31 at the hotel, located at 435 Sixth Avenue. That stretch lines up closely with last year's run, which The San Diego Union-Tribune reported went from Nov. 22 to Dec. 31 in 2025. This time around, organizers describe the decor as going even further than it did in its debut year.
KPBS and There San Diego give the run a November 21 through December 31 window.
Cocktails With a Pirate Twist
The drink menu leans into the theme with cocktails like the Chai Old Fashioned, which mixes Bulleit Rye with chai maple syrup and cardamom bitters, and the Garnet Garland, pairing Arette Classico Reposado with pomegranate concentrate, agave syrup, cranberry and orange bitters, per There San Diego. Rounding out the list are Naughty & Nice, Winter Wonderland and Captain's Grog, the outlet notes. The LandShark culinary team is also planning limited-time pirate-themed dishes, though specific menu details have not yet been announced.
Last year's pop-up, the same account notes, marked the tavern's first run, and this year's decor goes further than before. The comparison gives a sense of how the concept has grown since its debut, even as the kitchen keeps its new dishes under wraps for now.
Live Music and Pirate Sightings
Entertainment is a big part of the draw. The hotel advertises coastal tunes every Friday from 5 to 8 p.m. and DJ sets every Saturday from 7:30 to 10:30 p.m., a schedule that differs from the live music lineup the Union-Tribune described for 2025, which ran Wednesday through Saturday from 6 to 9 p.m.
Pirate character appearances are also on the calendar. The KPBS event listing and There San Diego describe appearances on select Saturday evenings in December from 7:30 to 9:30 p.m. Last year, according to the Union-Tribune, pirates made live appearances on Saturdays in December from 7 to 9 p.m. The pop-up is open daily, according to the hotel. Those with questions can reach Margaritaville Hotel San Diego directly at (619) 819-9500.
