Wednesday, December 24 – Christmas Eve
- DJ Nico @ Kraken Raw Bar 9:00 pm.
- Best of 2025 Voting @ The Daily Herald Online.
- Christmas Eve Dinner @ La Patrona 6:30–10:00 pm.
- Christmas Eve Dinner @ The Boon 6:00 pm.
- Ronny & Lee @ 3 Angle Bar 8:00 pm.
- Cedric & Fredo @ Hole in the Wall 9:00 pm.
- Karaoke @ Topper’s Restaurant & Bar 8:00 pm.
- Christmas with Cyndel @ Tortuga 6:30 pm.
- Pianist Tammy T @ Red Piano 9:00 pm.
Thursday, December 25 – Christmas Day
- Ronny Santana @ Pineapple Pete 6:30–9:30 pm.
- Christmas Dinner @ SALT at The Morgan 8:00 pm.
- Karaoke @ Topper’s Restaurant & Bar 8:00 pm.
- Pianist @ Red Piano 9:00 pm.
- Sweet Pan Music @ Fat Tony’s 6:00 pm.
- DJ @ Soggy Dollar Bar 9:00 pm.
- Eduardo @ Sint Maarten Yacht Club 7:00–10:00 pm.
- Live Music @ Rancho del Sol 7:00–10:00 pm.
- Best of 2025 Voting @ The Daily Herald Online.
Friday, December 26
- Ronny Santana @ Pineapple Pete 6:30–9:30 pm.
- Amin & Natalia @ Kraken Bar 9:30 pm.
- Audree Alexandrine @ Bold Buddha 7:00 pm.
- Pianist Tammy T @ Red Piano 9:00 pm.
- Alfredo Live @ Rendezvous Lounge 6:30 pm.
- Shantillia @ Tortuga 6:30 pm.
- DJs @ Soggy Dollar Bar 9:00 pm.
- Best of 2025 Voting @ The Daily Herald Online.
Saturday, December 27
- Saxophonist Gordon @ Pineapple Pete 6:30–9:30 pm.
- Live Music @ Tortuga 6:30 pm.
- UFC Fight @ Kraken Raw Bar 8:00 pm.
- Percy Rankin & the Bunfire Band @ Buccaneers 6:00–9:00 pm.
- Sexy Saturday Beach Party w/ DJ Madjin & Christine Gordon @ Boon Beach Bar 1:00 pm.
- Super Savings for Shoppers @ Blue Point 9:00 am–6:00 pm.
- Karaoke @ Topper’s Restaurant & Bar 8:00 pm.
- DJ EM @ Soggy Dollar Bar 9:00 pm.
- Sip & Paint @ Penka’s Fine Art Studio 7:30 pm.
- Pianist Tammy T @ Red Piano 9:00 pm.
- Saturday Night Spectacular Show @ Casino Royale.
- Boujee Saturdays @ Amore 10:00 pm.
- Best of 2025 Voting @ The Daily Herald Online.
Sunday, December 28
- Gordon on Saxophone @ Pineapple Pete 6:30–9:30 pm.
- Pianist Tammy T @ Red Piano 9:00 pm.
- Tea Dance Party @ Aloha Bar 7:30 pm.
- Live Jazz Band @ Rendezvous Lounge 1:00–4:00 pm. (Reservations recommended.)
- Sunday Funday @ Mary’s Boon 12:00–6:00 pm.
- Cydel & Jojo @ Sint Maarten Yacht Club 6:00 pm.
- Cuban Night w/ The Martinis @ Tortuga 6:00–9:00 pm.
- Island Church Service @ Caribbean Cinemas in Cole Bay 10:00–11:00 am.
- Eduardo @ Isola 7:30–9:30 pm.
- Karaoke Night @ Red Piano 9:00 pm.
- Gianfranco & Lee Hardesty @ Buccaneer Beach Bar 6:00–9:00 pm.
- Mr. Cole & the Untouchable Dancers @ Tropicana Princess Casino 8:00 pm.
- Super Sunday Deals @ Blue Point 10:00 am–2:00 pm.
- Karaoke @ Topper’s Restaurant & Bar 8:00 pm.
- Best of 2025 Voting @ The Daily Herald Online.
Monday, December 29
- Eduardo @ Pineapple Pete 7:00–10:00 pm.
- Jingle Jangle Movie Night @ Marigot Waterfront 7:00 pm.
- Michellee Parris @ Tortuga 6:30 pm.
- Karaoke @ Topper’s Restaurant & Bar 8:00 pm.
- Church Night w/ Live Band @ Red Piano 9:00 pm.
- Melting Pot Jam Band @ Huppel the Pub 8:00 pm.
- Best of 2025 Voting @ The Daily Herald Online.
Tuesday, December 30
- Eduardo @ Buccaneer 6:00–9:00 pm.
- Pianist Tammy T @ Red Piano 9:00 pm.
- Ricky da Phox @ Astra 7:30–10:30 pm.
- Latin Night @ Soggy Dollar Bar 8:30 pm.
- Salsa-Kizomba Classes @ Soggy Dollar Bar 7:00 pm.
- Best of 2025 Voting @ The Daily Herald Online.
