HAPPY NEW YEAR everyone! I hope that your holidays were filled with laughter, love and a whole lot of cheer! Things have been busy, busy, busy here on St. John, hence the delay in this month’s event calendar! This month, we have added the ongoing weekly events to the top of the calendar and an addition of up and coming events and activities that you can keep an eye on or plan your travel around.
Before we dig in on the exciting happenings, I want to briefly share with you a little info about the two businesses who are collaborating to make this calendar possible: Sailing Asante and Kapok Villas Boutique Resort.

Kapok Villas, located in the lovely Gifft Hill neighborhood, is ten minutes from the Cruz Bay Ferry Dock and many of the picture-perfect beaches on St. John’s North Shore. Family owned and operated for three generations; Kapok Villas is a perfect place to call “home” for solo travelers, couples, families or groups of up to 35 people. This is an amazing space to host your family for a reunion or guests for a wedding. Or simply a quiet escape nestled in lush tropical gardens. For more information, please email the hostess with the mostess: Kim Hart! You can also click the banner below to dig a little deeper into the amazing offerings of this lovely boutique resort nestled in the hills.

Sailing Asante is a small charter business owned and operated by residents of St. John. We started doing day charters on this beautiful 44-foot sailing vessel in November of 2020 (yes, I know!) and have been catering to the nature loving visitors of Love City ever since.

Captain Teddy and the crew cater to small groups, offering competitive pricing on private charters for up to six guests and include an open bar, premium snacks, fuel, experienced crew and puppy snuggles in the price of all trips. We always recommend beginning your St. John adventure with a day on Asante so that you can get all the tricks and tips from our crew. Maximizing your time on island in the most relaxing way possible. 🙂 For more information on full-day, half-day or sunset sails, shoot an email to Captain Teddy. Or you can grab some more details on our site before booking online by clicking the banner below. And now, on to the other fun stuff!

ONGOING EVENTS
Mondays
- Raintree Cafe | Cinnamon Bay Campground Chats (Sea Turtle Talk) | 6:00-7:00
- Annaberg | Cultural Demonstrations | 10:00AM-2:00PM
- Guided Reef Bay Hike | Taxi-In and Boat-Out Included | Sign up Required with Friends of Virgin Islands National Park
Tuesdays
- Raintree Cafe | Cinnamon Bay Campground Chats (Traditional Music & Crafts) | 6:00-7:00
- Upstairs Bar | Karaoke | 9:00-Midnight
- Johnny Lime | Open Mic | 5:00-8:00
- Annaberg | Cultural Demonstrations | 10:00AM-2:00PM
- Guided Reef Bay Hike | Taxi-In and Boat-Out Included | Sign up Required with Friends of Virgin Islands National Park
- Surf Club Cantina | Taco Tuesdays with Various Local DJ’s | 5:30-?
Wednesdays
- Raintree Cafe | Cinnamon Bay Campground Chats (Music of the Caribbean) | 6:00-7:00
- Upstairs Bar | BINGO | 5:00-7:00
- Johnny Lime | Trivia & Cookies for Community | 6:30-8:30
- Sundog Cafe | Wednesday Night Jam | 6:00-8:30
- Annaberg | Cultural Demonstrations | 10:00AM-2:00PM
Thursdays
- Raintree Cafe | Cinnamon Bay Campground Chats (Birds of St. John) | 6:00-7:00
- Miss Lucy’s | Open Mic | 5:30-9:00
- The Tap Room | Trivia with Banen | 7:00
Fridays
- Raintree Cafe | Cinnamon Bay Campground Chats (Coral Reef Ecosystems) | 6:00-7:00
- Sharky’s & Surf Club Cantina | Fridays w/ Lauren & Friends | 5:30-8:30
- Upstairs Bar | Karaoke | 9:00-12:00
Saturdays
Nothing yet!
Sundays
- The Windmill Bar | BINGO | 4PM-6PM
- Mongoose Junctions | Farmers Market | First Sunday of Every Month | 9:30-Noon

1/5
Windmill Bar | Ikema on Steel Pan | 11:30-2:30
Windmill Bar | Eva & Mark | 5:30-7:30
Love City Tacos | Moss Henry | 5:00-7:00
1/6
Windmill Bar | The Housewives with Sam on Sax | 4:30-7:30
1/7
Windmill Bar | Travis Riddle with Sam on Sax | 4:30-7:30
1/8
Beach Bar | Lourdes & The Switch | 7:00-10:00
Windmill Bar | Moss Henry | 5:30-7:30
Sundog Cafe | Eva & Mark | 6:00-8:30
1/9
Windmill Bar | Ikema on Steel Pan | 11:30-2:30
Windmill Bar | KASH’D Out | 5:30-8:30
Upstairs Bar | Friday Night Karaoke | 9:00-Midnight
Sundog Cafe | Ted Wyman | 6:00-8:30
1/10
Windmill Bar | KASH’D Out | 5:30-8:30
Bajo el Sol | “Lift Off!” – Richard Jurmain Book Signing | 4:00-6:00
Beach Bar | The Real Housewives of St. John | 7:00-10:00
Cruz Bay Ferry Dock | LOVE CITY SEAFOOD FEST | 2:00-10:00 | MORE INFO
1/11
Windmill Bar | KASH’D Out | 1:00-4:00
Sundog Cafe | Cuppa Joe – Sunday Brunch | 11:30A-1:30P
1/12
Windmill Bar | Ikema on Steel Pan | 11:30-2:30
Windmill Bar | Darin Keech & Friends | 4:30-7:30
Love City Tacos | Moss Henry | 5:00-7:00
1/13
Beach Bar | Mutt Mixer Happy Hour to Benefit the STJ Animal Care Center | 5:00-8:00
Windmill Bar | IslandGirlMusic – Erin Hart | 4:30-7:30
1/14
Windmill Bar | Eva & Mark | 4:30-7:30
1/15
Windmill Bar | Sol Driven Train | 5:30-8:30
Beach Bar | The Real Housewives of St. John | 7:00-10:00
Sundog Cafe | Eva & Mark | 6:00-8:30
1/16
Windmill Bar | Ikema on Steel Pan | 11:30-2:30
Windmill Bar | Sol Driven Train | 5:30-8:30
Sundog Cafe | Ted Wyman | 6:00-8:30
1/17
Windmill Bar | Sol Driven Train | 5:30-7:30
Beach Bar | Lourdes & The Switch | 7:00-10:00
1/18
Sundog Cafe | Cuppa Joe – Sunday Brunch | 11:30A-1:30P
1/19
Windmill Bar | Ikema on Steel Pan | 11:30-2:30
Windmill Bar | Eva & Mark | 4:30-7:30
Beach Bar | Sol Driven Train | 7:00-10:00
“Everybody can be great…because anybody can serve. You don’t have to have a college degree to serve. You don’t have to make your subject and verb agree to serve. You only need a heart full of grace. A soul generated by love.” -Martin Luther King, Jr.
1/20
Windmill Bar | IslandGirlMusic – Erin Hart | 4:30-7:30
Windmill Bar | Eva & Mark | 4:30-7:30
Tamarind Court | Tess Marie & Thomas Bryan Eaton | 5:30-8:30
1/21
Windmill Bar | Miss Tess | 4:30-7:30
1/22
Windmill Bar | Tony Jonez | 4:3-7:30
Tamarind Court | Tess Marie & Thomas Bryan Eaton | 5:30-8:30
Sundog Cafe | Eva & Mark | 6:00-8:30
1/23
Windmill Bar | Ikema on Steel Pan | 11:30-2:30
Windmill Bar | Miss Tess | 4:30-7:30
Sundog Cafe | Ted Wyman | 6:00-8:30
1/24
STJ Animal Care Center Glitter & Gold Gala | 5:30-9:00 | MORE INFO
Windmill Bar | Tony Jonez | 4:30-7:30
Beach Bar | Lourdes & The Switch | 7:00-10:00
1/25
Windmill Bar | Tony Jonez | 1:00-4:00
Sundog Cafe | Cuppa Joe – Sunday Brunch | 11:30A-1:30P
1/26
Windmill Bar | Ikema on Steel Pan | 11:30-2:30
Windmill Bar | Sally & George | 4:30-7:30
1/27
Windmill Bar | Blues Cruise Lunch Jam | Noon-3:00
Windmill Bar | IslandGirlMusic – Erin Hart | 4:30-7:30
Bajo el Sol Gallery & Art Bar | Rhyme & Lime Poetry Jam – Laugh to Keep From Crying | 7:00-9:00
Beach Bar | Blues Jam | 1:00-4:00
1/28
Windmill Bar | Eva & Mark | 4:30-7:30
Dr!nk | Shane Meade | 7:00-10:00
1/29
Windmill Bar | Sally & George | 4:30-7:30
Shambles | Shane Meade | 6:00-9:00
Beach Bar | The Real Housewives of St. John | 7:00-10:00
Sundog Cafe | Eva & Mark | 6:00-8:30
1/30
St. John School of the Arts | Broadway Comes to St. John – Friends & Family Show | 6:00-8:00 | MORE INFO
Windmill Bar | Sally & George | 4:30-7:30
Tamarind Court | Shane Meade | 5:30-8:30
Sundog Cafe | Ted Wyman | 6:00-8:30
Gifft Hill School | Farm to Table Dinner | 5:30-10:00 | TICKETS
1/31
Windmill Bar | Quelbe Resurrection | 4:30-7:30
The Tap Room | Shane Meade | 6:00-8:00
St. John School of the Arts | Broadway Comes to St. John – Angel Show | 6:00-10:00 MORE INFO
Skinny Legs | Catch N Keep | 6:00-9:00
SOON COME – SAVE THE DATES
The Windmill Bar | VI JAM FEST | March 5, 6, 7 | MORE INFO
St. John Cancer Fund’s LIGHT UP THE NIGHT | NPS Baseball Field – Cruz Bay | 5:00PM | MORE INFO
Gifft Hill School Auction | March 7 | MORE INFO
Lovango Resort & Beach Club | Friends of Virgin Islands National Park Gala | February 7 | MORE INFO & TICKETS
St. John Festival | Cruz Bay Customs Lot | June 27-July 4 | MORE INFO
If we have missed anything, please shoot me an email so we can update. Thanks for reading and follow along for more STJ info!
