May
11
Mon
2026
IKEMA ON STEEL PAN @ THE WINDMILL BAR
May 11 @ 11:30 AM – 2:30 PM

IKEMA ON STEEL PAN LIVE MUSIC -- SAINT JOHN ISLAND GUIDE

IKEMA ON STEEL PAN

Get swept away by the enchanting sounds of Ikema on Steel Pan at The Windmill Bar!  Immerse yourself in the Caribbean vibe as Ikema brings alive all the hits with skill and passion, making your St. John experience truly unforgettable.

Enjoy not only the mesmerizing music, but also the breathtaking views, top-notch entertainment, and delicious food and drinks that The Windmill Bar is renowned for.  Don’t miss out on this perfect blend of music and ambiance in one of St. John’s most scenic spots!

May
12
Tue
2026
OPEN MIC NIGHT IN CORAL BAY @ JOHNNY LIME
May 12 @ 5:00 PM – 8:00 PM

OPEN MIC NIGHT

JOHNNY LIME -- OPEN MIC NIGHT IN CORAL BAY -- SAINT JOHN ISLAND GUIDE

Join us at Johnny Lime in Coral Bay for a lively Open Mic Night, hosted by the talented Scotty Rolfsen. Whether you’re a local or visiting, Scotty sets the perfect island vibe, bringing together an eclectic mix of musicians for an unforgettable evening of music and fun. You never know which talented performers might take the stage—that’s part of the magic!

This true island jam welcomes all, so bring your instruments, your voice, your dance moves, or just your enthusiasm to soak in the great energy. Pair the incredible tunes with Johnny Lime’s legendary smoked meats, delicious sides, and tasty veggie options for an all-around amazing evening in Coral Bay.

JOHNNY LIME LOCATION

RICH GREENGOLD @ MID WAY CAFE & GRILL
May 12 @ 6:00 PM – 9:00 PM

RICH GREENGOLD -- ST. JOHN LIVE MUSIC -- SAINT JOHN ISLAND GUIDERICH GREENGOLD

Rich Greengold plays tenor sax, soprano sax, and chromatic harmonica.  Living in Coral Bay for over 35 years, he has played almost every venue on the island.  He often has a song list to request your favorite!

Come on out and be entertained by a local legend as you hang out at the Bar or enjoy some great local food at the Mid Way Cafe & Grill!

KARAOKE @ UPSTAIRS SPORTS BAR & GRILLE
May 12 @ 9:00 PM – May 13 @ 12:00 AM

UPSTAIRS SPORTS BAR & GRILLE -- SAINT JOHN ISLAND GUIDEKARAOKE EVERY TUESDAY!

In the heart of Cruz Bay, come on and sing your heart out at the Upstairs Sports Bar & Grille!  Now this is the way to meet others and have a blast!  Enjoy some great drinks and pub food at the Upstairs Bar & Grille.

UPSTAIRS SPORTS BAR & GRILLE LOCATION

May
13
Wed
2026
KARAOKE NIGHT VIBES @ MID WAY CAFE & GRILL
May 13 @ 6:00 PM – 9:00 PM

KARAOKE NIGHT VIBES -- MID WAY CAFE AND GRILL -- SAINT JOHN ISLAND GUIDE

Get ready to Sing Your Heart Out!  Come on out to Mid Way Cafe and Grill for some Karaoke Night Vibes every Wednesday!

 

WEDNESDAY NIGHT JAM @ SUN DOG CAFE
May 13 @ 6:00 PM – 8:30 PM

THE WEDNESDAY NIGHT JAM

WEDNESDAY NIGHT JAME SUN DOG CAFE -- SAINT JOHN ISLAND GUIDE

Join us for The Wednesday Night Jam at Sun Dog Cafe in St. John, where local musicians and special guests take the stage for an evening of live music and community vibes. From 6 PM to around 8:30 PM, immerse yourself in a lively atmosphere filled with talented performances and great company.

It’s the perfect midweek escape—don’t miss the chance to experience the rhythm and excitement of this unique jam session at Sun Dog!

SUN DOG CAFE LOCATION

May
14
Thu
2026
MARK WALLACE & EVA CHINN @ SUN DOG CAFE
May 14 @ 5:00 PM – 8:00 PM

MARK WALLACE & EVA CHINN

MARK WALLACE & EVA CHINN ST. JOHN LIVE MUSIC -- SAINT JOHN ISLAND GUIDE

Join us every Thursday evening at the Sun Dog Cafe as Mark Wallace & Eva Chinn serenade you with the best of Saint John. This dynamic duo brings a lively atmosphere to our open-air cafe, feeding off each other’s musical energy to deliver crowd-pleasing performances song after song.

Mark and Eva are beloved local musicians who never fail to delight audiences wherever they perform on the island. Come enjoy the perfect blend of music, atmosphere, and community spirit at the Sun Dog Cafe!

SUN DOG CAFE LOCATION

MISS LUCY’S OPEN MIC NIGHT @ MISS LUCY'S
May 14 @ 5:30 PM – 9:00 PM

ST. JOHN LIVE MUSIC -- MISS LUCY'S OPEN MIC NIGHT -- SAINT JOHN ISLAND GUIDE

MISS LUCY’S OPEN MIC NIGHT!

Every Thursday night, Miss Lucy’s in Friis Bay comes alive with the sounds of local and visiting musicians, hosted by the dynamic Lauren Jones Magnie. This outdoor island event is a gathering of locals and visitors alike, creating a vibrant atmosphere filled with music and community spirit. Guests are invited to bring chairs and enjoy the diverse talents on display, from soulful singers to talented instrumentalists.

Miss Lucy’s offers more than just music; it’s a culinary and cultural hub. Indulge in Caribbean delicacies and American favorites at the bar, complemented by a showcase of local handmade Caribbean wares and jewelry by Ital. Whether you’re a music enthusiast or simply looking to experience the authentic spirit of St. John, a visit to Miss Lucy’s on Thursday night promises an unforgettable evening of entertainment, flavors, and local craftsmanship against the scenic backdrop of Friis Bay, just beyond Coral Bay.

MISS LUCY’S LOCATION

LIVE MUSIC NIGHT @ CRUZ BAY LANDING
May 14 @ 6:00 PM – 9:00 PM
LIVE MUSIC NIGHT @ CRUZ BAY LANDING

Get ready for best of the best local musicians St. John has to offer to delight Guests at Cruz Bay Landing.  Nothing like enjoying an incredible meal or hanging out at the bar while being entertained island style with local musicians!  You’ll take these island vibes home with you!

SUNSET SOCIAL @ THE PARROT CLUB
May 14 @ 6:00 PM – 8:00 PM

LIVE MUSIC AT THE PARROT CLUB!

Enjoy the upbeat Live Music, Gaming, and a Full Service Bar!  You’ll be entertained by the best local musicians on St. John.  What a great way to soak in the Caribbean vibe while having lots of fun at the Parrot Club!

NIGHTLY EVENTS

TUESDAYS:  SPIN THE WHEEL — 7:30 – 10:00 PM

WEDNESDAYS:  LADIES NIGHT AND BALLOON POP RAFFLE — 7:00 – 10:00 PM

THURSDAYS:  SUNSET SOCIAL W/LIVE MUSIC — 6:00 – 8:00 PM

SATURDAY:  SPIN THE WHEEL — 7:30 – 10:00 PM

 

May
15
Fri
2026
IKEMA ON STEEL PAN @ THE WINDMILL BAR
May 15 @ 11:30 AM – 2:30 PM

IKEMA ON STEEL PAN LIVE MUSIC -- SAINT JOHN ISLAND GUIDE

IKEMA ON STEEL PAN

Get swept away by the enchanting sounds of Ikema on Steel Pan at The Windmill Bar!  Immerse yourself in the Caribbean vibe as Ikema brings alive all the hits with skill and passion, making your St. John experience truly unforgettable.

Enjoy not only the mesmerizing music, but also the breathtaking views, top-notch entertainment, and delicious food and drinks that The Windmill Bar is renowned for.  Don’t miss out on this perfect blend of music and ambiance in one of St. John’s most scenic spots!

RICH GREENGOLD @ JOHNNY LIME
May 15 @ 5:00 PM – 8:00 PM

RICH GREENGOLD -- ST. JOHN LIVE MUSIC -- SAINT JOHN ISLAND GUIDERICH GREENGOLD

Rich Greengold plays tenor sax, soprano sax, and chromatic harmonica.  Living in Coral Bay for over 35 years, he has played almost every venue on the island.  He often has a song list to request your favorite!

Come on out and be entertained by a local legend as you enjoy some of the best food and drinks in Coral Bay at Johnny Lime.  They have quite a few veggie options too!

TED WYMAN & FRIENDS @ SUN DOG CAFE
May 15 @ 5:00 PM – 8:00 PM

ST. JOHN LIVE MUSIC -- TED WYMAN

TED WYMAN & FRIENDS

Take the humor and stage presence of Jimmy Buffett, mix in the intelligence and craft of Warren Zevon, and add the energy and enthusiasm of Kenny Chesney and Bruce Springsteen, and you come up with Ted Wyman: a witty, charismatic, and energetic tour de force whose music is first and foremost about the audience experience, with each song designed to fit the event, the venue, the crowd, and the vibe.  A typical Ted Wyman performance features a blend of country and rock n’ roll music from both classic and modern eras, and everything in between.

Enjoy some great drinks, food, and entertainment at the Sun Dog Cafe.

SUN DOG CAFE LOCATION

May
17
Sun
2026
BRUNCH WITH RICH GREENGOLD @ SURF CLUB CANTINA
May 17 @ 10:00 AM – 1:00 PM

RICH GREENGOLD -- ST. JOHN LIVE MUSIC -- SAINT JOHN ISLAND GUIDERICH GREENGOLD

Rich Greengold plays tenor sax, soprano sax, and chromatic harmonica.  Living in Coral Bay for over 35 years, he has played almost every venue on the island.  He often has a song list to request your favorite!

Come on out and be entertained by a local legend as you enjoy a scrumptious Brunch at the Surf Club Cantina!

JAZZ BRUNCH WITH “CUPPA” JOE @ SUN DOG CAFE
May 17 @ 11:30 AM – 1:30 PM

“CUPPA” JOE SCIARRONNE

Enjoy a jazzy Sunday brunch with Guitarist Extraordinaire “Cuppa”Joe Sciarronne and the Sun Dog crew every Sunday morning! Joe, known for his incredible talent on the guitar, brings a smooth, vibrant jazz atmosphere that makes brunch at Sun Dog Café an event to remember. With decades of musical experience, Joe creates an inviting, soulful backdrop as you savor the delicious brunch offerings.

Indulge in some delicious mimosas while enjoying the island breeze and mellow tunes. Whether you’re unwinding after a long week or kicking off a new one, this is the ultimate Sunday treat. Come for the music, stay for the food, and bask in the best of St. John’s live entertainment! Brunch is served every Sunday from 9:00 AM to 12:00 Noon.

SUN DOG CAFE LOCATION

 

PAM AND BROHEEM @ CRUZ BAY LANDING
May 17 @ 5:30 PM – 8:30 PM

PAM & BROHEEM -- CRUZ BAY LANDING -- SAINT JOHN ISLAND GUIDE

FROM BROHEEM WITH LOVE

Get ready for these island favorites to delight Guests at the Cruz Bay Landing.  Nothing like enjoying an incredible meal or hanging out at the bar while being entertained island style with Pam Love’s magical voice while Broheem is kickin’ it on the Sax Island Style!  You’ll take these island vibes home with you!

CRUZ BAY LANDING LOCATION

May
18
Mon
2026
IKEMA ON STEEL PAN @ THE WINDMILL BAR
May 18 @ 11:30 AM – 2:30 PM

IKEMA ON STEEL PAN LIVE MUSIC -- SAINT JOHN ISLAND GUIDE

IKEMA ON STEEL PAN

Get swept away by the enchanting sounds of Ikema on Steel Pan at The Windmill Bar!  Immerse yourself in the Caribbean vibe as Ikema brings alive all the hits with skill and passion, making your St. John experience truly unforgettable.

Enjoy not only the mesmerizing music, but also the breathtaking views, top-notch entertainment, and delicious food and drinks that The Windmill Bar is renowned for.  Don’t miss out on this perfect blend of music and ambiance in one of St. John’s most scenic spots!

May
19
Tue
2026
OPEN MIC NIGHT IN CORAL BAY @ JOHNNY LIME
May 19 @ 5:00 PM – 8:00 PM

OPEN MIC NIGHT

JOHNNY LIME -- OPEN MIC NIGHT IN CORAL BAY -- SAINT JOHN ISLAND GUIDE

Join us at Johnny Lime in Coral Bay for a lively Open Mic Night, hosted by the talented Scotty Rolfsen. Whether you’re a local or visiting, Scotty sets the perfect island vibe, bringing together an eclectic mix of musicians for an unforgettable evening of music and fun. You never know which talented performers might take the stage—that’s part of the magic!

This true island jam welcomes all, so bring your instruments, your voice, your dance moves, or just your enthusiasm to soak in the great energy. Pair the incredible tunes with Johnny Lime’s legendary smoked meats, delicious sides, and tasty veggie options for an all-around amazing evening in Coral Bay.

JOHNNY LIME LOCATION

RICH GREENGOLD @ MID WAY CAFE & GRILL
May 19 @ 6:00 PM – 9:00 PM

RICH GREENGOLD -- ST. JOHN LIVE MUSIC -- SAINT JOHN ISLAND GUIDERICH GREENGOLD

Rich Greengold plays tenor sax, soprano sax, and chromatic harmonica.  Living in Coral Bay for over 35 years, he has played almost every venue on the island.  He often has a song list to request your favorite!

Come on out and be entertained by a local legend as you hang out at the Bar or enjoy some great local food at the Mid Way Cafe & Grill!

KARAOKE @ UPSTAIRS SPORTS BAR & GRILLE
May 19 @ 9:00 PM – May 20 @ 12:00 AM

UPSTAIRS SPORTS BAR & GRILLE -- SAINT JOHN ISLAND GUIDEKARAOKE EVERY TUESDAY!

In the heart of Cruz Bay, come on and sing your heart out at the Upstairs Sports Bar & Grille!  Now this is the way to meet others and have a blast!  Enjoy some great drinks and pub food at the Upstairs Bar & Grille.

UPSTAIRS SPORTS BAR & GRILLE LOCATION