What's on in Cayman Islands
89 upcoming events
Friday 3 July
—
Happy Fri-YAY
Vines to Ocean (V₂O)
Saturday 4 July
—
Next: Saturday, July 4
Jacks Beach Bar
—
Sushi Saturday
Vines to Ocean (V₂O)
Sunday 5 July
18:00
Cayman Islands Family Event
Grand Cayman venue
Monday 6 July
12:00
Constitution Day at Camana Bay
Camana Bay Harbour
Tuesday 7 July
19:30
Summer Moonlight & Movies
Camana Bay
Friday 10 July
18:00
Cayman Islands Culture Event
Grand Cayman venue
Friday 17 July
Sunday 19 July
12:00
World Cup Final Viewing Party
Hotel Indigo
Saturday 25 July
—
Concacaf Under-20 Championship
CONCACAF
Thursday 13 August
—
(before fees & tax)
Abita Kai — Grand Cayman Villas
Saturday 15 August
—
See Exhibition
National Gallery of the Cayman Islands
Tuesday 18 August
—
JUNIOR SUMMER CAMP
Cayman Islands Tennis Club
Friday 28 August
—
JUNIOR SUMMER CAMP
Cayman Islands Tennis Club
Tuesday 1 September
—
2026 North American Cup (hosted by Cayman Islands)
Cayman Islands Cricket Association
—
Fit Check #2 Time Trial
Cayman Cycling
—
Fall Matchplay
Cayman Islands Golf Association (CIGA)
—
After-School Programme (Fall 2026)
Cayman Pickleball & Tennis Academy
—
Stroke & Stride Series (3 rounds)
Cayman Islands Triathlon Association
Saturday 12 September
10:00
The Big Shave
Grand Cayman
Monday 21 September
—
Concacaf Nations League
CONCACAF
Wednesday 30 September
—
See Exhibition
National Gallery of the Cayman Islands
Thursday 1 October
—
Restaurant Month
Driftwood Bar & Grill
—
McGrath Tonner Duathlon
Cayman Islands Triathlon Association
Sunday 4 October
—
Cayman Cup Road Race
Cayman Cycling
—
RF Bank & Trust Cayman 7s Series Round 1
Cayman Rugby Football Union
Monday 5 October
—
TFCI CITC SINGLES OPEN 4
Cayman Islands Tennis Club
Sunday 11 October
—
RF Bank & Trust Cayman 7s Series Round 2
Cayman Rugby Football Union
Monday 12 October
17:00
Cayman Cocktail Week
Bars island-wide
Friday 23 October
—
Thu Oct 23 – Blind Tasting Flight Night
Le Petit Bar Cayman
Saturday 24 October
—
junior october mid-term camp
Cayman Islands Tennis Club
15:00
Oktoberfest Cayman
Grand Cayman
Sunday 25 October
—
RF Bank & Trust Cayman 7s Series Round 3
Cayman Rugby Football Union
Saturday 31 October
—
Halloween - October 31st
Explore Cayman annual events
Sunday 1 November
—
Fit Check #3 Time Trial
Cayman Cycling
—
MUFG Investor Services Triathlon
Cayman Islands Triathlon Association
—
Pirates Week Festival (dates TBA)
Cayman Islands
06:30
Cayman Islands Triathlon
George Town waterfront
Monday 2 November
—
TFCI CITC DOUBLES OPEN 4
Cayman Islands Tennis Club
Sunday 8 November
10:00
Pirates Week
George Town & districts
Monday 9 November
—
Concacaf Nations League
CONCACAF
Friday 13 November
—
Thu Nov 13 – Blind Tasting Flight Night
Le Petit Bar Cayman
Friday 20 November
19:00
Gimistory — International Storytelling Festival
Outdoor venues island-wide
Thursday 26 November
—
November 26th at noon.
Cayman Islands Tennis Club
Friday 27 November
17:30
Camana Bay Annual Tree Lighting
Camana Bay
Saturday 28 November
—
CIGA Pairs
Cayman Islands Golf Association (CIGA)
Monday 30 November
—
TFCI year end open
Cayman Islands Tennis Club
Tuesday 1 December
—
Christmas Party
Cayman Islands Tennis Club
Wednesday 2 December
—
Tue Dec 2 – Holiday Wine Trivia Night – Free
Le Petit Bar Cayman
Sunday 6 December
Friday 11 December
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Thu Dec 11 – Blind Tasting Flight Night
Le Petit Bar Cayman
Sunday 20 December
—
Saturday, December 20th and December 27th
Pane & Pasta - Italian Restaurant and pizza - Fresh Bakery
Friday 25 December
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Christmas Day - 25th December
Explore Cayman annual events
Wednesday 30 December
Thursday 31 December
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Fireworks at Camana Bay
Driftwood Bar & Grill
—
Monday Evening Hash Run (weekly)
Cayman Hash House Harriers
—
Annual CUC Youth & CARIFTA Track & Field Championships
Cayman Islands Athletic Association
—
CIBA Youth League (U12–U19, male and female)
Cayman Islands Basketball Association (CIBA)
—
Senior League (male and female)
Cayman Islands Basketball Association (CIBA)
—
CIFA Premier League 2025/26 Season
Cayman Islands Football Association (CIFA)
—
Women's League fixtures
Cayman Islands Football Association (CIFA)
—
Fast 5 Co-ed League
Cayman Islands Netball Association
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Mixed League
Cayman Islands Netball Association
—
Senior Women's League (Thursdays & Saturdays)
Cayman Islands Netball Association
—
Turtle Netters League (ages 5–10, Saturdays)
Cayman Islands Netball Association
—
Paradise Padel Tournament (monthly)
PHA Padel (Palm Heights)
—
Ladies Only Open Play (weekly Thursdays)
Cayman Pickleball & Tennis Academy
—
Caribbean Championships
Pickleball Cayman
—
Cruiser Racing (fourth Sunday monthly)
Cayman Islands Sailing Club
—
Dinghy Racing (first Sunday monthly)
Cayman Islands Sailing Club
—
J-22 Racing (third Sunday monthly)
Cayman Islands Sailing Club
—
Wednesday Night Hartley (weekly)
Cayman Islands Sailing Club
—
Box League / Shoot Out Tournament
South Sound Squash Club
—
Family Squash (last Sunday monthly)
South Sound Squash Club
—
LIG Services International Junior Tournament
South Sound Squash Club
—
Masters Open Tournament
South Sound Squash Club
—
Scotts Equipment SSSC Open Championships
South Sound Squash Club
—
CBAC Kick-off Swim Meet
Camana Bay Aquatic Club (CBAC)
—
Coconut Cup Swim Meet
Camana Bay Aquatic Club (CBAC)
—
Spring Splash Swim Meet
Camana Bay Aquatic Club (CBAC)
—
Doubles Social
Cayman Islands Tennis Club
—
Family Tennis Festival (monthly)
Cayman Islands Tennis Club
—
J30 International Junior Tournament
Cayman Islands Tennis Club
—
KPMG Junior Tournament
Cayman Islands Tennis Club
—
TFCI Singles Open (Beginner–Competitive)
Cayman Islands Tennis Club
—
Try This Tri (kids)
Cayman Islands Triathlon Association
Thursday 1 April
—
Annual Cross Island Relay
Cayman Hash House Harriers
Thursday 16 December
—
13% Occupancy Tax added to rates.
Kaibo Dreams – Grand Cayman Villas