57th Annual Agriculture Show

Stacy Watler Pavilion, Agricola Drive, Lower Valley, Box 1768, Grand Cayman KY1-1109, Cayman Islands, BWI. Bodden Town, Cayman Islands 18 Feb 2026

Light up the Night

#19 Grand Harbour, , KY1-1201 Prospect, Cayman Islands 7 Mar 2026

RED SKY AT NIGHT

Harquail Theatre 21 Mar 2026

Harvest Dinner with Guest Chef Nando Chang

The Brasserie, Cricket Square, George Town, KY1-1004 George Town, Cayman Islands 27 Feb 2026

EAST END SURF CHALLENGE & FISH TEA COOK OFF

East End Grand Cayman Cayman Islands BWI 26 Jan 2026

Valentine's Day Dinner & Gifts

The Brasserie, Cricket Square, George Town, KY1-1004 George Town, Cayman Islands 14 Feb 2026

Cayman Arts Festival 2026

George Town 5 Feb 2026

FOIE GRAS LUNCH 2026

Grand Old House 30 Jan 2026

2026 Addison Kelly Butterfly 5k

Camana Bay, Grand Cayman 7 Feb 2026

'A Calm Mind and Open Heart" Retreat

West Bay Road at Queens Court Plaza, KY1 1104 George Town, Cayman Islands 23 Jan 2026

Roots Reggae Tuesdays (featuring Rico Rolando)

Sandbar Daiquiri Bar and Grill 3 Feb 2026

Asado Night

389 West Bay Road Seven Mile Beach, George Town, Cayman Islands 30 Jan 2026

Lobster Night

389 West Bay Road Seven Mile Beach, George Town, Cayman Islands 28 Jan 2026

SWIRL: Best of New World Wines

The Brasserie, Cricket Square, George Town, KY1-1004 George Town, Cayman Islands 29 Jan 2026

Alex Panton Foundation's 2026 Youth Mental Health Symposium

Hotel Indigo Grand Cayman, an IHG Hotel (32 Seafire Way, Seven Mile Beach, West Bay, Grand Cayman, Cayman Islands) 21 Feb 2026

Winetasting 🍷 Bordeaux: Young and Aged — A Timeless Showdown

Grand Old House 11 Feb 2026

Grill & Chill Saturdays

786 Northwest Point RD, KY1-1301 West Bay, Cayman Islands 30 Jan 2026

IslandSoul Festival

Holiday Inn Resort Grand Cayman 31 Jan 2026

Cayman Islands — CayFest

Harquail Theatre 6 Mar 2026

Valentine's Dinner at Veranda

389 West Bay Road Seven Mile Beach, George Town, Cayman Islands 14 Feb 2026