Oct25
Gi & Rolando
Live music from Gi & Rolando.
🌴Lighthouse Hotel
- Learn More
- 9:00 AM to 11:00 AM
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The Island Social Calendar
In Key West, there’s always something worth celebrating. Legendary festivals spill onto Duval Street, live music fills the island, and food, art, culture, and a few wonderfully Key West traditions give every season its own reason to visit.
From five historic inns in the heart of Old Town, experience the events that bring the island to life, then come home to a stay with a story of its own.
Oct25
Paradise, Poured
Complimentary Pour of Roseblood Rosé.
🌴 Ella's Cottages
- Learn More
- 3:00 PM to 4:00 PM
- Specific-days
Oct25
Cypress Sangria
Complimentary house made Sangria.
🌴Ridley House
- Learn More
- 3:00 PM to 4:00 PM
- Specific-days
Oct25
Mallory Square Sunset
A nightly Key West tradition of sunsets and waterfront entertainment.
🌴 Mallory Square
- Learn More
- 4:00 PM to 7:00 PM
- Specific-days
Oct25
Happy Hour
A daily Key West tradition.
🌴 Bungalow Bar at Winslow's Bungalows
🌴 Isabel's at Lighthouse Hotel
- Learn More
- 4:00 PM to 6:00 PM
- Specific-days
Oct25
Compass Ritual
A little mystery and a signature toast await.
🌴 Nightly at 5:28 PM
🌴 Isabel's at Lighthouse Hotel
- Learn More
- All Day
- Oct 20 - Oct 20
Oct26
Rum, Lime, and Sunshine
Buy One, Get One Margaritas & Mojitos
🌴 Bungalow Bar at Winslow’s Bungalows
🌴 Isabel’s at Lighthouse Hotel
- Learn More
- 2:00 PM to 4:00 PM
- Specific-days
Oct28
Trop Rock’N Duval
Kick off Trop Rock N' Duval with Mick Fury.
🌴Winslow's' Bungalows
- Learn More
- 12:00 PM to 4:00 PM
- Oct 28 - Oct 28
Oct28
Wine Down Wednesday
Half off wines from 6pm to close.
🌴Winslow's Bungalows
- Learn More
- 4:00 PM to 8:00 PM
- Specific-days
Oct29
Throwback Thursday
Enjoy $10 Classic Cocktails.
🌴 Bungalow Bar at Winslow's Bungalows
- Learn More
- 11:00 AM to 8:00 PM
- Specific-days
Oct29
Farmer’s Market
Shop local produce, artisan foods, and handmade goods.
🌴Truman Waterfront Park
- Learn More
- 1:00 PM to 6:00 PM
- Thursdays
Oct29
Trop Rock’N Duval
Live Music and Poolside fun with Reggie Starrett
🌴 Winslow's Bungalows
- Learn More
- 2:00 PM to 5:00 PM
Oct25
Gi & Rolando
Live music from Gi & Rolando.
🌴Lighthouse Hotel
- Learn More
- 9:00 AM to 11:00 AM
Oct25
Paradise, Poured
Complimentary Pour of Roseblood Rosé.
🌴 Ella's Cottages
- Learn More
- 3:00 PM to 4:00 PM
- Specific-days
Oct25
Cypress Sangria
Complimentary house made Sangria.
🌴Ridley House
- Learn More
- 3:00 PM to 4:00 PM
- Specific-days
Oct25
Mallory Square Sunset
A nightly Key West tradition of sunsets and waterfront entertainment.
🌴 Mallory Square
- Learn More
- 4:00 PM to 7:00 PM
- Specific-days
Oct25
Happy Hour
A daily Key West tradition.
🌴 Bungalow Bar at Winslow's Bungalows
🌴 Isabel's at Lighthouse Hotel
- Learn More
- 4:00 PM to 6:00 PM
- Specific-days
Oct25
Compass Ritual
A little mystery and a signature toast await.
🌴 Nightly at 5:28 PM
🌴 Isabel's at Lighthouse Hotel
- Learn More
- All Day
- Oct 20 - Oct 20
Oct26
Rum, Lime, and Sunshine
Buy One, Get One Margaritas & Mojitos
🌴 Bungalow Bar at Winslow’s Bungalows
🌴 Isabel’s at Lighthouse Hotel
- Learn More
- 2:00 PM to 4:00 PM
- Specific-days
Oct28
Trop Rock’N Duval
Kick off Trop Rock N' Duval with Mick Fury.
🌴Winslow's' Bungalows
- Learn More
- 12:00 PM to 4:00 PM
- Oct 28 - Oct 28
Oct28
Wine Down Wednesday
Half off wines from 6pm to close.
🌴Winslow's Bungalows
- Learn More
- 4:00 PM to 8:00 PM
- Specific-days
Oct29
Throwback Thursday
Enjoy $10 Classic Cocktails.
🌴 Bungalow Bar at Winslow's Bungalows
- Learn More
- 11:00 AM to 8:00 PM
- Specific-days
Oct29
Farmer’s Market
Shop local produce, artisan foods, and handmade goods.
🌴Truman Waterfront Park
- Learn More
- 1:00 PM to 6:00 PM
- Thursdays
Oct29
Trop Rock’N Duval
Live Music and Poolside fun with Reggie Starrett
🌴 Winslow's Bungalows
- Learn More
- 2:00 PM to 5:00 PM
October 2026
SundaySun
MondayMon
TuesdayTue
WednesdayWed
ThursdayThu
FridayFri
SaturdaySat
1
| 16:00 | Mallory Square Sunset |
| 15:00 | Paradise, Poured |
| 13:00 | Farmer's Market |
| 11:00 | Throwback Thursday |
| 15:00 | Cypress Sangria |
| 16:00 | Happy Hour |
2
| 16:00 | Mallory Square Sunset |
| 15:00 | Paradise, Poured |
| 00:00 | Flocktail Friday |
| 15:00 | Cypress Sangria |
| 16:00 | Happy Hour |
3
| 16:00 | Mallory Square Sunset |
| 15:00 | Paradise, Poured |
| 09:00 | Toko Irie |
| 09:00 | Wichita Jack |
| 15:00 | Cypress Sangria |
| 16:00 | Happy Hour |
4
| 16:00 | Mallory Square Sunset |
| 15:00 | Paradise, Poured |
| 15:00 | Cypress Sangria |
| 16:00 | Happy Hour |
5
| 16:00 | Mallory Square Sunset |
| 15:00 | Paradise, Poured |
| 14:00 | Rum, Lime, and Sunshine |
| 15:00 | Cypress Sangria |
| 16:00 | Happy Hour |
6
| 16:00 | Mallory Square Sunset |
| 15:00 | Paradise, Poured |
| 15:00 | Cypress Sangria |
| 16:00 | Happy Hour |
7
| 16:00 | Mallory Square Sunset |
| 16:00 | Wine Down Wednesday |
| 15:00 | Paradise, Poured |
| 15:00 | Cypress Sangria |
| 16:00 | Happy Hour |
8
| 16:00 | Mallory Square Sunset |
| 15:00 | Paradise, Poured |
| 13:00 | Farmer's Market |
| 11:00 | Throwback Thursday |
| 15:00 | Cypress Sangria |
| 16:00 | Happy Hour |
9
| 16:00 | Mallory Square Sunset |
| 15:00 | Paradise, Poured |
| 00:00 | Flocktail Friday |
| 15:00 | Cypress Sangria |
| 16:00 | Happy Hour |
10
| 16:00 | Mallory Square Sunset |
| 15:00 | Paradise, Poured |
| 09:00 | Toko Irie |
| 14:00 | Nina Newton |
| 15:00 | Cypress Sangria |
| 16:00 | Happy Hour |
11
| 16:00 | Mallory Square Sunset |
| 15:00 | Paradise, Poured |
| 15:00 | Cypress Sangria |
| 16:00 | Happy Hour |
12
| 16:00 | Mallory Square Sunset |
| 15:00 | Paradise, Poured |
| 14:00 | Rum, Lime, and Sunshine |
| 15:00 | Cypress Sangria |
| 16:00 | Happy Hour |
13
| 16:00 | Mallory Square Sunset |
| 15:00 | Paradise, Poured |
| 15:00 | Cypress Sangria |
| 16:00 | Happy Hour |
14
| 16:00 | Mallory Square Sunset |
| 16:00 | Wine Down Wednesday |
| 15:00 | Paradise, Poured |
| 15:00 | Cypress Sangria |
| 16:00 | Happy Hour |
| 16:00 | Sam Carlson |
15
| 16:00 | Mallory Square Sunset |
| 15:00 | Paradise, Poured |
| 13:00 | Farmer's Market |
| 11:00 | Throwback Thursday |
| 15:00 | Cypress Sangria |
| 16:00 | Happy Hour |
| 16:00 | Jamie Sellers |
| 16:00 | Sam Carlson |
16
| 16:00 | Martin Sedlak |
| 16:00 | Mallory Square Sunset |
| 15:00 | Paradise, Poured |
| 00:00 | Fantasy Fest |
| 00:00 | Flocktail Friday |
| 15:00 | Cypress Sangria |
| 16:00 | Happy Hour |
| 16:00 | Wavy Davy |
17
| 16:00 | Mallory Square Sunset |
| 15:00 | Paradise, Poured |
| 09:00 | Toko Irie |
| 14:00 | Nina Newton |
| 15:00 | Cypress Sangria |
| 16:00 | Happy Hour |
18
| 16:00 | Mallory Square Sunset |
| 15:00 | Paradise, Poured |
| 10:00 | Key West Artisan Market |
| 00:00 | Goombay Festival |
| 09:00 | Martin Sedlak |
| 15:00 | Cypress Sangria |
| 16:00 | Happy Hour |
19
| 16:00 | Mallory Square Sunset |
| 15:00 | Paradise, Poured |
| 14:00 | Rum, Lime, and Sunshine |
| 15:00 | Cypress Sangria |
| 16:00 | Happy Hour |
20
| 16:00 | Mallory Square Sunset |
| 15:00 | Paradise, Poured |
| 12:00 | Greatest Hits Pool Party |
| 15:00 | Cypress Sangria |
| 16:00 | Happy Hour |
| 17:00 | Compass Ritual |
21
| 16:00 | Mallory Square Sunset |
| 16:00 | Wine Down Wednesday |
| 15:00 | Paradise, Poured |
| 15:00 | Cypress Sangria |
| 16:00 | Happy Hour |
| 16:00 | Sam Carlson |
| 17:00 | Compass Ritual |
22
| 16:00 | Mallory Square Sunset |
| 15:00 | Paradise, Poured |
| 13:00 | Farmer's Market |
| 11:00 | Throwback Thursday |
| 15:00 | Cypress Sangria |
| 16:00 | Happy Hour |
| 16:00 | Jamie Sellers |
| 16:00 | Sam Carlson |
| 17:00 | Compass Ritual |
23
| 16:00 | Mallory Square Sunset |
| 15:00 | Paradise, Poured |
| 00:00 | Flocktail Friday |
| 15:00 | Cypress Sangria |
| 16:00 | Happy Hour |
| 16:00 | Aaron Luka |
| 16:00 | Wavy Davy |
| 17:00 | Compass Ritual |
24
| 16:00 | Mallory Square Sunset |
| 15:00 | Paradise, Poured |
| 09:00 | Toko Irie |
| 14:00 | Nina Newton |
| 15:00 | Cypress Sangria |
| 16:00 | Happy Hour |
| 17:00 | Compass Ritual |
25
| 16:00 | Mallory Square Sunset |
| 15:00 | Paradise, Poured |
| 09:00 | Gi & Rolando |
| 15:00 | Cypress Sangria |
| 16:00 | Happy Hour |
| 17:00 | Compass Ritual |
26
| 16:00 | Mallory Square Sunset |
| 15:00 | Paradise, Poured |
| 14:00 | Rum, Lime, and Sunshine |
| 15:00 | Cypress Sangria |
| 16:00 | Happy Hour |
| 17:00 | Compass Ritual |
27
| 16:00 | Mallory Square Sunset |
| 15:00 | Paradise, Poured |
| 15:00 | Cypress Sangria |
| 16:00 | Happy Hour |
| 17:00 | Compass Ritual |
28
| 16:00 | Mallory Square Sunset |
| 16:00 | Wine Down Wednesday |
| 15:00 | Paradise, Poured |
| 12:00 | Trop Rock'N Duval |
| 15:00 | Cypress Sangria |
| 16:00 | Happy Hour |
| 17:00 | Compass Ritual |
29
| 16:00 | Mallory Square Sunset |
| 15:00 | Paradise, Poured |
| 14:00 | Trop Rock'N Duval |
| 13:00 | Farmer's Market |
| 11:00 | Throwback Thursday |
| 14:00 | Trop Rock'N Duval |
| 15:00 | Cypress Sangria |
| 16:00 | Happy Hour |
| 16:00 | Sam Carlson |
| 17:00 | Compass Ritual |
30
| 16:00 | Mallory Square Sunset |
| 15:00 | Paradise, Poured |
| 00:00 | Flocktail Friday |
| 15:00 | Cypress Sangria |
| 16:00 | Happy Hour |
| 17:00 | Compass Ritual |
31
| 16:00 | Trop Rock'N Duval |
| 16:00 | Mallory Square Sunset |
| 15:00 | Paradise, Poured |
| 09:00 | Toko Irie |
| 09:00 | Wichita Jack |
| 14:00 | Nina Newton |
| 15:00 | Cypress Sangria |
| 16:00 | Happy Hour |
| 17:00 | Compass Ritual |