Hello from Key West!

Thank you for joining the festivities
for our 29th Anniversary!

Key West offers a multitude of exciting experiences, from its diverse restaurants and vibrant nightlife to the numerous museums and art galleries. The wide range of water sports options adds an extra layer of adventure, making it an unforgettable destination.

And let’s not forget the intriguing fact of having 400 bars on an island that’s only 2 x 4 miles—truly a unique aspect of Key West’s charm! Your time on this magical island is sure to be filled with entertainment and discovery. Don’t forget to set aside some extra time to explore all that Key West has to offer. Keep checking this page for more updates!!!

BELOW ARE A FEW IMPORTANT RACE UPDATES:

Key West is the Southernmost City in the US. It is warmer and more humid this time of year than you may be used to. Hydration on the course is absolutely Vital! Our event is cup free which means you need to bring your own water bottle while you are on the course. There will be many aid stations (10) on the course where you can refill your bottle with either water or energy drink.

PACKET PICK-UP

Friday, January 15, 2027

  • 2:00 pm – 7:00 pm: Runner’s Expo/Packet Pick-up
    Location: Outside the Half Shell Raw Bar – 231 Margaret Street
  • 7:15 pm – 10:00 pm Special Late Bib Pick-Up at Fit2Run, 211 Duval Street (BIB’S ONLY. Shirts must be picked up at Runner Expo on Saturday between 1 pm and 6 pm)

Saturday, January 16, 2027

  • 1:00 pm – 6:00 pm: Runner’s Expo/Packet Pick-up
    Location: Outside the Half Shell Raw Bar – 231 Margaret Street
  • 7:00 pm – 10:00 pm Special Late Bib Pick-Up at Fit2Run, 211 Duval Street (BIB’S ONLY – Shirts must be picked up at Shirt Exchange on Sunday after the race at near Gear Check in the parking lot located in the finish line area)

DO YOU HAVE FRIENDS OR FAMILY THAT WOULD LIKE TO VOLUNTEER?

Each volunteer gets a shirt at volunteer check in and welcome to all events. We have dozens of jobs available to fit a variety of time schedules and abilities. Click Here to Volunteer.

RACE START:

Saturday, January 16, 2027

  • 7:00 am: 5K Start and Finish
    Location: Higg’s Beach on 1000 Atlantic Blvd.
  • 8:00 am: 10K Start and Finish
    Location: Higg’s Beach on 1000 Atlantic Blvd.

RACE FINISH: Higg’s Beach on 1000 Atlantic Blvd.

BAG CHECK – SATURDAY: 6:00 am – 6:45 am, in front of 1000 Atlantic Ave. – Saluté! On the Beach.

RESTROOMS/PORT-A-POTTIES: Race morning – Adjacent to Start/Finish Line at Saluté! On the Beach.

Sunday, January 17, 2027

  • 7:00 am: Half Marathon Racers MUST be in position by 6:30 am.
    7:30 am: 8K Start.
    Location: corner of Caroline Street & Trumbo Road/West Marine (less than two blocks from the Packet Pick-Up location.)

BAG CHECK: 6:00 am – 6:45 am on Race Day, in the parking lot by the finish line area in front of Waterfront Brewery. You can find your bag check tag on your bib.

RACE FINISH: Behind Waterfront Brewery.

WATER STATIONS: At the start & finish lines and approximately every 2 miles.

ENERGY DRINKS/GELS: Ultima Replenisher Sports Drink will be at most stations. Gels for sale at Expo

BIG AND LIL’ PECKER CHALLENGE

MUST USE RACE BIB FOR ALL 3 RACES. DO NOT FOLD OR MANGLE BIB.

Pick up your Big Pecker Medal or Lil’ Pecker hat at the Pecker Tent, Sunday after finishing your race. Must bring your bib to receive your Big Pecker Medal or Lil’ Pecker hat.

RACE SHIRTS: Only one race shirt per participant.

RESTROOMS/PORT-A-POTTIES:

  1. 200 yards behind the start line
  2. Half Shell Raw Bar
  3. The Boathouse
  4. Harpoon Harry’s
  5. Public restrooms between the Boathouse and Waterfront Brewery (yellow building with on the water side
  6. The Waterfront Brewery
  7. Schooner Wharf

AWARDS:

Saturday, January 16th, 2027 –

All 5K and 10K overall winners will be announced and age group winners will be available for pick up outside Saluté! On the Beach after the 10K at 9:30 am near the start/finish line.

Sunday, January 17th, 2027 –
8K and Half Marathon awards will be given out at tables near bag check. Overall Male/Female 1-3, Master Male/Female 1-3, and five year age groups Male/Female 1-3. Awards presented at 9:30 am for 8K; approx. 10:30 am for Half Marathon, raffles will follow. Age groups and walkers (Half Marathon only)

WE ARE A CUP FREE RACE!

Bring own cups for water/electrolyte drink! Because of the fragile nature of our marine environment, we won’t be using disposable cups at water stations. Most of the race is adjacent to the ocean, and because of the winds we normally see this time of year , we won’t be handing out disposable cups. Please bring your own reusable vessel for drinks. There will be silicone collapsible cups available for sale at the expo if you forget!

The Key West Papa’s Pilar Rum Stroll Sponsored By Papa’s Pilar Rum

Sunday, January 17th – 1:00 pm – 5:00 pm 

The Papa’s Pilar Rum Stroll Sponsored By Papa’s Pilar Rum. Featuring delicious Papa’s Pilar Rum Libation Special at each location! The Bib has 9 drink tickets that you will need to present at each location. To avoid long lines, feel free to visit the locations in any order.

  1. Hemingway Rum Company, Papa’s Pilar Distillery – 201 Simonton Street
  2. Schooner Wharf Bar – 202 William Street
  3. The Marker – 200 William Street
  4. Conch Republic Seafood Company – 631 Greene Street
  5. Ocean Key’s Sunset Pier – 0 Duval Street
  6. La Concha Tropicado Mojito Bar – 430 Duval Street
  7. First Flight Restaurant – 301 Whitehead Street
  8. RamsHead – 804 Whitehead Street
  9. Southernmost Beach Cafe – 1319 Duval Street

Key West Beach N’ Beer Mile!

Sunday, January 17th – 3:00 pm

The Beach N’ Beer Mile bib has 4 beer tickets on your bib. This casual and fun beer mile takes place on the beach at the Southernmost Beach Cafe, 1405 Duval Street, event starts at 3 pm. Look for the Key West Half Marathon sail flags and cones! Costumes are encouraged and we will be giving various prizes out for the best costumes.

You will need to pick up your Rum Stroll or Beer Mile shirt and bib at the registration tent on Friday, January 15 or Saturday January 16 ONLY. NO EXCEPTIONS. Look for the sign for Rum Stroll and Beer Mile.

For Late Arrivals after Saturday night, a last Pick up will be available at Shirt Exchange Sunday between 9 am- 11:30 am at the Shirt Exchange Table near Bag Check in the Municipal Parking Lot near the Finish line.

YOU WILL FORFEIT YOUR RUM STROLL AND BEER MILE ENTRY IF YOU DON’T ARRIVE WITH YOUR BIB ON SUNDAY, JANUARY 17TH AT EITHER EVENT!!! NO EXCEPTIONS.

2027 SCHEDULE OF EVENTS

Wednesday, January 13, 2027 (Day 1)

  • 11 am – 1:30 pm – Volunteer Check-In and Party
    Location: Sailfish Bar, Half Shell Raw Bar – 231 Margaret Street

Thursday, January 14, 2027 (Day 2)

  • 4:30 pm – 6:00 pm: Runner’s Meet & Greet – Sailfish Bar, Drink Specials
    Location:  Half Shell Raw Bar

Friday, January 15, 2027 (Day 3)

  • ALL DAY: ICE PIK Vodka Drink Specials – Frozen Butterfinger Mudslide $15 & Passionfruit ICE PIK Vodka Cocktail $9
    Location: Half Shell Raw Bar
  • 2:00 pm – 7:00 pm: Runner’s Expo/Packet Pick-up
    Location:  Outside the Half Shell Raw Bar
  • 7:15 pm – 10:00 pm Special Late Bib Pick-Up at Fit2Run, 211 Duval Street (BIB’S ONLY. Shirts must be picked up at Runner Expo on Saturday between 1 pm and 6 pm)

Saturday, January 16, 2027 (Day 4 – 5K & 10K)

  • Breakfast Special: Saluté! On the Beach! 1000 Atlantic Blvd. Will open early with a Three Breakfast Specials and Full Bar!
  • ALL DAY: Pasta Special – $26.99 – Includes Linguine & White or Red Clam Sauce, Garlic Bread and Side Salad.
    Location: Half Shell Raw Bar
  • ALL DAY: ICE PIK Vodka Drink Specials – Frozen Butterfinger Mudslide $15 & Passionfruit ICE PIK Vodka Cocktail $9
    Location: Half Shell Raw Bar
  • BAG CHECK: 6:00 am – 6:45 am, in front of 1000 Atlantic Ave. – Saluté! On the Beach.
  • 7:00 am: 5K Start and Finish
    Location: Higg’s Beach on 1000 Atlantic Blvd.
  • 8:00 am: 10K Start and Finish
    Location: Higg’s Beach on 1000 Atlantic Blvd.
  • 8:00 am – 11:00 am: 5K/10K Concert & Awards Party: Featuring Homebred Band – With Reggae Legend & Grammy Winner, Dave Richards
    Location:
    Outside Salute on the Beach, 1000 Atlantic Avenue
  • 9:30 am: All 5K and 10K overall winners will be announced and age group winners will be available for pick up outside Saluté! On the Beach after the 10K at 9:30 am near the start/finish line.
  • 1:00 pm – 6:00 pm: Runner’s Expo/Packet Pick-up
    Location: Outside the Half Shell Raw Bar
  • 3:30 pm – Presentation by Dr. Kellee Reed. Introduction to Mike Raymond – Man Kicks Bucket at Bucket List Trip
  • 7:00 pm – 10:00 pm Special Late Bib Pick-Up at Fit2Run, 211 Duval Street (BIB’S ONLY – Shirts must be picked up at Shirt Exchange on Sunday after the race at near Gear Check in the parking lot located in the finish line area)

Sunday, January 17, 2027 (Day 5 – Half Marathon & 8K)

  • ALL DAY: $8 Bloody Mary and Mimosa Drink Specials
    Location: Half Shell Raw Bar
  • ALL DAY: ICE PIK Vodka Drink Specials – Frozen Butterfinger Mudslide $15 & Passionfruit ICE PIK Vodka Cocktail $9
    Location: Half Shell Raw Bar
  • BAG CHECK: 6:00 am – 6:45 am on Race Day, in the parking lot by the finish line area in front of Waterfront Brewery.
  • 7:00 am: Half Marathon
  • 7:30 am: 8K Start
    Location: corner of Caroline Street & Trumbo Road/West Marine (less than two blocks from the Packet Pick-Up location.)
    RACE FINISH: Behind Waterfront Brewery.
  • 8:30 am – 12:30 pm: Concert & Awards Party: Featuring The Cayo Ritmo Big Band
    Location: Outside Half Shell Raw Bar
  • 9:30 am: 8K Awards at tables near bag check
  • 10:30 am: Half Marathon Awards at tables near bag check
  • 1:00 pm – 5:00 pm  The Key West Papa’s Pilar Rum Stroll Sponsored By Papa’s Pilar Rum
    Featuring delicious Papa’s Pilar Rum Libation Special at each location!

    1. Hemingway Rum Company, Papa’s Pilar Distillery – 201 Simonton Street
    2. Schooner Wharf Bar – 202 William Street
    3. The Marker – 200 William Street
    4. Conch Republic Seafood Company – 631 Greene Street
    5. Ocean Key Sunset Pier – 0 Duval Street
    6. La Concha Tropicado Mojito Bar – 430 Duval Street
    7. First Flight Restaurant – 301 Whitehead Street
    8. RamsHead – 804 Whitehead Street
    9. Southernmost Beach Cafe – 1319 Duval Street
  • 3:00 pm Key West Beach N’ Beer Mile! Outside of the Southern Most Beach Cafe: 1405 Duval St, Key West, FL 33040
    4 Loops, 4 Beers, Custom Shirt. Race is NOT TIMED!
    Prizes awarded for:
    1. Best Team Spirit
    2. Best Dressed
    3. Least Dressed
  • 4:00 pm – 6:00 pm: Cool Down & Recover Pool Party at the Blue Flamingo Resort. Free Entry! Live Music and Drink Specials. 3820 N Roosevelt Blvd, Key West, FL 33040. 
  • 4:00 pm – 6:00 pm: Key West Farewell Party
    Location:  Salty Oyster with Live Entertainment at the Perry Hotel located 7001 Shrimp Road, Key West, FL 33040.  Happy Hour pricing is 50% off well drinks and draft beers. And continue on to Matt’s Stock Island Happy Hour also at the Perry Hotel!!!

Monday, January 18, 2027 (Day 6)

    • 4:00 – 6:00 pm: Marathon Farewell Party and Happy Hour at the Blu Bistro at the Skipjack Resort in Marathon. 20% off all Menu items and Drinks All Day! Just mention you participate d in the Key west Half Marathon
      Location: SKIPJACK RESORT & MARINA – 19 Sombrero Blvd, Marathon, FL 33050

Post Race Concert Featuring The Cayo Ritmo Big Band

Cayo Ritmo in Spanish means Island Rhythm. The Band plays American & Caribbean Dance Music, Funk, Pop, R&B, Reggae, Cha-Cha, Calypso and Latin Jazz with Key West’s Finest Musicians!

b29bf772-fe64-4b81-9804-edb8f28795a4-bjtgvv
e83c46c2-ed3c-45d7-8104-7244cd0dd1da-bjtgvv

SATURDAY PARKING: There is ample parking near Salute Restaurant, 1000 Atlantic Blvd. Across the street at the Dog Parks and by the Bocce Courts by the Wildlife Bird Center, 1801 White Street.

SUNDAY PARKING: Ample parking within a block of start/finish area.

SUNDAY ARRIVE BY 5:30 am. We strongly suggest you arrive by taxi or bicycle or Uber and Lyft are available. City of Key West lots: Corner of Grinnell/Caroline and Margaret/Caroline, Conch Harbor Marina. Mallory Square lot and Opal Resort lots are within 1/4 mile of start/finish.

IV Hydration Station Offering IV vitamin infusions for Energy boost, athletic prep and recovery, immune boost and much more!

Charity Partner

We would like to thank our main charity partner, key west sunrise rotary, who uses all the proceeds to fund scholarships
For key west high school students.

Classic Harbor Line is proud to offer Key West Half Marathon or 5K participants a free ticket aboard the Schooner America 2.0 on the Classic Day Sail or Champagne Sunset Sail with the purchase of at least one additional adult ticket.
Call Tom at (305) 293-7245 and mention this promotion to book! Offer good 01/10-01/27.

www.sail-keywest.com

Contact Us

We're not around right now. But you can send us an email and we'll get back to you, asap.

Not readable? Change text. captcha txt