Monday
October
18
1:00 pm - 4:00 pm
Sunset Pier

Live at Sunset Pier

Featuring:  Rolando Rojas

Live music right over the water at the Sunset Pier! Gorgeous harbor views, tropical libations and island-inspired snacks.

Sunset Pier Menu

Monday
October
18
6:00 pm - 8:00 pm
Sunset Pier

Live at Sunset Pier

Featuring:  Rolando Rojas

Join us at the Sunset Pier for waterfront live music, breathtaking sunset views and delicious cocktails and bites.

Sunset Pier Menu

Wednesday
October
20
SpaTerre

SpaTerre Ultimate Bliss Special

Relax and rejuvenate the natural way!

The Ultimate Bliss, CBD Package

Relax like never before with this package designed to create a state of bliss using quality CBD infused products. First, slough away dead skin cells and uncover a fresh radiant skin using CBD infused Lavender and gray sea salt scrub. Then enjoy a CBD Warm Oil scalp massage while cocooned in our CBD lavender body mask. Finally, sink into total relaxation during a full body massage using CBD infused massage oil.

$295; Add a CBD Ritual Bath for deeper relaxation for $90

Call to reserve your appointment, 305-295-7017.

Wednesday
October
20
1:00 pm - 4:00 pm
Sunset Pier

Live at Sunset Pier

Featuring:  Kim Jade Fry

Live music right over the water at the Sunset Pier! Gorgeous harbor views, tropical libations and island-inspired snacks.

Sunset Pier Menu

Wednesday
October
20
6:00 pm - 8:00 pm
Sunset Pier

Live at Sunset Pier

Featuring:  Jerrod & Friends

Join us at the Sunset Pier for waterfront live music, breathtaking sunset views and delicious cocktails and bites.

Sunset Pier Menu

Thursday
October
21
6:00 pm
Sunset Pier

Great American Trainwreck

Americana/Bluegrass/Southern Rock from the PNW – this will be a FREE show for all to enjoy! Live entertainment, stunning views and the best in island libations right over the water! Portion of proceeds to benefit Mote Marine Laboratory’s Center for Coral Reef Research & Restoration. Come for the concert, stay for the cause.

 

Fantasy Fest
Friday
October
22

Fantasy Fest

Event Dates 10/22-10/31

The origins of Fantasy Fest date back to 1979 when a group of business owners decided to come up with an event to attract visitors during the slow season. What began as a simple, yet audacious costume parade has since turned into a multi-day event. The festival has since added several events and activities that serve as fundraisers for community groups and non-profit organizations.

Key West Fantasy Fest is going to be lively this year! Charge your creative juices and enjoy some partying, playing and plain old having a great time!

Learn More

Friday
October
22
SpaTerre

Signature Spa Specials

Be transformed with a little pampering in paradise! Try our Signature Facial or the Detox Duval Wrap.

Each treatment 50 minutes for $109

Call to reserve your appointment, 305-295-7017. Learn More

Friday
October
22
SpaTerre

Swedish Massage Special

Unwind with this gentle, relaxing massage that improves circulation and vitality. This massage uses our lightest touch.

50 minutes for $109 (for a limited time only!)

Call to reserve your appointment, 305-295-7017. Learn More

Friday
October
22
1:00 pm - 4:00 pm
Sunset Pier

Live at Sunset Pier

Featuring:  Rick Fusco

Live music right over the water at the Sunset Pier! Gorgeous harbor views, tropical libations and island-inspired snacks.

Sunset Pier Menu

Friday
October
22
6:00 pm - 8:00 pm
Sunset Pier

Live at Sunset Pier

Featuring:  Claire Finley

Join us at the Sunset Pier for waterfront live music, breathtaking sunset views and delicious cocktails and bites.

Sunset Pier Menu

Saturday
October
23
6:00 pm
Sunset Pier

That Arena Rock Show

That Arena Rock Show is the ultimate high energy tribute to “Classic” Rock N’ Roll. Performing legendary rock anthems that ruled the airwaves in the 70s and 80s. Including artists like: Led Zeppelin, Aerosmith, AC/DC, Bon Jovi, and Guns N Roses to name a few. This show will take you on a trip back in time, turning every sized venue into an arena for a night, and this Key West show is FREE for all guests of the Sunset Pier to enjoy. Get your lighters out and your fist in the air. This rock show is more than just music – it’s an experience! Portion of proceeds to benefit Mote Marine Laboratory’s Center for Coral Reef Research & Restoration. Come for the concert, stay for the cause.

 

Sunday
October
24
1:00 pm - 4:00 pm
Sunset Pier

Live at Sunset Pier

Featuring:  The Frito Lays

Live music right over the water at the Sunset Pier! Gorgeous harbor views, tropical libations and island-inspired snacks.

Sunset Pier Menu

Sunday
October
24
6:00 pm - 8:00 pm
Sunset Pier

Live at Sunset Pier

Featuring:  The Robert Albury Band

Join us at the Sunset Pier for waterfront live music, breathtaking sunset views and delicious cocktails and bites.

Sunset Pier Menu

Monday
October
25
1:00 pm - 4:00 pm
Sunset Pier

Live at Sunset Pier

Featuring:  Rolando Rojas

Live music right over the water at the Sunset Pier! Gorgeous harbor views, tropical libations and island-inspired snacks.

Sunset Pier Menu

Monday
October
25
6:00 pm - 8:00 pm
Sunset Pier

Live at Sunset Pier

Featuring:  Rolando Rojas

Join us at the Sunset Pier for waterfront live music, breathtaking sunset views and delicious cocktails and bites.

Sunset Pier Menu

Tuesday
October
26
1:00 pm - 4:00 pm
Sunset Pier

Live at Sunset Pier

Featuring:  Ross Brown

Live music right over the water at the Sunset Pier! Gorgeous harbor views, tropical libations and island-inspired snacks.

Sunset Pier Menu

Tuesday
October
26
6:00 pm - 8:00 pm
Sunset Pier

Live at Sunset Pier

Featuring:  Ross Brown

Join us at the Sunset Pier for waterfront live music, breathtaking sunset views and delicious cocktails and bites.

Sunset Pier Menu

Wednesday
October
27
SpaTerre

SpaTerre Body Scrub Special

Relax and rejuvenate the natural way!

Peaceful Glow CBD Body Scrub
French Gray Sea Salt combined with CBD infused Grapeseed oil exfoliates and nourishes skin during this relaxing body scrub.

50 minutes $170; Add a CBD Ritual Bath for deeper relaxation for $90

Call to reserve your appointment, 305-295-7017.

Wednesday
October
27
1:00 pm - 4:00 pm
Sunset Pier

Live at Sunset Pier

Featuring:  Kim Jade Fry

Live music right over the water at the Sunset Pier! Gorgeous harbor views, tropical libations and island-inspired snacks.

Sunset Pier Menu

Wednesday
October
27
6:00 pm - 8:00 pm
Sunset Pier

Live at Sunset Pier

Featuring:  Jerrod & Friends

Join us at the Sunset Pier for waterfront live music, breathtaking sunset views and delicious cocktails and bites.

Sunset Pier Menu

Thursday
October
28
1:00 pm - 4:00 pm
Sunset Pier

Live at Sunset Pier

Featuring:  Marjory Lee

Live music right over the water at the Sunset Pier! Gorgeous harbor views, tropical libations and island-inspired snacks.

Sunset Pier Menu

Thursday
October
28
6:00 pm - 8:00 pm
Sunset Pier

Live at Sunset Pier

Featuring:  Sharese 

Join us at the Sunset Pier for waterfront live music, breathtaking sunset views and delicious cocktails and bites.

Sunset Pier Menu

Friday
October
29
SpaTerre

Signature Spa Specials

Be transformed with a little pampering in paradise! Try our Signature Facial or the Detox Duval Wrap.

Each treatment 50 minutes for $109

Call to reserve your appointment, 305-295-7017. Learn More

Friday
October
29
SpaTerre

Swedish Massage Special

Unwind with this gentle, relaxing massage that improves circulation and vitality. This massage uses our lightest touch.

50 minutes for $109 (for a limited time only!)

Call to reserve your appointment, 305-295-7017. Learn More

Friday
October
29
1:00 pm - 4:00 pm
Sunset Pier

Live at Sunset Pier

Featuring:  Rick Fusco

Live music right over the water at the Sunset Pier! Gorgeous harbor views, tropical libations and island-inspired snacks.

Sunset Pier Menu

Friday
October
29
8:00 pm - 11:00 pm
Sunset Pier

20th Annual Living Art Expo

A showcase of the human form as a living canvas. Contestant entries are open to Female, Male or Group models competing for the title of Best Overall Living Art of Fantasy Fest 2021 and $3000 in cash and prizes. Best Overall wins $1000 in cash.

VIP will include back stage access with the models, 3-hour open bar, and a pasta station dinner.

Tickets are $95 or $150 for table seating (sold in pairs).

Buy Tickets

For entry information contact the Sunset Pier 305-295-7047 or dining@oceankey.com.

Fantasy Fest Website

Sunday
October
31
1:00 pm - 4:00 pm
Sunset Pier

Live at Sunset Pier

Featuring:  The Frito Lays

Live music right over the water at the Sunset Pier! Gorgeous harbor views, tropical libations and island-inspired snacks.

Sunset Pier Menu

Sunday
October
31
6:00 pm - 8:00 pm
Sunset Pier

Live at Sunset Pier

Featuring:  The Robert Albury Band

Join us at the Sunset Pier for waterfront live music, breathtaking sunset views and delicious cocktails and bites.

Sunset Pier Menu

Parrot Heads
Wednesday
November
3

Parrot Heads, Annual Meeting of the Minds

Event Dates 11/3-11/7

Get your own little taste of Margaritaville by migrating to Key West along with the rest of the Parrot Heads. Parrot Head chapters from all over the world flock to Key West for an annual Meeting of The Minds, a four-day convention that celebrates friendship, charitable “partying with a purpose” and Jimmy Buffet’s music. The Parrot Head convention annually attracts about 3,500 attendees on the week following Fantasy Fest and is regarded as one of the best things to do in Key West around the beginning of November.

Learn More

Wednesday
November
3
SpaTerre

SpaTerre Mani/Pedi Special

Ultimate CBD Mani/Pedi Experience

  • Calms Anxiety
  • Relieves Pain & Inflammation
  • Deep Relaxation
  • Super Hydrating

Call to reserve your appointment, 305-295-7017.

Wednesday
November
3
6:00 pm
Sunset Pier

Live at Sunset Pier

Featuring:  Trop Rock Junkies

Join us at the Sunset Pier for waterfront live music, breathtaking sunset views and delicious cocktails and bites.

Sunset Pier Menu

OKR Boat Race
Sunday
November
7

Race World Offshore Championships

Event Dates 11/7-11/14

Experience the most powerful of water activities in Key West with the Race World Offshore World Championships. Watch as the world’s biggest and fastest boats attain speeds of up to 180 mph over the six-mile course on the Gulf side of the island. Over the course of the season, from May to November, teams from all around the world compete in National Series Points races which eventually determine the overall winner. Most of the Super Boat racers are out on the water in a different locale every weekend. Take a shore side seat for this exciting watersport action.

Learn More

Monday
November
8
5:00 pm - 7:00 pm
Sunset Pier

Live at Sunset Pier

Featuring:  The Wheeland Brothers

Join us at the Sunset Pier for waterfront live music, breathtaking sunset views and delicious cocktails and bites.

Sunset Pier Menu

Tuesday
November
9
5:00 pm - 7:00 pm
Sunset Pier

Live at Sunset Pier

Featuring:  The Wheeland Brothers

Join us at the Sunset Pier for waterfront live music, breathtaking sunset views and delicious cocktails and bites.

Sunset Pier Menu

Friday
January
14

RokIsland Fest

Event Dates 1/14-1/17

The inaugural RokIsland Fest, where the world’s greatest rock bands will descend upon our island paradise for a 4-day music festival. Events will take place at the Truman Waterfront Park Amphitheater, a beautifully designed facility on the Gulf waters of Key West, as well as at the Sunset Pier. Tickets are on sale now and going fast. Get ready to pack your bags for an epic week of ROCK!

Learn More

Sunday
January
16

Half Marathon & 5K

The annual Key West Half Marathon & 5K Run is recognized by Runners World magazine as one of the 10 great half-marathons of the winter season. This competitive race follows a 13.1-mile course through Old Town Key West past historic landmarks and the island’s scenic waterfront.

If you’re planning on joining the half-marathon or 5k run, make Ocean Key Resort & Spa your home base. You’ll be able to relax before and after the race, in true Keys style. Be sure to book a massage after the race, to soothe your tired muscles!

Learn More

Tuesday
January
25

Mile 0 Fest

Event Dates 1/25-1/29

Mile 0 Fest is a boutique destination festival. Called by attendees the ‘the friendliest and best fest’ out there. Bringing the best of “Red Dirt & Americana Music” to Paradise every year. Join us at venues around the island including the Sunset Pier!

Learn More

Wednesday
May
4

The Key West Songwriters Festival

Event Dates 5/4-5/8

The Key West Songwriters Festival is the largest festival of its kind in the world. Celebrating its 26th year. The festival revolves around five days and nights where live music bliss introduces crowds to the faces, voices and stories behind the songs. Join us at many venues around the island including the Sunset Pier!

Learn More

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