2 large sailboats on the water during a gorgeous sunset

Sunset Sails

There is nothing quite like a Key West sunset, and the second-best place to view one (after the Sunset Pier, of course) is out on the water. Whether you’re listening to live music on a catamaran, enjoying a fine glass of wine on a sailboat or enjoying a gourmet meal aboard a yacht, a sunset sail is an absolute must during your trip.

Contact our concierge to reserve this experience.

Date

May 9, 2026 - July 31, 2026

Time

Saturday's, Varies (sunset)

Location

Off-Site (Key West waters)

Calendar of Events

Jul21
Double Dip Snorkel Trip
Explore the turquoise waters of the 3rd largest coral barrier reef, teeming with fish, coral, sea turtles and more.

Date: May 12, 2026 - July 31, 2026
Time: Tuesday's, 2:00 pm – 5:00 pm
Location: Off-Site (Catamaran / Key West reef)

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Jul21
Live at Sunset Pier - Reggae Lou & The Kind Buds
Join us at the Sunset Pier for waterfront live music, breathtaking sunset views and delicious cocktails and bites.

Date: July 16, 21, 23, 28, 30, 2026
Time: 7:00 pm - 9:00 pm
Location: Sunset Pier

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Jul22
Zero Duval Scavenger Hunt
Experience a one-of-a-kind, interactive scavenger hunt in the downtown area of Old Town, starting at Zero Duval.

Date: May 13, 2026 - July 31, 2026
Time: Wednesday's, 10:00 am – 12:00 pm
Location: Old Town Key West (starts at Zero Duval)

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Jul22
Muddle & Mingle
We invite locals and resort guests to a spirited midday escape, blending cocktail craft, island flavor and Sweet Bird flair.

Date: July 6, 2026 - August 30, 2026
Time: 12:00 PM
Location: Sweet Bird Bar

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Jul22
Live at Sunset Pier – Jerico Rockability Quartet
Join us at the Sunset Pier for waterfront live music, breathtaking sunset views and delicious cocktails and bites.

Date: Wednesdays & Fridays | July 1 - 31, 2026
Time: 7:00 pm - 9:00 pm
Location: Sunset Pier

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Jul23
SpaTerre VOYA Treatments
Relax and rejuvenate the natural way! VOYA Organic Seaweed Treatments.

Date: May 14, 2026 - July 31, 2026
Time: Thursday's, All day (by appointment)
Location: SpaTerre

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Jul23
SpaTerre VOYA Treatments
Vortex Cleansing deeply cleanses and hydrates, Hydrapeel exfoliation resurfaces without irritation

Date: May 12, 2026 - July 31, 2026
Time: Tuesday's, All day (by appointment)
Location: SpaTerre

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Jul23
Hemingway Days
Fans of Ernest Hemingway’s literary greatness and vigorous life – including scores of bearded Hemingway look-alikes

Date: July 23 - 27, 2026
Time: Varies by event
Location: Key West (Sloppy Joe's Bar, 201 Duval St., and other venues)

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Jul23
Haunted Tours
Explore the SPOOKY side of Key West with a haunted historical tour.

Date: May 14, 2026 - July 31, 2026
Time: Thursday evenings (varies by operator)
Location: Off-Site (Key West – walking or trolley tour)

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Jul23
Romance at Hot Tin Roof
Add some romance to your dining experience with a chilled bottle of Lallier Reserve Brut champagne and your table decorated with rose petals

Date: May 14, 2026 - July 31, 2026
Time: Thursday's, During Hot Tin Roof dining hours
Location: Hot Tin Roof

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