Sunset Sail Key West

Sunset Sail Key West Sunset Sail Key West is a locally owned, independent charter company operating historic schooners and sailing yachts in Key West.
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We offer shared and private sunset sails aboard our own fleet of storied sailing yachts. There's no better way to experience the Florida Keys than right on the water, and there's no better charter to trust with your tour than Sunset Sail Key West. With years of experience and a lifetime of passion, our fleet of locally owned sailboats and personable sailors will show you all the beauty that Key We

st has to offer. As you join us for a sunset, starlight, or snorkel sail, you'll find that the sparkling waters of the Florida Keys have a way of bringing people together. Our dedicated team is flexible, accommodating, and dedicated to making your sailing experience as smooth and personalized as possible.

Summer, sunshine and wind in the sails! It’s your charter!
06/04/2026

Summer, sunshine and wind in the sails! It’s your charter!

Fair winds to the good ship When And If and her fearless crew! May your trip be easy and the wind at your back! We cann...
06/02/2026

Fair winds to the good ship When And If and her fearless crew! May your trip be easy and the wind at your back! We cannot wait for you to be back in November!

05/25/2026

This is what it’s all about!!

05/25/2026

Special. Unique. Meaningful. This is Sunset Sail Key West! Reserve your private charter and leave all your worries at the dock!

05/23/2026

Congratulations to Chrystal and Everett and thank you Weddings To Go for a beautiful and memorable ceremony!

Less than 2 weeks of sailing in Key West aboard the historic Schooner When And If from the Key West Historic Seaport! Ho...
05/19/2026

Less than 2 weeks of sailing in Key West aboard the historic Schooner When And If from the Key West Historic Seaport! Hop onboard for a majestic sail before we depart for the Sail4th 250 celebrations!

Summer sailing on Key West’s first and most versatile sloop S/V High Tide! Private charters for tropical sailing vibes! ...
05/19/2026

Summer sailing on Key West’s first and most versatile sloop S/V High Tide!
Private charters for tropical sailing vibes! 🏝️⛵️😎
Choose from a variety of options!
- A short and sweet harbor day sail ⛵️☀️
- 3 hr chill out lily pad sail 🩱☀️⛵️
- 4hr snorkel/ dolphin watch 🐬🤿⛵️
** or our specialty!!
Relaxed and perfect for any occasion
— 2hr Sunset Sail! 🌅⛵️🥂

USCG Certified for 12 Guests
Licensed Captain and knowledgeable crew
No charge for BYOB
Bottled water, cooler filled with ice included
*Ad ons available, fully customizable!
Call 305-587-4488 or book online at
https://sunsetsailkeywest.com

Shout out to all of the Conch Republic who came out to celebrate and participate in the 44th annual Conch Republic Indep...
04/26/2026

Shout out to all of the Conch Republic who came out to celebrate and participate in the 44th annual Conch Republic Independence Celebration! Victory was once again ours! A reminder that good humor and good fun brings us all together and that is what the Conch Republic is all about!

Address

202 William Street
Key West, FL
33040

Opening Hours

Monday 8am - 10pm
Tuesday 8am - 10pm
Wednesday 8am - 10pm
Thursday 8am - 10pm
Friday 8am - 10pm
Saturday 8am - 10pm
Sunday 8am - 10pm

Telephone

+13055874488

Website

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