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The Perfect End To An Island Day

Private Charter Sunset Sailing

Take in the sunset without the crowds with a private charter at Sunset Sail Key West. Choose from one of our unique classic boats and enjoy the sunset in style as you glide through the aqua blue waters of the keys with your friends and family, or on a romantic trip for two.

Choose Your Private Charter Sailboat

Ht ss
2 Hours
1-6 guests $395
7-10 guests +$75pp
Complimentary ice, bottled water and soft drinks – BYOB!
key-west-sailing-charters
2 Hours
1-6 guests $495
Complimentary ice, bottled water and soft drinks – BYOB!
Sunset Sail Key West - Sail When and If - Freas Photography-25.2
2 Hours
1-6 guests $395
Complimentary ice, bottled water and soft drinks – BYOB!
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2 Hours
32 guests $2,600
Complimentary ice, bottled water and La Croix – BYOB!

Looking for a special something? Try our private charter add-ons and packages!

A Shared Sunset Experience

With room for up to 28 people to enjoy the gorgeous Key West sunset, the antique schooner yacht When And If is the most elegant sunset sail in town. Take in the unobstructed view in the peace and calm of blue-ocean sailing, with a delicious shared cheese platter and all your new friends!

2 Hours
$79pp

Call us to book: (305) 587-4488