Our Top Picks for Key West Sunset Cruises

From lively group cruises to private luxury charters—find the perfect way to experience a Key West sunset.

Public Sunset Options

Live Music Happy Hour Sunset Cruise
A lively “happy hour on the water” with a local musician, open well bar, and light appetizers. Cruise into the sunset aboard a spacious sailing catamaran.
2 hours • ~60 guests • $69.95 per person

Classic Schooner Sail
Sail aboard the last known Chesapeake Bugeye schooner for a quiet, classic sunset experience through Key West’s backcountrywaters. Open bar.
2 hours • Max 22 guests • $109 per person

Sunset Dinner Cruise
 A vibrant sunset cruise featuring a tropical buffet, open bar, and live music as you sail through Key West’s waters. Upgrade to premium spirits for $19.95.
2 hours • $89.95 per person

Private Sunset Charters

Private Sunset Sail
A relaxed, private sail with breathtaking sunset views—perfect for families or a romantic evening.
2 hours (additional time available) • $645 for up to 6 guests

 

Private Powerboat
Cruise the coastline on a private 24’ center console with unobstructed sunset views. Simple, fun, and unforgettable.
2 hours • Up to 6 guests • $399 total

Luxury Catamaran (Up to 13 Guests)
Experience Key West in comfort aboard a private luxury catamaran—spacious, smooth, and designed for the ultimate sunset cruise.
3 hours • Call 305-290-2049 for availability & pricing