Sunset & Dinner Cruises in Key West

39 boats available

The best out of 39 deals in Key West - enter dates to check availability

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Top Sunset & Dinner Cruises in Key West

Showing top 10 charters
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Listing image
Meet the Captain
Center console silhouette

33 ft

•

up to 6

Kilo Whiskey Charters

5.0
/5
(15 reviews)
 
Key West
Sunset Harbor Tour - 3 Hour Trip
+6
Instant Confirmation
Price for up to 6 people
US $500
Listing image
Meet the Captain
Other silhouette

20 ft

•

up to 6

Tiki Boat Adventures - Key West

5.0
/5
(13 reviews)
 
Key West
2 Hour Trip – Sunset Cruise
+3
Instant Confirmation
Price for up to 6 people
US $425
Listing image
Meet the Captain
Headboat silhouette

55 ft

•

up to 40

Cora Beth

4.8
/5
(2 reviews)
•
716 external reviews
 
Key West
2 Hour Trip –Sunset Cocktail Cruise
Price for up to 40 people
US $750
Listing image
Meet the Captain
Center console silhouette

24 ft

•

up to 6

Good Times Key West 24’ Center Console.

5.0
/5
(2 reviews)
•
372 external reviews
 
Key West
4hr PM – Dolphin,Sandbar,Snorkel
+2
Instant Confirmation
Price for up to 2 people
US $700
Listing image
Meet the Captain
Motor yacht silhouette

35 ft

•

up to 6

Good Times Key West 35’ Offshore Express

4.9
/5
(372 external reviews)
 
Key West
2 Hour – Sunset Cruise
+3
Instant Confirmation
Price for up to 6 people
US $800
Listing image
Meet the Captain
Deck boat silhouette

26 ft

•

up to 12

Salty Bottom Boats – Tiki

5.0
/5
(11 reviews)
 
Key West
2 Hr – Tiki Sunset Trip
Price for up to 12 people
US $479
Listing image
Meet the Captain
Catamaran silhouette

25 ft

•

up to 6

Something Fishy Charters

5.0
/5
(9 reviews)
 
Key West
Half Day Custom Trip – 10:00 AM
+3
Instant Confirmation
Price for up to 6 people
US $490
Listing image
Catamaran silhouette

65 ft

•

up to 25

Sunset Watersports Key West – Sunset Sail

5.0
/5
(3 reviews)
 
Key West
2 Hour – Sunset Sail with Open Bar
Per person
US $79
Listing image
Meet the Captain
Sportfishing silhouette

35 ft

•

up to 6

Screaming Lines Adventures

4.9
/5
(161 external reviews)
 
Key West
3 Hour – Sunset Trip
+2
Price for up to 6 people
US $400
Listing image
Runabout silhouette

8 ft

•

up to 6

Lady of the Sea LLC

 
Key West
2 Hr – Mallory Square Sunset Cruise
+3
Instant Confirmation
Price for up to 6 people
US $375
Listing image
Meet the Captain
Center console silhouette

33 ft

•

up to 6

Kilo Whiskey Charters

5.0
/5
(15 reviews)
 
Key West
Sunset Harbor Tour - 3 Hour Trip
+6
Instant Confirmation
Price for up to 6 people
US $500
Listing image
Meet the Captain
Other silhouette

20 ft

•

up to 6

Tiki Boat Adventures - Key West

5.0
/5
(13 reviews)
 
Key West
2 Hour Trip – Sunset Cruise
+3
Instant Confirmation
Price for up to 6 people
US $425
Listing image
Meet the Captain
Headboat silhouette

55 ft

•

up to 40

Cora Beth

4.8
/5
(2 reviews)
•
716 external reviews
 
Key West
2 Hour Trip –Sunset Cocktail Cruise
Price for up to 40 people
US $750
Listing image
Meet the Captain
Center console silhouette

24 ft

•

up to 6

Good Times Key West 24’ Center Console.

5.0
/5
(2 reviews)
•
372 external reviews
 
Key West
4hr PM – Dolphin,Sandbar,Snorkel
+2
Instant Confirmation
Price for up to 2 people
US $700
Listing image
Meet the Captain
Motor yacht silhouette

35 ft

•

up to 6

Good Times Key West 35’ Offshore Express

4.9
/5
(372 external reviews)
 
Key West
2 Hour – Sunset Cruise
+3
Instant Confirmation
Price for up to 6 people
US $800
Listing image
Meet the Captain
Deck boat silhouette

26 ft

•

up to 12

Salty Bottom Boats – Tiki

5.0
/5
(11 reviews)
 
Key West
2 Hr – Tiki Sunset Trip
Price for up to 12 people
US $479
Listing image
Meet the Captain
Catamaran silhouette

25 ft

•

up to 6

Something Fishy Charters

5.0
/5
(9 reviews)
 
Key West
Half Day Custom Trip – 10:00 AM
+3
Instant Confirmation
Price for up to 6 people
US $490
Listing image
Catamaran silhouette

65 ft

•

up to 25

Sunset Watersports Key West – Sunset Sail

5.0
/5
(3 reviews)
 
Key West
2 Hour – Sunset Sail with Open Bar
Per person
US $79
Listing image
Meet the Captain
Sportfishing silhouette

35 ft

•

up to 6

Screaming Lines Adventures

4.9
/5
(161 external reviews)
 
Key West
3 Hour – Sunset Trip
+2
Price for up to 6 people
US $400
Listing image
Runabout silhouette

8 ft

•

up to 6

Lady of the Sea LLC

 
Key West
2 Hr – Mallory Square Sunset Cruise
+3
Instant Confirmation
Price for up to 6 people
US $375
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