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“Stop In”

Kelly's Caribbean Bar & Grill
Ranked #152 of 448 Restaurants in Key West
Cuisines: Caribbean
More restaurant details
Restaurant details
Good for: Local cuisine, Large groups, Romantic
Dining options: Lunch, Dinner, Breakfast, Late Night, Reservations
Description: Located at 301 Whitehead St., on the corner of Whitehead and Caroline, stands one of Key West's most impressive and historic buildings - Kelly's Caribbean. Well known for being the birthplace of Pan American World Airways, Pan-Am's first tickets were sold out of this very building in 1927. Pan Am was the principal and largest international air carriers in the United States from 1927 until its collapse on December 4, 1991. Founded in 1927 as a scheduled air mail and passenger service operating between Key West, Florida and Havana, Cuba, the airline became a major company credited with many innovations that shaped the international airline industry, including the widespread use of jet aircraft, jumbo jets and computerized reservation systems. Our Namesake - Kelly McGillis Kelly's was opened in 1992 by Fred Tillman and Actress, Kelly McGillis. We are proud to carry Kelly McGillis' name! Noted for her various movie roles - Top Gun, Witness, The Accused - Kelly now resides in North Carolina but she does keep a watchful eye on the Kelly's Caribbean. Should you stop on by Kelly's Caribbean...we do have her Top Gun Jacket in the "Crash Bar" area.
Saint Louis, Missouri
Level 6 Contributor
123 reviews
67 restaurant reviews
common_n_restaurant_reviews_1bd8 34 helpful votes
“Stop In”
Reviewed February 20, 2014

A nice reprieve from the heat, snuck in to find a ‘rum-punch’. The bartender was friendly and accommodating.

Visited February 2014
Thank RoadWarriorInHeels
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.
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1,163 reviews from our community

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Rating summary
Date | Rating
  • Danish first
  • Dutch first
  • English first
  • French first
  • German first
  • Italian first
  • Portuguese first
  • Spanish first
  • Swedish first
  • Any
English first
Grand Cayman
Level 6 Contributor
105 reviews
42 restaurant reviews
common_n_restaurant_reviews_1bd8 30 helpful votes
“Hard Woorking staff”
Reviewed February 19, 2014

The staff here were incredible - hard working, moving tables and chairs, it was just rather sad they had so much to do and so little time to help the customer! After a long wait, decided not to order food and went elsewhere.

  • Visited January 2014
    • Value
    • Atmosphere
    • Service
Thank Grownup56
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.
Level 2 Contributor
7 reviews
4 restaurant reviews
common_n_restaurant_reviews_1bd8 10 helpful votes
“Disappointing Lunch at Kelly's”
Reviewed February 19, 2014

Conch Chowder was not very good, mostly tomato with no trace of conch.
Outside seating could be cleaner.
Restaurant was not read to serve.

  • Visited February 2014
    • Value
    • Atmosphere
    • Service
    • Food
Thank UncleFrank
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.
Level 6 Contributor
101 reviews
44 restaurant reviews
common_n_restaurant_reviews_1bd8 56 helpful votes
“Great bar service, but food was meh!”
Reviewed February 18, 2014

Great bar, great drinks, and great bartenders, but food was really not that memorable. We asked to replace our first waiter who was a jerk to us, and the replacement, while nice, just wasn't that attentive. I will not return.

Visited January 2014
Thank GeauxTiguhs
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.
Newnan, Georgia
Level 6 Contributor
164 reviews
86 restaurant reviews
common_n_restaurant_reviews_1bd8 48 helpful votes
“Given other options, not worth the visit.”
Reviewed February 16, 2014

Visited based on a recommendation, even though the Trip Advisor reviews were marginal. The signature "Key Lime Margaritas" are way too sweet for our taste and the Thai Chili wings were mushy and also very sweet. Regular Margaritas, Craft beer and Shrimp Bacon Quesadilla were good. Given the other options on the island, would not go here again.

Visited February 2014
Thank BK1946
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.

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