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Kelly's Caribbean Bar & Grill

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301 Whitehead St, Key West, FL 33040-6542
+1 305-293-7897
11:00 - 22:00
Closed now
See all hours
Sun - Sat 11:00 - 22:00
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1,064 Reviews from our TripAdvisor Community

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Showing 1,016: English reviews
Level Contributor
16 reviews
5 restaurant reviews
common_n_restaurant_reviews_1bd8 8 helpful votes
5 of 5 bubbles Reviewed yesterday NEW

Go for the margaritas, several to choose from, sip and enjoy, classic tropical look with banyon trees, outdoor courtyard, not far from Duval, but classier, quieter and much more relaxing.

Thank phaase
Chapel Hill
Level Contributor
164 reviews
53 restaurant reviews
common_n_restaurant_reviews_1bd8 62 helpful votes
5 of 5 bubbles Reviewed 2 days ago NEW

We stopped for lunch and a break in site seeing and had a great lunch on the patio. The food was delicious and the fish was extremely fresh. Service was quick and efficient and the wait staff were knowledgeable and helpful. They actually seemed to be having fun and not just going through the motions. Our group ate the fresh... More 

Thank Pat D
Winston Salem, North Carolina
Level Contributor
75 reviews
45 restaurant reviews
common_n_restaurant_reviews_1bd8 17 helpful votes
5 of 5 bubbles Reviewed 5 days ago NEW via mobile

We have enjoyed margaritas and nachos for several nights at Kelly's. Patrick is a great bartender and very attentive to patrons. The Happy Hour is the best and we will be back.

Thank LizDarla
Herndon, Virginia
Level Contributor
118 reviews
78 restaurant reviews
common_n_restaurant_reviews_1bd8 57 helpful votes
3 of 5 bubbles Reviewed 5 days ago NEW

We were looking for a pre-dinner drink off the main drag and this fit the bill. The beers were good but sad to say the only happy hour snack we tried was not. The 'tempura' shrimp were soggy, floury and indigestible. Possibly another choice would have been better. We moved on for dinner (see "Sarabeth's.)

Thank shenandoah1506
Level Contributor
3 reviews
4 of 5 bubbles Reviewed 6 days ago NEW

We were told by family members that this was a great place - apparently once owned by Kelly McGillis and her now ex-husband. I ordered the pecan crusted mahi and my husband had a similar dish. I also ordered a glass of wine to complement my dinner choice and we sat outside on the lit patio at a small table... More 

Thank Honey S
Plainsboro, New Jersey
1 review
5 of 5 bubbles Reviewed 6 days ago NEW

We had our reception (25 people) at Kelly’s Caribbean Bar and Grill in December 2016, and used the upstairs area. It was so beautiful, elegant, and romantic. The lights on the trees and the lights strung in the open area were so pretty, and really set the mood (it felt like a dream). Chuck is great at making sure you... More 

Thank mcclaryh8
New York City, New York
Level Contributor
46 reviews
23 restaurant reviews
common_n_restaurant_reviews_1bd8 31 helpful votes
5 of 5 bubbles Reviewed 1 week ago via mobile

Very nice atmosphere ...we sat outside on the back patio for lunch. The food and cocktails were outstanding, and the service was excellent. The place was formerly owned by Kelly McGillis so it's interesting to stop by the little display area in front that features some of her memorabilia including the cool jacket she wore in Top Gun.

Thank Gisele C
Coeur d'Alene, Idaho, United States
Level Contributor
38 reviews
21 restaurant reviews
common_n_restaurant_reviews_1bd8 9 helpful votes
5 of 5 bubbles Reviewed 1 week ago via mobile

Dropped in for Happy hour. Doug gave great service and made some delicious drinks. This place has a ton of character with a great history to go with it. The outdoor patio is a tropical garden. This is a great place to start your night!

Thank Heath J
Naples, Florida
Level Contributor
283 reviews
202 restaurant reviews
common_n_restaurant_reviews_1bd8 137 helpful votes
4 of 5 bubbles Reviewed 1 week ago

Great to sit outdoors under the trees for lunch. Had some good local brews and wonderful sandwiches. Portions are huge so easy to split.

Thank Brad M
Wingate, North Carolina
Level Contributor
39 reviews
30 restaurant reviews
common_n_restaurant_reviews_1bd8 7 helpful votes
5 of 5 bubbles Reviewed 1 week ago via mobile

My brother-in-law treated everyone to dinner at Kelly's, and we were not disappointed. OMG! The warm coconut pineapple bread served before dinner was amazing!!! Most of our party ordered the balsamic glaze shrimp and scallop special with mashed potatoes and veggies, and we were very pleased with our choice. We decided to order and share both dessert options. The Key... More 

Thank CZiegler04

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Restaurant Details

Rating summary
  • Food
    4 of 5 bubbles
    3.5 of 5 bubbles
  • Value
    3.5 of 5 bubbles
    4 of 5 bubbles
American, Bar, Seafood, Caribbean, Gluten Free Options
Restaurant features
Takeout, Reservations, Outdoor Seating, Seating, Waitstaff, Television, Wheelchair Accessible, Serves Alcohol, Full Bar, Accepts American Express, Accepts Mastercard, Accepts Visa, Free Wifi, Accepts Discover, Highchairs Available
Good for
Open Hours
11:00 - 22:00
11:00 - 22:00
11:00 - 22:00
11:00 - 22:00
11:00 - 22:00
11:00 - 22:00
11:00 - 22:00
Location and Contact Information
  • Address: 301 Whitehead St, Key West, FL 33040-6542
  • Location: United States  >  Florida (FL)  >  Florida Keys  >  Key West
  • Phone Number: +1 305-293-7897
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.

Questions & Answers

Here's what previous visitors have asked, with answers from representatives of Kelly's Caribbean Bar & Grill and other visitors
1 question
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Norfolk, Virginia
over a year ago

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Questions? Get answers from Kelly's Caribbean Bar & Grill staff and past visitors.
Posting guidelines
Typical questions asked:
  • Do you have gluten-free options?
  • Is there a dress code?
  • Do you allow dogs on the outdoor patio?