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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
Website
Today
11:00 - 22:00
Closed now
All hours
Hours:
Sun - Sat 11:00 - 22:00
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1,042 Reviews from our TripAdvisor Community

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Showing 995: English reviews
PONTE VEDRA BEACH
Level Contributor
158 reviews
68 restaurant reviews
common_n_restaurant_reviews_1bd8 72 helpful votes
5 of 5 bubbles Reviewed 2 days ago NEW

This place is one of the better dining venues in Key West owned by Kelly Mcgillis the Top Gun Actress. The Food was outstanding. Very attractive outdoor dining in a court yard under Banyon trees. A place not to be missed.

Helpful?
Thank CactusBadger
Jason B, Manager at Kelly's Caribbean Bar & Grill, responded to this review

Thank you so much for your feedback, we are glad that you enjoyed Kelly's! We look forward to seeing you again soon. More 

Jupiter, Florida
2 reviews
5 of 5 bubbles Reviewed 2 days ago NEW

I had my wedding reception at Kelly's November 2016. From the initial contact with Chuck to the actual reception everything went smoothly and as planned. Chuck the manager was open to changes that I wanted to make and the entire event was set up perfectly. We rented the upstairs area which was worth every penny. The reception was at night... More 

Helpful?
Thank FL0RIDA-nativegirl
Jason B, Manager at Kelly's Caribbean Bar & Grill, responded to this review

Thanks for your fabulous review! We are so happy that everything turned out so well for your wedding reception. Come visit us again soon! More 

Chicago, Illinois
Level Contributor
32 reviews
14 restaurant reviews
common_n_restaurant_reviews_1bd8 4 helpful votes
3 of 5 bubbles Reviewed 2 days ago NEW via mobile

We first had drinks and food at the bar. That was fine and fun. Then we moved downstairs for dinner. The food was very good but served luke warm. Our server was very friendly but forgot to bring several items and had to be reminded. The atmosphere was very nice.

Helpful?
Thank lovethesun016
Jason B, Manager at Kelly's Caribbean Bar & Grill, responded to this review

Thank you for taking the time to give us feedback. I apologize that the service you received wasn't up to par. If possible, I would like to know who your server was so that I can address your concerns directly. You can call the restaurant at 305-293-8484 or email me at kellyskeyw@aol.com. Also if you are in town, please stop... More 

Toronto, Canada
Level Contributor
187 reviews
113 restaurant reviews
common_n_restaurant_reviews_1bd8 122 helpful votes
4 of 5 bubbles Reviewed 2 days ago NEW

We frequent Kelly's a couple of times a week every time we are in KW. Always good, but the night we stopped by with our grandkids during happy hour, our server Jake made our night. He was attentive, made the kids feel welcome and had us all in good humor. As usual food and drinks were priced fairly. Give it... More 

Helpful?
Thank Saltydogcafe
Jason B, Manager at Kelly's Caribbean Bar & Grill, responded to this review

Thank you so much for your feedback! I am glad that you had such a great experience with Jake, I will share your feedback with him. More 

Chapel Hill, North Carolina
Level Contributor
25 reviews
15 restaurant reviews
common_n_restaurant_reviews_1bd8 3 helpful votes
3 of 5 bubbles Reviewed 1 week ago NEW

Coconut shrimp were really good, other entrees were fine but nothing special. Great outdoor seating. Most notable, unfortunately, was the really bad service. I don't think our server was trained very well.

Helpful?
Thank tarheel617
Jason B, Manager at Kelly's Caribbean Bar & Grill, responded to this review

Thank you for taking the time to let us know how we are doing. I apologize that our service was off. If possible, I would like to know who your server was so that I may address your concerns directly. You can call the restaurant at 305-293-8484, email kellykeyw@aol.com, or stop by the restaurant and ask for me if you... More 

Key West, Florida
Level Contributor
24 reviews
18 restaurant reviews
common_n_restaurant_reviews_1bd8 14 helpful votes
3 of 5 bubbles Reviewed 1 week ago

Recently some friends and I dined at Kelly's ...we were met and sat with no issue a short time later our server stopped by the table inquiring if we would like to place a drink order, we inquired about their beers as they have a microbrewery onsite and were advised that they had only 2 of 3 beers available there... More 

Helpful?
Thank b s
Hayward, California
Level Contributor
4 reviews
common_n_restaurant_reviews_1bd8 1 helpful vote
4 of 5 bubbles Reviewed 2 weeks ago

While visiting Key West over our Thanksgiving Holiday we found this place that was able to accommodate our party of 10 with short notice. They had a Thanksgiving Meal being served. We were happy to find the Traditional and Southern Thanksgiving choices. We had a great waitress and were very pleased with our appetizer choices of tomato and mozzarella and... More 

Helpful?
Thank Kelly R
Jason B, Manager at Kelly's Caribbean Bar & Grill, responded to this review

We all thank you so much for your great review, and are glad you enjoyed Thanksgiving at Kelly's. We look forward to seeing you again in the future! More 

Level Contributor
17 reviews
8 restaurant reviews
common_n_restaurant_reviews_1bd8 3 helpful votes
3 of 5 bubbles Reviewed 2 weeks ago

The situation of the establishment is good just off Duval Street, but nothing memorable about the Place other than being the original Home of PANAM Airways......and that was what made me look it up, nothing to see other than a sign on the outside of the Building and nothing made of this piece of history inside a disappointment and a... More 

Helpful?
Thank Christopher H
Jason B, Manager at Kelly's Caribbean Bar & Grill, responded to this review

We apologize that your experience did not meet your expectations, and it definitely sounds like it did not meet the standards we hold ourselves to either. Please give us another chance the next time you are around, and we will be sure to change your minds. Please ask for me personally. More 

Level Contributor
123 reviews
107 restaurant reviews
common_n_restaurant_reviews_1bd8 24 helpful votes
5 of 5 bubbles Reviewed 3 weeks ago via mobile

1/2 price drinks and appetizers. Good well drinks Chicken wings, tempura shrimp and all are very good. Historical area. Give it a try

Helpful?
Thank Louis S
Jason B, Manager at Kelly's Caribbean Bar & Grill, responded to this review

Thanks for your recent review. I am glad that you enjoyed our happy hour while in town. We look forward to seeing you again soon! More 

Level Contributor
16 reviews
14 restaurant reviews
common_n_restaurant_reviews_1bd8 3 helpful votes
5 of 5 bubbles Reviewed 3 weeks ago via mobile

We went here for happy hour several times while on vacation. The staff are friendly, the drinks are good and priced cheap, and the appetizers are really good. We had the wings and they were big and juicy. A great place!!!

Helpful?
Thank BigBoulder
Jason B, Manager at Kelly's Caribbean Bar & Grill, responded to this review

Thanks for your great review! Our Happy Hour is very popular with both locals and tourists alike, and we are glad you enjoyed it enough for multiple visits. We look forward to seeing you again in the future. More 

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Restaurant Details

Rating summary
  • Food
    4 of 5 bubbles
    Service
    3.5 of 5 bubbles
  • Value
    3.5 of 5 bubbles
    Atmosphere
    4 of 5 bubbles
Cuisine
American, Bar, Seafood, Caribbean, Pub, Gluten Free Options
Meals
Brunch, After-hours
Restaurant features
Takeout, Outdoor Seating, Seating, Waitstaff, Television, Wheelchair Accessible, Serves Alcohol, Full Bar, Accepts American Express, Accepts Mastercard, Accepts Visa, Accepts Discover, Reservations, Highchairs Available, Free Wifi
Good for
Kids
Open Hours
Sunday
11:00 - 22:00
Monday
11:00 - 22:00
Tuesday
11:00 - 22:00
Wednesday
11:00 - 22:00
Thursday
11:00 - 22:00
Friday
11:00 - 22:00
Saturday
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
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.

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?