We noticed that you're using an unsupported browser. The TripAdvisor website may not display properly.
We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.
New! Find and book your ideal hotel on TripAdvisor — and get the lowest prices

Kelly's Caribbean Bar & Grill

Map
Satellite
Map updates are paused. Zoom in to see updated info.
Reset zoom
Updating Map...
Get directions
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
More Info
Add Photo Write a Review

1,038 Reviews from our TripAdvisor Community

Traveller rating
Traveller type
Time of year
Language
  • More
Showing 991: English reviews
Chapel Hill, North Carolina
Level Contributor
25 reviews
15 restaurant reviews
common_n_restaurant_reviews_1bd8 3 helpful votes
3 of 5 bubbles Reviewed 3 days 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
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 1 week 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
121 reviews
105 restaurant reviews
common_n_restaurant_reviews_1bd8 24 helpful votes
5 of 5 bubbles Reviewed 2 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 

Level Contributor
15 reviews
8 restaurant reviews
common_n_restaurant_reviews_1bd8 5 helpful votes
5 of 5 bubbles Reviewed 4 weeks ago

A must-visit for happy hour. The Beer Cheese and Pretzel Dip is addictive! Loved the Key Lime Margaritas and Fish Tacos too. It's a few steps off Duval, with a big, open patio. Highly recommend.

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

Thanks for your fantastic review! We are glad the you enjoyed our happy hour and look forward to seeing you again soon. More 

Santa Ana, Costa Rica
Level Contributor
231 reviews
158 restaurant reviews
common_n_restaurant_reviews_1bd8 79 helpful votes
3 of 5 bubbles Reviewed 4 weeks ago

Always enjoyed the fried plantains and tropical menu at Kelly's.. Now it seemed to be basic American period... Not bad food, but not impressive in anyway...

Helpful?
Thank islandjerr
Level Contributor
6 reviews
5 restaurant reviews
common_n_restaurant_reviews_1bd8 2 helpful votes
3 of 5 bubbles Reviewed 30 October 2016 via mobile

We have been going to Key West yearly since 1988. We now visit there twice a year. We have probably walked by Kelly's a hundred times and it always looked so inviting. So this trip we decided to go there for lunch; since we had never been there, we did not know when the best time would be. We chose... More 

Helpful?
2 Thank hugs44
Tamarac, Florida
Level Contributor
266 reviews
248 restaurant reviews
common_n_restaurant_reviews_1bd8 88 helpful votes
3 of 5 bubbles Reviewed 29 October 2016

aaron, our server, was excellent.. we had delicious conch chowders and the daily special coconut encrusted yellowtail snapper. i found the snapper way too sweet. several of us had the cheese cake key lime pie, and thought it was just "ok". there are so many great restaurants in key west and unfortunately this one has fallen off my list.

Helpful?
Thank sarge-in-fla

Travellers who viewed Kelly's Caribbean Bar & Grill also viewed

Key West, Florida Keys
Key West, Florida Keys
 
Key West, Florida Keys
Key West, Florida Keys
 
Key West, Florida Keys
 

Been to Kelly's Caribbean Bar & Grill? Share your experiences!

Write a Review Add Photos & Videos

Is This Your TripAdvisor Listing?

Own or manage this property? Claim your listing for free to respond to reviews, update your profile and much more.

Claim Your Listing
Improve this listing

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
Ask a question
Norfolk, Virginia
over a year ago

See all questions (1)

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?