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  4. Florida Keys - Monroe County
  5. Key West

First Flight Island Restaurant & Brewery

4.5
4.5
898 Reviews
$30 and under
Seafood
First Flight Island Restaurant and Brewery is located in the home of Pan Americans office, where the first American international flight ticket Key West- Havana, Cuba was bought on October 28th 1927. The restaurant features a beautiful garden dining area nestled under the canopies of 2 Strangler Figs, an inside dining room with Pan American memorabilia and an indoor- outdoor crash bar made from an airplane wing.This is also the birthplace of the Southernmost Brewery in the States where 3 flagship and seasonal beers are made by Brewmaster Andrew Koennecke. The restaurant menu focuses on locally sourced seafood, house brew braised dishes and fresh seasonal ingredients. The menu changes throughout the year by Executive Chef Ben Schneller who supplements tradition with an island twist.

Make a reservation

2 people

7:00 PM


Booked 20 times today

Additional information

  • Dining style

    Casual Elegant

  • Cuisines

    Seafood, Brewery, Gastro Pub

  • Hours of operation

    Lunch Daily 11:00 am–4:00 pm Gastro Pub Dining Daily 11:00 am–10:00 pm Dinner Daily 4:00 pm–10:00 pm Happy Hour Daily 4:00 pm–6:00 pm

  • Phone number

    (305) 293-8484

  • Payment options

    AMEX, Discover, MasterCard, Visa

  • Dress code

    Business Casual

  • Executive chef

    Ben Schneller

  • Private party contact

    Jackie Gibson: (305) 293-8484

  • Neighborhood

    Key West

  • Cross street

    Caroline Street

  • Parking details

    There is metered parking on both Whitehead Street and the cross Street Caroline. Busiest parking times is right before sunset

  • Additional

    Banquet, Bar/Lounge, Beer, Beer Garden, Cocktails, Corkage Fee, Full Bar, Gluten-free Options, Happy Hour, Late Night, Non-Smoking, Outdoor Smoking Area, Patio/Outdoor Dining, Patio/Outdoor Dining, Private Room, Takeout, View, Wheelchair Access, Wine

Popular dishes

What 898 people are saying

Overall ratings and reviews

Reviews can only be made by diners who have eaten at this restaurant

4.5
4.5 based on recent ratings
  • 4.4Food
  • 4.5Service
  • 4.6Ambience
  • 4.3Value

NoiseModerate

Loved For

  • Key West / Florida Keys

    Outdoor Dining

  • Key West / Florida Keys

    Vibrant Bar Scene

  • Key West / Florida Keys

    Seafood

  • Key West / Florida Keys

    Most Booked

  • Florida Keys - Monroe County

    Outdoor Dining

  • Florida Keys - Monroe County

    Vibrant Bar Scene

  • Florida Keys - Monroe County

    Seafood

  • Florida Keys - Monroe County

    Most Booked

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  1. OT

    OpenTable Diner

    New York Area

    4 reviews

    5.0

    4 reviews

    Dined today

    overall5food5service4ambience5
    Great place for dinner. Food was delicious, good service, great ambience. Beer made on sight, live music across the street. We sat outside in the garden, not sure if there is indoor seating except at the bar. Price was fantastic for two people. We will definitely go again.
  2. DZ

    DebbyZ

    Tampa

    18 reviews

    vip
    5.0

    18 reviews

    Dined 1 day ago

    overall5food5service5ambience5
    Great diverse menu with something for everyone. Service is excellent.
  3. OT

    OpenTable Diner

    Charlotte

    3 reviews

    5.0

    3 reviews

    Dined 1 day ago

    overall5food4service5ambience5
    My family and I took my dad here as a surprise on our vacation. He is a pilot and LOVED the theme of this place as well as the history. He says he plans to tell all of his flight crews about it when they visit key west. The food was good. The drinks/beer were good to. It’s a cool place since they have their own brewery right there!
  4. OT

    OpenTable Diner

    San Francisco

    1 review

    3.0

    1 review

    Dined 2 days ago

    overall3food5service3ambience5
    Food was awesome. Waitress was MIA much of the time and got our order wrong
  5. MG

    MaritzaG

    New York Area

    9 reviews

    4.0

    9 reviews

    Dined 3 days ago

    overall4food4service5ambience4
    Really a nice place. The food was good and the drinks were great! Great dinner overall.
  6. OT

    OpenTable Diner

    Western NC

    7 reviews

    5.0

    7 reviews

    Dined 4 days ago

    overall5food5service5ambience4
    Great whole snapper, salads and even our little guy got some chicken that he loved! All around great. Sit inside if possible and try the chocolate Key Lime pie!
  7. EH

    EHMIV

    1 review

    5.0

    1 review

    Dined 6 days ago

    overall5food5service5ambience5
    Outside dining with the roosters. “Pussers Painkiller very good. When you want a good meal and sit in a quieter atmosphere, this is the place.
  8. DF

    DonnaF

    1 review

    3.0

    1 review

    Dined on June 26, 2022

    overall3food3service2ambience3
    Salads were very good as were the fried ravioli and very big pretzel
  9. J

    Jean

    Tampa

    1 review

    3.0

    1 review

    Dined on June 22, 2022

    overall3food4service3ambience2
    Waitress could have been friendlier. We all had stomach issues that night after diner.
  10. W

    Westburbsdiners1

    New Mexico

    14 reviews

    5.0

    14 reviews

    Dined on June 19, 2022

    overall5food5service4ambience5
    Our server was well versed on the menu and candid with recommendations, which we sincerely appreciated. Delicious food.
  11. KF

    KateF

    Washington DC

    2 reviews

    5.0

    2 reviews

    Dined on June 19, 2022

    overall5food5service5ambience5
    Great service, great food, great ambiance!! IPAs we’re delicious. We had the deviled eggs and bake brie to start. So yummy. Our kids had the butter noodles, kids burger and Mac and cheese - they ate more than they usually do at dinner! Adults had everything from the special to the fish tacos, to the seafood pasta and it was very well portioned and delicious. We can’t wait to go back!!
  12. F

    Frank

    Charleston

    6 reviews

    2.0

    6 reviews

    Dined on June 19, 2022

    overall2food3service1ambience2
    Expected more island ambiance and better food. Service was inattentive. Not a good time at all.
  13. OT

    OpenTable Diner

    San Antonio

    2 reviews

    5.0

    2 reviews

    Dined on June 15, 2022

    overall5food5service5ambience5
    I ate here with my husband and 8 year old son. We all loved our food and the atmosphere was fantastic, especially for my husband who is a bit of an aviation fanatic!
  14. KS

    KristynS

    San Diego

    1 review

    5.0

    1 review

    Dined on June 13, 2022

    overall5food5service5ambience5
    We had an excellent dinner at First Flight! The patio is a lovely setting for dinner, and we enjoyed listening to the music at Hank’s across the street. Everything we ordered was delicious!
  15. DG

    DeenaG

    Atlanta

    18 reviews

    5.0

    18 reviews

    Dined on June 7, 2022

    overall5food5service5ambience5
    Excellent food! Great place on Key West
  16. OT

    OpenTable Diner

    San Francisco

    1 review

    5.0

    1 review

    Dined on June 7, 2022

    overall5food5service5ambience5
    My favorite place on the island. Great bar with garden view!
  17. OT

    OpenTable Diner

    1 review

    5.0

    1 review

    Dined on June 6, 2022

    overall5food5service4ambience5
    Started outside the flies were terrible we thought we would be picked up and Carry to dual they were so large. We ask to be moved inside and they accommodated us without hesitation. The food was amazing and would gladly return.
  18. WC

    WhitneyC

    Chicago

    2 reviews

    5.0

    2 reviews

    Dined on June 6, 2022

    overall5food5service5ambience5
    My husband and I love trying new craft beers so we thought this would be a fun dinner spot during our vacation to Key West. We LOVED it! The beers were excellent and we had the seafood Alfredo and the island chicken pasta. Both were excellent. The staff was quick and so friendly. We will be back!
  19. PC

    PattyC

    1 review

    5.0

    1 review

    Dined on June 2, 2022

    overall5food5service5ambience4
    We ate at the open patio. As soon as the food was served, we were swarmed by flies which was worse with one of our meals making it unpleasant for enjoying the experience, but the food was tasty. Maybe we were there at the wrong time of day.
  20. D

    Danika

    Grand Rapids

    1 review

    3.0

    1 review

    Dined on May 31, 2022

    overall3food5service5ambience4
    We made a reservation for 4:30 so we could enjoy happy hour. Once we were sitting down, they told us happy hour was only on the "bar seating" area. That was frustrating since it was 5 feet from where we were sitting but we couldn't get those prices. We got our bill and moved to the bar area. Also music was too loud.
  21. LB

    LauraB

    Chicago

    1 review

    vip
    5.0

    1 review

    Dined on May 30, 2022

    overall5food5service5ambience5
    Casual and fun atmosphere.
  22. P

    Pete

    Minneapolis

    2 reviews

    5.0

    2 reviews

    Dined on May 30, 2022

    overall5food5service5ambience5
    We had a very good time here. We ate outdoor with the chickens at our feet. Everything's is a few dollars to expensive but that seems to be the Key West way.
  23. HM

    HollyM

    Naples

    6 reviews

    vip
    4.0

    6 reviews

    Dined on May 29, 2022

    overall4food4service4ambience4
    Very good, island pasta delicious, cute patio.
  24. BC

    BobC

    New York Area

    34 reviews

    vip
    4.0

    34 reviews

    Dined on May 27, 2022

    overall4food4service5ambience5
    Went to First Flight last night for a light dinner and to check out their brews. Overall, a very good place for dinner! I had the burger which was cooked well and loved the fries. My wife had the brisket sandwich that was excellent. As for the beer- I was looking for a lager, which they don’t have in their repertoire, having mostly IPA’s. They were very good, but not what I was looking for. Overall, worth a visit when you’re on Key West.
  25. NB

    NicoleB

    New Orleans

    4 reviews

    5.0

    4 reviews

    Dined on May 24, 2022

    overall5food5service5ambience5
    We went for our honeymoon and we’re greeted with a glass of champagne to celebrate. We had the scallops and brisket Mac and cheese, both were insanely delicious! We got the Painkiller cocktail which was unreal! So good!! We fully enjoyed our time here.
  26. OT

    OpenTable Diner

    Atlanta

    1 review

    5.0

    1 review

    Dined on May 23, 2022

    overall5food5service5ambience4
    We brought in dish that we had caught that day for them to cook. The presentation was AMAZING and the fish was delicious. Everyone who walked by our table asked about it. The only downside of the meal was we were seated by the wall and the mosquitos were terrible. I had to wrap napkins around my legs. We finally asked the waiter if we could move to a different table and they were very accommodating. Another family also asked to move and they were also moved quickly.
  27. M

    Mark

    Atlantic City

    102 reviews

    vip
    5.0

    102 reviews

    Dined on May 23, 2022

    overall5food5service5ambience5
    Great food and service. Beautiful courtyard to dine in. Will definitely be back.
  28. OT

    OpenTable Diner

    Cincinnati

    1 review

    5.0

    1 review

    Dined on May 22, 2022

    overall5food5service5ambience5
    Highly recommend this restaurant for their outdoor dining patio. The atmosphere was amazing. Enjoyed our dinner while listening to a band play at the bar across the street.
  29. JS

    JenniferS

    West Palm Beach

    5 reviews

    5.0

    5 reviews

    Dined on May 20, 2022

    overall5food5service5ambience5
    Been coming to Key West for years and have recently decided to try new places each time. Everything was Excellent from the moment we were greeted at the host stand to the bartenders (Damien) was Awesome!! Service was great and food was incredible.
  30. DD

    DougD

    1 review

    5.0

    1 review

    Dined on May 20, 2022

    overall5food5service5ambience5
    We started with the mac and cheese. It was so good that we thought the fish tacos were going to be disappointing after it. I even told the waiter that the tacos had a very high bar set by the mac and cheese. The tacos did not disappoint. This was the best meal we had eaten all week. We had spent triple the price at other places with the food being pretty but not tasty. We will definitely eat here a few times on our next visit to the keys.
  31. Z

    Zielinski35

    Detroit

    10 reviews

    5.0

    10 reviews

    Dined on May 20, 2022

    overall5food5service5ambience5
    Very nice waitress and great ambiance. Glad it didn’t rain as we enjoyed the outdoor seating. A wedding was using the balcony floor. While they were a joyous group it didn’t bother the regular customers. Food was excellent. We got fish tacos and a French dip Swiss and shaved beef.
  32. MD

    MarianneD

    Chicago

    140 reviews

    vip
    4.0

    140 reviews

    Dined on May 20, 2022

    overall4food4service5ambience4
    I’ve been to this restaurant before when Kelly McGillis owned it and it was Kelly’s Caribbean Bar, Grill & Brewery. This is my 1st visit to First Flight. There’s a lot of history to this building as it was the first Pan-American office back in 1927. The restaurant has a great outdoor space and bar area. There are also tables indoors to beat the heat. We had our final toast to our family vacation…I had a skinny Paloma, the best I had in Key West. This was our last dinner before leaving for home in Chicago so I ate a little lighter because of traveling the next day. My family shared the deviled eggs with fried jalapeños. The deviled eggs were creamy, but I skipped on the fried jalapeños. For dinner, I had the di parma flatbread appetizer. I was surprised at the perfect pizza crust, not a flatbread at all. Delicious salty prosciutto with melted mozzarella and peppery arugula, it was delicious! It was pretty crowded when we went, so I recommend making reservations. Stop here for the brewery, if not for the good food. My son had a flight of beers that he enjoyed.
  33. ER

    ERAH

    1 review

    3.0

    1 review

    Dined on May 20, 2022

    overall3food2service3ambience3
    Very expensive meals The quality is correct but no more
  34. c

    clsr7777

    Oklahoma City

    34 reviews

    vip
    5.0

    34 reviews

    Dined on May 17, 2022

    overall5food5service5ambience5
    First Flight has the best patio in Key West with the beautiful palms and green plants within and surrounding the entire area! Our Seared Tuna and the Filet entrees were perfectly cooked and seasoned. The bar area has a good happy hour from 4-6 where we had drinks and the fried ravioli appetizer. Great place for dinner!
  35. MH

    MichaelH

    New England

    1 review

    4.0

    1 review

    Dined on May 16, 2022

    overall4food4service4ambience4
    Great food and service. The music from Hank's can be overwhelming sometimes if you sit close to Caroline St.
  36. JL

    JulieL

    New York Area

    29 reviews

    vip
    5.0

    29 reviews

    Dined on May 15, 2022

    overall5food5service5ambience5
    Always a great meal with great service and ambiance. First Flight is always on our list of restaurants for our trips to Key West. Love this place.
  37. P

    Poucho

    Charlotte

    27 reviews

    vip
    5.0

    27 reviews

    Dined on May 14, 2022

    overall5food5service5ambience5
    Delicious food, great service, lovely outdoor garden setting! Highly recommend whatever the fresh fish special is for the day !!
  38. OT

    OpenTable Diner

    Detroit

    3 reviews

    5.0

    3 reviews

    Dined on May 13, 2022

    overall5food5service5ambience5
    Food was great. Everyone loved their meals. The snapper was terrific! The service was great!
  39. AM

    AaronM

    Tampa

    21 reviews

    vip
    4.0

    21 reviews

    Dined on May 12, 2022

    overall4food4service3ambience4
    Have been to this eatery many times over the years and always enjoy it. Ate here twice during our recent visit to KW. The outdoor seating in the courtyard is great. Food and drinks were tasty. Good menu selections and not overpriced. Only disappointed by our service. Some staff seemed disinterested and were inattentive, others were fine.
  40. f

    foodluver

    Atlanta

    29 reviews

    vip
    5.0

    29 reviews

    Dined on May 8, 2022

    overall5food5service5ambience5
    What a nice experience! The service, the FOOD! EXCELLENT! I would certainly recommend First Flight to everyone.

Safety precautions

  • Cleaning & sanitizing

    • Surfaces sanitized between seatings
    • Digital, disposable or sanitized menu provided
    • Sealed or wrapped utensils used
    • Common areas deep-cleaned daily
    • Sanitizer or wipes provided for customers
  • Physical distancing

    • Limited number of seated diners
    • Distancing maintained in common areas
    • Extra space between tables
  • Protective equipment

    • Waitstaff wear masks
    • Diners must wear masks unless eating or drinking
  • Screening

    • Sick staff prohibited in the workplace

FAQs

First Flight Island Restaurant & Brewery offers takeout which you can order by calling the restaurant at (305) 293-8484.

First Flight Island Restaurant & Brewery is rated 4.5 stars by 898 OpenTable diners.

Yes, you can generally book this restaurant by choosing the date, time and party size on OpenTable.

Make a reservation

2 people

7:00 PM


Booked 20 times today
Google Map for First Flight Island Restaurant & Brewery

301 Whitehead St Key West, FL 33040

Additional information

  • Cross street

    Caroline Street

  • Neighborhood

    Key West

  • Hours of operation

    Lunch Daily 11:00 am–4:00 pm Gastro Pub Dining Daily 11:00 am–10:00 pm Dinner Daily 4:00 pm–10:00 pm Happy Hour Daily 4:00 pm–6:00 pm

  • Cuisines

    Seafood, Brewery, Gastro Pub

  • Dining style

    Casual Elegant

  • Dress code

    Business Casual

  • Parking details

    There is metered parking on both Whitehead Street and the cross Street Caroline. Busiest parking times is right before sunset

  • Payment options

    AMEX, Discover, MasterCard, Visa

  • Executive chef

    Ben Schneller

  • Additional

    Banquet, Bar/Lounge, Beer, Beer Garden, Cocktails, Corkage Fee, Full Bar, Gluten-free Options, Happy Hour, Late Night, Non-Smoking, Outdoor Smoking Area, Patio/Outdoor Dining, Patio/Outdoor Dining, Private Room, Takeout, View, Wheelchair Access, Wine

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