Enable JavaScript to run this app.
Skip to Main Content
OpenTable logo
  1. Home
  2. United States
  3. Key West / Florida Keys
  4. Florida Keys - Monroe County
  5. Key West

First Flight Island Restaurant & Brewery

4.5
4.5
930 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 18 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 930 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
  • 4.5Food
  • 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

  • Florida Keys - Monroe County

    Outdoor Dining

  • Florida Keys - Monroe County

    Vibrant Bar Scene

  • Florida Keys - Monroe County

    Seafood

Sort by

Filters

  1. MA

    MAGUSA

    Tampa

    10 reviews

    2.0

    10 reviews

    Dined 3 days ago

    overall2food2service1ambience4
    Waitress was lost, rude and miserable to be at work
  2. l

    luv2dine

    Denver

    119 reviews

    vip
    5.0

    119 reviews

    Dined 6 days ago

    overall5food5service5ambience5
    Absolutely top-notch! Our server, Igor, was amazing-so professional, friendly, and efficient-his beer recommendations were spot on! Food, drink and the key lime pie were delicious! From start to finish it was a great dining experience. Definitely will be back!
  3. OT

    OpenTable Diner

    Las Vegas

    1 review

    5.0

    1 review

    Dined on August 10, 2022

    overall5food5service5ambience5
    Delicious! Great service!
  4. s

    sylvie

    Key West

    6 reviews

    3.0

    6 reviews

    Dined on August 10, 2022

    overall3food3service3ambience3
    Table réservée depuis 10 jours pas prête on veux nous installer à la sortie des wc… poissons bon mais restaurant restaurant très cher , pas d organisation sur les réservations
  5. OT

    OpenTable Diner

    Yorkshire

    10 reviews

    5.0

    10 reviews

    Dined on August 6, 2022

    overall5food5service5ambience5
    Loved this place. Service, location, food and beverage selection all fantastic. We had Brussels sprouts and fried Brie as starters - delicious. All main meals were at Leo fantastic- especially the brewery burger and fish tacos. Damian, our waiter, was particularly helpful/friendly.
  6. M

    Mchammer

    Tampa

    1 review

    5.0

    1 review

    Dined on August 6, 2022

    overall5food5service5ambience5
    Great evening ambiance! Food and beer selection was great! Highly recommend!
  7. OT

    OpenTable Diner

    New Orleans

    11 reviews

    3.0

    11 reviews

    Dined on August 6, 2022

    overall3food3service3ambience3
    There were chickens walking around the inside of the restaurant.
  8. OT

    OpenTable Diner

    Seattle

    1 review

    5.0

    1 review

    Dined on August 6, 2022

    overall5food5service5ambience5
    Our favorite meal in Key West! Great ambiance, fun live music across the street, food was very good and waiter was excellent. We enjoyed everything from cocktails to desert and every thing was great! Highly recommend!
  9. MD

    MarionD

    Naples

    7 reviews

    5.0

    7 reviews

    Dined on August 5, 2022

    overall5food5service5ambience5
    Our waiter Igor took very good care of us!
  10. OT

    OpenTable Diner

    Key West

    9 reviews

    4.0

    9 reviews

    Dined on July 30, 2022

    overall4food4service4ambience3
    The swordfish was great. I think I licked the plate clean. We will be back for more soon.
  11. OT

    OpenTable Diner

    Unspecified

    1 review

    3.0

    1 review

    Dined on July 30, 2022

    overall3food3service3ambience5
    We were a family of four on vacation in Key West. This was our first meal in the city, and the food was okay, the service was okay, but the ambience is nice under the trees with the lights. They do have an off-menu “kid’s menu” if you are dining with the little ones. Our kids had chicken strips, French fries and brisket Mac & cheese. They enjoyed it. My 14 year old said it fell right in the middle as far as quality of kid’s menu food goes. I had the fish tacos, which had a very flavorful slaw. The fish was over cooked, but otherwise had a good flavor. My husband did not enjoy his yellowtail, it was like rubber. The food arrived before our drinks, which we found very odd. Fresh meals rarely arrive before you get a drink on the table, suspiciously fast. Overall, it would be a great place for date night drinks and apps, not good for much else. We won’t return.
  12. OT

    OpenTable Diner

    Columbus

    3 reviews

    3.0

    3 reviews

    Dined on July 28, 2022

    overall3food3service5ambience3
    Joint birthday celebration. Food was good but not great. They were just a little off the mark with the dishes - as examples - my main course was a great piece of fish and well cooked, bit bland and my husbands dinner was over loaded with blue cheese which completely overpowered the dish (and we both love blue cheese). Service and ambience were wonderful. We would give it a second try as they may have had an off day.
  13. OT

    OpenTable Diner

    Tampa

    22 reviews

    vip
    3.0

    22 reviews

    Dined on July 28, 2022

    overall3food4service2ambience5
    We’ve been here before and had an excellent experience. This time the service was horrible. They weren’t short staffed or anything. Waiter forgot to put in our apps, forgot to bring drinks from the bar, we had to go hand him the check and then he lost our credit card saying we never gave it to him. My husband literally got up from the table and put it in his hand because he never came back. He then went and looked for it and he had set it down somewhere. Love the ambiance but doubt we will go back anytime soon.
  14. N

    None

    Louisville

    1 review

    1.0

    1 review

    Dined on July 27, 2022

    overall1food3service1ambience4
    Took way too long for just appa /drinks and they weren’t even busy! Said they had no specials… weird experiences, we have always loved this place!
  15. OT

    OpenTable Diner

    Salt Lake City

    2 reviews

    5.0

    2 reviews

    Dined on July 25, 2022

    overall5food5service4ambience5
    Great historical place to dine! Food was excellent. You can’t go wrong!
  16. OT

    OpenTable Diner

    Cleveland

    2 reviews

    5.0

    2 reviews

    Dined on July 23, 2022

    overall5food5service5ambience5
    Good food, great patio!
  17. OT

    OpenTable Diner

    West Palm Beach

    4 reviews

    5.0

    4 reviews

    Dined on July 23, 2022

    overall5food5service5ambience5
    Such a great dining experience! Banquet manager Brittani was an outstanding host🙌
  18. PP

    PamP

    New Orleans

    2 reviews

    5.0

    2 reviews

    Dined on July 23, 2022

    overall5food4service4ambience4
    The history of this building is very cool - they've done a good job of restoring some of the PanAm info without being over the top. Courtyard is great, but choice to eat inside when it's KW hot.
  19. KR

    KatiaR

    San Francisco

    3 reviews

    5.0

    3 reviews

    Dined on July 23, 2022

    overall5food5service5ambience5
    The food was fabulous - Branzino stuffed with crab meat. seafood pasta and fish tacos as well. the server was amazing "Igor". it started to rain and he had a table set up indoors. then it stopped and he brought us back out in the garden y just in time for dinner. wonderful service! will be back and recommend.
  20. BC

    BrettC

    1 review

    3.0

    1 review

    Dined on July 21, 2022

    overall3food2service5ambience4
    Fish taco- a fairly simple dish, however the rice was hard & dry - the red beans were soupy- as in right from an Undrained canned & heated/served . As for the tacos themselves- eh nothing special.
  21. JC

    JanC

    Philadelphia

    10 reviews

    vip
    5.0

    10 reviews

    Dined on July 21, 2022

    overall5food5service5ambience5
    Happy hour menu (4 to 6pm) is an excellent bargain. Both the food (bar menu and dinner menu) and drinks were delicious. The whole snapper was tasty as well as the tuna entree. The atmosphere is fun and we enjoyed the music being played across the street. Service was prompt and attentive - thank you Damian. Highly recommend visiting this historic establishment (old Pan Am office).
  22. DV

    DeniseV

    Tampa

    13 reviews

    5.0

    13 reviews

    Dined on July 20, 2022

    overall5food4service4ambience4
    Fun key west experience. We really wanted to try the deviled eggs, and they ran out. It’s a bit pricey, however the food was good.
  23. AM

    AbbeyM

    Tulsa

    3 reviews

    5.0

    3 reviews

    Dined on July 17, 2022

    overall5food5service4ambience4
    Garden seating, live band playing across the street, resident island chickens roaming about. Food and drink were fabulous (literally had pretty much one of everything because of our group size) and everything was decently priced compared to more tourist style restaurants closer to the water. 10/10 recommend and we will be back in our next trip to key west 🏝
  24. d

    denisew

    London

    3 reviews

    4.0

    3 reviews

    Dined on July 17, 2022

    overall4food3service4ambience4
    Lovely courtyard setting. Too quick service - in & out in under an hour & $90 bill! Food was ok - usual $14 for a load of green leaves called a summer salad - not great. Burger over cooked
  25. m

    marke

    1 review

    1.0

    1 review

    Dined on July 15, 2022

    overall1food1service2ambience1
    Food was bland and unappetizing. Chickens running around the restaurant were disgusting and it’s hard to imagine how anyone would find it to be charming. Would not recommend given all the other options around Key West.
  26. LH

    LeslieH

    New York Area

    4 reviews

    vip
    5.0

    4 reviews

    Dined on July 14, 2022

    overall5food5service5ambience5
    Vacation Dinner! Great outdoor place! Rooster and hens abound and crow. Upscale food at reasonable prices. We had the ahi tuna, sea bass, filet minion, and the chicken salad. The fried Brie app with strawberries and apples was awesome. God wine selection as well. Server was basically perfect! So nice, attentive but not too attentive. We laughed with our parents and had a great evening.
  27. OT

    OpenTable Diner

    New York Area

    2 reviews

    vip
    5.0

    2 reviews

    Dined on July 13, 2022

    overall5food5service5ambience5
    My wedding and ceremony was amazing. Great food and staff
  28. A

    Andee

    Boise

    22 reviews

    vip
    3.0

    22 reviews

    Dined on July 11, 2022

    overall3food3service5ambience1
    Decided to try this restaurant after reading lots of positive reviews. Unfortunately, my husband and I had a terrible experience. While the servers were awesome, the heat being outdoors, all the annoying roosters roaming around, and the horrible horrible flies just killed it for us. After trying to eat while fighting off flies for about 30 minutes, we finally asked to box our food and took it home. The steamed clams were ok but too much chorizo in it lost the clam flavor. We are still waiting to eat our seafood pasta and whole fried red snapper after losing our appetite last night. Kudos to the servers who were really great. Too bad the environment was awful.
  29. N

    Nadine

    1 review

    5.0

    1 review

    Dined on July 10, 2022

    overall5food5service5ambience5
    Our waitress was amazing. She was the sweetest and went ABOVE AND BEYOND. The food was delicious and the environment was great.
  30. PT

    PeterT

    West Palm Beach

    1 review

    5.0

    1 review

    Dined on July 9, 2022

    overall5food5service5ambience5
    Very good atmosphere and terrific food. Our server was great, so friendly and attentive.
  31. OT

    OpenTable Diner

    Orange County

    1 review

    4.0

    1 review

    Dined on July 6, 2022

    overall4food5service4ambience4
    Food was great. Beer was not. We tried two of their craft beers, both were disappointing. Great service as well. Nice place, but ask for samples of the beers before you commit.
  32. T

    Thumper

    1 review

    3.0

    1 review

    Dined on July 4, 2022

    overall3food3service2ambience3
    Sent message prior explaining it was anniversary and that we ate there after getting married 22 years ago asked for a specific seating area, this was ignored we were put facing the sun and had to move. Waiter was surly and uninterested barely spoke to us. Food was nice but over priced. Plates not cleared before main course arrived. We tipped based on our experience and then ended up with a full on confrontation from waiter demanding a 20% tip. Terrible experience that left us feeling like we'd never come back to keys. This will definitely be our last visit.
  33. OT

    OpenTable Diner

    New York Area

    7 reviews

    5.0

    7 reviews

    Dined on July 3, 2022

    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.
  34. DZ

    DebbyZ

    Tampa

    18 reviews

    vip
    5.0

    18 reviews

    Dined on July 3, 2022

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

    OpenTable Diner

    Charlotte

    3 reviews

    5.0

    3 reviews

    Dined on July 2, 2022

    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!
  36. MH

    MHMH

    New York Area

    3 reviews

    3.0

    3 reviews

    Dined on July 2, 2022

    overall3food3service3ambience3
    Good. I thought the food was okay, nothing too memorable. I had the house Pilsner and it was good.
  37. OT

    OpenTable Diner

    San Francisco

    1 review

    3.0

    1 review

    Dined on July 2, 2022

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

    MaritzaG

    New York Area

    9 reviews

    4.0

    9 reviews

    Dined on June 30, 2022

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

    OpenTable Diner

    Western NC

    7 reviews

    5.0

    7 reviews

    Dined on June 29, 2022

    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!
  40. EH

    EHMIV

    1 review

    5.0

    1 review

    Dined on June 28, 2022

    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.

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 930 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 18 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

Copyright © 2022 OpenTable, Inc. 1 Montgomery St Ste 700, San Francisco CA 94104 - All rights reserved.
OpenTable is part of Booking Holdings, the world leader in online travel and related services.
Booking LogoPriceline LogoKAYAK LogoAgoda LogoRentalcars LogoOpenTable Logo