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  4. Florida Keys - Monroe County
  5. Key West

First Flight Island Restaurant & Brewery

4.4
4.4
1073 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 30 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 1,073 people are saying

Overall ratings and reviews

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

4.4
4.4 based on recent ratings
  • 4.3Food
  • 4.4Service
  • 4.6Ambience
  • 4.2Value

NoiseModerate

Loved For

  • Key West / Florida Keys

    Great for outdoor dining

  • Key West / Florida Keys

    Lively

  • Key West / Florida Keys

    Seafood

  • Key West / Florida Keys

    Most Booked

  • Florida Keys - Monroe County

    Great for outdoor dining

  • Florida Keys - Monroe County

    Lively

  • Florida Keys - Monroe County

    Seafood

  • Florida Keys - Monroe County

    Most Booked

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  1. NYCtravelers

    New York Area

    42 reviews

    vip
    5.0

    42 reviews

    Dined 2 days ago

    overall5food5service5ambience5
    The brisket Mac and cheese as an appetizer was SO good. We then had the Caesar and split the fish tacos. Also very delicious. Would totally recommend checking this restaurant out!
  2. jojobangs

    New England

    54 reviews

    4.0

    54 reviews

    Dined 2 days ago

    overall4food4service4ambience5
    Overall very nice. It’s a beautiful spot and the drinks and food were goo.
  3. OldNavy

    Philadelphia

    9 reviews

    vip
    5.0

    9 reviews

    Dined 3 days ago

    overall5food5service5ambience4
    This was our third visit to First Flight as my wife as I were celebrating our return to Key West. Every aspect of our dinner was fantastic including the wonderful presentation, taste and quantity of the food, our attentive and friendly waitress and the ambiance of your courtyard. I will mention, however, that as soon as my red snapper was served, my dish was immediately invaded by flies. I do not perceive this as a fault on your part, and it was interesting in that neither my wife’s scallops nor our Brussel sprouts were touched, but the snapper was clearly a target. Nonetheless, our waitress immediately addressed the issues by offering us a secluded table inside. Dinner, from then on, was a total delight and the snapper was absolutely delicious. We have recommended First Flight to all of our friends traveling to Key West, and none have been disappointed. All the Best, Mark Pachuta
  4. MicheleL

    Tahoe

    4 reviews

    5.0

    4 reviews

    Dined 3 days ago

    overall5food4service5ambience5
    Good food in a beautiful setting. Great back story and good beer
  5. Hef51

    Minneapolis

    13 reviews

    4.0

    13 reviews

    Dined 4 days ago

    overall4food4service3ambience5
    Food was nice. We ended up being the lost table so service took awhile until we finally asked for a waiter. Once that was sorted out things got significantly better. Shaded courtyard is beautiful and lovely at night.
  6. MKoc

    Philadelphia

    50 reviews

    vip
    5.0

    50 reviews

    Dined 5 days ago

    overall5food4service5ambience4
    Wonderful evening with a first time female server who acted like a pro! And Chris had his eye on everything, so we were happy and well cared for. Thank you!
  7. Laurie

    Chicago

    9 reviews

    vip
    3.0

    9 reviews

    Dined 5 days ago

    overall3food3service4ambience2
    Limited menu. Tuna was very good. Like most places in key west, high priced, rather average quality.
  8. andys

    Atlantic City

    10 reviews

    3.0

    10 reviews

    Dined 5 days ago

    overall3food2service5ambience5
    We’ve always really enjoyed coming in the first place. The outdoor dining area is beautiful and the service is usually very attentive. The food has been mostly excellent as well unfortunately, while dining last night, though our servers were excellent, the food was subpar. the burger was dry, roll, stale. The brisket mac & cheese was flavorless, the croutons on the salad, stale. The rest of the food was just OK. It felt bad to spend $200 and come away dissatisfied. The restaurant was kind enough to remove 10% from the overall bill, which was appreciated. I would still recommend the restaurant and would give it another chance.
  9. LindaT

    Key West

    16 reviews

    vip
    5.0

    16 reviews

    Dined 7 days ago

    overall5food5service5ambience4
    First Flight is a local gem. The food and service are very good. The place is charming. I have been there many times and will continue to go back.
  10. OpenTable Diner

    San Francisco

    13 reviews

    vip
    2.0

    13 reviews

    Dined on March 15, 2023

    overall2food1service1ambience4
    Very disappointed. Heard so many good things. Food had no flavor. We sat for over 15 minutes when we overhead server remark "that's not my table" to host. Very mediocre.
  11. jaynep

    1 review

    5.0

    1 review

    Dined on March 14, 2023

    overall5food4service5ambience5
    We ate early at 630 and had a great server. The beer flights were well priced and good variety . The freah catch of the day was amazing. Didn't like key lime pie with chocolate crust but everything else was top notch.
  12. Cheryl

    Western NC

    59 reviews

    vip
    5.0

    59 reviews

    Dined on March 13, 2023

    overall5food5service5ambience5
    Great dining experience with our visiting family
  13. cski

    New York Area

    24 reviews

    vip
    3.0

    24 reviews

    Dined on March 12, 2023

    overall3food3service2ambience3
    Sat outside and flys everywhere. Good just ok. Happy good
  14. OpenTable Diner

    1 review

    4.0

    1 review

    Dined on March 10, 2023

    overall4food3service5ambience4
    Beautiful outdoor dining with good variety on the menu. Noise varied from peaceful to blaring, depending upon the situation at the bar across the street.
  15. KellyB

    New England

    14 reviews

    2.0

    14 reviews

    Dined on March 10, 2023

    overall2food3service4ambience1
    Great service .. fair happy hour good choices. Sat down in dining area and was attacked by flies when food arrived. Couldn’t eat our meal.
  16. Warde

    Tampa

    42 reviews

    vip
    5.0

    42 reviews

    Dined on March 9, 2023

    overall5food4service5ambience5
    Beautiful outdoor seating, noisy due to live music upstairs and also at Garbo’s across Caroline Street so it was noisy. Also if the fans were on I think the flies would have been less of an annoyance. For appetizers we got the tuna poke, the Brussels sprouts, and the deviled eggs. All were delicious; however, the fried pieces of peppers alongside the deviled eggs were lousy… greasy and almost 100% coating with nothing inside. The Brussels sprouts were so good though… sweet, nutty, perfectly cooked. I would definitely have those again! The poke was also very good, obviously the tuna was fresh and the preparation was spicy. For entrees we had fish tacos, swordfish, a burger, and the seared tuna. The fish tacos were meh, but everything else was very impressive. They did a beautiful job cooking the swordfish. The tuna was so soft and buttery, and the zucchini/squash side was perfect. The burger is huge and juicy, but the onion ring had that terrible greasy batter coating like what came with the deviled eggs so my advice is to ask to have the onion ring s on the side or, even better, left off the plate entirely. We are locals so will be back again, as they are extremely dog friendly and the service was absolutely perfect.
  17. RhondaM

    E. Tennessee

    1 review

    3.0

    1 review

    Dined on March 8, 2023

    overall3food2service3ambience4
    We ate at 915 one of their sister restaurants and it was delish so we tried this one. Shrimp was rubbery, pork was dry and rice was under cooked and crunchy. Disappointed in the food but patio was nice.
  18. OpenTable Diner

    Key West

    6 reviews

    vip
    4.0

    6 reviews

    Dined on March 7, 2023

    overall4food5service5ambience5
    Atmosphere was great and service exceptional!
  19. Missy

    San Francisco

    1 review

    3.0

    1 review

    Dined on March 6, 2023

    overall3food3service2ambience4
    We had high hopes for dinner at First Flight but we were disappointed. The food was just ok (for the price) and the server was not very attentive. We liked the atmosphere and the location was very convenient.
  20. lindas

    New York Area

    8 reviews

    vip
    5.0

    8 reviews

    Dined on March 6, 2023

    overall5food5service5ambience5
    Loved everything about this restaurant.. a must try if you are in Key West
  21. OpenTable Diner

    New York Area

    6 reviews

    vip
    4.0

    6 reviews

    Dined on March 3, 2023

    overall4food4service4ambience4
    Good food and nice atmosphere.
  22. Maggie

    New York Area

    13 reviews

    5.0

    13 reviews

    Dined on February 28, 2023

    overall5food5service5ambience5
    So sorry for the delayed response. Had dinner with family on Feb 28th. What a magical place, the patio is beautiful. Everything from the drinks (great Margaritas) appetizers to entrees was amazing. Fish tacos so fresh and seasoned well. Caribbean pork was so good, tender and the spices were fantastic. The staff was exceptional. Everyone made sure we had our drinks and food and appreciate checking back to see if we needed anything. Great job!
  23. Atcdrew

    Atlanta Metro

    26 reviews

    3.0

    26 reviews

    Dined on February 26, 2023

    overall3food3service5ambience5
    Overall it was just ok. The ambiance and service were great. Food was just ok. Shrimp cocktail appetizer was over cooked and the shrimp were small. Tuna was ok and the burger was pretty good. The prices for the entrees rivaled that of a fine dining restaurant, which this was not. The bathroom was gross. When you have some menu items that are just shy of $100, have some clean bathrooms.
  24. OpenTable Diner

    New York Area

    8 reviews

    vip
    4.0

    8 reviews

    Dined on February 25, 2023

    overall4food5service4ambience4
    We really enjoyed the outside deck and food. Wings, tuna and
  25. OpenTable Diner

    Chicago

    2 reviews

    3.0

    2 reviews

    Dined on February 24, 2023

    overall3food3service3ambience2
    Just okay, service slow, food average, they had the main floor restaurant closed for a wedding. They had the balcony opened for diners, heard the entire speech from the best man while trying to eat our dinner. Would not return.
  26. Yummy

    Philadelphia

    28 reviews

    vip
    4.0

    28 reviews

    Dined on February 24, 2023

    overall4food4service5ambience5
    Nice selection of food and drinks. Excellent flavors. Friendly service.
  27. OpenTable Diner

    New England

    102 reviews

    vip
    5.0

    102 reviews

    Dined on February 23, 2023

    overall5food5service5ambience5
    Food was great, nice menu selection, good waiter, loud band across the street but we could still have a conversation. They have a great Happy Hour also.
  28. LindaS

    Philadelphia

    2 reviews

    4.0

    2 reviews

    Dined on February 22, 2023

    overall4food4service5ambience5
    Food was good, Chris, our server excellent. Was fun place to take the family. Will return.
  29. mary

    New England

    17 reviews

    5.0

    17 reviews

    Dined on February 22, 2023

    overall5food5service5ambience5
    We were a variety of ages but great food for everyone. Thank you
  30. OpenTable Diner

    Baltimore

    1 review

    4.0

    1 review

    Dined on February 20, 2023

    overall4food5service5ambience4
    The meal, service and outdoor dining were wonderful. But the restrooms….absolutely disgusting! With all the money flowing through the restaurant they should be able to afford a decent makeover and keep them spotless and well stocked with soap and towels.
  31. TinaW

    New Mexico

    46 reviews

    vip
    5.0

    46 reviews

    Dined on February 20, 2023

    overall5food5service4ambience5
    Nice! Great outdoor spot food was very good. Music across the street service was fine. All and all very good-
  32. luv4food

    Cincinnati

    17 reviews

    vip
    4.0

    17 reviews

    Dined on February 19, 2023

    overall4food5service3ambience3
    Had the wings and the blackened grouper. The wings were okay but the grouper was fantastic. Don’t think they can make up their mind if they want to be a bar restaurant or an upscale one. Prices and some of the food is there for an upscale but the atmosphere and staff are not.
  33. SteveA

    Columbus

    16 reviews

    vip
    2.0

    16 reviews

    Dined on February 18, 2023

    overall2food1service1ambience1
    Where do I start. The restaurant was old and dirty. We were seated on the second floor having to climb old steps that were arrow and uneven. The food was horrible. Me and my friend both ordered salads. Neither came with enough dressing to tie the ingredients together. The service was horrible. Our waiter was waiting on close to 7 tables. He never checked back on us once. I ordered a burger medium rare. It came rare with only to outside browned.
  34. JohnS

    1 review

    4.0

    1 review

    Dined on February 16, 2023

    overall4food4service5ambience5
    Very nice atmosphere. Service was excellent and food was good. Good location and good beer .
  35. Shalah

    Wicklow

    2 reviews

    5.0

    2 reviews

    Dined on February 15, 2023

    overall5food5service5ambience4
    Today is my birthday. My husband and I had a wonderful dinner. It is the best meal we have had since we arrived in Key West and we have eaten in a different restaurant for every meal since we arrived on Monday.
  36. OpenTable Diner

    Atlanta Metro

    2 reviews

    3.0

    2 reviews

    Dined on February 15, 2023

    overall3food3service4ambience4
    Food was meh. Service was great, ambiance was nice. The band from the outdoor bar across the street was very loud
  37. JuliaB

    1 review

    5.0

    1 review

    Dined on February 14, 2023

    overall5food5service5ambience5
    Food and ambience were great. Service was amazing and quick. Beer was awesome. Music was playing next door. We could hear from our seat so we didn’t have to go over there for a good time. Great little place off the beaten path. Definitely stop or make reservations. I’ll be back!
  38. Lauren

    New York Area

    1 review

    vip
    2.0

    1 review

    Dined on February 12, 2023

    overall2food1service3ambience4
    Unfortunately the food was disappointing.
  39. OpenTable Diner

    Naples

    5 reviews

    5.0

    5 reviews

    Dined on February 11, 2023

    overall5food5service4ambience5
    Beautifully decorated with white lights and foliage. Menu has just the right number of options without being overwhelming. I had the seafood pasta which was delicious with shrimp and clams. My husband had the Caribbean pork which was also delicious. Our server was polite and attentive. We will go back!!
  40. Tommyg

    New York Area

    30 reviews

    vip
    5.0

    30 reviews

    Dined on February 7, 2023

    overall5food5service5ambience5
    We loved this place, great ambience with indoor or outdoor dining. Our waiter was great, suggested great beers for my flight and was very personable. The food was excellent and plentiful. Live music from across the way added to the good time we had.

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 4.4 stars by 1073 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 30 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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