First Flight Island Restaurant & Brewery

Name: First Flight Island Restaurant & Brewery
Address: 301 Whitehead St, Key West, FL, United States, 33040
Telephone: (305) 293-8484
Price range: $30 and under
Rating: 4.5

4.5

893 Reviews

$30 and under

Seafood

Top Tags:

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

Party Size

2 people

DateTime

Jul 2, 2022

7:00 PM

Booked 15 times today

Order delivery or takeout

Takeout

(305) 293-8484

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
Website
http://firstflightkw.com/
Payment options
AMEX, Discover, MasterCard, Visa
Dress code
Business Casual
Executive chef
Ben Schneller
Private party contact
Jackie Gibson: (305) 293-8484

Location
301 Whitehead St Key West, FL 33040
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

Featured in

Popular dishes

Ahi Tuna Poke*$14.00
Ginger & honey marinated ahi tuna, cucumber, sweet soy, toasted coconut, wonton
Shrimp Cocktail$16.00
House made cocktail sauce, mango salsa
Diver Scallops*$21.00
Pan seared diver scallops, chorizo-pesto risotto, sweet corn salsa
Beer Steamed Clams$18.00
One pound steamed clams, fennel, chorizo, Main Squeeze citrus wheat, toast points
Fried Brie$14.00
Crispy panko crusted, green apple, strawberries, passionfruit honey, toast points
Brussels Sprouts$12.00
Pan charred, caramelized in honey dijon
Beef Brisket Mac & Cheese$16.00
Cavatappi pasta, house three cheese blend, braised beef brisket
Brewery Wings$15.00
Jumbo wings, breaded or not, house made ranch. Choice: buffalo - old bay butter - jerk - sweet chili
Di Parma Flatbread$14.00
Prosciutto, arugula, mozzarella, rosemary infused olive oil
Hop Farm Flatbread$13.00
Heirloom cherry tomatoes, mozzarella, ipa-hop infused pesto, aged balsamic drizzle
Hummus Trio$12.00
Chef's hummus trio, corn tortilla, crudite
Deviled Eggs$11.00
House made recipe, beer battered jalapeno

Field

Add Grilled or Blackened: Chicken $7, Shrimp or Mahi $8, Tuna $9

Black & Blue$21.00
Blackened shrimp, blue cheese crumbles, strawberry, candied walnut, field greens, creamy balsamic
Caesar$13.00
Romaine, shaved parmesan, garlic croutons, cherry tomato, house made dressing
Summer$14.00
Artisan mixed greens, green apple, cucumber, grilled pineapple, cherry tomatoes, toasted almonds, citrus vinaigrette

Mains

Chefs Catch
Chef daily selection of locally sourced seafood
- MP
Swordfish$36.00
Grilled swordfish, roasted jalapeno cream sauce, avocado-jasmine rice, asparagus
Whole Snapper$35.00
Local yellowtail snapper, fried golden brown, jasmine rice, chef's sautéed vegetable, sweet chili sauce
Seafood Fettuccini$36.00
Hand made fettuccini, local fish, clams, shrimp, basil parmesan cream sauce
Seared Tuna*$34.00
Rare seared ahi tuna steak, jasmine rice, stir fry vegetables, wasabi crema
Fish Tacos$20.00
Blackened local fish, citrus slaw, mango salsa, chipotle-lime crema, island rice & red beans
Caribbean Pork$32.00
Mojo glazed pork tenderloin, caribbean red beans & rice, sweet plantains
Island Chicken Pasta$27.00
Blackened chicken breast, chefs sautéed vegetables, Caribbean alfredo tossed over penne pasta
Filet Mignon*$54.00
Char-grilled 8oz filet, blue cheese mashed potato, grilled asparagus, wild mushroom & bourbon demi glace
NY Strip & Frites*$47.00
12oz NY strip, brewery fries, truffle herb butter
The Brewery Burger*$21.00
8oz ground kobe beef, bacon, aged white cheddar, beer battered onion ring, arugula, brioche bun

What 893 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
4.6Service
4.6Ambience
4.3Value

Noise • Moderate

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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Filters

MG
MaritzaG
New York Area
9 reviews
4.0
9 reviews
Dined 1 day ago
overall4food4service5ambience4
Really a nice place. The food was good and the drinks were great! Great dinner overall.
EH
EHMIV
1 review
5.0
1 review
Dined 3 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.
DF
DonnaF
1 review
3.0
1 review
Dined 5 days ago
overall3food3service2ambience3
Salads were very good as were the fried ravioli and very big pretzel
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.
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.
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!!
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.
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!
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!
DG
DeenaG
Atlanta
18 reviews
5.0
18 reviews
Dined on June 7, 2022
overall5food5service5ambience5
Excellent food! Great place on Key West
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!
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.
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!
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.
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.
LB
LauraB
Chicago
1 review
vip
5.0
1 review
Dined on May 30, 2022
overall5food5service5ambience5
Casual and fun atmosphere.
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.
HM
HollyM
Naples
6 reviews
vip
4.0
6 reviews
Dined on May 29, 2022
overall4food4service4ambience4
Very good, island pasta delicious, cute patio.
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.
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.
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.
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.
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.
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.
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.
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.
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.
ER
ERAH
1 review
3.0
1 review
Dined on May 20, 2022
overall3food2service3ambience3
Very expensive meals The quality is correct but no more
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!
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.
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.
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 !!
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!
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.
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.
c
chefdkh
San Francisco
4 reviews
vip
4.0
4 reviews
Dined on May 8, 2022
overall4food4service5ambience4
Our server Igor was the best. He paid close attention to our requests and followed through gracefully with everyone. What a treasure
MP
MargetteP
1 review
4.0
1 review
Dined on May 5, 2022
overall4food4service4ambience4
Great meal, service was great...quiet place off the business of Duval. Will definitely come back again.
D
David
Tampa
6 reviews
5.0
6 reviews
Dined on May 3, 2022
overall5food5service5ambience5
The food was great and the ambiance was even better. Great place to go as a couple or with a large group of friends.
CK
CindyK
Warwickshire
4 reviews
vip
5.0
4 reviews
Dined on May 3, 2022
overall5food5service5ambience4
Wonderful ! Celebrated my birthday. Food was great and service was fantastic.
BD
BrianD
Central Coast
6 reviews
5.0
6 reviews
Dined on May 1, 2022
overall5food4service5ambience3
The service and food was excellent. The noise from the bar across the street was annoying, guess I’m not much of a rap aficionado…

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 893 OpenTable diners.

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

Make a reservation

Party Size

2 people

DateTime

Jul 2, 2022

7:00 PM

Booked 15 times today

Order delivery or takeout

Takeout

(305) 293-8484

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

Website
http://firstflightkw.com/
Phone number
(305) 293-8484
Private party contact
Jackie Gibson: (305) 293-8484

First Flight Island Restaurant & Brewery

Make a reservation

Order delivery or takeout

Takeout

Additional information

22 Key West / Florida Keys Restaurants to Love This Valentine's Day

The Best Bars for Foodies in the Florida Keys

The Best Breakfast Restaurants in the Florida Keys

Fish Tacos

Whole Snapper

Key Lime Margarita

For the Table

Ahi Tuna Poke*$14.00

Shrimp Cocktail$16.00

Diver Scallops*$21.00

Beer Steamed Clams$18.00

Fried Brie$14.00

Brussels Sprouts$12.00

Beef Brisket Mac & Cheese$16.00

Brewery Wings$15.00

Di Parma Flatbread$14.00

Hop Farm Flatbread$13.00

Hummus Trio$12.00

Deviled Eggs$11.00

Field

Black & Blue$21.00

Caesar$13.00

Summer$14.00

Mains

Chefs Catch

Swordfish$36.00

Whole Snapper$35.00

Seafood Fettuccini$36.00

Seared Tuna*$34.00

Fish Tacos$20.00

Caribbean Pork$32.00

Island Chicken Pasta$27.00

Filet Mignon*$54.00

NY Strip & Frites*$47.00

The Brewery Burger*$21.00

Overall ratings and reviews

Loved For

Sort by

Filters

Cleaning & sanitizing

Physical distancing

Protective equipment

Screening

FAQs

Does First Flight Island Restaurant & Brewery offer delivery through OpenTable or takeout?

How is First Flight Island Restaurant & Brewery restaurant rated?

Is First Flight Island Restaurant & Brewery currently accepting reservations?

Make a reservation

Order delivery or takeout

Takeout

Additional information

Featured in

22 Key West / Florida Keys Restaurants to Love This Valentine's Day

The Best Bars for Foodies in the Florida Keys

The Best Breakfast Restaurants in the Florida Keys