Florida Keys: Enjoying Garden Canopy Dining at First Flight

Florida Keys: Enjoying Garden Canopy Dining at First Flight
22 Jun 2018

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Disclosure: Our food was covered by First Flight Island Restaurant & Brewery and The Florida Keys. All opinions are my own.

Located in an historic building at the corner of Whitehead and Caroline is First Flight Island Restaurant & Brewery, a fun and vibrant addition to the Kew West food scene. This location formerly housed Kelly’s Caribbean Bar Grill & Brewery, as in actress Kelly McGillis from Top Gun.

The history of this building predates Kelly’s though… it was the birthplace of Pan American World Airways. Pan Am, the largest international air carrier in the USA from 1927 to 1991, sold their first tickets in this very building.

Keeping with tradition, First Flight has not so subtle hints of the historic building’s heritage woven into its decor. It truly is a beautiful building, with a fun Key West atmosphere.

Garden Canopy Dining

The outdoor dining experience at First Flight is wonderful. Sitting under a garden canopy of tall trees, with patio lanterns strung overhead, enjoying a delicious meal. There is not much better than that. Just up the stairs and through the doors is the Southernmost Brewery in the USA. Named for the Sikorsky sea plane that plunging through the ceiling, the aluminum wing drinking surface of the Crash Bar is a popular hangout for local “fly-boys” in the US military, who if a frequent visitor, have their own personalized drinking mug. The Tree-Top Deck on the second floor offers a great view of the canopy garden.

What I Ate For Dinner at First Flight

Having spent the previous few days eating big meals, we decide to do smaller, shareable appetizers, finished off with desserts we could share.

The fist dish we ordered was the Shrimp Ceviche. This beautifully prepared and very colourful dish was packed with flavour. The citrus popped, the shrimp were tasty, and the fresh tortilla chips added a nice crunchy texture to the overall bite. Very yummy!

First Flight stuffed avocado

Now I am not one to normally eat a lot avocado, unless it is in something. So when the Street Corn Avocado dish came out, I was a little curious. Fire roasted street corn salsa, avocado, chipotle aioli. This beautiful combo of flavours worked well together. I was pleasantly surprised, and would definitely order this appetizer again.

The Seared Scallops were my favourite dish of the night. I ordered this one for myself. Diver scallops, basil risotto, chorizo, jalapeño & corn salsa. The large diver scallops were beautifully seared, and the combination of flavours was amazing. The basil risotto had a great taste and texture. This savoury dish was absolutely perfect.

First Flight fish tacos

After those delicious scallops, I was in the mood for First Flight’s Fish Tacos. Blackened local fish, citrus slaw, avocado aioli, pickled sweet onion, pico de gallo, with a side of hand cut fries. These were really good, and the fish was prepared just right.

For our first of two desserts, we had Oreo Key Lime Pie. Yep, you read that correctly. Oreo cookie crust, and Oreo cookie pieces in the Key me pie filling. The tartness of the lime was a little overpowered by the sweetness of the Oreo cookie pieces, but it was still a delicious slice of pie. Save room for it!

First Flight fried peanut butter and jelly sandwich

The second dessert we ordered was the Fried Peanut Butter and Jelly Sandwich with Vanilla Ice Cream. Oh. Em. Gee. I like peanut butter and jelly sandwiches as much as the next person, but this took that classic childhood favourite to a whole new level! With the addition of ice cream and the sweet chocolate drizzle, this dessert is sinfully good. If you have room, give it a try!

Overall, our dinner at First Flight Island Restaurant & Brewery was a great experience. I loved dining under the trees and patio lanterns, with new friends, warm temperatures, and a cool breeze in the air.

First Flight menu

First Flight Menu

First Flight serves lunch and dinner. The lunch menu has hand food on it, which is available to order at dinner time as well, so I combined the two menus here.


Street Corn Avocado: fire roasted street corn salsa, avocado, chipotle aioli.

Shrimp Ceviche: citrus marinated Key West shrimp, fried corn tortilla.

Grilled Octopus: char-grilled mediterranean octopus, smashed fingerling potatoes, shaved fennel, lemon vinaigrette.

Devil Eggs: house made with fried jalapeño.

Chicken Wings: Chef Moses’s six hour confit wings, house made ranch, served buffalo – old bay – garlic & parmesan.

Beef Brisket Mac & Cheese: cavatappi pasta, house three cheese blend, braised beef brisket.

Mussels Fra Diavolo: pan tossed mussels, spicy marinara, grilled ciabatta.

Hummus Trio: chef’s hummus trio with grilled flatbread.

Tuna Poke Bowl: marinated sushi grade ahi tuna, white rice, pickled asian vegetable, soy finish.

Beer Steamed Clams: one pound house beer steamed clams, fennel, chorizo, grilled ciabatta.

Seared Scallops: diver scallops, basil risotto, chorizo, jalapeño & corn salsa.

Charred Brussels Sprouts: caramelized in honey dijon.

First Flight Fries: thick steak fries, cajun aioli.


Lobster: warm water lobster, mozzarella, applewood smoked bacon, beer steamed sweet onion, shaved black truffle.

BBQ Brisket: braised beef brisket, street corn salsa, three cheese blend, fried onion, BBQ sauce.

Hop Farm: heirloom cherry tomatoes, organic mozzarella, ipa-hop infused pesto, aged balsamic drizzle.

Di Parma: proscuitto, arugula, mozzarella, rosemary infused olive oil.


Kale Caesar: baby kale & romaine mix, shaved parmesan, fried prosciutto, garlic croutons, house made caesar.

Black & Blue: blackened shrimp & blue cheese crumbles, strawberry, candied walnut, baby spinach, creamy balsamic.

Garden Fresh Caprese: organic mozzarella, garden picked basil, marinated heirloom tomato, balsamic reduction.

Greek: baby arugula, heirloom tomato, pickled sweet onion, kalamata olives, feta cheese, red wine vinaigrette.


Hogfish: locally sourced hogfish, coconut rice, charred cherry tomatoes, citrus beurre blanc.

Grouper: local black grouper, lump crab, jasmine rice, grilled asparagus, key lime hollandaise.

Whole Snapper: golden brown locally sourced yellowtail snapper, jasmine rice, chefs sautéed vegetable, pineapple chutney.

Lobster Tail: warm water spiny lobster, garden vegetable risotto,
grilled asparagus, preserved lemon butter.

Seafood Linguini: house made linguini, black grouper, clams, shrimp,
basil parmesan cream sauce.


Organic Chicken: organic Ashley Farms chicken, wild mushroom risotto, charred brussel sprouts, pan demi.

Skirt Steak: 8oz grass fed skirt steak, steak frites, blistered cherry tomatoes, roast garlic chimichurri.

Short Rib: braised bone-in short rib, rustic root vegetable polenta, port wine demi.

Filet Mignon: 8oz grilled filet, blue cheese mashed potato, grilled asparagus, wild mushroom & bourbon pan sauce.

Hand Food

Garden Panini: avocado, cucumber, organic mozzarella, aged balsamic.

Braised Brisket Panini: house beef brisket, swiss, caramelized onion, port wine demi.

Tropical Chicken Sandwich: grilled pineapple, avocado aioli, tomato.

Fish Tacos: blackened local fish, citrus slaw, avocado aioli, pickled sweet onion, pico de gallo.

Brewery Burger: 8oz ground kobe beef & bacon patty. Aged white cheddar, beer battered onion ring, arugula, brioche, fries.

Classic Burger: seasoned beef, choice of cheese, lettuce, tomato, onion, lemon-herb remoulade.

Black Bean Burger: organic black bean burger, swiss cheese, street corn salsa, cajun aioli.

First Flight garden canopy from street

Location and Hours

First Flight Island Restaurant & Brewery is located at:
301 Whitehead Street
Key West, Florida 33040
Phone: (305) 293-8484

Open daily from 11:00am – Midnight
Garden Dining; Until 10:00pm
Brewery: 11:00am – 10:00pm

First Flight welcome sign

Get Social with First Flight Island Restaurant & Brewery

Be sure to follow First Flight Island Restaurant & Brewery’s updates on Facebook, and Instagram.

Big Daddy

If you would like me to review your product, service, restaurant, or travel destination, please send me an email at craig@bigdaddykreativ.ca or tweet me at @BigDaddyKreativ

Craig Silva

Craig is a husband, father, team leader, travel and food writer, senior youth group coordinator, designer, brander, community builder, volunteer, and social media strategist. He likes to travel, go camping, go on road trips, watch movies, build stuff, operate the grill, and sing with his band. Craig is a member of the Travel Media Association of Canada. If you are a PR agency or brand and would like Craig to review a travel destination, vehicle, restaurant, product or service, please send him an email.

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