A Wine Lovers Travel Guide: The Florida Keys

As Canadians, we’re no strangers to beautiful South Florida. Each year, we escape the harsh winter weather to live our best “Snow Bird” lives down on the sunny and beautiful Gulf Coast. 😆

And yet, each time before we go (and when we return home) it seems we’re bombarded with the same questions…

So, glasses of bubbly in hand, we put our heads together and thought… “Why not put together a wine lovers travel guide to some of our favourite cities and non-wine producing destinations?” Just because they don’t make wine somewhere, doesn’t mean there aren’t fantastic food and beverage experiences for wine lovers and foodies alike.

So, this post marks the first instalment of a new series, where we share our favourite sparkling spots and effervescent experiences (including our favourite wine bars, restaurants, things to do, and hidden gems) in some of our favourite cities and non-wine producing regions. So you can leave Alexa at home… because, we got you! 😎🙌

First Stop: Islamorada

Located about 1.5 hours south of Miami, Islamorada is a village encompassing six of the Florida Keys and is known for its beautiful coral reefs, fishing and water sports. It has an up-scale small-town atmosphere, with stunning vistas and sunsets, plenty of great restaurants, breweries, quaint shops and art galleries.

As the drive from Miami to Key West is a bit of a trek – 3.5 hours on a single lane highway, and if you get stuck behind The Golden Girls in a Sebring those 3.5 hours may feel more like 5 – we recommend making a pit-stop in Islamorada for a night. It’s the mid-way point between Miami and Key West, and it’s a great reminder that “the Florida Keys” are not just Key West!

Islamorada – Food, Drink + Experiences

Florida Keys Brewing Co.

Islamorada is known as the sport fishing capital of the world, and has the longstanding reputation of being a drinking town with a fishing problem. We found that quite funny! 😆

The Florida Keys Brewing Co. is the first microbrewery in what’s known as the Upper Keys (the section that’s closer to the mainland). It is located in the fun and funky Morada Way Arts and Cultural District on Islamorada. So, it’s fitting that this colourful, inspired brewery offers flight of beers in an indoor and outdoor art-infused setting, allowing you to check out artwork, play some games (including a Golden Girls’ version of Clue!) and to relax and listen to some music while sipping a refreshing beverage (including non-alcoholic options). They also offer tours of their growing facilities – which we had the pleasure of experiencing! 

The Florida Keys Brewing Co. tasting room consistently features twenty draught beer options, some of which rotate seasonally but which always express a sense of innovation and ingenuity (including the use of locally grown ingredients, such as lemongrass – which found itself into a draught beer that we tried). While their diverse and delicious lineup of rotating brews keeps customers coming back for something new and exciting, Florida Keys Brewing Co. has recently upscaled and now sells three of their staple beers, including Spearfish Amber, to retailers in the Keys and in abutting counties. They’re committed to remaining a local craft product, and people come from all over for these refreshing brews. (And yes, we do love beer, as it’s sparkling and perfectly fitting for us lovers of all things effervescent!).

We had the pleasure of proprietor Craig McBay taking us around the facility on a relaxed weekday afternoon. Well, we should say that it was relaxed for us, as Craig is one busy man. The Burlington, Ontario native not only owns and runs the Florida Keys Brewing Co. with his wife Cheryl, but he also is active in the local Chamber of Commerce and supports the Morada Way Arts and Cultural District and has a family (one kid and one parrot, which keep him busy). We appreciated him taking us through his growing facility, sharing his journey into microbrewing and the story of the Florida Keys Brewing Co. – which is really a family venture. His wife designs much of the packaging, and that sense of art and personal imprint is apparent in the packaging, styling of the space and of course the tap room and the beers!

Islamorada Beer Company

Just a stones throw from our first stop, we arrived at the Islamorada Beer Company. Named after the island it was founded on, the Islamorada Beer Company really came to be when some local beer lovers dreamed up brewing their own suds in this sunny corner of the Florida Keys.

As with most ideas down here, this one was dreamt up on a fishing boat, and evolved into a brewery with a goal to make quality local craft beer that complements the relaxing, sunny and tropical Florida Keys lifestyle. We found this reflected in the brews – like the “No Wake Zone” Coconut Key Lime Ale – and in their branding and colourful tap room. We enjoyed a tasty, distinctly Florida Keys welcome with the array of inspired beers.

As we also learned from hostess with the mostest Larissa, that brewing Florida Keys craft beer is a passion for the company and we would agree that is shown by the quality of Islamorada Beer Company’s suds. Some of the brews are made on site, and are available the tap bar. Most, however, are made on the mainland and distributed widely across the US so be on the lookout for a taste of Islamorada.

And recently they’ve expanded with the launch of their new distillery next door! The first distillery in Islamorada, they specialize in rum – the Dark Barrel Aged being our favourite – along with a super cool range of canned craft cocktails.

Lorelei Restaurant & Cabana Bar

Now, we love us a dive bar. And Lorelei’s, located a stone’s throw away from Islamorada’s upscale Cheeca Resort (where we had the pleasure of staying), is a local institution on the island. While there are plenty of mid-range and fancy options for dinner, we were really feeling like something old school. And, we sure found it!

From the mermaid décor, to the spacious outdoor bar and bandshell in front of a covered cabana, Lorelei’s lived up to its name. The restaurant is roadhouse-style, and faces the bayfront and a small marina, specializing in seafood and is known for its live music and incredible sunset views. You may not find sparkling on the menu, but the experience of a draught beer or margarita, coconut shrimp and some live music and a sunset, shared with some locals, is a real treat and a quintessential Keys experience!

Islamorada – Where to Stay

Cheeca Lodge & Spa

One of our goals in coming to the Florida Keys, aside from finding our sparkle and sharing those sparkling experiences, was to relax. And we sure did, at Islamorada’s Cheeca Lodge & Spa.

This beautiful resort is located on just over 10 hectres (about 27 acres) of lush, immaculately maintained tropical gardens and 300 metres (or 1000 feet) of private waterfront with its own pier. From the sparkling reception, to the warm staff and attentive service, we felt truly at ease. And, it’s fair to say that Cheeca Lodge & Spa was exactly what we were looking for and the most luxurious resort that you’ll find Islamorada.

Located within walking distance to the Florida Keys Brewing Co. and Islamorada Brewing, Cheeca is spread out over a series of buildings fanning out from the main reception building that has a restaurant, bar and shops attached to it. The main restaurant serves breakfast, lunch and dinner and others are available – such as the Mia Cucina pizzeria. Included in your stay are a number of facilities, including golfing and some water sports activities. 

We had the pleasure of staying in a beach-facing bungalow, which contained four small single-storey rooms with parking underneath and included an enclosed lanaii and just a stone’s throw from the waterfront area. On that front (no pun intended), the waterfront area includes a small natural beach and shallow area for swimming, and a man-made extension and beautiful pool area… perfect spot for a glass of bubbles!

Next Stop: Key West

The most happening spot in The Florida Keys, Key West is paradise in every sense of the word. The most southern point in Florida, located just 90 miles north of Cuba, boasts something for absolutely everyone. From water sports and diving excursions, to shopping, theatre, fabulous museums, art galleries, incredible seafood, nightlife, and of course… amazing wine bars with an island flair!

Key West – Food, Drink + Experiences

Wine-O Bar

Wine-O Bar is located in the La Concha Hotel, the tallest structure in Key West, and offers an extensive collection of wines including popular favourites, sommelier selected cult-classics and some hard-to-find wines from a variety of wineries around the US and top wine regions.

Perhaps unsurprising given that Wine-O Bar is located in an upscale hotel, it is outfitted with extravagant furnishings and decor. We can’t lie, we loved the bit of extra on this stretch of the legendary Duval Street. Furnishings aside, they offer over 200 bottles from around the world! We enjoyed a bottle of Iron Horse Vineyard’s 2014 Oceans Reserve Blanc de Blancs, which was elegant, affordable and deliciously topical (we’re surrounded by ocean here in Key West, so it made sense right?). That aside, the wine showed its age and we were all the happier for it, enjoying a rich and nutty bubbly while watching Duval Street buzz away. 

If you’re interested in the sweet side of life, they also offer an array of chocolates for your enjoyment!

Alonzos Oyster Bar

Located in the beautiful waterfront area of Key West, Alonzo’s Oyster Bar Is a seafood focused restaurant that is well loved by tourists and locals. This happening spot also offers great seafood probably one of the best happy hours in the Keys.

We enjoyed our Oysters Muscovy with a bottle of a Sophia Brut Rosé, while watching this part of Key West teem with nightlife. Sitting on the patio is your best bet, as it’s the most atmospheric spot in the restaurant, but indoors will offer you that seaside, coastal feeling if it’s too cold or rainy.

Other selections of bubbles are available, and certainly prove that there’s no better pairing than oysters and sparkling wine!

ViV Wine Bistro

A favourite of ours on our recent trip to Key West, ViV Wine Bistro is a wine and cheese bar offering a wonderful selection of fine, authentic Old & New World natural wines to pair with hand selected European cheeses and custom charcuterie boards. What can we say, other than oui, oui!

ViV Wine Bistro is like stepping into the world of an authentic French delicatessen, except you’re right in the heart of Key West. So, maybe that St. Martin feeling?

It was established in 2014, and ViV Wine Bistro hand selects their natural wines, cheese and charcuterie with inspiration from their homeland of France. They emphasize and take pride in food by using only fresh, organic, and natural ingredients. This applies to the wines as well, which are biodynamic, natural and downright delicious. We enjoyed a Pet Nat from Meinklang, a producer in Austria together with a selection of delicious French cheeses on the patio while enjoying the unique and tropical Key West vibe.

Wines are available by the glass or bottle, and can be enjoyed on site with a small corkage fee. We highly encourage you to stay and enjoy some natural bubbles, because we sure did!

Matt’s Stock Island Kitchen & Bar

When we think of the Keys, we think of a relaxed island vibe and fresh and flavourful ingredients reflecting the bounty of the sea. Well, Matt’s Stock Island Kitchen & Bar has both in spades. Featuring a clean and modern design that fits nicely with The Perry Hotel which it calls home, this wonderful restaurant is built on the philosophy that the ingredients they use speak for themselves. They specializes in American Coastal Comfort Food served family-style on the waterfront, located at the state-of-the-art Stock Island Marina. So, exactly is American Coastal Comfort Food?

Mostly built around seafood and other ingredients available in coastal areas such as the Florida Keys, the menu is fresh but inventive (maybe that’s the American part), as we experienced with the epic seafood tower, or three tier tackle box!

From crab claws, to oysters, to tuna tartare and ceviche in Key Lime juice, it’s hard to pickle a more perfectly fitting appetizer for this beautiful part of Florida. Everything was fresh, and beautifully presented but completely unpretentious, which we felt placed us firmly in the Florida Keys. We may have also been close to heaven, with a glass or two of perfectly paired Billecart Salmon Brut Reserve.

Now, for the main course we each tried a local favourite – fresh Florida Grouper and Florida Lobster. Cooked perfectly, these two dishes remind us that there’s so much bounty in this party of the world and that freshness does not need complication to be enjoyed. Lightly seasoned and presented with complimentary sides, our mains reflected that American Coastal Comfort Food vibe that Matt’s Stock Island Kitchen & Bar is all about.

While we enjoyed our meal with champagne, their wine and beverage list was diverse but built around coastal cuisine so there is something for everyone… though we recommend bubbles with your fresh seafood, ok?

Fun fact: you bring in your own fresh catch for Matt’s Stock Island Kitchen & Bar to prepare for you. Whether you come in with your own catch from a fishing adventure, or are looking to explore some great coastal comfort foods, we can guarantee you’ll want to try everything on the menu!

Having dined here and experienced the attentive but not obtrusive service, we can say that it’s no surprise that Matt’s Stock Island Kitchen & Bar was the winner of OpenTable’s 2019 Diners’ Choice award for Best Dining, Ambiance, Seafood, and Lunch, and named #2 out of the Top 10 Restaurants in Key West by TimeOut magazine. We highly recommend it!

Hemingway Rum Company

Author and all around renaissance man Ernest Hemingway was known for his love of cocktails. He worked in Toronto during World War II, and Hemingway’s in Yorkville is a reminder of his presence on home turf. He’s made an imprint on Paris, Cuba and other places that he found himself in.

Of everywhere he traveled in the world, Ernest Hemingway chose Key West to call home. The sea, the sun, his beautiful plantation style home, his many loves and his elegant and apropos boat famously named Pilar all kept him here.

So, it’s fitting that Hemingway Rum Company, located in a beautifully refurbished tobacco warehouse in the waterfront area of Key West, chose to create local, artisanal, small batch rum to reflect Ernest’s passion and interests.

Called Papa’s Pilar, because he liked to be called Papa and his beloved and over the top boat was named Pilar, the brand is crafted on site by rum makers to produce a unique spirit. Made from sugar cane sourced in the French Caribbean and mainland USA, the resulting rums are distilled and blended in Key West and aged in a variety of vessels to achieve different imprints on the final product. Not unlike wine, the finished rums reflect the makers’ production choices.

The Blonde Rum is youthful, zesty with hints of coconut, key lime and mild toast and caramel. It’s companion, the Dark Rum, is aged for a longer period of time and provides a richer, darker experience. Finally, the Marchesa, named after an island the Ernest was stranded on during an intense storm, is much like the darker rum but smoother, more elegant and with nuttier notes.

When you visit, you’ll learn about Hemingway Rum at their Brand Experience Center & Innovation Hub, with a guided tour through the history of rum and learn what makes this spirit so remarkable. Having been taken through the process and distillery by the rum make, we can is say it was a pleasure to learn about the brand, and to discover new stories about Hemingway, as well as take home a unique gift.

Best of all, Ontario friends – you’ll soon be able to experience Papa’s Pilar in the LCBO!

VINOS on Duval

Located on Duval Street just next to the Tropical Inn, Vinos on Duval is a small wine shop overlooking Key West’s main drag – but don’t worry, a visit won’t be a drag for you!

We found the spot to be relaxing, and a refreshing change of pace from the hustle and bustle. From the lovely elevated patio, to the dimly lit and cool interior, you’ll find that the space is intimate and invites conversation. So, sharing a glass or bottle of wine with a nibble or two won’t be a problem.

Vinos on Duval has an extensive selection of reds, whites and sparkling wine from American and international producers. As the wine list is constantly changing, we don’t think it makes sense to highlight what’s on offer now but we do want to point out that they have some great happy hour specials. From a $5 Sangria special (perfect for someone in your party that’s not a wine connoisseur or if you’re seeking some quick refreshment from the heat) to their by-the-glass Veuve Clicquot special, there’s plenty of options here to keep you busy before dinner or your next attraction in Key West.

Key West – Attractions

Ernest Hemingway House

Located on the second highest point of Key West, the Ernest Hemingway House a unique, historical property that was once home to Ernest Hemingway, one of America’s most honored and respected authors (and a character with a very interesting, and storied, personal life!). The French colonial style manor was originally built by a salvage wrecker – or, person looting from ship wrecks for which the area was known – using limestone quarried from Key West.

Ernest eventually bought the house and lived here for more than ten years of his life (although he eventually left, he kept the deed to this house). As learned at the Hemingway Rum Co., he enjoyed Key West very much, chose to call it home and reflected on this beautiful setting. It’s not surprising – aside from being a beautiful, placid place to live, back in the day, it would have been a wonderful place to write and a demanding place to live (he did have an adventurous side, so that fits!). 

A visit here is a step back in time, with guided tours available for guests. As part of a tour, you can visit the interior rooms of the house, enjoy the views from the balconies, visit the outbuildings, as well as wander gardens that inspired the most noted period of Hemingway’s writing career. 

A wander through the lush grounds will also introduce you some of the forty cats that live on the property. Now, if you’re not a cat lover, this may not appeal to you but for those of us that love our furry, feline friends, the cats here are no ordinary cats. Nope! They’ve all got six toes, descending in one way or another from an O.G. with the same condition – apparently, Hemingway’s sons reminisced about his father breading the cats, first in the Florida Keys and then in Cuba. A testament to the high quality construction of this old house is that it has never been destroyed by any hurricane, not even Irma (in fact, employees and cats remained on the island and were not harmed during this last, intense storm).

Conch Tour Train

A great way to explore Key West is by the Conch Tour Train.

Since 1958, the Conch Tour Train has treated guests to a close-up view of many of Key West’s iconic sites – the Southernmost Point, Mallory Square, The Harry S. Truman Little White House, Overseas Railroad Museum, the Key West Aquarium and so much more. 

We enjoyed the low-key, but entertaining vibe of the Conch Tour Train, which while not a train and rather a bus, reflects on the once prominent and important rail industry that when brought to Key West, finally and firmly connected it to the mainland (you’ll see the old rail bridges on your drive in).

While on the tour, a guide (called an engineer, another train reference) will offer interesting and amusing points and historical facts, trivia and humour, and recount fascinating stories of the interesting people that make Key West so unique. On our tour, we were learned that Key West natives are called Conchs (that’s pronounced ‘Conks’), that there were once many trees on the island (including Key West mahogany, sapodillas and more common species, like black and Russian olives) which were used for housing, firewood and soap production, and that most of the island is not suitable for farming or burial due to it’s porous, and hard, limestone soil. You’d think, being in such a temperate climate, that growing crops would be a cinch – but alas!

Duvall St & Mallory Square

Duval Street is Key West’s main drag, a classic downtown street with many shops, bars and entertainment-focussed establishments (like theatres). It runs north and south from the Gulf of Mexico to the Atlantic Ocean, is just over 2 kilometres (1.25 miles) in length and was named after the first territorial governor of Florida. Did he like to party? We’re not certain, but what we are certain of is that the street he gives his name to is lined by an immense amount of bars and plenty of places to find some sparkling wine!

On one end of Duval Street is Mallory Square, known locally for a “Sunset Celebration,” which basically involves watching the sun set at the end of the day. A square chock full of vendors, arts and crafts exhibitors, street performers and food carts is nearby, offering that wonderful ‘Port of Call’ and island feeling. If you need a spot to grab a souvenir, this would be it!

Where to Stay

Whether you’re looking for a laid back pool-side vibe, or a spot right in the centre of the action, we’ve got all your bases covered! 😎

The Perry Hotel Key West

The Perry Key West Hotel is a state-of-the-art, contemporary boutique hotel located in the emerging Stock Island area of Key West and anchoring a lively, working marina. This sleek, modern space includes a beautiful (and insanely Instagrammable) pool area and in-house restaurant, which is focussed on fresh seafood (and allows those with a boat to bring in their own catch, how fun!). From a design perspective, it’s firmly rooted in the Florida Keys (with nautical and natural, wood-focussed touches throughout), with a dash of that glam, Palm Springs resort hotel vibe. We won’t lie, we loved it!

Removed from the hustle and bustle of Duval Street and the cruise crowd, the Perry is an airy and relax space that puts you in the heart of living and working Key West (you’re in a marina, that feeds into State Harbor and the Atlantic Ocean, after all). As our first stay in Key West, it was a wonderful introduction into the vibe and feel of the island, putting us in touch with so many great nautical activities, such kayaking, snorkeling and fishing. In truth, we had very little time to partake in any, so we settled for a leisurely walk around the marina and a bit of lounging around the beautiful pool, which was overlooked by palm trees and the main hotel building. 

Our check in process began with a glass of sparkling wine – an effervescent start, we’d say! From the bright lobby, which is connected to the in-house restaurant and bar, we made our way to our beautiful suite. Like the rest of the hotel, we felt firmly rooted in Key West – through design touches, the drift-food inspired colour palate and art – and, all the while, we enjoyed all the modern conveniences. Spacious stand up shower, plenty of room for luggage, a desk and seating area (for a bit of early-in-the-day work and end-of-day relaxation) and a lovely balcony, overlooking that pool we were just raving about. We must say, spent quite a bit of time on our beautiful balcony, taking in the views of the pool and marina, in our robes and with a glass of Billecart Salmon Brut. Sipping champagne with a view of the pool, Stock Island Marina and the not too distant sea is not too shabby of a gig, right?

As we learned, the hotel’s name is an homage to an American man who had a big imprint on the navy in the US – Commodore Perry. This, of course, makes sense when you tour the island and see the strong naval presence and outpouring of support for the troops on the island. We don’t know what Commodore Perry was like, or his personal taste, but as we mentioned before, the hotel is beautifully outfitted. After millions spent on renovations, development and improvements to the area, the Perry is bring a little sparkle to Stock Island. 

Now, with that said, you’re not too far from traditional attractions – and the Perry’s shuttle service is a great option for connecting with all that glitters on the island (departing on the hour, and saving you an Uber ride). The bars and restaurants of Duval Street, the shopping and artisanal goods, as well as the awesome nightlife are within easy reach from the Perry Hotel. You’ll just have the benefit of retiring to a beautiful space, and a wonderful, relaxing night’s sleep after a great day (or night) out!

The Gardens Hotel

Our second stay in the beautiful Keys was at the historic and stately The Gardens Hotel, located just off of Duval Street. Located on one of the largest estates on the island, this hotel harkens back to genteel days of yore, but without any of the trappings of that time period – and, with some pretty epic wine focussed conveniences, like the Florida Keys first enomatic wine bar!

The Gardens Hotel is comprised of several luxurious guest suites, set in either the main house on the property or in the surrounding buildings. Each is set among lush gardens, which given this hotel its name – as we learned upon check in, the Gardens Hotel features one of the oldest tropical gardens in Florida. Being so close to Duval Street, we found it to be a tranquil slice of heaven! The gardens include a variety of pathways, fountains, a gazebo and an aviary, offering a sense of peace and calm.

While a historic hotel, The Gardens is outfitted with all the bells and whistles (beyond the beautiful gardens and enomatic wine bar that we were excited to experience), including a heated pool and relaxing pool area. Every morning also begins with an expansive breakfast spread and coffee in the pool and conservatory/living room areas and most evenings include a live jazz performance. How else to enjoy a beautiful evening in the Keys, right?

Now, we’d be remiss to not touch on the enomatic wine bar at the Gardens Hotel. When built, it was the first and only of its kind in the Florida Keys (though there’s one more somewhere in this chain of islands). A state-of-the-art system of dispensers allow for the distribution of individual chilled or room temperature wine samples from a variety of bottle selections, some of which were quite high end. In less wine nerd terms, it’s a great opportunity to try a variety of samples of wines – held in appropriate conditions and not deteriorating from being opened – from a variety of producers. It makes for a great conversation and opportunity to expand your palate, and reflecting on the choices, we will say that there’s something for everyone. We were given a card upon checking in, and that card was used to record which wines and how much of a sample we enjoyed. The wines can be enjoyed anywhere on the property and we may, or may not, have enjoyed a glass of wine (which is the largest sample size) in the gazebo, overlooking the pool and listening to the birds in the aviary. If that’s not your jam, there’s also a wine bar in the hotel by the pool area where Champagne is served by the glass (sadly, no sparklings were available in the enomatic wine bar).

Our guestroom was located in one of the outbuildings, overlooking a lovely fountain and courtyard area, and included access to a second-storey wrap around porch that gave us the opportunity to take in the views and enjoy simple pleasures (like watching the lush palm trees sway in the breeze, as the sun was preparing to set). Outfitted with a more classic, southern style, our room included a comfortable four post bed, small desk and drawer area and a flat-screen television (but who has time for tv these days?). We definitely found our sparkle at The Gardens, enjoying a glass of champagne on the beautiful porch, that’s for sure! And, with a five minute commute to attractions, including many LGBTQ+ bars, such as Aqua Lounge and the 801 Drag Cabaret, it’s a great’s spot to not only find your sparkle in the Florida Keys, but to also let your inner rainbow free! 

Having stayed at this beautiful boutique hotel, we can say that it’s no surprise that the Gardens Hotel was voted “The Prettiest Hotel in Key West” by The New York Time’s List and was also featured in the book “1000 Places to See Before You Die.”