Tuesday, July 13, 2021

{travel guide: Key West 2021}

"Wait you LIVE in Key West?! Tell me everything!"

"What should I do? Where should I eat? Where should I stay? What's your favorite spot?"

Friends... I present to you: A Local's Guide to Key West

You've come to the right spot! I've been living on this magical island for almost 2 years now and let's just say a) I never want to move and b) I have been allllmost everywhere now lol. At some point I will flush out each category in separate blog posts but I much prefer everything to be in one spot - don't you?

I'm answering how to get there, where to stay, where to eat, favorite happy hours, best coffee places, what to see and do, etc!! [side note: September is normally the quietest month here so keep that in mind - times and openings are always subject to change]

Working on my KW Bachelorette post still FYI!


If you have the option I would drive because it's a stunning trip along the water! Fair warning that traffic could be bad at times because US-1 is one lane north and one lane south. Be sure to schedule in time to make stops along the way [check out my last blog post that includes driving stops here]. 

A few spots to stop by if you're driving:

- Caribbean Club (Key Largo)
- Pilot House (Key Largo)
- Craig's (Plantation Key) [under new ownership since I've been]
- Robbie's (Islamorada)
- Morada Bay Beach Cafe (Islamorada)
- Sombrero Beach (Marathon)
- Sea Turtle Hospital (Marathon)
- National Key Deer Refuge (Big Pine)
- Square Grouper (Marathon & Islamorada)
- Baby's Coffee (Sugarloaf)

However, flying is still an option - the KW airport is tiny so if you're an anxious person just be aware of that. You'll deplane on the runway, walk down a ladder, and then head towards the airport building where there are 2 carousels to grab your luggage - there is also a cocktail bar inside :) It's easy to grab an uber/taxi from there. 


I always like to recommend AirBNB's in Old Town - this supports the local economy in a big way and is the best way to get a flavor of the island too! There are tons of historic houses and everything is very colorful - not just the flora but the houses. If you look at a map, staying "left" of White Street will keep you close to Duval St (the main "going out" strip) and within walking/biking distance of places to eat, visit, and drink.

There are also lots of amazing hotels that I've been lucky to visit and experience [this entire list has a pool on property as well]. Please note, that these are personal preferences and places I've had the chance to see/explore in person. These hotels range wiiiidely in price so there's something for every budget. For example, I stayed at the Blue Marlin in college on spring break and loved it (it has also recently been redone haha). In no particular order:

- Parrot Key*
- Hyatt Centric
- The Grand Maloney
- The Paradise Inn
- The Reach*
- Marquesa Hotel*
- The Marker
- Kimpton Hotels (Ridley House*, Winslow's Bungalows, Ella's Cottages, Lighthouse Hotel*)
- Southernmost House*
- Pier House*
- The Perry (on Stock Island - left picture)*
- Blue Marlin Motel
- The Porch on Frances Inn (no pool)
- The Capitana*
- Little Palm Island (if you stay here no need to leave for anything)*

*places I would personally recommend for honeymooners - a little bit more luxe, private, and off the beaten path.


Renting bikes is my preference because they're easy to lock up and find spots to park! Plus, you end up saving so much money not using ubers! Key West is very friendly to bikers in regards to sharing the road but still be careful and look both ways. Most bike places will recommend another if they're sold out which makes me super happy - they all look out for each other.

We have rented beach cruiser bikes for our guests from Island Bicycles because they have the cleanest bikes and best prices (around $10 a day or $60 for a weekly rate). Call ahead to reserve (seriously, reserve your bikes haha) and get 10% off too [305-292-9707]

Eaton Bikes is another local bikeshop around the corner from our house that we love. Kyle has taken his personal bike here a couple of times for adjustments and I personally used Eaton Bikes for my sister's bach here (top tier service - five stars!!). Prices vary but are on average $18 a day, $10 a day after that and $55 for a week. They also have tandem bikes and trailers for kids to sit in! Call ahead to reserve, they will also drop off your bikes for you if they're able. They have discounts for reserving online too [305-294-8188].

Scooters are another fun option!! I'm obviously a fan since that's how I get around :) We bought our 2-seater from Sunshine Scooters so that's the place I'd recommend. There are tons of other places but double check to see if your hotel has them to rent! Sunshine Scooters is $30-45 for the day and $99-179 for the week. I believe they will deliver and pick up from where you're staying too. Make sure to reserve them online at least 24 hours in advance. [305-414-2976]


There are Starbucks on the island but take my word for it and do NOT go to one... enjoy the local spots!!

- Cuban Coffee Queen - three locations (best chai lattes)*
- Keys Coffee (great matcha lattes)*
- La Grignote
- Old Town Bakery (Kyle's favorite - pictured on left above)*
- Red Buoy Coffee (inside Glazed Donuts)
- Sandy's Cafe
- Funky Rooster (middle photo)
- The Koffie House
- Banana Cafe (great brunch too)
- Frenchie's Cafe

*favorite spots


This list may seem long but there's some amazing food here! I personally prefer to eat outside because I work inside all day... Yes, I know it's hot :) but there's lots of shade and fans available - bring a hat too!! I would recommend making reservations for dinner right now because travelers are always flocking to the island. It's free to reserve/cancel and better safe than sorry! Note that I haven't included every single restaurant... that would be a lot!


- Banana Cafe
- Blue Macaw
- The Breakfast Club, Too
- Louie's Backyard*^
- Pepe's


- Amigo's
- Blue Heaven
- B.O.'s Fish Wagon (cash only)
- Hot Tin Roof
- Latitude's (Sunset Key)*^
- LL's Test Kitchen (Stock Island)
- Louie's Backyard*^
- Moondog Cafe
- Roostica (Stock Island)
- Salute


- Amigo's
    (tex-mex in downtown area)
- Azure*
- Bagatelle
- Bel Mare*^
    (romantic fine dining ambiance in heart of harbor)
- Blackfin Bistro
    (delicious wagyu burger)
- First Flight
    (a favorite spot to grab HH dinner)
- Flaming Buoy*
- Four Marlin's*
    (a hidden gem in The Reach Hotel - great water views)
- Firefly
    (southern cuisine in historic Bahama Village)
- La Trattoria
- Latitude's (Sunset Key)*^
    (reservations are a must because it's on a private island $$$)
- Little Pearl*^
    (a neighborhood favorite - luxe and worth every penny)
- Lola's*^
    (two seating times and reservations go fast. BYOB. couple owned and run)
- Louie's Backyard*^
    (my all time favorite. incredible food with great sunset and water views!)
- Martin's*
    (great martinis and tapas - I recommend the lemon drop martini)
- Mangia Mangia
    (Italian food - pasta is made in house daily)
- MisoHappy
    (sushi, drinks, and a really fun atmosphere)
- Nine One Five
    (I love being able to sit on the porches and people watch)
- Onlywood Pizzeria
    (two locations - each slightly different. The downtown location is my favorite to sit outside)
- Paradise Restaurant
- Santiago's Bodega*
    (local's favorite spot. Well priced, fantastic tapas, and great sangria. Bahama Village)
- Thirsty Mermaid*
    (small restaurant. sister spot to little pearl. fresh seafood. great wine)
- Southernmost Fresh Co
- Conch Republic (they will cook your fresh caught fish for you!)
    (many consider this a tourist spot since it's huge on the harbor but I love their options for cooking
    your fresh caught fish. great spicy margaritas)

*great for date night 

I always get this question so my top favorite spots are (in order):

- Louie's*^
- Little Pearl*
- Lola's*^
- Hot Tin Roof (brunch)
- Thirsty Mermaid* (HH)

^these are also some of the most romantic spots on the island


This island has a bar everywhere you turn... Honestly, the best thing to do is walk down Duval Street and see what looks like fun and THEN go down the side streets! The side streets have my favorite spots. Don't be afraid to go up the Keys a bit to check out Stock Island. Most places have Happy Hour drink and food specials (again, future blog post coming with full list of every HH) that Kyle and I love to do for an early dinner during the week. These are my favorite spots to grab a drink right now (my favorites change a lot lol):

Bagatelle [4-6pm; 1/2 price drinks and $5 apps]
Boathouse * [currently relocating to a new spot on the waterfront and not open yet - will update once it's up and running]
- Champagne Room [3-4pm $3 bubbles, 4-5pm $4 bubbles, 5-6pm $5 bubbles; $2 grenades of "champagne of beers"; Monday - 1/2 price bottles of wine 3-11pm]
First Flight * [4-6pm; 1/2 off selected cocktails and $5 house made beer and glasses of wine; $5 happy hour food menu]
The Grand Cafe [4-6pm; 1/2 price wine, cocktails, and beer; 1/2 price apps]
- Green Parrot + [4-7pm M-Tr; 4-5:30 Friday; discounts on selected drinks and beers]
Hank's * + [4-7pm; beer $4 domestic and $5 draft, $6 sangria, $5 well drinks, $6 Stoli Bloody; Garbo's Grill food truck in the back - $8 Umami Burger and $10 taco trio] 
Mary Ellen's * + [M-Fr 12-6pm & Sat-Sun 3-6pm; 2-for-1 all wine, wells, and draft beers/cocktails; all week 3-6pm $5 food specials; Mondays = drunk spelling bee; Thursdays = vibrator races]
Off the Hook + [4-6pm & 9:30-11:30pm; drink specials and special HH menu] 
Old Town Tavern [4-7pm and 11-1am; 1/2 off wines and well drinks; 25% off beer; 1/2 off flatbreads and shared plates]
- Onlywood Pizza * [Nov 1 - March 31 = 4:30-6pm; April 1 - Oct 31 = 5-7pm; 50% off signature drinks, well and call drinks, wines by the glass and beers; special HH menu]
Santiago's * [3-6pm; 1/2 price drinks (amazing sangria); $5 tapas]
Seaside Cafe at Southernmost House [no HH but right on the water with a great food truck]
Smokin' Tuna + [3-6pm; daily drink specials; 2-for-1 premium well drinks] +
- Thirsty Mermaid * [ 4-6pm; $2 pints private label Mermaid Lager; $5 plates of 1/2 dozen oysters, ceviche du jour, and special HH menu]
- Vino's on Duval * [4-7pm; $5 sangria; sundays - $5 mimosas]
- VIV wine Bistro [4-6pm; 1/2 off available selection of daily wines; $4-7 tapas]

*favorite happy hours :)

+ live music

working on a post for my favorite margaritas around the island!!!


If you ask me what ONE thing you have to do while you're in Key West... it would be to get out on the water. Get your cute self on a boat and feel the wind whip through your hair and then you can see what it's really like to be down here :)

Danger Charters Wind & Wine Sunset Sail - I've said it a million times but this is my absolute favorite way to watch the sunset! On a sailboat, with a wine tasting, and little apps being passed around. It's mesmerizing to watch the sail and tasting 7+ wines ain't so bad either haha. (Boat pictured above) If you're here visiting on your honeymoon this is a must must do... trust me!!! (Locals - be sure to call to get 30% off. Must have a valid ID at check-in.)
Sunset Sail - There are multiple companies down here that offer sunset sails. Some with champagne, sangria, beer, open bar, etc. Some have live music and some are on a catamaran. It all depends on what you're looking for. Check out Sunset Sail, Sebago, Fury, & Danger Charters.
Fury Ultimate Adventure - this is an all day adventure on a catamaran that includes snorkeling, jet skiing, water park, kayaking, parasailing, and a banana boat! Breakfast and lunch are provided along with drinks after you're tired of all the activities! (Locals - be sure to call to get discounted rate. Must have a valid ID at check-in.)
Fishing Charter - Deep Sea or Flats Guides are available depending on the type of fish you want to catch. If you're interested in fishing please send me an email and I can put you in touch with one of my friends that are guides down here! southernanchors@gmail.com
Hang out at a sandbar - Snipe's (where the rope swing is), Marvin, Mud Keys, Boca Grande, and Jewfish Basin are favorite local ones [see below for charter recommendations]
Paddle boarding, kayaking, jet skiing, etc! There are tons of rental companies around the island (and lots are located at hotels). Barefoot Billy's and Lazy Dog are popular with my friends!
Go snorkeling or diving at the reefs - we love Sand Key! [see below for charter recommendations]
- Dry Tortugas - take the ferry or a little plan there... enough said! It's still on my bucket list and I cannot wait to go!
Charter a boat - Recommendations from friends and people that have visited before and chartered a boat for a day on the water: Aquaholics, Key West Charters, Boundless Charters, Fun in the Sun, Fish N Chicks, Sol Chaser Charters. If I had to pick JUST ONE... go with Aquaholics. I'm lucky to call the owners my friends and they're some of the best people on this island! (Locals - be sure to call to get discounted rate. Must have a valid ID at check-in.)


If you go out fishing and are lucky enough to catch dinner there are multiple restaurants and hotels that will cook it for you! Just be sure to have your guide filet it properly!

- Benihana
- Blue Heaven
- Café Sole
- Conch Republic (our personal favorite spot for cooking fish)
- DJ's Clam Shack
- Dante's
- Grand Café
- Hogfish Bar & Grill
- Hurricane Hole
- Louie's Backyard
- Martin's on Duval
- Pepe's
- Pinchers Crab Shack

- Casa Marina Resort
- Hyatt Key West
- Marriott Beachside
- Ocean's Edge
- Ocean Key Resort
- Pier House Resort
- Opal Key Resort and Marina


Something to keep in mind: there may be lines or advanced ticket reservations necessary.

Hemingway's House - so much history and SO many cats! I've been 5+ times and never get tired of learning more about Ernest Hemingway. He had such a fascinating life and the photos, posters, and articles all over the house detail it very well. Plus, the cats still roam free and are taken care of by veterinarians that volunteer. They're famous for their 6 toes!
Key West Lighthouse - Across the street from Hemingway's house and a great piece of history plus spectacular views.
Southernmost Point - there is almost always a line at this famous picture spot!
Truman Waterfront - checkout out the USCGC Ingham, a splash water park perfect for kids, large grassy lawn, sunset views, and a Farmer's Market every Thursday evening until sunset!
Key West Garden Club - located near Higg's Beach this incredible garden is kept alive by a group of volunteers with serious green thumbs
- Key West Theater - check out their list of upcoming events and plan to take in a show while enjoying a drink! This gorgeous theater is covered in Dade County Pine and sure to show you some local talent!
Rum Distillery - this was the first legal rum distillery in Key West! They have daily free private tours and tastings. I can't wait for everything to open back up because they used to have a mojito making class and I'm dying to go!
Nature and Butterfly Conservatory - is there anything more magical than thousands of butterflies and hoping one will land on you? Plus, the flamingos are pretty cool!
Conch Train - I've personally never gone on the Conch Train but it's very well known around the island! This is the best way to take in all of the sights and learn a lot about the history of the island. I've actually biked behind it so many times that I know some history facts from over hearing things haha.
Ghost Tour - Another tour train I've never gone on but knowing how Key West does theatrics and costumes (RIP Fantasy Fest 2020) I can only imaaaagine how much fun this ghost tour is haha. Plus, there are so many stories and fables from this island... the cigar houses... mafia... bank robberies... if this is your thing I bet it's a hoot.
Art Shack and Soul House - if you tire of the water and sun these two spots on Stock Island are hidden gems of incredible local artists. Easiest to get to by car or scooter. (If you go I recommend stopping by Hogfish, Roostica, or Matt's at The Perry Hotel to round out your Stock Island trip).
Bahama Village - home to the famous Blue Heaven but also some cute little shops and great artists. It's worth a quick walk down Petronia St. Plus, the new arch on the corner of Duval was just reinstalled... look for the rainbow sidewalks :)
Shops at Mallory Square - Home to local artists like Cocky Key West, Key West Soaps, & Ocean Blues Studio. The building itself is full of history but the art inside is perfect for when you just need to shop! Located at 291 Front Street. (If you want to get a Key West shirt you've got to get one from Cocky... that's how you truly get a souvenir... from a local!!!)


Key West isn't exactly known for it's beaches so keep that in mind. Lots of hotels on the water have docks and sun chairs that overlook the water which is fun and you can still take a dip in the ocean. However, if you still need to lay in the sand these are our best beaches:

Ft. Zachary Taylor State Park - (right photo) costs $ to get in but this is a big beach with great water to swim in. There’s a little beach shack, picnic tables, grills, and plenty of trees to hang a hammock on. Since this is a state park, alcohol isn't allowed... but as long as you have no labels and are using cups you should be fine... just play it cool/safe. You can rent chairs and umbrellas for the day - totally worth it just get there early so they don't sell out. If you need to leave and come back just let the guys know bc they are truly yours for the whole day!
Higgs Beach - a personal favorite spot to watch the sunrise. Complete with pier to walk out on and volleyball courts. There’s a park nearby too. Salutè is the restaurant overlooking everything!
Smathers Beach - (left photo) aka the party beach during spring break. If you arrive via the airport you’ll drive by this! Farthest away from Duval St but kayak rentals available here. I love watching the sunrise here because it's nice and quiet with people walking their dogs or enjoying a workout
South Beach - (middle picture) small and next to the Southernmost Hotel. There’s a Starbucks and cafe (plus bar) right on the sand with chairs you can rent. Warning - this spot can be crowded since it’s at the end of Duval St!
Simonton Beach - personal favorite since it's tiiiiny and right next to Lagerheads Bar where you can grab a drink and some fish tacos! Worth renting a $10 chair for the day - make sure to try the fish tacos. Located at north end of Simonton St.
Dog Beach - exactly what you think it is haha small and at the south end of Vernon Ave right next to Louie's Backyard


Q: Should I bother packing makeup?

A: Okay this question cracks me up and is GOOD!!! I think you can totally downsize on what you bring. I personally don't wear foundation so concealer and bronzer are my go-to's! If I'm hanging out at the pool during the day I normally only wear sunscreen, concealer, and mascara. If I go out at night I'll do a bit more (usually cream products) but just remember you may get a little shinier than usual with the heat and humidity - embrace it!!! Work that glow :) I would think a lot of powder and foundation would melt off? I can tell you honestly that most girls don't wear makeup out on the boats either - lash extensions are popular here. I just make sure my eyebrows are dyed and I'm happy with no makeup lol sunglasses all day everyday, baby!!

Q: Any good smoothie or juice places?

A: YES! The Raw Machine on Duval St (far right photo above!) is amazing!! I also love Date and Thyme for smoothies. There's a place called Grain and Berry that's farther up Roosevelt too I highly recommend.

Q: Is taking the ferry to eat at Latitudes worth the time and effort?

A: Personally, I think yes! I've always heard that brunch is better than dinner because the sunset can be really scorching until the sun goes down! I love being able to see the blue water during the day too - it's a little less fancy/fussy. The ferry is super easy to take back and forth too. Heads up that reservations are extremely booked out right now!

Q: Is going to a beach a must or will hanging at our hotel pool suffice?

A: You've got to get in the Ocean or Gulf at least once while you're here!!! I recommend going to Ft. Zach and renting an umbrella and chair for the day. Or if you're on the island Sunday night check out the live music at Higg's Beach (far left photo above) - that's a great way to see the ocean, pack a picnic (stop by our local grocery store, Fausto's), and just hang out with the locals while listening to amazing music from groups like Coconut Victrola.

Q: AirBNB's vs Hotels?

A: Airbnb's ALWAYS over hotels!!! You will get more of a feel for the eclectic island vibe and can probably find a spot in Old Town!

Q: Honeymoon / romantic spots?

A: I did my best to mark these above in my answers!

Q: Best time of year to visit? Best day? Mid-week better than weekends?

A: I love Key West in March - May right before it gets crazy hot. But anytime of the year is amazing :) December and January are wonderful with the cooler temps but people don't believe me when I say you won't want to be hanging out in the ocean and it gets chilly!! That ocean wind is no joke!! It's also glorious here in October with Fantasy Fest (NOT for children...). As I mentioned above September is normally the month where businesses close down and take a break. Any day of the week is perfect to visit because it's a hospitality town. But you can probably guess the busiest travel days are Sundays!

Q: Golf cart rentals?

A: The only one I've personally experienced are Conch Electric Cars! The spot is right by the ferry building. I've never rented a golf cart before - I can imagine they're convenient if you have elderly people with you that can't ride a bike or scooter. However, parking is tricky on the small streets and most spots are pay per hour or marked as residential. I personally would try to avoid the headache. (But I know when my mom and mimi finally visit I will be renting a golf cart lol)

Q: Hotels with shuttles?

A: This varies hotel by hotel and is constantly changing. For example, I saw a Havana Cabana shuttle the other day and when I stayed there (6-7 years ago) they didn't have one. The best bet is to call and ask. However, I don't think this should be a deal maker or breaker. The airport is 5 minutes away and renting a scooter or bike is truly the way to go.

Q: What was my favorite place in KW before I moved here?

A: I loved Irish Kevin's and Blue Heaven! Those were the most talked about spots amongst my naive college friends :) I still love Blue Heaven I just don't hang out at Irish Kevin's anymore because it's really crowded!

Q: What's the safest place to run while I'm there?

A: The easiest place to run is along the water by Smathers Beach. If you're an early riser then I love going down to the city marina and running along the dock.. starting at the ferry, past schooners, past conch republic, and to A&B Marina. Then I will continue through Truman Annex, to the Ingham Museum, and eventually home :) you can make any run 2 miles or 5 miles with weaving in and out streets!

Q: Do you think KW is a good honeymoon destination?

A: I think it's a great location to honeymoon!!! Pick a wonderful place with a pool, book a sunset cruise, grab happy hour, and make nice dinner reservations and you're set!

Q: How warm will it be in December/January?

A: On average it's been 75-67 during the "colder months". I think that time of year is the best to visit an island because everywhere else is actually cold haha. I carry a light jacket, jean jacket or sweater when I go out and can get away with jeans (and sandals). You'll see lots of people still wearing sundresses, skirts, and shorts too - especially if the sun is out. The water will be colder as well so keep that in mind. I always encourage people to bring a wind breaker because you truly never know what the temps will actually be with wind chill (no joke it's been high 50s before).

Q: What is it like with COVID?

A: Please head to this post for most recent updates - and a guide that's tailored to outdoor restaurants, etc.

Love Always,

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