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Florida Key Recommendations?


BearSchlong

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Wife and her friend were day drinking and doing google tourism and now we have plane tickets to MIA for late April/Early May, Covid be damned.

I'm looking for the following

  1. Where should we stay in the Keys?  We'll be there for 6 nights total, and plan to do a few nights at different places.
  2. Fishing - any guide recommendations?  The other couple has a Contender 31 and spends a ton of time offshore but obviously we're not trailering.
  3. Can't miss attractions?  Restaurants?

I've been to Key West for a few days but didn't venture north.

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That upper Keys area was really hammered by a hurricane a couple of years ago, but it seems to be coming back with lots of new construction.  Was there last in the Spring of 2019 and we stayed at a basic internet rental condo on the gulf side of Key Largo (nice beaches and pretty water on that side) for a couple of nights before heading on down to the Key West bacchanalia. 

Snorkeling tours at the John Pennekamp Coral Reef State Park off of Key Largo are a really good time.  Can't recall which outfitter we used, but it was a half-day trip in the afternoon.  Skipper's Dockside in Key Largo is a fun restaurant with outdoor seating on a boat harbor, so lots of boat activity to watch, if you like that sort of thing.  I don't think I ate anything besides calamari, ceviche, and conch the last time I was down that way -- and I regret none of it!

Edited by DalTxHornFan
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I hit the Keys several times a year - they are only a 2.5 hour drive so easy trip

Upper Keys:

Hotel

The Postcard Inn in Islamorada is great. Great Tiki Bar - lot's of fishing charters leave from their marina MM84

Restaurants

Jimmy Johnson's Big Chill in Key Largo - nice place to have a drink - overlooks the bay MM104

Loralei - known for sunset celebration - a bit touristy - MM 82

Robbie's - also touristy, tarpon feeding, you can do a snorkel trip from here to alligator reef MM77

The Square Grouper is great restaurant, my favorite in Upper Keys, MM 80

I usually skip the middle keys and then head to Key West

Hotel

I stay at the Hyatt Centric in Key West - north end of the island on Front Street, just off Duval

Other good hotels: Pier House, La Concha, Southern Most and there are a ton of B&Bs

To me the location is key as you won't want to drive too much in KW, you may save some money being further from Old Town, but you end up paying for cabs to get to and from the hotel

Bars/Restaurants

Sloppy Joe's, Irish Kevin's, Captain Tony's, Smokin Tuna, Hog's Breath are the big ones on Duval, good live music/entertainment - all worth a visit for at least a drink

Other spots on/near Duval - Tiki House, The Green Room, Tattoos and Scars and Fogarty's

There are some decent places in the bight as well - Conch Republic Seafood, Waterfront Brewery, Schooner Warf, Half Shell Raw Bar

If you are tired of the touristy places - there is a small bar called the Retro Room on Simonton in the same building as the Divers Direct. More of a local low key place, I think it opens around 2. Trivia on Sunday nights, I drank with Nick Swarsdon there once

Amigos is  good place for dinner, food is ok but if you get a seat by the street you can watch the drunk people try and throw coins in the Grouper's mouth at captain tony's

Two Friends is great for breakfast as is Blue Moon

Louie's back yard nice place for drinks

Rent a golf cart and explore - The Key West Cemetery is cool, there are more dead people on the island than there are living people. 

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We spent a week in the Upper Keys a few years back.  Had a blast.  We stayed at Playa Largo (Marriott property).  Pretty nice.  Good pool.  Good beach.  Good restaurant on site.

I second Robbie's and Loralei.  Both lots of fun, but a bit touristy.  

Hobo's Cafe in Key Largo had great food.  Loved the hogfish.  

Green Turtle Inn on Islamorada was some of the best breakfast I've ever had.  

We had fun in a big rain storm at the Tiki Bar.  Typical bar experience.

DM if you want a good inland fishing guide.  We went with a guy that was top notch out of Tavernier.  Super professional and put us on the fish.  

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Doc’s diner in Key Largo has a good breakfast. Not sure where they get their eggs but it is the orangest yolk you will see.  
 

Robbies is fun for the kids and feeding the tarpon.  Forget what key they are on but drive thru some of the residential areas and see the key deer. Extremely small. Long time ago renting mopeds in key west was fun cause you could race against all the crew. Probably too crowded for that now. 

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14 minutes ago, Shaddie said:

Doc’s diner in Key Largo has a good breakfast. Not sure where they get their eggs but it is the orangest yolk you will see.  
 

Robbies is fun for the kids and feeding the tarpon.  Forget what key they are on but drive thru some of the residential areas and see the key deer. Extremely small. Long time ago renting mopeds in key west was fun cause you could race against all the crew. Probably too crowded for that now. 

The key deer are on big pine

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I was there back in October.  I enjoyed:

  • both breweries in Islamorada: Islamorada and Florida Keys
  • Key Fisheries in Marathon is a good fish shack.  Real fun part was that they aerate the water which attracts tarpon, shark, and other fish.
  •  Bahia Honda State Park has beautiful waters and is a great place to swim and snorkel.  Not much of a beach, but enough for a great time.
  • Waterfront Brewery and First Flight Brewery in Key West.

 

Next time I visit I want to take the tour to Dry Tortugas Natl. Park / Ft. Jefferson.

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I was there back in October.  I enjoyed:
  • both breweries in Islamorada: Islamorada and Florida Keys
  • Key Fisheries in Marathon is a good fish shack.  Real fun part was that they aerate the water which attracts tarpon, shark, and other fish.
  •  Bahia Honda State Park has beautiful waters and is a great place to swim and snorkel.  Not much of a beach, but enough for a great time.
  • Waterfront Brewery and First Flight Brewery in Key West.
 
Next time I visit I want to take the tour to Dry Tortugas Natl. Park / Ft. Jefferson.

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Monroe (named after Monroe county where the key are) approves of Florida Key Brewing
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Bahia Honda is a great place to snorkel off the beach.  John Pennekamp Coral Reef State Park is good.  Just up-voting these previously recommended places.

If you have a day (or most of a day) Dry Tortuga is a good excursion and worth the time. 

We have stayed at the Sheraton on the Atlantic Side in Key West.  They had a shuttle running to Duval area.  Stayed at a Hampton Inn on the Gulf side in Key Largo.  There was a canal close by that manatees swam up and down.

We stayed at an older hotel on Duval street, built in the 20's but I can't recall the name of it.  It was great for convenience.  

The vibe down there on Duval street is worth the trip.  Lots of folks just hitting bars and drinking without all of the alcohol fueled dipshittery you would find on 6th street.

Also, the beach at Fort Zach provided for some great ,um, scenery.  Lot's of fit European women there on one of my trips.  

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Sounds like you've already got your upper/middle keys lodging worked out, but I'll second Playa Largo resort in Key Largo. Took the family there for a week in 2019 and they had a great time. Nice beach by Keys standards (seriously, if nice beaches are your thing, skip the Keys and go to Marco Island or Naples. Gulf side Keys beaches are like lagoon side beaches in the Caribbean) great resort pool, a couple restaurants and bars on site. If you're into Keys Sportfishing history at all, Robbie's and Loralei are where most of the famous tournaments start/finish. Also, the Worldwide Sportsman (Bass Pro) in Islamorada has the sister ship to Hemmingway's Pilar in the middle of the store. You can walk around and even climb in. (It's really not that interesting unless you're an uber-geek for fishing history like me)

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1 hour ago, Pescado_Rojo said:

Sounds like you've already got your upper/middle keys lodging worked out, but I'll second Playa Largo resort in Key Largo. Took the family there for a week in 2019 and they had a great time. Nice beach by Keys standards (seriously, if nice beaches are your thing, skip the Keys and go to Marco Island or Naples. Gulf side Keys beaches are like lagoon side beaches in the Caribbean) great resort pool, a couple restaurants and bars on site. If you're into Keys Sportfishing history at all, Robbie's and Loralei are where most of the famous tournaments start/finish. Also, the Worldwide Sportsman (Bass Pro) in Islamorada has the sister ship to Hemmingway's Pilar in the middle of the store. You can walk around and even climb in. (It's really not that interesting unless you're an uber-geek for fishing history like me)

The red tide can be an issue right now on the Gulf side, if you entertain this idea stay down in Marco it is not usually bad there and there is a nice newly renovated Marriott. I was there last weekend no signs of it (fish kill, coughing etc.),

Heading up to Cabbage Key on the boat this weekend (north of Fort Myers near Boca Grande) it is not supposed to be bad there right now, but that can change on any given day this time of the year.

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Spent about a week there a few years ago and the thing that stands out the most was having a really fun day at Morada Bay in Islamorada.  Really cool super chill beach restaurant and bar.  Live music, felt more Caribbean and less Florida tourism than pretty much everything else we did on the trip.  Wife and daughter (no pics) loved it.

Chartered a really cheap fishing trip one day and apparently you get what you pay for because it suuuucked.  Fucking thing was basically an overgrown canoe and it could not handle things once we got very far offshore.  So pay extra for a better boat on that.  At least get something with a bathroom...the girls were none too happy when told by our guide that they’d have to use a bucket if they needed to go.  We turned back after being out for about 20 mins.  It was miserable.

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8 hours ago, Ogie Ogilthorpe said:

The red tide can be an issue right now on the Gulf side, if you entertain this idea stay down in Marco it is not usually bad there and there is a nice newly renovated Marriott. I was there last weekend no signs of it (fish kill, coughing etc.),

Heading up to Cabbage Key on the boat this weekend (north of Fort Myers near Boca Grande) it is not supposed to be bad there right now, but that can change on any given day this time of the year.

Always a good time to be had at Cabbage Key. Cheers!

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Keys Fisheries in Marathon like @Sundodger already mentioned. We would drive down explicitly for their lobster reubens a couple times a year back when we lived in Miami. There's a little "crow's nest" of a bar near the marina (almost like a kid's clubhouse or tree fort) that's nice to watch the sunset from, but not sure whether you're interested in chilling at a very small (10-20 person?) bar. It's totally separate from the main seating area, so don't let it dissuade you. 

The stone crabs are the freshest and cheapest you'll find anywhere. 

https://www.keysfisheries.com/

Also, take Card Sound Road from Florida City to Key Largo and hit the rev limiter of your rental car. Aside from the Florida Turnpike to get to Florida City, the rest of your drive will be at the pace of the slowest driving vehicle somewhere ahead of you. Just roll with it...

Edited by Prepuce of Doom
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On 2/9/2021 at 2:12 PM, Ogie Ogilthorpe said:

The red tide can be an issue right now on the Gulf side, if you entertain this idea stay down in Marco it is not usually bad there and there is a nice newly renovated Marriott. I was there last weekend no signs of it (fish kill, coughing etc.),

Heading up to Cabbage Key on the boat this weekend (north of Fort Myers near Boca Grande) it is not supposed to be bad there right now, but that can change on any given day this time of the year.

We were at Cabbage Key around Christmas and the longest boat I have seen come in there rolled in. His balls hung way lower than mine, because there is no way I would have attempted to get back there in it.

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  • 2 months later...

Going down to Miami Beach in June with wife and 15 year old boys.  Was looking at a few days in the Keys as well but any preference to Key West over Marathon over Key Largo?  Goal is to do nothing but eat, fish, snorkel and sit by pool/water with a drink in hand.  With the teens in tow, the bar/nightlife and wife shopping scene not as important (we'll get that on Miami Beach). Looks like more and slightly cheaper housing/hotels in KL and it looks like a car rental is a must to get down to either.... I'm trying to talk myself out of the drive all the way out to KW...

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On 2/8/2021 at 9:09 PM, Sundodger said:

Next time I visit I want to take the tour to Dry Tortugas Natl. Park / Ft. Jefferson.

it's awesome.  definitely one of the most unique national parks in the system.  i went on May 6 a few years ago.  i remember because it was the day after Cinco de Mayo, and i almost threw up on the ferry ride.  several people did.  it's a little bit of a jaunt.  but once you get there, it's a cool fort to explore and a great place to swim on a hot day.

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8 hours ago, Grimas said:

Going down to Miami Beach in June with wife and 15 year old boys.  Was looking at a few days in the Keys as well but any preference to Key West over Marathon over Key Largo?  Goal is to do nothing but eat, fish, snorkel and sit by pool/water with a drink in hand.  With the teens in tow, the bar/nightlife and wife shopping scene not as important (we'll get that on Miami Beach). Looks like more and slightly cheaper housing/hotels in KL and it looks like a car rental is a must to get down to either.... I'm trying to talk myself out of the drive all the way out to KW...

I would skip Key west with Kids in tow, at least for a few more years. Key Largo has great snorkeling at John Pennekamp park. Marathon is another hour down the road and not rally worth it unless you go all the way to KW. Islamorada is great, about 10-15 miles past Key Largo so you can drive up to Key Largo for things to do but Islamorada has more of a Keys feel to it, you can go to robbies and feed the tarpon and they have a snorkel boat that goes out to Alligator Reef.

Key Largo - shortest drive, great snorkeling/diving, more of a town feel than Keys feel

Key West - great time, great bars there are some kid friendly things but mostly for 21+ crowd it is called Duval Street, not Sesame Street

Marathon - most town feel of all the keys

Islamorada - close to Key Largo if you want to do things there, more of a Keys vibe, tons of fishing, 

You can't go wrong with any of the  four.

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I ended up booking the Islander Resort on Islamorada for 5 nights. After digging through recent reviews the past day, it seems Covid has really messed up all the resorts in general in the Keys with crappy (or no) housekeeping as most of them have complaints of having dirty rooms seem to be the common thread.  Bummer that stone crab season ends in May and damn, what happened to rental car prices?!!? $88/day out of Miami for an intermediate?

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3 hours ago, Grimas said:

what happened to rental car prices?!!? $88/day out of Miami for an intermediate?

Start of covid rental companies sold off most cars and didn’t order new ones. My corporate rate has went up and I sometimes have take what’s left on the lot. Renting without corporate rate is not good right now. 

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6 hours ago, Grimas said:

I ended up booking the Islander Resort on Islamorada for 5 nights. After digging through recent reviews the past day, it seems Covid has really messed up all the resorts in general in the Keys with crappy (or no) housekeeping as most of them have complaints of having dirty rooms seem to be the common thread.  Bummer that stone crab season ends in May and damn, what happened to rental car prices?!!? $88/day out of Miami for an intermediate?

I have never stayed there but I have some friends who have and they keep going back. It is right across from Lorelei, a little touristy but not bad and they have a sunset celebration every night.

Be sure to hit the Square Grouper about a mile down the road, great food, and there are 2 breweries Islamorada Brewing and Florida Key brewing company. May not be kid friendly but you can walk to both from the Islander

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7 hours ago, Grimas said:

I ended up booking the Islander Resort on Islamorada for 5 nights. After digging through recent reviews the past day, it seems Covid has really messed up all the resorts in general in the Keys with crappy (or no) housekeeping as most of them have complaints of having dirty rooms seem to be the common thread.  Bummer that stone crab season ends in May and damn, what happened to rental car prices?!!? $88/day out of Miami for an intermediate?

Good choice.  The Islander is nice.  Given your group, Islamorada is a great spot.  Plenty of restaurants in Islamorada and Key Lago.  The drive is manageable from Miami.  Robbie's is fun and has decent food.  Lorelei's and the Sand Bar are great spots for a drink.  Hit up the Green Turtle Inn for breakfast one day.  

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8 hours ago, Shaddie said:

Start of covid rental companies sold off most cars and didn’t order new ones. My corporate rate has went up and I sometimes have take what’s left on the lot. Renting without corporate rate is not good right now. 

Stupid me thinking I could find the best rates for car rental online...  Punched in my corporate card and got a week of a large sedan for $290 (from the airport as the local place on S. Beach is closed on Sunday) all in...  Thanks!

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9 hours ago, Shaddie said:

Start of covid rental companies sold off most cars and didn’t order new ones. My corporate rate has went up and I sometimes have take what’s left on the lot. Renting without corporate rate is not good right now. 

I saw some prices in orlando for spring break that topped $300 per day.  Yep sold off cars

 

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20 hours ago, Grimas said:

I ended up booking the Islander Resort on Islamorada for 5 nights. After digging through recent reviews the past day, it seems Covid has really messed up all the resorts in general in the Keys with crappy (or no) housekeeping as most of them have complaints of having dirty rooms seem to be the common thread.  Bummer that stone crab season ends in May and damn, what happened to rental car prices?!!? $88/day out of Miami for an intermediate?

Flew into Palm Springs yesterday and the rental car counters were a complete clusterfuck. I felt bad for the customers who were getting fucked as well as the poor college-age girls behind the counter that were getting their asses ripped by aforementioned customers. 
We’re flying into Fort Lauderdale next month and driving to Key West. I prepaid for the rental car. Hoping that was the right thing to do. 

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  • 1 month later...
5 hours ago, Grimas said:

Headed out tomorrow... Can’t wait to shut work off for 2 weeks and luckily the Horns are on the way to Omaha so I have another excuse to go to a sports bar this weekend...

Hate to tell ya...ya don’t have to go to the Keys to find a sports bar. 

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  • 1 year later...

Please help me narrow all this down...dizzying array of choices above. Keys may not be what I want. Don't want to fish, golf or bar hop. Just want sandy beach where kids can swim and I can sit on my butt and watch. Something similar to condo in Port A or in Hawaii. Perhaps Keys is not my spot. 

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9 minutes ago, Not that Bob said:

Please help me narrow all this down...dizzying array of choices above. Keys may not be what I want. Don't want to fish, golf or bar hop. Just want sandy beach where kids can swim and I can sit on my butt and watch. Something similar to condo in Port A or in Hawaii. Perhaps Keys is not my spot. 

Probably not.

You might be better off looking at the west coast of FL, or the panhandle.  Or the Carolinas.  I once had a nice condo beach vacation on Ocean Isle Beach.  Check out the Brunswick Islands, perhaps.  Places to stay, plus nice house rental options too.  

Edited by After irth
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I'll second the recommendation for the west coast or panhandle if you just want a beach. To help you narrow it down my favorite vacation spot on the west coast is Sanibel Island. Everywhere else that I've been is way more built up with miles of 10+ story condos. If you don't mind over built spots I'm also a fan of Madeira Beach and try to be close to John's Pass so you can walk there in the evenings for food. Driving can be annoying and it's nice to just walk across the road and pick up dinner easily. I think we ate at the pizza joint there every other night.

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3 hours ago, Not that Bob said:

Please help me narrow all this down...dizzying array of choices above. Keys may not be what I want. Don't want to fish, golf or bar hop. Just want sandy beach where kids can swim and I can sit on my butt and watch. Something similar to condo in Port A or in Hawaii. Perhaps Keys is not my spot. 

This is not the place for that. Go to Cancun. 

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