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1st time in Key West

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Toronto, Canada
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1st time in Key West

Hi there,

My boyfriend and I will be travelling to Key West in mid-May. We'll fly into Miami and drive down through the Keys. We are both extremely excited to finally able to visit the Keys. This will be our first time there. We had planned to go last November when we were in Florida but time wouldn't let us so this time around, we're making it our first trip in Florida.

We would love some suggestions on places to stay, things to do, restaurants, bars/clubs. We are both on a budget but don't mind spending a little more for a little luxury. We both love to walk and sightsee, both loves music and loves to dance, but I would like a little romance thrown in as well. Any suggestions we can get would be great.

Thanks in advance.

Lincoln, NE
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1. Re: 1st time in Key West

Seven Fish would be a good place for a somewhat expensive but worth it romantic dinner. Key West B&B (The Popular House) is a very nice place to stay, but not overpriced, and is in a great location. The Schooner Wharf Bar is a good spot to dance to island music if that's your thing. A lot of bars have Happy Hour specials that make drinking and eating a bit cheaper, so I would check into that. Blue Heaven is great for breakfast/brunch. B.O.'s Fish Wagon is a cheap lunch spot that looks like it's built from hurricane wreckage. Don't let the look of the place scare you off though. Kermit's Key Lime Shoppe for key lime pie is a must too.

If you'll be driving down from Miami and passing through Marathon/Bayside around lunch or dinner, a good place to grab a quick bite to eat is Seven Mile Grill, located just before the Seven Mile Bridge.

Have a great time. My wife and I went there while we were dating, got married there, and have been back several times since.

Marathon, Florida
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for Marathon, Islamorada
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14,507 posts
33 reviews
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2. Re: 1st time in Key West

Are you looking to stay only in KW? Or need suggestions for in the Keys as well?

Chester County, PA
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3. Re: 1st time in Key West

Good question Bluewater. Don't bypass the Keys to get to key West.

Now with that caveat, I have not spent much time in the "Keys" - just Key West. Other than a few gems, others can provide you more details than you can handle regarding everything from MM4 north. Let them know

As far as Key West goes, it's nothing like Florida. We hate Florida. Knowing nothing about you except that you're on a budget, want to eat good, drink good, walk, sightsee, lovin' and dancin' , you're going to the right place. You can do all of these things and probably a lot more you've never heard of or considered. Here are two threads to get you started:

Drinking/Happy Hour


Just plain weird stuff and why we love it


key west
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3,350 posts
15 reviews
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4. Re: 1st time in Key West

and don't plan on going to Seven Fish for romance unless you like romancing with the next table over. The food is wonderful but tables are so close you almost have to talk to your neighbors. This could be fun but not romantic in my book. I would pick Pieces, Azur or Marquessa for romantic, somewhat splurgy dining.

Key West, Florida
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24 reviews
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5. Re: 1st time in Key West

For a romantic dinner that will not break the bank, I would suggest Lattitudes (somewhat pricey, but not cost prohibitive). For a romantic one-on-one drink atmosphere, the roof at La Concha, OR if you are really daring, a drink or two at Garden of Eden (clothing optional).

Personally, I would go with no itinerary at all, and let the chips fall where they may. To me, Key West is romance personified, and romance will find you where ever you happen to be.

Have fun, and be sure to let us all know what you did and what you enjoyed with a "trip report"!!

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10 reviews
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6. Re: 1st time in Key West

By reading your post, I think Key West would be ideal!!! If you enjoy luxury and dont mind spending a lil, may I suggest staying at Ocean Key. It is romantic, sits right on the water and has the best location in Key West ( 0 Duval Streeet). It is right in the heart of the action. The restaraunts and bars are everywhere , just read the forums and search the Key West page here on T.A. it will not steer you wrong. I know you will enjoy your trip!!! Keep us posted!!

New Jersey
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for Key West
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7. Re: 1st time in Key West

This video is good because in about a minute it shows you how much fun you can have on a sunset sail...


Thsi particular one leaves from a slip in front of the Ocean Key Resort so you could show up early and have a drink at the Tiki Bar there.


Grand Rapids mi
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for South Haven
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8. Re: 1st time in Key West

read read read..............this forum there are hundreds (thousands?) of answers to your questions. just keep reading, my one piece of advice...don't overplan. maybe pick one thing out each day to do, but don't try to schedule evry minute.and....start planning on yur next trip...KW is made for you!

New York
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39 posts
9 reviews
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9. Re: 1st time in Key West

Just got back from our first trip to key west. The thing I would recommend is the Sunset Cruise. It's like a 2 hour cocktail party on a catamaran with a 3 piece band. We met the nicest people and had a blast drinking and dancing with them.

Tarpon Springs...
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105 posts
12 reviews
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10. Re: 1st time in Key West

well i am no expert on key west by any means. we have just booked our second trip to key west.

however, our first time we went for 9 days and enjoyed many things. there are so many places to have good food and cocktails i don't think you can go to wrong. musci will be everywhere. i'm not a seafood lover so some of the others maybe able to tell you about local seafood. there is an italian restaurant we discovered while riding bikes called mangia mangia. it's not located in the hub of duval st. but they make the pasta there and the time we went it was not crowded at all. food was yummy.

as far as things to do, if you like beaches and snorkeling i would recommend ft zacahry taylor on your own. we drove back up to bahia honda key and key largo to do some snorkeling as well. this time we have booked the dry tortugas. we've seen the hemingway house and the six toed cats, audobon house and have done a few other side tours. there is so much to see in key west, that walking around the neighborhoods can be charming within itself. the sunset show at mallory square is a must.

we rented bikes our first time down and will take our own this time.

i can't offer much in thje way of advice on where to stay. our first trip was based on bringing a pet. this time we booked a place based primarily on price and are taking our chances on the type of place it will be. we are not expecting much other than a clean room, very basic amentites. we decided we would rather spend money on dining and entertainment and have a clean place to lay our head sat night. we are in our 30's and travel frequently. hope this helps. feel free to email me if you want to know more.