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First time Key West visit!

by cooke350 Online Now Feb 13, 2013 at 2:03 PM

My wife & I will be going to Key West in May to celebrate our 40th birthdays. Looking for information from locals, such as must-do's, must-see's, etc. Also, anything we should expect or be prepared for that time of year, like crowds, gatherings, parking, getting around? What's the best beach for relaxing? Safe local bar, club for dancing? Any neighborhoods we should avoid after dark? Anyway, looking for insider tips!

We'll more than likely be staying at the Inn at Key West. Before we commit to that, any suggestions on the hotel would be nice, too.

About us...From Northern Minnesota, looking forward to some beach time, relaxation, shopping, dining, drinks, nightlife. Maybe a tour and/or kayaking? On a bit of a budget, so we'd be looking for frugal suggestions. We're only there for 3 nights, and with drive time there & back, we'll have Thurs evening, all day Fri, and all day Sat to cram in as much stuff as we can!

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27 Answers
  • martensd's Profile Photo

    Re: First time Key West visit!

    by martensd Online Now Feb 13, 2013 at 3:16 PM

    Check out the posts and other forum Q & A about Key West. That will help you get started. I assume you are driving from Miami and back. Personally I like to stop and sightsee a bit going down (or up), even though I was a local (Big Pine Key). Great places to eat along the way which helps since KW tends to be pricey for good food. Places like Porkey's in Marathon and No Name Pub in Big Pine Key (hard to find but worth it) Check out the keys and keywest.com websites to get some ideas. Do not know the Hotel, but maybe check out the B & B's for a more homey stay. For the most part KW is pretty safe. Duval St. is "THEE PLACE TO BE" but we found some very cool bars just of Duval. Just wander around and stop in for a look. Of course you need to be aware that there are gay bars around. No worries just may not be your thing. There was this club on Roosevelt (I can not remember the name) Before you got downtown and near a marina that was alot of fun. It was a Russian place. I will try to find out the name. Weather should be nice at that time of the year. Hope that helps a little. David

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  • irvbur's Profile Photo

    Re: First time Key West visit!

    by irvbur Online Now Feb 13, 2013 at 4:02 PM

    Using a HoHo (hop-on, Hop-off) sightseeing bus is usually a great way to get an overview. It worked fine for us last Fall.

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  • Agraichen's Profile Photo

    Re: First time Key West visit!

    by Agraichen Online Now Feb 13, 2013 at 6:10 PM

    I enjoy Captain Tony's Bar and the Hog's Breath. Hog's is more than just a bit toursity but they usually have good music.

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  • SONG's Profile Photo

    Re:

    by SONG Online Now Feb 13, 2013 at 7:53 PM

    Another VT member and I took a trip to Key West last May and the weather was perfect!!! We also drove from Miami and enjoyed the drive down. The scenery was beautiful and the aqua waters mesmerizing. It took about 5 hours, if I remember correctly. We took one of the sunset sailing tours and found it to be well worth the price. A VTer was actually the skipper of the ship. Not sure if Chris is still there. I would recommend visiting the beach at the Waldorf Astoria , which of course is a private beach, but you can at least look at it, walk on it, and even recline in one of the hammocks IF you happen to eat lunch there or have a cocktail out on the patio, next to the beach.. It is the nicest beach we saw while at KW. I was pretty disappointed in the other beaches. I have quite a few photos of this trip on my homepage under Travels....Key West and Palm Island. : "Colorful Key West, Florida" - Key West by SONG "Little Palm Island, Florida" - Palm Island by SONG

    Feel free to email me at if you have any more questions.

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  • grandmaR's Profile Photo

    Re: First time Key West visit!

    by grandmaR Online Now Feb 14, 2013 at 7:39 AM

    We lived in Key West in the 60s and May was nice but hot. The Royal Poinciana trees will be in bloom - most tourists don't get to see those because they only visit in the winter.  Parking is almost always a problem in Key West no matter what the time of year.  Ive never stayed at the Inn at Key West, so check on whether parking there is free.

    As was noted in a previous answer, Key West beaches are not the main attractions.  The better beaches in the Keys are the Bahia Honda beaches, but that is a state park.  Another state park in Key West which really has the best beach is the Fort Taylor State Park  If you stay on the east side of the island the best hotel beach is at the Casa Marina which is of course expensive, but it is the only hotel beach that I would recommend unreservedly.  It is a bit out of the way for being at the heart of the bar action though. 

    There are kayaking tours in Marathon, and possibly some on Boca Chica.  Mostly these will be tours of the mangrove swamps and the canals.  I would recommend maybe renting a bike as it is possible to bike around the whole island very easily. 

    Free and inexpensive - you must go to Mallory Square for the sunset celebration - free unless you count cost for parking

    Shopping - beware of the T-shirt stores.  If you want cheap T-shirts, stop at the Flea Market at Big Pine on your way back on Sunday

    Tour - I recommend the Conch Train tour.  It gives an good overview of the town

    Bars - the Duval Crawl is the thing -stroll along Duval street and go to places that look interesting.  I can't recommend anything specific because it's not our thing- maybe Finnegan's Wake.  Very popular restaurants include the Blue Heaven for breakfast, Turtle Kraals or Kelly's or lunch.   Rusty Anchor Restaurant on Stock Island is hard to find but might be nice for dinner.

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  • grandmaR's Profile Photo

    Re: First time Key West visit!

    by grandmaR Online Now Feb 19, 2013 at 9:05 AM

    I do not recommend either the Truman Little White House or the Mel Fisher Museum as they are way more expensive than what you get. Better to go to the Oldest House Museum which is really good and authentic and the East Martello Tower.  Hemingway house is also expensive unless you are a fan of his.

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  • Re: First time Key West visit!

    by cooke350 Online Now Feb 19, 2013 at 12:53 PM

    Thanks for all the advice! We plan on doing the conch tour and things like the aqarium and a museum or two. We're also looking forward to relaxing on a beach, maybe some kayaking and/or bike riding. As for bars and eating, we're more into places that the "locals" go to when we're traveling, although I'm sure we'll check out the bars on Duval. I haven't booked the hotel yet, as I'm still not sure if the location is ideal for what we'd like to do. I called the hotel and spoke with someone about our concerns and there were a lot of positives, like free parking, concierge services for setting up rentals, etc. He did say there are a couple of nice beaches within a mile of the hotel, but I can't find them online. Does anyone know which ones they'd be? The hotel is the Inn at Key West at 3420 N Roosevelt Blvd.

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  • martensd's Profile Photo

    Re: First time Key West visit!

    by martensd Online Now Feb 19, 2013 at 1:36 PM

    I admit I did like the Hemmingway House, but then, I was an English Major in College. Roosevelt is the Main road splitting off US 1. Right to the main drag and left towards the airport. The hotel you mention is a bit far from the downtown area but I would not worry too much about that since you can get there a number of ways. It is not close to the beach area which is near the airport and I believe off Boca Chica Rd. Another VT'er mentioned Zachary Taylor Park as having a good beach and I agree totally, although I have never seen many people at that beach. The park is near the Naval Air Station Annex in Old town section. Parking downtown (old town) off Duval can be a pain, but I have always found a space down the side streets. Other options are renting a scooter, bicycle and taking a cab. Check out the side streets and you may find some of the places the locals go for food and drink as well as the "New Town" area off Roosevelt and before you get into KW on US 1. Key West is small and easy to get around so while your hotel may not be in the hot spot you are within 15 minutes driving time to most everything. David

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  • grandmaR's Profile Photo

    Re: First time Key West visit!

    by grandmaR Online Now Feb 19, 2013 at 3:14 PM

    Roosevelt is on the east side of the island (Ocean side) and the beach along that side is manmade but is a very active beach. I am not sure that Key West has much 'local' bar scene. The locals will be working in the bars and the ones drinking will be the tourists. If I wanted to wander around Old Town and the aquarium (which I agree is nice), I'd book someplace you could walk from there, if you can find one with free parking. Otherwise, you will be driving and trying to find a place to park every day. Incidentally there are city buses. I have lived there, visited by car and rented a place on the old heliport (Navy base), come by cruise ship, come on our own boat and taken a mooring or gone to a marina, and gone to stay at a condo on Roosevelt, but I haven't actually stayed at a hotel in Key West.

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  • martensd's Profile Photo

    Re: First time Key West visit!

    by martensd Online Now Feb 19, 2013 at 4:43 PM

    I believe that Roosevelt is both on the ocean side and the gulf (West) side. When you enter off US 1 you can go left (east) toward the airport or to the right towards New Town and the marina's, But both are considered Roosevelt. The hotel that was being looked is one that you have to follow to the right. There are more hotels and businesses on that side.

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  • grandmaR's Profile Photo

    Re: First time Key West visit!

    by grandmaR Online Now Feb 19, 2013 at 7:31 PM

    martensd wrote: I believe that Roosevelt is both on the ocean side and the gulf (West) side. When you enter off US 1 you can go left (east) toward the airport or to the right towards New Town and the marina's, But both are considered Roosevelt. The hotel that was being looked is one that you have to follow to the right. There are more hotels and businesses on that side.

    Yes you are right - I think of Roosevelt as being over there by the airport down to the West Martello tower because Roosevelt on the west side turns into Truman about halfway down.  They call it North Roosevelt.  I DO NOT recommend any accommodations on North Roosevelt because there's really no transportation there except for a car and the beaches aren't as good.   I talked to a couple of people who were there at one of those hotels right after you get to Key West from Stock Island, and they were quite annoyed at being so far out of town.  They felt it had been misrepresented. They can of course promise free parking because they are so far out of town.  I'd recommend either staying down on South Roosevelt at the Casa Marina or south of that, or a little north at the Sheraton or the condo next door where at least the beach is right across the street,  or over on the other side at someplace like the Westin or the Banyon Resort.  The Crown Plaza is right in the center of the action but that is an old hotel and I don't know how nice it is. 

     

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  • DEBBBEDB's Profile Photo

    Re: First time Key West visit!

    by DEBBBEDB Online Now Feb 19, 2013 at 9:03 PM

    Our favorite restaurants are Camille's, Blue Heaven and Finnegan's Wake. We also like to get naked wings and then go to Peppers of Key West and sample their hot sauces on them.

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  • martensd's Profile Photo

    Re: First time Key West visit!

    by martensd Online Now Feb 20, 2013 at 7:54 AM

    Very true, N. Roosevelt does change to Truman. I only refer to it as Roosevelt since the hotel being looked at has a Roosevelt address. I hardly ever came down S. Roosevelt as I was always heading to New Town or Old Town.

    Gram- The old adage "To each Their Own" applies to our answers. LOL. I always stay on N. Roosevelt because I had points for free rooms at Comfort and Quality Inns. (Not good rooms BTW...but free) And even though it is a few miles from the "Action". I never had a problem getting around. I always found a parking space when in my car or my motorcycle. Once we rented scooters and we easily got around and when we hit Duval at night we always took a cab. Of course when I lived on Big Pine Key, I just drove home.

    I really had no interests in the beaches but have gone to the Z.T. State Park beach which was pretty nice but I believe you have to pay to get in.

    I did stay at the Crown Plaza once and I have to say, that was a fantastic hotel room....but I had to pay for parking and the room was almost $400 a day so I do not know if that fits into their budget.

    As far as Stock Island, I once tried to find a seafood market/restaurant down on 3rd and discovered it closed down. The only other thing I remember about that area is a restaurant I think is called "Hogfish" which was pretty good.

    Lastly, I agree with Deb on Camille's. GREAT Breakfast but usually a line to get in.

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  • grandmaR's Profile Photo

    Re: First time Key West visit!

    by grandmaR Online Now Feb 20, 2013 at 8:44 AM

    martensd wrote: Very true, N. Roosevelt does change to Truman. I only refer to it as Roosevelt since the hotel being looked at has a Roosevelt address. I hardly ever came down S. Roosevelt as I was always heading to New Town or Old Town.

    I almost always go left because the traffic that way is less unless I was going out to Sigsbee to the commissary.

    Gram- The old adage "To each Their Own" applies to our answers. LOL. I always stay on N. Roosevelt because I had points for free rooms at Comfort and Quality Inns. (Not good rooms BTW...but free) And even though it is a few miles from the "Action". I never had a problem getting around. I always found a parking space when in my car or my motorcycle. Once we rented scooters and we easily got around and when we hit Duval at night we always took a cab. Of course when I lived on Big Pine Key, I just drove home.

    My point was that is you wanted to be where you could walk to the things going on in Old Town, that N. Roosevelt is not a good place to be.  Even the Casa Marina on S Roosevelt is fairly far from town (although with a good beach). 

    When we were there on a boat with only one bicycle for land transportation, I investigated renting one of those little tiny electric cars, or motor scooters and found the electric car was over twice as expensive as a regular car and two motor scooters would also be more expensive than a regular car.  But the original person who asked will have a car and my opinion is that they would be better to stay closer to town and maybe rent bikes because the parking is a problem especially if you don't know the town well.   A lot of the spaces are metered.  (I'd also advise to park in the municipal lots where possible)

    I really had no interests in the beaches but have gone to the Z.T. State Park beach which was pretty nice but I believe you have to pay to get in.

    It is a State Park, and the admission fee gives you adminsion to the Fort which is very interesting.  Offers picnicking, swimming, snorkeling, and fishing. Visitors can also enjoy a short nature trail and bicycling within the park. The beachfront Cayo Hueso CafĂ© offers snacks, cold beverages, beach sundries, and souvenirs.

    Admission Fees: $6.00* per vehicle. Limit 2-8 people per vehicle. $2.00* Pedestrians, bicyclists, * Plus $.50 per person Monroe County Surcharge.  So two people in a car would be $7.00 and two people on bikes would be $5.00

    I did stay at the Crown Plaza once and I have to say, that was a fantastic hotel room....but I had to pay for parking and the room was almost $400 a day so I do not know if that fits into their budget.

    I think most places down in town are going to be more expensive, so the decision has to be made as to whether you want convenient to the action and pay more for it, or whether you are going to be OK with a little more effort to get to town.  I would also ask about the beach that the hotel has if I was going to stay on North Roosevelt.

    As far as Stock Island, I once tried to find a seafood market/restaurant down on 3rd and discovered it closed down. The only other thing I remember about that area is a restaurant I think is called "Hogfish" which was pretty good.

    The restaurant that we ate at on Stock Island was the Rusty Anchor. 

    Lastly, I agree with Deb on Camille's. GREAT Breakfast but usually a line to get in.

     

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  • grandmaR's Profile Photo

    Re: First time Key West visit!

    by grandmaR Online Now Feb 20, 2013 at 8:46 AM

    DEBBBEDB wrote: Our favorite restaurants are Camille's, Blue Heaven and Finnegan's Wake. We also like to get naked wings and then go to Peppers of Key West and sample their hot sauces on them.
     My sister went to Peppers and she enjoyed it.

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  • Re: First time Key West visit!

    by cooke350 Online Now Feb 20, 2013 at 1:44 PM

    We've been researching the hotels and have decided against the Inn at Key West, as we'd like to be closer to Duval and Mallory Square. Looking at location, pricing, and reviews, we're now considering Eden House. It looks like it's about a 6 block walk to Duval along Eaton St. Can anyone tell me if this is a safe area to walk at night?

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  • martensd's Profile Photo

    Re: First time Key West visit!

    by martensd Online Now Feb 20, 2013 at 10:04 PM

    All points well taken. Cheers David

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  • martensd's Profile Photo

    Re: First time Key West visit!

    by martensd Online Now Feb 20, 2013 at 10:15 PM

    Some of those side streets can get pretty dark. But if memory serves, I think that area is not bad. I have heard good things about Eden House but have never stayed there. I personally feel KW is pretty safe.

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    Re: First time Key West visit!

    by martensd Online Now Feb 20, 2013 at 10:15 PM

    Some of those side streets can get pretty dark. But if memory serves, I think that area is not bad. I have heard good things about Eden House but have never stayed there. I personally feel KW is pretty safe.

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  • TRimer's Profile Photo

    Re: First time Key West visit!

    by TRimer Online Now Feb 26, 2013 at 3:41 PM

    We were just in Key West two weeks ago. We had been there 6 years ago and had a totally different experience. The first time we stayed at the Hilton (we had points) and did a lot of the touristy things. We did a tall ship cruise which was great. Watched the sunset every night at Mallory Square (a unique view is to have drinks at the hotel bar which overlooks the Square). Drank at Captn Tonys, Margaritaville (we are parrotheads) and Hogs Breath to name a few. This trip was more about relaxing. Stayed at the Mermaid and the Alligator B&B (amazing). Ate at Blue Heaven, Santiagos Bodega and Michaels. Tried to eat at Better than Sex but it was a 45 minute wait.

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  • Re: First time Key West visit!

    by cooke350 Online Now Feb 28, 2013 at 8:15 AM

    We finally decided on where we're staying! We booked a suite at the Galleon Resort. The location looks like it'll be perfect! I can't begin to tell everyone how excited we are to get down to Key West! Looking forward to driving through Miami, Key Largo, etc on the way, too. We're already planning on going back and we haven't even been there yet! We're assuming we'll enjoy it immensely! Thanks for all of the info from everyone, this site is terrific!

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    Re: First time Key West visit!

    by rdywenur Online Now Mar 14, 2013 at 12:19 PM

    I just came back from a cruise and stopped at Key West. I took the Conch Tour and got to see most of the city. Not enough time to explore and see at least one sight. I do have a flyer from Hop on Hop Off which has a nice map and listings of Trolley Stops, Points of Interest/Attractions and Restaurants/Shopping. I can scan it and email it to you if you like.

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  • Re: First time Key West visit!

    by cooke350 Online Now Mar 14, 2013 at 12:41 PM

    Thanks! Yes, that would be great! Send it to cooke350@msn.com!

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    by rdywenur Online Now Mar 15, 2013 at 8:54 AM

    you should have it by now. I sent it in pdf format so you can print it out

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    Re: First time Key West visit!

    by rdywenur Online Now Mar 15, 2013 at 9:10 AM

    BTW when I said not enough time it was because I was on a Carnival Tour. so my time was limited. The Conch Tour Train lasts about 1 1/2 hrs. First we went to the places we wanted to collect free gifts with our coupons from ship. Then stopped at the Key Lime Co. for a slice of pie (ummm) then took the tour. I wanted to see Hemingway House but that takes a good hour or more to go thru and ship would leave without us if we missed it. Lots of walking so bring good walking shoes, water, and wear a hat.

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  • Re: First time Key West visit!

    by cooke350 Online Now Mar 25, 2013 at 12:30 PM

    All of the answers have been soooo helpful! Thank you everyone! So, we're thinking about maybe renting kayaks for a few hours. Are there some nice sand bars/beaches that you can easily kayak to?

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  • martensd's Profile Photo

    Re: First time Key West visit!

    by martensd Online Now Mar 25, 2013 at 1:36 PM

    Here are a couple of websites that might interest you.

    The clearly unique might be pretty new. I never saw them before, but it looks pretty cool.

    The lazy dog had both guided tours and rental of just the kayaks.

    clearlyuniquecharters.com/Ho...

    lazydog.com/?utm_source=TDC_...

    Enjoy

    David

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