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1st Time to Florida Keys - Key West/Islamorada

1st Time to Florida Keys - Key West/Islamorada

Old Feb 21st, 2024, 01:52 PM
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1st Time to Florida Keys - Key West/Islamorada

Greetings all,

My husband and I will be traveling to Key West the first week of April for a BIG BIRTHDAY celebration. Believe it or not, this will be our first time. We will be there for 6 nights and thought it would be nice to break the time up between Key West and Islamorada. However, I just realized that they are about 2.5 hrs apart. We are flying int and out of Key West.

I’m looking for your expert travel advice on lodging and location, restaurants, and ideas on best way to get from Key West to Islamorada and back again. Is it worth it? We didn’t want to rent a car because I don’t think we will need it in Key West. We are not usually fans of taking buses but not sure if there are other options.

We were looking at Parrot Key, La Mer and The Saint in Key West. Any feedback on those. We want to be close to restaurants, shopping, action BUT…we are not what I would call party people. Don’t want a bunch of partying going on while we are trying to sleep 😊. We want to enjoy a nice pool, the ocean, and be able to walk to other sights, etc.

In Islamirada we were looking at Cheeca Lodge and that’s as far as we got.

Would love to hear of your experiences, recommendations, and input.

Thank you!

Last edited by ciaociao; Feb 21st, 2024 at 02:02 PM.
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Old Feb 21st, 2024, 07:32 PM
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I have heard very good reports about Cheeca Lodge and Islamorada.
Relatives and friends( not traveling together) who recently visited KeyWest said it had changed, not for the better.Crowded, noisy etc, and they were all so disappointed. I donít know where they stayed but said it was also very expensive.
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Old Feb 22nd, 2024, 05:24 AM
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Hi Happy Trvlr,

Appreciate the feedback. Not what I want to hear but I would rather be informed and aware. Sadly, nothing seems to be what it used to be . Maybe we should look at spending more time in Islamorada than in Key West. I will keep researching and hope to hear back from others.

Thank you!!
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Old Feb 22nd, 2024, 06:53 AM
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I have a cousin who lives in Florida and the Cheeca Lodge is her favorite destination in the Keys. We were in the Keys last year after a weekend wedding in Miami and I think you will really need a car to get around. You won't necessarily need the car in Key West but for driving to Islamorada and stopping in Marathon you would want one. This was our second time in Key West and the first was just on an afternoon cruise stop with our kids so we didn't do all that much. It was very hot and humid at the end of April but hopefully the weather will be better earlier in the month. While we will enjoy an afternoon drink and a drink. with dinner we are not much for partying and Key West seems to be a lot about happy hours and lots of drinking. We did enjoy walking around and looking at the architecture, as well as visiting the Hemingway House and the Truman Little White House. In Islamorada we only stayed one night as we needed to be back at the Miami Airport for a 3 PM flight. We did have an enjoyable dinner at the Islamorada Fish Company with an awesome sunset.
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Old Feb 23rd, 2024, 08:05 AM
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Before doing any touring in Key West, visit the museum. It is near the cruise port. Unfortunately, we saved it until last and were sorry we did not know the history of Key West until we were leaving. It was one of the more interesting museums we have visited with local history of development of Key West, information and lots of photos of famous people who planned the town, the society of earlier times and art.
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Old Feb 23rd, 2024, 11:34 AM
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Hi Madam397 and Sassafrass! Yeah, thanks for your advice. We are booked at Checca Lodge for 4 nights and will have a car there so we can enjoy Islamirada, Marathon, etc. Very excited. We are going to stay 2 nights in Key West. Still looking at accommodations. We definitely check out the Fish Company in Islamorada and in Key West Hemingway and Truman house. Sassafrass, I will put the museum on my list too. Is that the Mell Fisher museum? Someone told me that was good to see as well (shipwreck museum).

Thanks again you guys. If you have any other recommendations for restaurants, things to do or see...I'm all ears! thank you.
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Old Feb 23rd, 2024, 12:30 PM
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Look at Lazy Days Restaurant and The Square Grouper in Islamorada.
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Old Feb 23rd, 2024, 12:57 PM
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Hi mcheryl, Lazy Days looks great. It's on the list now. I can't wait to try all the fresh seafood there and throughout the keys! Thank you....
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Old Feb 24th, 2024, 07:47 AM
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https://keysweekly.com/42/a-tale-of-...ys-beginnings/
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Old Feb 24th, 2024, 08:02 AM
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Hi Sassafrass. thank you. Great history and back story. Soaking it all up!!!
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Old Feb 24th, 2024, 08:27 AM
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We had a nice breakfast in Islamorada at a French patisserie. We also had a nice breakfast in Key West at Breakfast Too. There is an Asian Fusian restaurant right near the Frencg patisserie and the entrance to Cheeca. The entrance is also near the small monument to those who perished in the 1938 hurricane. It is right on the. main road and there is a church right next to it.
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Old Feb 25th, 2024, 05:16 AM
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The museum that is really good is the Museum of Art and History in the old Customs House
https://www.smithsonianmag.com/museu...t-history-4DV/

It is one of the most interesting local museums I have ever visited. It has excellent, life size figures, sculptures, sets, exhibits and replicas of Hemingway, the rail stations, etc. Often, little museums and some houses are kind of forgettable, but not this one. We also really enjoyed the Hemingway House.

We also toured the oldest house. It was only mildly interesting, and IMHO, kind of a waste. I wish we had spent that time and money seeing a different museum.

Last edited by Sassafrass; Feb 25th, 2024 at 05:25 AM. Reason: More info.
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Old Feb 25th, 2024, 07:40 AM
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Madam and Sassafrass, you guys are great. I really do appreciate your insights. I'm putting my list together of restaurants and places to see as we speak. Thanks for contributing to that. I think this trip is just what we needed. I will report back when we return and will continue to monitor the forum for great tidbits!

My thanks and appreciation!
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Old Feb 25th, 2024, 08:24 AM
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That museum sounds interesting. If I ever get back to Key West, I will remember it. A friend's daughter had recommended the African Queen boat ride out of Key Largo as someone has bought and refurbished the boat that was in the the classic film. The timing wasn't good enough for our drive back to the airport day or on the day heading down as we didn't know what the traffic situation would be like, plus we wanted to have breakfast at local hot spot, Harriette's which was great but located as you were heading out of Key Largo to head to Islamorada.
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Old Feb 27th, 2024, 06:43 PM
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I've spent some time in Islamorada and in my opinion, THE place to stay in THE MOORINGS, not Cheeca Lodge. Cheeca is a very large property but they get a convention trade and I was not wowed when I visited (but did not stay there). The Moorings, just to the south, is among my favorites of any lodging I've stayed at in the US. It's not a hotel, but individual cottages spread over a former coconut grove. Some are right facing the beach while others are set back into the foliage amidst trees dripping with Spanish moss and orchids. They are in various sizes and prices; if you think about staying there I could offer advice as we've spent time in about 4 of their cottages.

. The wooden cottages, in the style of The Keys, have little kitchens, well equipped, and some even have laundry. They are charming, but with all mod cons like big tv, a/c, etc etc.
They do not serve any meals, so you are pretty much on your own--I found it VERY romantic. You may not ever see any other guests except at the pool where there might be a few.


You can walk to various restaurants from there, and of course the staff can organize any kinds of activities like kayaking, fishing, etc. It is such a gorgeous unique property. One caveat is that I have not been since that big hurricane devastated The Keys but from all reports, the resort is back to normal. Also, they have a fantastic heated swimming pool. I cannot recommend that place more h highly, although it is expensive.

Last edited by ekscrunchy; Feb 27th, 2024 at 06:46 PM.
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Old Feb 29th, 2024, 01:39 AM
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We just did a trip to Key West and loved it. We are not partiers by any means. Loved the Hemingway House and Truman Little White House mentioned above. Our favorite thing was taking a sail on the Argo Navis. https://sailargonavis.com/ Excellent, friendly crew with cocktails and passed appetizers. We wanted something that wasn't a party boat, and it was perfect. We really enjoyed Moondog Cafe https://moondogcafe.com/. Cute restaurant with great baked goods. We stayed at the Hyatt Centric. Ocean Key Resort is also good, but rates had increased a lot since our last stay. That area of town is easily walkable and on the water with nice views. El Meson de Pepe has good Cuban food. And of course you'll want to get some Key lime pie.
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Old Mar 1st, 2024, 08:25 AM
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Hello ekscruncy and volcanogirl!

I will look at the Moorings. Good to know about that. We are booked at Cheeca so maybe Moorings another time. I always like to keep a short list of places to stay though! Volcanogirl, you must have read my mind. We always like to take a sail and finding the right company, captain, boat etc. is key. Definitely going to check this out and the restaurants. Many thanks!!
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Old Mar 2nd, 2024, 06:10 PM
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We have stayed at the La Mer house in Key West and loved it. You are on the other end of Duval from most of the bars and night life. It is adults only and there is a beach right behind the property.
Key West has a lot of things to do besides drinking. The museums, Hemingway House, The Truman Annex, The Butterfly Conservatory are all great. Our favorite is snorkeling at Fort Zachary Taylor.

I’ve never stayed in Islamorada, but have driven through there plenty of times. The restaurant, Lorelei has great coconut shrimp.
https://www.loreleicabanabar.com/

Marathon has plenty of great restaurants and the Seven Mile Bridge. We love to walk out on the part that allows it. You can see so much ocean life just by walking out there and looking.

Enjoy your time in the Keys.

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