Help a Reader Travel: Key West

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Welcome to another post of helping a reader travel!

This weekly post is to help readers get a ton of travel advice from thousand of Deals We Like blog readers. Thus far, we’ve been able to help other readers travel to a slew of domestic and international destinations. Check out recent destinations and comment on suggestions here.

So this weeks travel destination includes Banff. I received the following email from reader Richard:

“I am looking to take my family to Key West this winter. I am traveling from the East Coast and getting there seems to be a little challenging. I am leading towards flying into Miami and then driving, since flights are much cheaper and no direct flights to Key West. Would anyone suggest this, and is there anything worthwhile to stop at along the way? Once in Key West, any hotels you’d recommend staying at? I have a bunch of points from various hotel programs, so would like a major chain hotel that is also family friendly. Also, any suggestions on things to do and places to eat? Thanks!”

If you’ve ever been to Banff, let’s help out reader Richard and I am sure many other interested readers!

Also, if you have any upcoming travel where you need some help, feel free to email me at to be a featured “Help a Reader Travel” Monday special. Thanks!

The responses below are not provided or commissioned by the bank advertiser. Responses have not been reviewed, approved or otherwise endorsed by the bank advertiser. It is not the bank advertiser's responsibility to ensure all posts and/or questions are answered.


  1. I’ve heard that the drive gets to be rather long and tedious. Have they considered the Key West Express Ferry from Ft. Myers? I haven’t taken it myself but that will probably be my option in October when I’ll go there over a long weekend and don’t want to spend the majority of it in a car.

  2. We flew to Miami and then drove to key west. It’s a beautiful drive, especially towards the end and very easy to do.

    We stayed at the Speakeasy Inn ($140/night) and loved it. Great for families as you get suite rooms with a microwave, couch, etc.

    If you have points definitely shoot for the Westin. It’s stunning and in the best location. Even if you aren’t staying there be sure to do happy hour there. We got there on the early side to get a good seat and it was the best place to see the sunset.

    Everything in key west is very walkable so you dont really need a car once you are there.

    One of our favorite sites we saw was Truman’s Little White House – really cool history

  3. Thanks, I will be heading down to keywest with family and friends this winter as well, and have made reservation for the Hyatt Keywest on points. We are flying into Miami and will drive to Keywest. How would you compare the Hyatt Keywest to the Westin, any suggestions? (I am Hyatt diamond and my friend is SPG platinum). Thank you!

  4. My husband and I took a weeklong trip to Key West last year to celebrate our 26th wedding anniversary. We used our Southwest points (including “companion pass” for his flights) to fly into Ft Lauderdale and out of Fort Myers. We rented a black mustang convertible and drove to Miami and stayed the Turnbury Isle Golf resort (an Autograph hotel using Marriott points) which I would highly recommend as it was one of our favorite places during this trip. We also stayed in Key Largo, Key West, and Naples (all on Marriott points). Another favorite place we stayed was the Ritz Carlton Naples golf resort which has complimentary shuttle service to their other resort on the beach in Naples which is an outstanding resort on an incredible beach.

  5. My husband and I are currently planning a trip to Key West. We live in PA and plan on flying in Fort Lauderdale or Miami…whoever seems to have the cheapest tickets. We will then take the scenic drive towards Key West and stop about 1/2 way there to enjoy a relaxing night or two at one of the other Keys. I have gotten a lot of tips from If you are unfamiliar with this site – it’s a great resource to see what others think of area activities, hotels, etc.

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