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Another first timer - just wanted to introduce myself

Springfield MO
4 posts
2 reviews
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Another first timer - just wanted to introduce myself

My husband and I will be heading to the Keys in April. Flying into Miami and driving down to Key West. Staying three nights and then staying another three nights in the upper keys and flying back home. We are both in our 30s and do not have kids.

Last year we went to Hawaii and I was obsessed with planning. When a trip fell through the first day, I let it bother me a little too much! Once I was able to chill out, we had a fabulous time.

This trip, I don't want to make the same mistake but it's in my nature to want to plan. I am getting great information by reading reviews and forum posts. I've viewed blogs and photos posted here and they are amazing - so colorful - and the food pics, wow!

Are you a vacation planner or fly by the seat of your pants type of person? What works best for a Keys trip?

Thank you!


Key Colony Beach...
Destination Expert
for Florida Keys
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7,661 posts
23 reviews
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1. Re: Another first timer - just wanted to introduce myself

If you over plan, you will have a sucky time.

Plan 1 or 2 things each day, and then hope you don't get them all done.

If you have a minute by minute itinerary, you will focus more on getting to the next item on your list rather than enjoying what you are doing.

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1,695 posts
148 reviews
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2. Re: Another first timer - just wanted to introduce myself

When I go to the Keys, I usually plan one or two highlight activities/side trips. Then I go with the flow. In KW take the Old Town trolley tour, this will give you orientation and general layout. You can get on and off at stops that interest you. A sunset sail one day is nice to do, usually can make a reservation the day before(check the weather). Not sure what your interest are but, most activities can be booked the day before or morning of the day you want to go. You should try to narrow down a couple of activities for your stay in KW. Last word relax, get on island time and be spontaneous.

Edited: 20 January 2013, 15:38
Hilton, New York
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110 posts
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3. Re: Another first timer - just wanted to introduce myself

We have more fun by just letting the fun happen!! Just walking around and looking at all the sights is great. The colorful houses are so nice to look. I know you'll have a wonderful time...you're in the Keys for goodness sakes!

Williamsville, New...
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545 posts
67 reviews
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4. Re: Another first timer - just wanted to introduce myself

I agree with the above posts. Plan on a couple things, maybe a sunset cruise or kayak/snorkeling excursion. Then let the day take you where it does. Don't let it get to you if you miss something...it will be there on your next visit. The best thing about Key West is even if you go & just hang out & walk/bike around you will fill your day.

St. Clair Shores...
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107 posts
1 review
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5. Re: Another first timer - just wanted to introduce myself

We have airfare and a place to stay. No other plans are made. We always find things to do if we choose to.

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3,800 posts
3 reviews
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6. Re: Another first timer - just wanted to introduce myself

Welcome Shannon, we use KW as our relaxing vacation, we don't plan on anything until we get there. but being your first time check out the "things to do" in the upper left side of this page. This will give you a chance to see what you mite like.


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111 posts
8 reviews
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7. Re: Another first timer - just wanted to introduce myself

When we go on other vacations, I plan 1 or 2 excursions for the whole trip and the rest of the time go with the flow. When Im in Key West I make a list of Happy Hours and restaurants I want to visit, and the rest of the time is pool or beach time.

Key West, Florida
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8. Re: Another first timer - just wanted to introduce myself

I think planning is LOTS of fun, so I encourage you to do as much research as you can and make as many plans as you'd like. To me, that's part of the fun of a vacation and extends your enjoyment of the trip long before you go. The anticipation is part of the experience!

That said, having a plan, and being tied to it are two completely different things. If you treat your plan as a grab bag of stuff you might like to do if the opportunity, mood, weather, hangover (?) allows, that's way different from having an hour by hour list of things to do and see that you must check off.

As others have said, one of the best parts of a trip to the Keys is letting the beauty of the area and the friendliness of the people unfold around you, proving an opportunity for experiencing things that unexpectedly come along your way. If you're too busy running from thing to thing,,you might miss the best parts. Parts that no one could recommend for you because they will be experiences that only you will have.

Good luck with the planning and have a great trip! I hope you keep us posted on how it all goes.

Appleton, Wisconsin
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503 posts
11 reviews
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9. Re: Another first timer - just wanted to introduce myself

I, like many here, stalk the forum for weeks before each trip, but rarely plan a thing. Take a conch train or trolley tour on the first full day. They give you some history and take you past a lot of the sights. Then you have a better idea of what you want to see. Then, just let each day happen naturally.

Grand Rapids mi
Destination Expert
for South Haven
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1,761 posts
48 reviews
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10. Re: Another first timer - just wanted to introduce myself

agree with everyone's comments........but KWSTEPS says it best !