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first trip (surprise engagement) Oct 24-30

Boulder, CO
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first trip (surprise engagement) Oct 24-30

I'm surprising my girlfriend with a trip to Key West in about a month. We're statying at the Sheraton Suites across from Smathers Beach October 24th - 30th. And, I'm "popping the question" at some point down there.

I know that this is the week leading up to the Fantasy Fest celebration, so it might not be the most romantic time to be in Key West, but I figure we'll still enjoy it coming from Denver and all...

Right now, I'm planning on booking a snorkel trip and a renting a car to drive down the keys & try and find a secluded beach. Other than the typical tourist attractions like Douval St., the Southermost Point, Hemmingways House, etc., I was wondering if anyone could give me some tips on what to do when I'm there. And the more romantic, the better.

Thanks, all & wish me luck!!!

Pjk
New Jersey
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for Key West
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1. Re: first trip (surprise engagement) Oct 24-30

There are several nice sunset sails out of Key West. This one on Danger takes a max of 20 people, is a wine tasting, and probably won't be filled in Oct...

http://www.dangercharters.com/

And this one, The Floridays, has a champagne sunset sail, says they take 30 people, but this too will not be filled...

http://www.floridays.org/

They are on the other side of the island form you, but the Suites run a shuttle.

Pjk

Fort Myers Beach...
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for Key West
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2. Re: first trip (surprise engagement) Oct 24-30

Take her to Little Palm Island to pop the question, it's the most romantic place in the Keys (maybe anywhere).

You will take a boat aot to the island and have dinner on the beach and time it so you are there at sunset (the beach faces west).

You get the boat at MM 28.5 on Little Torch Key so you will need the car.

Ask (beg) for a table on the beach and tell them what you are planning to do.

Last time we were there on Dec. 27 th for our 33 rd aniversery, they printed menues with oyr name and what we were celibrating. They will do almost anything you ask like I had a dozen roses delivered to the table during dinner.

While we were there that night there was another couple there and he got on his knees and poped the question.

Rolla, Missouri
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3. Re: first trip (surprise engagement) Oct 24-30

You may find this strange, but i find walks through cemetery's romantic and there is a great one in Key West. keywesttravelguide.com/key-west-cemetery-map…

If she has by now hopefully accepted the proposal of a life together, than a twilight stroll through the cemetery imaging lifes gone before while planning your life in the future can be very cool. you can contemplate the mark on this life you want to leave behind as your personal legacies.

Rolla, Missouri
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4. Re: first trip (surprise engagement) Oct 24-30

bottomtime's idea is cool, but i am a loner romancer. i would propose on that secluded beach and then "let the party begin."

Arlington, TX
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for Fort Worth
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5. Re: first trip (surprise engagement) Oct 24-30

Bahia Honda is a great sunset if you have a car.

Rooftop Bar @ Hotel la Concha is a wonderful Sunset; sunset is always romantic to me.

patio dining @ mangia mangia is casually romantic

I find an evening stroll thru the lovely homes and harbor area quite romantic.

mi
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6. Re: first trip (surprise engagement) Oct 24-30

If money is no object, then Little Torch Key would be a great spot. If you don't have unlimited money, but are willing to spluge, Sunset Key would be a great alternative and even Louie's Backyard. If Sunset Key is too much, then I would also agree with the others that the sunset cruise is a good option (however it probably won't be a young crowd, if that matters). If you are on a budget, find a pier along Smathers or South Beach.

(don't, I repeat don't do it in the cemetary .... ohbo you are one unique fella)

Montgomery Alabama
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7. Re: first trip (surprise engagement) Oct 24-30

Little Palm island is my recommendation. I was there in June, it is very romantic and i saw another couple get engaged. I would do it there if anywhere in the world

Indianapolis...
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8. Re: first trip (surprise engagement) Oct 24-30

We had our Anniversary dinner at Latitudes on Sunset Key and it was very romantic (my wife loved it, you can check out my review) tripadvisor.com/ShowUserReviews-g34345-d6807…

There was another couple there that had just gotten engaged and she looked pretty impressed. The beach isn't secluded but after sunset there are very few, if any, people on the beach. We went for a walk and didn't see anyone. I do like bottom's idea, we didn't have a car so it was inconvenient for us. Just remember to do everything you can to make sure that when you make reservation to explain what is going on. Good Luck!

Pjk
New Jersey
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9. Re: first trip (surprise engagement) Oct 24-30

In case you are wondering, this is Sunset Key,

http://www.sunsetkeyisland.com/

It's reached by a shuttle from near the Mallory Docks in Key West which would be just above the island in the photo. The pier is where it lands and lets off passengers, and IIRC the restaurant is in the beach area to the left of the pier. Not a bad idea.

Pjk

South Florida...
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10. Re: first trip (surprise engagement) Oct 24-30

Little Palm Island as my vote. Its is as romantic as you can get.