Hilton Head or Key West - Where would you go?

[katmittens]

Not sure if it is ok to ask this since one of my possible destinations is Key West in Florida, but hoping someone has been to DVC at HH and to Key West in Florida. What is better. Just will be DH and myself in Oct. I will be spending a few days at one of these places either before or after Disney. I have a studio booked at HH and a studio at BWV for four nites and then 2 nites in Key West. I may have to drop one or the other, HH or Key West. What is there to do at both places. Any info would be appreciated.

 

[chum]

Tough question.
I like both but now live on Hilton Head.
Key West is adult oriented.
HHI is still a family destination.
HHI is not as hard to get to but the drive through the Keys is special.
Beaches are better in HHI but the fishing is better in the Keys.
Golf is better in HHI.
Mopeds in Key West and bikes in HHI.
HHI has more restaurants but plenty of unique spots in the Keys.
HHI is the second largest island after Long Island and Key West is the southern most point of the US.
Key West feels more like a tourist town.
Good history in both spots.
I loved the Key West of the late 70's and wish it was still that way.
Hilton Head is better off now than 35 years ago.

I don't think you can go wrong with either.
Flip a coin?

 

[podsnel]

I agree, i like them both, but they are so different. Both are very special and unique destinations. Key West is more like an anything goes party town (although of course there's lots of history, too, with Hemingway's home, Truman, etc). Key West feels beachier to me, even though the beaches are much smaller. HHI is more refined, more "southern charm". 400 year old live oaks gracefully shading everything, bike paths, huge beaches, great golf and tennis, tons of dolphins and birds. Both do have great restaurants, and both have extremely welcoming and friendly natives! Oh no! You can't cut out either!!

 

[mecllap]

Looks like part of the decision might relate to how you are getting back and forth to those places. Key West is worth seeing once and you can "see" a lot of it with a full day there, but it's worth more time than that if you like what it has to offer. It's a 7-9 hour drive from Orlando.
Hilton Head is delightful and relaxing, but similar to lots of other places on the Atlantic Coast (well, of course, it has its own personality, too). It's more like a 5-hour drive from Orlando, and altho it's 45 minutes east of the freeway, could be a good place to visit on a driving trip to/from Penn. If this is your only chance to see one or the other, I'd vote for Key West. Chances are, you'll want to go back to either one to spend more time.

 

[mecllap]

eta: Oops -- sorry that a duplicate post occurred.

(I went to both on a Florida trip in November, and a day in Key West was enough for me, but I would enjoy going back. I will be much more likely to go back to Hilton Head, tho -- it appeals to me more now, and I hate to think that's a factor of age, but in my 30's-40's I would have been all about Key West as a top choice).

 

[5forDiz]

Haven't been to Key West as of yet but DH has and he said if you have 2 days to visit there to/from Orlando it would probably be enjoyable but if he had to pick one or other it would be HHI especially for restaurants & beaches.

If you will be driving would definitely stop overnight at HHI traveling to or from Florida ( our family enjoys HHI so much we often stop both ways on our drive ).

You'll most likely get more relaxation time in on your drive heading back home as it is approximately 335 miles from WDW to the Sea Pines Circle on HHI near Disney resort via Cross Island Pkway.

It typically takes around 5 and half hours total with majority of drive on I95 and then last 30 miles from Exit 8-Hardeeville east to island unless you stop off in Savannah on way and work you way up from there to Bluffton & then over to HHI, this will take longer because it's local routes from Savannah.

If we can't get DVC resort we bid a room on priceline at Resort Level on HHI and if the bid is accepted you'll get either Westin, Hilton, Crowne Plaza or Marriott Beach which are all very nice oceanfront properties ( usually during summer months which is popular time on HHI we get bid accepted at around $80 per night, during October probably can get accepted between $60 - 80 ).

Have fun planning, it sounds like a wonderful trip

 

[katmittens]

Thanks for great suggestions. First we will be driving down to Florida. My plans now are to leave at 4 in the afternoon and drive and stay in Winchester, Va. Then the next day stay outside of HH or in HH if I can get a good deal. Checking into a studio at HH for Fri and Sat. Disney world on Sun. at Riverside for the nite and then 3 nites in a studio at BW. Leaving BW on Thursday and staying in the Keys Thurs, Fri and Sat. Leaving to come home on Sun and staying in Ga, Mon staying in Va. and Tues. home. Fourteen days!. This will be the longest we have been away. DS and DD are both back at home and working. DD just graduated from college so if no job she will be substituting (art teacher) and DS is an attorney and will only be here the rest of this year till Aug of 2011, so since I have a cat sitter I figure I will take advantage of it. We have been trying to see different parts of Fla, for future retirement, I don't think I would go to Key West or Miami, too far south, but DH has always wanted to go there, so I think we will try it. We have been to HH before and loved it so it will be good to be back there since it has been about 10 years since we have been there.

 

[Smoochies]

I’m a Florida girl, so I am biased and would vote for Key West over HH, personally. However, being that you’re traveling in October (not sure of your exact dates), I would mention that if it’s the end of October, Key West has Fantasy Fest around then and if you’re on the conservative side, it may be a bit much…it gets pretty wild down there then.

Whatever you decide, I’m sure you’ll have a great trip!

 

[pb4ugo]

chum summed up the differences pretty nicely. having been to both hh and kw, i would say that it depends on what you/dh like to do. great dining and shopping at either location; hh golf is way better; kw history is more convenient; kw will likely be warmer in oct than hh; one nite in hh will only give you the desire to return. but if you are considering retirement locations, i hafta suggest that you take a 1 hr drive north of orlando to go and see the villages! the villages is like a theme park for adults! if you don't know of it, get a sneak peak at all the villages has to offer at http://www.thevillages.com/. i am not affiliated with the sales staff - dh and i are just snowbirds there! and we like to stay at disney's hhi resort for a few days on our way back to nj each spring. you can't beat it for ambiance and the laid back atmosphere while the rest of the island has all the get-up-and-go that one might desire. sorry if you hafta give up one side or the other of disneyworld - that's a tough decision!

 

[katmittens]

Thanks for the info about The Villages. We have thought about going there to see what it is all about. A friend of DH's wants us to stop at their place in New Smyrna Beach for a day or two. They have a house there and stay for the winter. Oh well looks like this vacation will be extended a few more days. I don't mind that a bit.