<p>We are early in the process of looking at spots to buy a vacation/retirement home for the cold winter months. Hilton Head is on the list and so we’re looking for opinions, experiences, information. At some point this winter, we plan on visiting and having a look around, meeting with a realtor, and exploring. So, visiting info is also appreciated. Thank you!</p>
<p>I don’t know where you are coming from, but Winter at Hilton Head isn’t exactly toasty. While there will be plenty of nice days, the Atlantic gets pretty darn cold and January and February certainly aren’t swimming months.</p>
<p>Certainly activities like walking, golfing and tennis are generally manageable, but Hilton Head is pretty quiet in the Winter.</p>
<p>I agree that HHI is not going to be a warm winter destination. I’ve walked on the beach with no jacket in December, but I’ve also been freezing on Thanksgiving there. On the other hand, the winter months are quiet and peaceful, and HHI has to be one of the most beautiful places on Earth. There’s no light pollution, there are miles of trails for walking/biking, and the beaches are pristine. There are a variety of housing choices and a huge inventory on the market, so you should be able to find something you like whatever your price range. Golf and tennis are the main activities, along with biking on the beach and some excellent restaurants.</p>
<p>We live in Toronto and are not looking for summer/swimming temps in the winter. Otherwise we’d be focussing on Florida, which we’re not interested in. 
My H is a golfer and we enjoy biking and walking, so those would be our main outdoor activities. Oh, and quiet is good!</p>
<p>I went there a couple of years ago and was surprised at how manicured the place is. It’s all private developments as far as I could tell with a guard booth at each entry. (I couldn’t figure out why this was necessary. To keep out tourist riff-raff?). A ton of golf courses. It seemed very quiet.</p>
<p>My family started vacationing at Hilton Head in 1962 when the only thing at Sea Pines was one golf course and a motel. We watched it explode into a city with shopping centers, six lane highways, ridiculous traffic. When my father built his ocean front house in the late 1970s, Hilton Head was already far too down the growth curve for the quiet beachfront place he was looking for, so he built at another island up near Beaufort (Fripp Island). I probably wouldn’t recommend that unless you are specifically looking for ocean front and/or beach resort, but I do have a gated community that would be worth checking out. It was all built out about 20 years ago, so it’s all mature landscaping. Two golf courses. Beautiful houses and landscaping, but manageable in size for the most part - single-family houses are mostly in the $300k to $750k range, not the million dollar prices on Hilton Head. Lovely Club House with dining, tennis and so forth. About ten minutes from grocery shopping, doctors offices, banks, etc. And, infinitely quieter and less “city” than Hilton Head. I would say that more than half of the houses are full-time residences, the others being part-year winter/spring residences. No vacation rentals at all.</p>
<p>[Dataw</a> Island Official Site | Dataw Island, SC](<a href=“http://www.dataw.org/]Dataw”>http://www.dataw.org/)</p>
<p>When you do a trip, check out all the gated communities on Hilton Head, but reserve a day to drive up and see some of the developments around Beaufort. There are quite a few and they might appeal to you if you are looking for something with less of a touristy/feel. It will also give you a better sense of the Low Country. Hilton Head is kind of its own little world.</p>
<p>As far as weather goes. It’s pretty comfortable golfing whether 10 months a year (if you count August as comfortable) and you can play year round on nice days. It almost never freezes, maybe one or two nights a year. Spring starts early and is just spectacular through May. June, July, and August are hot for yankees, but people just play golf at sunrise and hang out in the airconditioning in the heat of the day.</p>
<p>We’ve been vacationing on HHI for the past 11 years and love it. Of course, we go in July/August while you’re looking more at the winter months. Friends of ours retired on HHI and absolutely love life there.</p>
<p>Have you tried Hilton Head Life’s forums? I don’t know the url so I can’t post a link but if you google Hilton Head Life you’ll easily find the message boards there.</p>
<p>alwaysamom, If Hilton Head doesn’t turn out to be the place for you, I would highly recommend going a little further south and checking out St. Simon’s Island GA. </p>
<p>My fifty-seven yr. old sister recently bought a condo there for vacations and future retirement. DH and I spent a week in May and a week in July at her place. It was just beautiful…golf,biking/walking paths all over the island,real estate priced from very reasonable to over the top, a really cool little downtown that runs right down to the big community pier/waterfront park. St. Simon’s has a more “homey” feel than many resorts because there are a lot of year round residents there. </p>
<p>Sorry for the hijack!</p>
<p>We spent many end-of-October weeks on Hilton Head (had to stop going when kids got too old to miss a week of school - couldn’t talk in-laws into a different time share week :)). LOVE IT!!! Friends from Michigan live in Sea Pines Plantation year-round & absolutely love it. They have many year-round friends on the island.</p>
<p>I can’t really recommend any places, as we haven’t visited in several years & things are always changing. I can say, though, that I would much prefer retirement on HHI to retirement anywhere in Florida.</p>
<p>mousegray, a gated community is actually a requirement for us. Even though such communities are ubiquitous in many areas of the U.S., they are virtually non-existent in Canada, however, the fact that we will not be living in the house full-time means that this will be one layer of our security arrangements.</p>
<p>i-dad, thank you for your input. I had a look last night at some real estate listings on Fripp and Dataw Islands. I’ll pass them along to my H whose research is more golf-focussed. The two communities on HH that interest him most, at the moment, are Long Cove and Wexford. He’s looking for a private course, and also, we’re not interested in renting the house out when we’re not there. I’ll delve a little further into the areas around Beaufort. Thanks, again!</p>
<p>wharfrat, I haven’t had a look at the HH forums but I’ll add that to my to do list. Thank you for the suggestion.</p>
<p>packmom, thank you for recommending St Simon’s Island. It’s on my H’s list, as I believe he knows a golfer who lives there. </p>
<p>kelsmom, thank you. Seems that we agree on Florida. We have many friends who have winter places in Florida but it just doesn’t appeal to us. My H has golfed all over Florida through the years but never found a spot that he really wanted to return to again. His absolute favorite golf location is Pinehurst but he wants something with the chance of being just a tad warmer in the winter months. Hence, our research on HHI.</p>
<p>When our kids were small we spent several vacation weeks on Hilton Head and loved it. One thing you might want to look into if you start narrowing in on a particular home: Hilton Head has become a popular destination for college “senior weeks” (the week between end of classes and graduation). For the last several years, the senior classes of both Colgate and Bucknell have been at HH during the same week; Williams seniors go a few weeks later. Hundreds of 21 year olds roadtrip to HH and rent homes for a week in May. My son and 20 (!) or so of his fraternity brothers loved their large oceanfront rental home … but I wouldn’t want my retirement home to be the house next door.</p>
<p>My parents had a house in Port Royal Plantation on HH for many years. It is on the Atlantic side, with a wonderful long walkable beach, and is almost all (like probably 98% or more) single-family houses with a very, very few small groups of joined “patio homes.” The thing that set Port Royal apart was that there were NO apartments/condos at all, and short term rentals (even for a couple of weeks) were NOT allowed at all. There’s a golf course–which I gather is very good, although I am not a golfer-- and clubhouse, and a beach club with a pool. Tennis courts, lagoons, etc. Great for walking and biking. People whose focus is boating who want moorings would probably pick another plantation. People who wanted to rent out their place would definitely pick another plantation. </p>
<p>They eventually decided to sell their place and build something similar on the water in the Beaufort area. They got tired of being on an island, especially when everyone had to evacuate for hurricanes over a single bridge! They ended up not building the other place, but IIRC the “plantation” was called something like “Bull’s Head,” and it was on a high bluff on the water. Sounded like a nice place, and Beaufort is a pretty town.</p>
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<p>I would not recommend Fripp unless you are specifically looking for an oceanfront house. And watching my father maintain an ocean front house for 25 years, I would not recommend absentee ownership of oceanfront property. It’s endless – the boarding up for hurricanes, the replacement central air compressors that corrode in the salt air. He loved it for very long time, but he also lived there full-time. When he hit his 70s, it just got to be too much. He was happy to sell it and move away from the immediate coast. Fripp’s golf courses and resort management have never been stable. They’ve always wanted to turn it into a resort and been at odds with the single family homeowners.</p>
<p>In contrast, Dataw was never intented to be a resort. It never has had any vacation rentals. Very limited multi-family – just some fairway villas – four two-bedroom condos with garages per building on the golf course (my great aunt owned one) that were really nice for a single person. Everything else is single-family detached some on large lots, some on low-maintenance California style lots. It was always intended to be a gated residential golf/tennis/club oriented development. Two very well-maintained private golf courses that have no vacation daily fee usage – just the members (home owners and some full-time memberships sold to other Beaufort area residents).</p>
<p>I’m not first hand familiar with the two newer Hilton Head properties you mention, so I’m useless on those. My days staying at Hilton Head were back when Sea Pines was the only game in town. I remember when the first two non-Sea Pines resorts were developed, Port Royal and Palmetto Dunes. I had several high school friends who owned some of the very first houses built in Sea Pines. I’ve gone deep sea fishing from the Harbor Town marina back when it was so new there weren’t even any boats there.</p>
<p>Everyone has different priorities. Go visit and focus more on the lifestyle you are looking for, especially projecting forward when you may move full-time. Before purchasing anywhere, I would recommend maybe doing a rental in off-season and again in peak season so you can really see what you are getting in for. What you see in January may not be what you see over Easter or 4th of July weekends!</p>
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<p>Bingo. Sounds familiar to me. Oceanfront is a young man’s game.</p>
<p>On the hurricane evacuations, my dad just got to where he went a day before the evacuation orders. Just got out early, beat the traffic, and settled into a hotel room in Columbia, Augusta, or Aiken with some cards for bridge and gin for martinis. Board the house up with well worn sheets of plywood cut to size for each window and sliding door. Turn off the water. And, hope it’s all there when you come back. He was lucky. Never had ocean in his house. Worst damage was wood shingles blown off.</p>
<p>The comments about temperature are correct. If you are looking for beach weather in the winter months, you need to get to Naples or further south. It freezes in Jacksonville in the winter.</p>
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<p>i-dad, thanks again for all your input. We’re planning on visiting at some point in the next few months. I understand your point about visiting at different times of year, but we won’t be moving there full-time even after retirement. My guess is that we’ll definitely use it at different times of year, as will our family, but we have no plans to live there year round. I agree with you about beachfront, and we really have no particular desire to be in a beachfront property. Beach access would be nice for walking or the occasional sitting and reading, but we’re not ‘go down to the beach early to mark our spot for the day’ people. :)</p>
<p>dadx, exactly. That’s why we’re not looking for beach weather in the winter months.</p>
<p>alwaysamom, if you are looking for golf I would look into Port Royal. Although the plantation is beachfront, and there is easy access, most of the houses are not. And the golf course–there may be several-- is good enough to be used for pro tournaments.</p>
<p>After 10 years in Folly Field (older homes, not a plantation, mid-island) we stayed in Shipyard last summer. We enjoyed it tremendously there.</p>
<p>We’ve spent a lot of time today, on our respective laptops, looking at different areas on HH. Such fun! It’s always interesting to look at real estate in a new area. One surprising thing we’ve noted is that you can have pools there with no fencing requirement! That is unheard of where we live, where many people have pools, too. You not only have very strict fencing requirements but also must have a gate that locks, and the city must inspect and approve it prior to the pool being filled. </p>
<p>Have been in touch with a realtor and are compiling our wishlist of features, locations, requirements, etc. On HHI and the surrounding communities, there are 5000+ properties for sale, which is amazing to me. Now we need to find a week when we can visit and explore in person. Thank you all again for your help!</p>
<p>Alwaysamom, what fun! Living in Georgia, when our kids were small, we spent many great summer vacations in a (rented) big house in Sea Pines with good friends, babysitters in tow–10 or 11 people in all–and have wonderful memories. In those days, buying a beach house was way out of our financial reach, and since it’s a 5 hour drive, not realistic for a weekend getaway. </p>
<p>We loved the biking–all our kids learned to ride bikes there–and walking on the beach was terrific. </p>
<p>Keep us posted on what you end up buying.</p>