Photo by Muffy Aldrich
The Modern Guide to The Thing Before Preppy

Thursday, December 7, 2023

Reader Question: Winter Getaways for Warmth and Sun that are more Preppy than Resort?

 A reader question for the community:

Hi, fellow Saltwater New Englanders! 

I hope you're all enjoying the festive season and staying warm. I love the charm and beauty of New England in winter, but I also wouldn't mind some warmth and sun after Christmas. Do you have any recommendations for places to go?  Are there better parts in Florida or an island that are more preppy than resort? I'd love to hear your suggestions and experiences. Thanks!

41 comments:

  1. Replies
    1. Bermuda isn't so warm in December/January, but it's a great place to visit.

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    2. Agree with Andrew on Bermuda. Love to spend time there but my preferred time of year to go is early spring versus winter.

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    3. Okay, you take Port Royal road out of Kingston up the hill past the cement factory and down the other side and on the left 2171 Magenta Drive. Blue Mountain Grille for dinner.

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    4. It's lovely up here in the mountains; nice and cool. I'll be waiting for you.

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    5. Ah, Miss Taro. Terrance Young asked her not to play the role as a Chinese woman but as a Mid Atlantic woman who isn't real but a woman about whom men dream. As a lad I certainly did.

      Will

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    6. 60 years on and Miss Taro still looks lovely! Just watch out for her nail varnish.

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    7. Cary Grant - the quintessential Mid-Atlantic Gentleman - and Doris Day, loved Bermuda. But perhaps too warm for a Touch of Mink

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  2. Palm Beach, just find non-resort lodging. Before Hurricane Ian, I would have recommended renting a house or cottage on Sanibel Island, but I think it's still in early stages of rebuilding many businesses.

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    1. Housing is mainly intact, but Sanibel’s hospitality is sadly no more. Even South Seas remains closed to all but bare bones operations; literally food trucks 🥺

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  3. The Jamaica Inn, in Jamaica. It’s low-key, old fashioned, and gorgeous. You dress for dinner. Every room has an ocean view and a private veranda

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  4. Virtually every major city has an hotel that has that feel about it and a few local institutions around which a local prep subculture revolves. I would find a Sun Belt city, plan things to do, and jump in. For example, in Houston River Oaks and West University have that vibe, as do the bars and restaurants around them.

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  5. Although it is a resort, we hope that you will visit us at Sea Island, GA. www.seaisland.com

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    1. Can second Sea Island. Wonderful accommodations and fantastic golf

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    2. Shhhh! Let's keep Sea Island special.

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    3. We would visit the Cloister every year if only they would get rid of the ridiculous weight limit for dogs!

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  6. I know a great place, but you cahn't get theah from heah.

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  7. Sea Island is great. I spent a fair amount of time there and Saint Simon's Island when I did I stint at the Federal Law Enforcement Training Center in Brunswick. I feel like it's still one of the few coastal hidden gems of the South.

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    1. It won’t stay hidden long if you keep telling people about it! Just kidding. It is a great place with plenty of options for activities all year round. I hope you were able to get a government rate for the Cloister.

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    2. I was there last January and the traffic would say otherwise as far as being hidden.

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  8. Why would I want to get away? I like my life and my home if that were true, I will change something.

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    1. Seasonality. Indoor tennis gets old in the cold 🥺

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  9. In the spirit of my grandmother's maxim, "live modestly and travel well" we have spent many trips at various Belmond Resorts around the world. You will pay a handsome price to be there but the barrier to entry will ensure you are treated well and surrounded by those that appreciate the desire for solitude and tranquility. Otherwise, charter a boat!

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  10. Replies
    1. See the earlier comments above. Bermuda is lovely but not a place to go for a winter getaway, when it's the low season. Spring - early summer is the best time to go if you're looking for warmth, per the original poster's question.

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  11. How about leaning into all the enjoyment that winter has to offer? Skiing, skating, snowshoeing, fireplaces, sweaters, hot cocoa, hot toddies, etc. To everything there is a season.

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    1. I relished ski trips north & west while living in Florida. Now I relish winter trips to Florida. Grass is always greener 🤣

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  12. I used to live in Winter Park, Florida, and highly recommend visiting. I miss it very much for its charm, beauty and character. Be sure to take the scenic boat tour through lovely lakes and canals.

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  13. I've heard that Apalachicola, Florida is laid back with nearby secluded beaches plus a historical downtown with good seafood. At least that was my older brother's experience when his wife spent a winter's month or so there and he visited between business trips. Anyone been there ? There's a small local airport for access. Hope the peninsula hasn't been wiped out by storms....

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  14. Yes. We have been to Apalachicola. It is quiet and lovely. The nearby barrier island is pristine. It is not easy to get to Apalachicola. That’s what makes it worth the trip.

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  15. I went to Madeira last January and it was lovely and warm, not hot. Typical temperatures were around 60-75 near the ocean and 40-55 in the mountains. It was also the off-season, so quite affordable. Flew from New York and spent a couple days in Lisbon on either side, as well.

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    1. Madeira and Lisbon! Excellent suggestion. Nazare also, up the coast from Lisbon. Spectacular beaches and the premier 'Big Surf' location in the world. Google it.

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  16. Go to the Hotel del Coronado. It is a lovely throwback.

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    1. Yes, but you have to cross that terrifying bridge.

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  17. I heartily recommend Malaga in Spain. It won't be hot but it will be warm enough for shirtsleeves during the day. The beautiful downtown is just off of the beach/coast. (It's also lovely leading up to Christmas with fabulous, over the top but gorgeous Christmas lights!) Nice museums, great restaurants-- go go go!

    --EM

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  18. We spent 6 winters in Palm Beach. That was more than enough. You can do better.

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  19. Admiral's Inn in Antigua. Quiet and low key. Just don't go the week of the Antiqua Classic which is in mid-April.

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  20. Harbour Island, Bahamas and thank me later. We like "Coral Sands" (tasteful small bungalows and main house)

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  21. 1000 Islands... the Skull and Bones even has an island up there.

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  22. Living in the UK it’s either the Canaries or further afield the summer of South Africa

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  23. Not sure it counts for winter warmth, but Kiawah is an excellent destination at Christmas.

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