Sarasota/Venice definitely has lots of culture in January and it is much more low key than a lot of the Miami and northward areas. There is live theatre, opera, dinner theater, boat excursions, the Ringling Museum of Art, etc. etc. You will want to rent a car, and you may want to fly into Tampa or Ft. Myers in order to get a better price from the airlines. They are only a short drive away. It can be expensive to fly into Sarasota. Venice is even more laid back than Sarasota, but you are close enough to enjoy the amenities in Sarasota. I would recommend Sanibel rather than Captiva based on the village vibe you want. You would fly into Ft. Myers to go there as well.

New Smyrna Beach and Palm Coast are very nice if you want ocean breezes but not the rush of tourist culture--Nascar, motorcycles, spring break, etc. New Smyrna, south of Daytona, has an artsy feel. Both NS and PC are college towns--branches of Daytona State College. Music in the Amphitheater. Access to beaches is very good. PC is north of the cities of Daytona and Ormond Beach. Ormond has lots of nice restaurants and a not so crowded gorgeous beach. Palm Coast is new, celebrating it's 10th anniversary. Pop. is 60,000. It's equidistant to St. Augustine and Daytona. Has gorgeous new resorts on the beach. St. Augustine is a 45 min. drive. It has awful traffic and little parking available. It makes a nice day trip from PC. Lots of fun historical events.

Oh, Palm Coast is on the north edge of the citrus belt. It's about as warm as DAytona Beach whereas St. Aug can get cold, especially on the beach in Jan-Feb. Today it was near 90.

Also, On a day trip to St. Augustine, stay for the evening. The city is still all in holiday lights!

Fly into Ft. Myers, rent a car and take the short drive to Sanibel and (connected by bridge)Captiva. Stay at Tween Waters Inn on Captiva. There are great restaurants on both islands and interesting shopping, as well. Paddle through the Ding Darling Sanctuary. Your Tween Waters beach is heavenly, and the Sanibel beaches are, too. Shelling is great fun and very productive. Even though you won't get your little town, I bet you will return year after year.

I get real happy every time I go to Sanibel. My kids are always happy on Sanibel. My husband is always happy on Sanibel. Get my drift? There are no strip malls but there are nice shops. No francise restaurants other than a Subway, a Dairy Queen and a 7/11 but there are lots of good restaurants that are sophisticated if that's your style or kid friendly if that's a better fit. We bgan going there years ago when our family really needed some downtime, a chance to talk to each other and rest. We're now on the next generation and the kids still love to rent bikes, play volley ball on the beach and pick up shells. It is a real vacation.

anna74, St. Augustine, FL has history, art galleries, good & reasonably priced restaurants, (outlet) shopping, nice beaches, etc. It's also off the radar for most tourists. In January, it may be cool (compared to South Florida), but way warmer than Boston.

A few links:
http://www.staugustine.com/visit/
http://www.visitflorida.com/St_Augustine
http://www.getaway4florida.com/
http://www.getaway4florida.com/nights/

Hi Anna,
Looks like you've got a lot of tips already...here's mine: West Palm Beach has the nicest downtown in South Florida because it's pedestrian friendly, offers a lot of cultural activities, has a historic old Florida flair which is gone almost everywhere else in South Florida and is right accross the bridge from Palm Beach with it's historic mansions, beautiful beaches, bike paths and world class restaurants. It is true that the weather can be cool in Jan...but day time temperatures are, really almost without exception, in the 70s and often 80 degrees. I'm originally from here, lived away for 22 years mostly in Europe and loved coming back a few years ago...opened a B & B with historic cottages...check it out: www.grandview-gardens.com

RickRose,
Welcome to Fodors. Those are some good suggestions, but please remember that there is no advertising here.

Hi Orlando_Vic, thanks for bringing that to my attention, I'm new at participating on travel forums and still learning what the rules are...by reading the above posts, I thought it was OK to link into websites for tips. Where are the participating guidelines for this site? Anyway, thanks again!

natinwpb, You said "As for Singer Island it has a nice beach but it is a horrible area & I would not recommend it for a family". We have been going to Singer Island for years as a family & we, along with thousands of other families, love Singer Island. When is the last time you were there?

Hello again, RickRose.
It's all here in the Subscriber's Agreement, section 5(A) http://www.fodors.com/about/subagree/.

Yes, it is O.K. to link to websites as long as one does not personally profit from it. At least that's my understanding of it. Does anyone else have a different interpretation?

No, I am not the police here.

Yes, I am glad you're here to share ideas about your travel experiences. Again, Welcome!

There have been several posters over the years, some current, who are owners or managers of hotels, B&B's, restaurants, and the like, but they take care not to promote their own businesses. That's how I understand the rules: you're welcome to share advice and expertise, but must steer clear of plugging your own place. I agree with OrlandoVic, welcome, RickRose, your advice will be appreciated!

Bookmarking.

I'm sorry you don't want to go to a larger city. We've been to Ft. Lauderdale the past two Januarys and had fabulous times. So much to see and do, even walking--nice wide sidewalks along the ocean and on Las Olas Blvd (all stroller convenient for3 year-old), range of interesting restaurants, not so rushed in that month, gloriously warm & bright. Several times we tried the Gulf Coast in "winter." Just once was it was really nice--Fort Myers Beach & Sanibel. In Sarasota one year it was upper 50s every morning for a week!

Second or third or fourth the idea of Sanibel/Captiva. There is no real town center but lots of small shopping areas, miles of bike path (you can even rent a surrey like bike for the family.) There are miles of gorgeous beach, shelling is excellent, and there are a few nice playgrounds...in Periwinkel Park Shopping Center and across from The Bean Coffee Shop both mid island. Tarpon Bay Outfitters has boat trips as well as kayak rentals on Sanibel. There are also places on Captiva. "Tween Waters is lovely and takes you the length of Sanibel to get there. Doc Ford's Restaurant is my current favorite.

Oh, and someone above said people are divided on East Coast vs. West Coast of Florida and like one or the other....well I love both. We often fly into Miami, spend a night or two in South Beach enjoying it all and then drive across Tamiami Trail stop at Shark Valley and then relax on Sanibel!! Makes a fantastic trip.

I'm kind of stunned by the suggestion of Marco Island, which does have a nice beach, but the whole place is kind of a strip mall city with wall to wall condos and convention hotels on the beach. It's kind of the exact opposite of how Delray has managed to preserve their "quaintness". And yes, I too think if you like Delray, you'd probably like Naples -- especially staying within a few blocks of the beach and within the downtown area. One of Naples most unique features is that within the city itself with a small exception at the north end, the entire beach is public access and is ONLY private homes, no condos or hotels.

Vero Beach/Orchid Island (the barrier island part of Vero.)
upscale, wonderful restaurants, gorgeous wide beach, great bike and running paths, sweet downtown, sophisticated, well to do population.