[chaggertyjr]

I know there a probably tons of threads on this already, but I like fresh, up to date answers!
My wife and I were looking at Florida as a potential move in 2016. We are originally from Long Island, NY, so we are big fans of having the beach nearby! I also plan on buying a sailboat as soon as I save up the funds. We currently live in Chesapeake, VA (3rd MOST BORING city in the country) and can't stand it. Very spotty, and every good neighborhood is surrounded by crap neighborhoods. It is also very boring where we live, and need to drive 30 minutes or so just to get food at somewhere other than applebee's or shop at a decent store.

I want to take her to the gulf coast for Valentine's day this year as a surprise, but I want it to be a practical trip, too. So, the faster I get responses, the faster I can book the trip for us!

We like cities/towns that have a lot of mom and pop or locally owned restaurants and shops. We are not fans of all the chain restaurants. She wants there to be ample shopping (I just want a beach within a 25 minute drive and a place to keep my future sailboat within the same distance). Affordability would be great ($300,000 would be a safe max).
We also like areas that have a sense of community. We both enjoy things like farmer's markets, food/music festivals, and downtown that has at least a little night life.
However, we do have our first little one on the way, and we will be moving there with her mother and younger sister who will be 14 by that time, so schools and safety are the priorities.
We are sick of traffic jams, so I think the Tampa area may be out of the question, but I like to hear opinions.
Punta Gorda sounds like it might fit the bill, or Cape Coral. I keep finding mixed reviews for their neighboring towns though (port charlotte and fort myers).
We have been reading tons and tons of things on where we would like to move.
For comparison, we love the types of amenities and culture that Charleston, SC and Savannah, GA offer. They just don't fit the bill for us for their own reasons. We know FL will be very hot, and we are OK with that.
Keep in mind, close burbs just outside of a great place with many activities could fit the bill, too, as long as the burbs aren't super boring! We are open to suggestions!
Please help!

[macrodome2]

Punta Gorda and Port Charlotte would be good for a sailboat, but don't really have good beaches. Look at Google Map and follow the coastline.

You might want to check out Estero, just south of Ft. Myers. It's a little further to a beach, but there is plenty of shopping close by and you're close enough to get to Naples or Ft. Myers.

Take a look at the Bradenton-Sarasota-Venice forum to check out that area. Although Venice has a downtown it would probably be too old. North Port would be younger, but it doesn't have a downtown. Englewood might be worth a look. Sarasota may be your best possibility. As you move up north of Sarasota to Bradenton you're going to run into more people and more traffic.

I've seen some people recommend Palm Harbor and Safety Harbor further north, but I'm not familiar with that area.

[Fl1150]

Sarasota, North Port, Cape Coral are options.

[kyle19125]

Originally Posted by chaggertyjr

I know there a probably tons of threads on this already, but I like fresh, up to date answers!
My wife and I were looking at Florida as a potential move in 2016. We are originally from Long Island, NY, so we are big fans of having the beach nearby! I also plan on buying a sailboat as soon as I save up the funds. We currently live in Chesapeake, VA (3rd MOST BORING city in the country) and can't stand it. Very spotty, and every good neighborhood is surrounded by crap neighborhoods. It is also very boring where we live, and need to drive 30 minutes or so just to get food at somewhere other than applebee's or shop at a decent store.

I want to take her to the gulf coast for Valentine's day this year as a surprise, but I want it to be a practical trip, too. So, the faster I get responses, the faster I can book the trip for us!

We like cities/towns that have a lot of mom and pop or locally owned restaurants and shops. We are not fans of all the chain restaurants. She wants there to be ample shopping (I just want a beach within a 25 minute drive and a place to keep my future sailboat within the same distance). Affordability would be great ($300,000 would be a safe max).
We also like areas that have a sense of community. We both enjoy things like farmer's markets, food/music festivals, and downtown that has at least a little night life.
However, we do have our first little one on the way, and we will be moving there with her mother and younger sister who will be 14 by that time, so schools and safety are the priorities.
We are sick of traffic jams, so I think the Tampa area may be out of the question, but I like to hear opinions.
Punta Gorda sounds like it might fit the bill, or Cape Coral. I keep finding mixed reviews for their neighboring towns though (port charlotte and fort myers).
We have been reading tons and tons of things on where we would like to move.
For comparison, we love the types of amenities and culture that Charleston, SC and Savannah, GA offer. They just don't fit the bill for us for their own reasons. We know FL will be very hot, and we are OK with that.
Keep in mind, close burbs just outside of a great place with many activities could fit the bill, too, as long as the burbs aren't super boring! We are open to suggestions!
Please help!

Originally Posted by macrodome2

I've seen some people recommend Palm Harbor and Safety Harbor further north, but I'm not familiar with that area.

I would highly recommend Safety Harbor and Palm Harbor given your boating interests as well as the safe/good schools aspect. I would also add neighboring Dunedin, as well as a good bit of Tarpon Springs and all of East Lake. All have plenty of independent shops/restaurants and easy access to Tampa/St Petersburg/Clearwater amenities without truly bad traffic most of the time.

[gypsychic]

Sarasota, Safety Harbor, Dunedin would be good places to look. Sarasota (where I live) has TONS of shopping, loads of unique restaurants (we have the chains too) and some of the most beautiful beaches on the Gulf coast. Have fun!