Orlando weekend with some local flavor (Tampa, Winter Park: condo, hotel, house)

[BrianGC]

So, even though I grew up in Tampa and came over to the theme parks frequently, I have very little knowledge about the city of Orlando itself. My girlfriend and I are visiting family in the Bay area for the holidays, but we decided to take an excursion for two days to O-town.

Our plan is to arrive in Orlando late morning on Saturday 12/22 and explore the non-touristy areas that day. Hit up some nightlife that night, then do Sea World (the only big tourist thing we're doing) on Sunday until around mid-afternoon. Explore some more of the city Sunday evening and more nightlife later, then head back to Tampa on Monday 12/24 after brunch.

My main question is what are the cool non-touristy neighborhoods/places to hit up? We like walk-able areas with local restaurants, breweries, bars, live music spots, night clubs, etc. I'm basically trying to pinpoint where our Airbnb/hotel should be. I know it's a short visit, but we want to optimize our time.

Thanks in advance

[bmw335xi]

Originally Posted by BrianGC

So, even though I grew up in Tampa and came over to the theme parks frequently, I have very little knowledge about the city of Orlando itself. My girlfriend and I are visiting family in the Bay area for the holidays, but we decided to take an excursion for two days to O-town.

Our plan is to arrive in Orlando late morning on Saturday 12/22 and explore the non-touristy areas that day. Hit up some nightlife that night, then do Sea World (the only big tourist thing we're doing) on Sunday until around mid-afternoon. Explore some more of the city Sunday evening and more nightlife later, then head back to Tampa on Monday 12/24 after brunch.

My main question is what are the cool non-touristy neighborhoods/places to hit up? We like walk-able areas with local restaurants, breweries, bars, live music spots, night clubs, etc. I'm basically trying to pinpoint where our Airbnb/hotel should be. I know it's a short visit, but we want to optimize our time.

Thanks in advance

I’d aim for an airbnb anywhere from Lake Eola / Thornton Park up to Winter Park. So that whole area in between. If you want to post a specific listing location feel free to do so here or in a direct message.

Downtown Orlando has fun night life, on the weekends. I like Aero Club, free cover, the roof is house music, courtyard is mixture, there is a reggae room and a hip hop room too. There are some cool speakeasy type bars too. Walkable areas would be parts of downtown along Orange Ave, Central Ave, Lake Eola. There is also Park Avenue in Winter Park. There is also Baldwin Park. Every Sunday Lake Eola has a farmers market. If you want specific restaurant recommendations let me know what type of cuisine and I’d be happy to give you some. There are also local breweries in these areas. Yelp.com is a good resource but feel free to ask me specific things too.

[Arcenal813]

Downtown Winter Park is a must, going by your criteria.

For night clubs, there's downtown itself, but be aware that it's mostly filled with some fairly dingy establishments where most people are getting plastered. It does get pretty busy during evening/nights though, so you might enjoy how active it gets. If the Orange Ave/Magnolia Ave scene is a bit too rowdy for you, you might enjoy Central Ave going East towards Thornton Park better, where there are patio bars and quieter pubs along the way.

There are some really cool local spots along Mills North of Colonial up to around Virginia Ave. Much more of a "local" scene.
Same with East of there along Corrine Dr. heading East. Corrine especially will have some places with some nice brew pubs and the like.

Then, immediately East of there is Baldwin Park, which is sort of a mini urban area of its own. The entire place is walkable, and the main drag is lined with shops, bars, restaurants, etc. It's a bit more on the upscale side of things.

There's also College Park along Edgewater which people seem to enjoy. Not my favorite, but it's popular.

All of this is close to downtown.

If you don't mind venturing off a little, downtown Winter Garden and Downtown Mount Dora also have what you're looking for. Downtown Mount Dora is more retiree-heavy though, but still enjoyable, and is home to one of Central Florida's top restaurants (1921.)
There is also a really nice brewery pub along Highland St that crafts its own brews. Be warned that they are VERY strong... And tasty... You'll have no problem downing 2 rocking red ales, for instance, but would be best walking some of it off before driving away. The neighborhoods around are nice though, and you can catch some pretty amazing sunsets on Lake Dora, which is directly adjacent to downtown.

[Arcenal813]

I also suggest getting an Airbnb downtown near Lake Eola.
There are quite a few condo listings, and even I, as a local, have used them. They tend to be expensive, but you can find them at reasonable rates when booking last-minute if the places are vacant.

[kyle19125]

Originally Posted by Arcenal352

I also suggest getting an Airbnb downtown near Lake Eola.
There are quite a few condo listings, and even I, as a local, have used them. They tend to be expensive, but you can find them at reasonable rates when booking last-minute if the places are vacant.

I agree though would suggest the much more established site VRBO over Airbnb, which has some sketchy reputation failings. https://www.vrbo.com/results?petIncl...%20FL%2C%20USA

[bmw335xi]

Originally Posted by kyle19125

I agree though would suggest the much more established site VRBO over Airbnb, which has some sketchy reputation failings. https://www.vrbo.com/results?petIncl...%20FL%2C%20USA

Only grandpas use VBRO lol. JK sort of...

[brinkofsunshine]

Milk Mart is happening on the 22nd in the Milk District on Robinson St./Bumby Ave. It’s a local maker’s market, usually several vendors selling art, vintage clothes, screen print tees, soaps, etc. There’s also a bunch of popular spots in that area like Drunken Monkey for coffee, Pom Pom’s Teahouse and Sandwiches, and Gringos Locos (tacos) as well as a few hole-in-the-wall hipster bars. Nextdoor to the Milk District is Mills50 which is part Vietnamese neighborhoood part artsy hipster hood with popular live music bars (Will’s Pub/Lil Indies, Uncle Lou’s). Also nearby is Audubon Park which is home to East End Market (food hall with some small stores) and a bunch of various locally owned vintage stores, bakeries, coffee spots, etc.

[drive carephilly]

The Winter Park Farmer's Market is Saturday morning until about noon.

The Market in Orlando is on Sundays at the southeast corner of the Lake and goes until about 4pm. There's not much "farmer" there but it's definitely worth going for the food as much as for the scene.

If you're looking for an airbnb I'd say to try to stick to either side of Mills. Anywhere north of 408 puts you within walking distance of a lot. There's a ton of great food in all directions within a 1/2 mile of that intersection of Mills and Colonial. A lot of fun places to drink as well . . . and as was mentioned above the Milk District (Bumby/Robinson) has some fun bars with a laidback vibe.

[kyle19125]

Originally Posted by bmw335xi

Only grandpas use VBRO lol. JK sort of...

Must be a lot of us grandpas given the popularity of the site. Not to mention they screen landlords and charge an annual subscription ($499) which helps weed out the creepers that Airbnb has made a name for having an abundance of.

[Ping322]

I highly recommend spending talking walking around the town of Winter Park's main shopping and dining strip, Park Ave, about 5 minutes drive north of downtown in Lake Eola.

The breakfast at Briarpatch on Park Ave is spectacular.

I'd also recommend taking a scenic boat tour of Winter Park. The boats leave regularly. There's also a super low-key, 9-hole, family friendly golf course at one end of Park Ave.