Orlando, The City Beautiful: A guest post from my friend Kristin

Greetings Dears! This is the first guest post in this is my journey, It’s from my friend Kristin from www.sippingypsy.com she is a great experienced writer and has wonderful reviews of food and cocktails. I am sure you will enjoy reading this post as I also did.

Lake Eola

Orlando….The City Beautiful.  Home to millions of people from all over this amazing planet, and destination for even millions more for the warm Florida sunshine and all things theme park and entertainment.  While I wasn’t born in Orlando, I would visit here almost every year growing up, and once old enough and out on my own, moving here was top on my priority.  In nearing 2 decades based out of this beautiful town, I feel like I can confidently call Orlando ‘home’.  I’m proud of her diversity and while she can’t really boast the historic appeal of centuries-old landmarks she does have pockets of charming neighborhoods with a network of people that are hardworking, dedicated and the backbone of a city that thrives on tourism, but celebrates home and community.

It has been exciting to watch downtown Orlando blossom over the past decade.  Her skyline is modest, but downtown Orlando has its own rhythm.  One of my favorite locations is Lake Eola.  Speckled with local restaurants and bars and an outdoor theater that hosts everything from Shakespeare plays to concerts.  I’ve enjoyed many an evening at the Eola Wine Company after a romantic stroll around the lake.  Festivals, markets and shows set up home along the picturesque bank of Lake Eola.  I use The City Of Orlando webpage to catch what’s going on around the lake to plan when to spend the afternoon downtown. Every Sunday people flock to the Orlando Farmers Market to stock up on fresh produce and home crafted goods in a strong commitment to supporting local.  Just a few blocks from Lake Eola are the clubs and bars on and adjacent to Church Street and the home of my favorite pizza spot in all my travels,  Gitto’s Pizza.  Gitto’s has faithfully been helping club and bar goers sober up for as long as I can remember.  While you won’t find me personally in these night clubs, I will still make it a point to get to Gitto’s for my regular pizza fix. Not too far up the street is Mathers Social Gathering, I do enjoy frequenting this swanky spot.  Designed to feel like a speakeasy, you have to dress to impress to even be considered to come in…and once inside the first floor lobby, good luck finding the way up to the bar…but don’t give up.  Mathers is a chic spot with excellent cocktails, definitely a go to for Orlando locals.  Want great entertainment outside of the parks? The Dr Phillips Center is Broadway here in Orlando.  Amazing shows and plays come to downtown Orlando.  Treat yourself to a live show, and dinner at Ceviche…it will be a memorable evening!

Baldwin Park

The neighborhoods surrounding downtown Orlando offer each their own unique charm and truly amazing spots for food, cocktails and shopping.   Baldwin Park is another sophisticated area built on the picturesque Lake Baldwin.  There is a cornucopia of delicious and local spots up and down New Broad Street.  Again, save time to stroll around the park, and step in and out of local shops to find unique clothes and gifts that you won’t find in mainstream shops.  Baldwin Park is also active with social events and festivals around their lake, I use Baldwin Park Events to plan out when to venture to this great neighborhood. If you make it to Baldwin Park, please, do yourself a huge favor and visit The Nest.

The Nest with menu

I love a good cocktail.  Many bars claim to be ‘craft cocktail bars’, but few impress me like this spot.  The Nest is a cozy charming spot that I discovered based on my travels to St. Augustine Fl and the original bar Odd Birds.  I love the eclectic décor and playful drink menu.


The ‘foodie’ hot spot in Orlando right now is definitely Winter Park.  There has been a revolution of farm to table, organic and locally owned restaurants and bars.  This posh neighborhood is active and thriving and can easily keep you busy for the whole day.  Check out City Of Winter Park for the events calendar.  I usually try to space my time to enjoy lunch and dinner up on this side of town. The Ravenous Pig is one of my favorite spots for lunch before I hit Park Ave for some shopping.  In the evening, the decision of where to eat becomes a little more complicated.  The usual candidates depending on cuisine preference would be Domu for ramen, Annas for amazing authentic Polish cuisine, or Prato for a swanky environment with great Italian food.

Cocoa beach

The other great advantage to staying in Orlando during your trip to Florida is her central location and easy day trips to other great spots in Florida and Southern Georgia.  For a relaxing beach day you can head west for the relaxing Gulf of Mexico and enjoy Clearwater Beach.  There a several amazing restaurants up and down the beach for fresh seafood and great cocktails.  If you want the option for surfing, head east to the beaches along the Atlantic Ocean.  Daytona Beach is an active pulsing beach with lots of activities and entertainment.  I prefer Cocoa Beach and usually park at the pier for my afternoon.  Orlando may not have centuries old castles, but we do have the beautiful and charming St. Augustine.  This city packs in a lot of history and entertainment.  For a day trip to St. Augustine I like to start out at the St. Augustine Distillery and grab lunch at Ice Plant upstairs.  I stock up on several bottles from the Distillery to take home…their Gin is one of my favorite.  The rest of the day is easy to spend in the historic district along Saint George St.  Please enjoy a cocktail at Odd Birds.  This eclectic spot hosts my pick for some of the best cocktails I have had in my travels.

Kristin on Lake Baldwin

I hope this post helps as you plan your trip to Orlando.  She is a growing city that is ever evolving and changing.  When you arrive, grab a drink and talk with the locals….ask them where some of their favorite spots are and enjoy!

Sippin Gypsy


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4 thoughts on “Orlando, The City Beautiful: A guest post from my friend Kristin

Add yours

  1. Orlando is definitely a good base to explore all of Florida, and there are so many great places to stay. As for the restaurant scene, I am not really familiar, but the Winter Park area sounds like my cup of tea! I’ll have to try out some of these places on my next visit to the city.


  2. What a well written blog on Orlando! Sippin gypsy really makes makes me want to go to Orlando again. Cocoa beach is also one of my favorite beaches of Orlando.


  3. Beautiful post on Orlando! I have friends there and they say it never ceases to amaze them. I can now see why. And I admire the fact that you always dreamt of moving back there and you finally did.


  4. Orlando looks and sounds amazing! I visited Florida as a child (for Disney and Universal Studios of course!) but don’t think I really appreciated the state itself as much as I should. Would love to go back now I’m a grown up and explore Orlando and Miami !

    Liked by 1 person

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