The Cutest Orlando Weekend Itinerary for Your Couples’ Getaway

A woman wearing a coral tank top and sunglasses sits in a kayak with a man in a baseball cap, grey shirt and dark shorts on open water.

Jennifer Graven

Jennifer lives in Orlando, Florida, with her boyfriend, Will, and her pup, Wally. She’s a designer by trade but dabbles in all things creative. Her creativity is at its finest while planning international excursions, outdoor adventures and surprise date nights for her besties and boyfriend. She’s an explorer by nature and enjoys the outdoors as much as she loves tasting her way through a new city.

Where do Orlando locals hang out when they’re not at the theme parks?

Trust me — we love catching a fireworks show at Disney’s Magic Kingdom_® Theme Park and bar hopping our way through Universal Orlando’s CityWalk^™, but sometimes we need to get away and just relax.

And relaxing doesn’t have to be boring, my friends.

Recently, my boyfriend, Will, and I took a “staycation” at Orlando Breeze Resort, and we came up with this Orlando weekend itinerary — aka the perfect guide for planning a cute, romantic and active couples’ getaway.

It’s great for exploring all the magic Central Florida has to offer, without having to go to the theme parks.

A woman in a red shirt, black pants and sunglasses stands next to a sign near a man with a black shirt and sunglasses outdoors. ^{Hi there! I’m Jennifer and this is my boyfriend, Will.}

Will and I live in downtown Orlando and spend a lot of our free time checking out local restaurants, breweries, activities and experiences.

There are so many hidden gems throughout the city, and we jump at any opportunity to play local tour guides to friends and family who visit.

But even after over a decade of exploring, there are always new experiences popping up, and we never run out of things to try.

This itinerary has a mix of activities we’ve done before (and loved) and new ones we’ve been excited to try — and they’re all right near the resort we called “home” for the weekend.

We hope it helps you get some ideas for your next couples’ getaway with your special someone!

A man (right) wears a red button-up shirt next to a woman (left) wearing a navy dress while holding wine near winery vendor stalls outdoors. ^{Lakeridge Winery}

Day 1: Exploring the Resort & ICON Park^®

Orlando Breeze Resort is easy to access throughout all of Central Florida and it’s surrounded by more restaurants and activities than this entire blog could ever hold.

The area around it probably has enough restaurants and attractions to fill a month-long stay.

We were most excited to be able to relax at the resort, and whenever we were ready for some entertainment, a short ride would have so many opportunities at our fingertips.

Arriving at Orlando Breeze Resort

As we were driving to the resort, we got a glimpse of the pool and already knew it was going to be a great weekend.

And to make it even better, the friendly woman at the front desk who helped us check in informed us that there were two entirely separate pool areas.

We also got a sneak peek at the mini golf course on the way to our room, and it’s by far one of the most fun courses we’ve ever seen at a hotel or resort.

Our 2-Bedroom Lodge villa was fantastic and very spacious, too. We instantly regretted only booking a weekend instead of an entire week.

Bedroom with bed, window and access to patio/balcony in a two-bedroom villa at Orlando Breeze Resort in Florida. ^{Our Two-bedroom Lodge villa, aka our “home” for our little getaway}

Will was impressed by the full kitchen and living room area, while I knew I’d be spending plenty of time on our TWO balconies.

But honestly, my favorite part was the bathroom.

From the jacuzzi tub to the TWO sinks and TWO showerheads, down to the little details like the Bath & Body Works Coconut Lime Shampoo (my favorite), I wanted to take it home with me.

Left: A woman in black apparel sits in a large, white jacuzzi tub. Right: A woman in black stands in a walk-in shower with two large showerheads. ^{A bathroom truly fit for a queen 👑}

The resort was spotless, central to everything and packed with amenities, and we were so excited to be there for the weekend.

Here’s what Will had to say about it: “Orlando Breeze Resort was the perfect spot for a chill and relaxing three-day staycation. The location was pretty ideal because it’s close to Clermont (which is where we spent a lot of our weekend) and the theme parks (if you want to add them into your own itinerary).”

Friday Night Food & Football at ICON Park®

As UCF alumni, we had to start our vacation off right by cheering on our college football team. What better place to do that than under the iconic Ferris wheel at ICON Park?

We met up with some friends at Buffalo Wild Wings and watched the game on the big screen with an endless supply of beer and wings.

Unfortunately, the Knights lost, but it’s hard to stay disappointed very long when you’re at one of the most romantic places in Orlando.

Left: A man and woman in sports apparel share a toast with beers at a bar. Right: A man and woman in sports apparel stand in front of an illuminated Ferris wheel at night. ^{Buffalo Wild Wings for the game, followed by the perfect photo op with The Wheel at ICON Park™}

If you’ve never been to ICON Park before, we would recommend:

Taking selfies at the Museum of Illusions
Dancing to live music at Tin Roof
Satisfying your sweet tooth at Sugar Factory
And taking in the views from the top of the Ferris wheel

Day 2: Taking a Day Trip to Clermont for Hiking, Drinks & Food

We started our Saturday by grabbing some coffee from a nearby Starbucks and taking a walk around the resort’s gorgeous property.

Luckily, we had thrown a couple yard games in our car before the trip and decided to take advantage of the huge field behind our building with a little lawn darts tournament...

a woman in a red tank top and black leggings throws lawn darts while standing in an open grass field. ^{I think it’s very important to note that I was the lawn dart champion that day.}

Taking a Hike at Lake Louisa State Park

Knowing we had our sights set on exploring new bars and restaurants later in the day, we decided to get in a little exercise first.

Will remembered visiting Lake Louisa State Park several years back and suggested we try out some of its hiking trails since I’d never been.

While we had only planned a trail or two, we were shocked to see the park has 9 trails, 7 lakes, a beach and a playground. And it offers kayaking, horseback riding and bicycle rentals.

We ended up hiking two trails, but we can’t wait to go back when we have more time to do kayaking or horseback riding.

Left: Overlooking the waters and trees of Lake Louisa State Park under a cloudy sky. Right: A man and woman in recreational apparel stand on white sand surrounded by water and palm and moss trees under a cloudy sky. ^{Lake Louisa State Park}

Picnic and Wine Tasting at Lakeridge Winery

After feeling like accomplished hikers, it was time for lunch and a drink.

There’s a Publix grocery store only three minutes away from the resort, so we stopped to pick up picnic supplies and then headed to Lakeridge Winery & Vineyards.

We set up a picnic outside of the winery with a gorgeous view of the vineyards.

Honestly? I never wanted to leave that spot, but the wine inside was calling my name.

A man (left) wears a red button-up shirt and dark shorts while seated on a picnic blanket next to a woman (right) wearing a navy dress near a row of vineyard trees. ^{Picnic party of 2 at Lakeridge Winery}

We did the free winery tour and wine tasting, sampling several wines and learning about the muscadine grapes they grow on property.

The winery offers live music every weekend from noon to 4 p.m., so we watched the band while drinking the blueberry pomegranate wine slushie, which I highly recommend you try!

Brewery Hopping in Downtown Clermont

Less than a 15-minute drive from Lakeridge Winery, there are two craft breweries that are walking distance apart.

At Suncreek Brewery, we tried a Hazy IPA and Mango Cider while listening to live music.

There are two restaurants inside the brewery, Michael’s Ali Coal Fired Pizza and Mac’d Out. We ordered the mac and cheese as an appetizer, and we were in heaven.

Left: A man and woman hold beers in glasses on a covered outdoor patio. Right: Two different glasses hold two types of beer on a bar top. ^{First up, Suncreek Brewery, then Clermont Brewing}

Next up was Clermont brewing. It was only a couple blocks away, and we checked out some of the downtown shops on our walk over.

We’ve been to Clermont Brewing before and would highly recommend eating there. It has everything from sushi to salads to sliders, and all of it is delicious.

Will said, “Out of everything, I was most excited about the breweries because we don’t get over to Clermont very often, so it was nice to get out and try them.”

Dinner at The Southern on 8th

While we were having a drink at Clermont Brewing, we made a reservation for a brand-new restaurant we’d seen on our drive in, The Southern on 8th. (It was only a two-block walk away.)

The ambiance felt like a southern speakeasy and the service was fantastic.

Will got the pork chop, I tried the hot chicken sandwich, and we ordered a bread pudding to-go. We’ve been raving about this place ever since.

Two white, plated dishes containing a sandwich (back) and pork chop (front) placed on a dark tabletop. ^{The Southern on 8th}

Day 3: Enjoying the Resort Day of Our Dreams

We started off our last morning drinking coffee on our balcony. (Did I mention we had two balconies?)

We were looking forward to spending the day at the resort and planned out which activities we wanted to do.

Feeling Nostalgic in the Arcade

Will and I are both huge fans of arcades. I couldn’t wait to get my hands on the Pac Man machine, and he was determined to beat the high score on the basketball game.

We spent at least an hour in the arcade playing air hockey, shooting spaceships and trying to beat each other’s scores.

A man in a grey t-shirt stands at a neon-colored air hockey table in an indoor arcade. ^{Will takes air hockey VERY seriously}

Getting Competitive on the Mini Golf Course

We go on mini golf dates quite often, and I can honestly tell you that Orlando Breeze Resort’s mini golf course was more fun than any of the courses by our house.

The best part? It’s free for resort guests! You can get your clubs, golf balls and scorecards at the Activity Center.

We had the course all to ourselves that morning and had a great time discovering all the unexpected twists and turns that were built into each hole.

Will wants it to go on the record that he won this game … but little does he know, we’ll be back and he’s going down next time!

Left: A woman in black holds a mini golf putter on an outdoor course. Right: A man in patriotic swim trunks and a camo tank holds a mini golf putter on an outdoor course. ^{We’re gonna need a rematch on mini golf.}

Relaxing & Recharging at the Pool

Before leaving, we grabbed some Publix subs from down the street and headed to the main pool next to the clubhouse.

After a long weekend of exploring Orlando Breeze Resort and all the fun nearby, it was nice to soak up the sun and relax poolside.

I loved that there was a hot tub and that the resort has two separate pool areas. They also have grills and tables all around the pool area, so it would be a great spot to grill out next time we visit.

Will said, “The outdoor area is ideal for a family gathering and to do a BBQ with a mix of shade and sun.”

A man wades in an outdoor pool on a blue and white striped inflatable near a resort building. ^{The main pool area at Orlando Breeze Resort}

We were sad to be leaving, but we knew we’d be back. On our next trip, I’m looking forward to getting in the hot tub, and Will can’t wait to use the private movie theater.

For us personally, the best part about Orlando Breeze Resort was being in an area full of fun things to do that we don’t make it out to often enough.

We loved visiting local spots on this trip, but we’ve also come up with some ideas for next time, like:

Venturing out to the theme parks (since they’re so close)
Checking out Disney Springs, Universal CityWalk and International Drive (also very close by)
Playing a round of golf at one of the nearby courses
Sampling our way through the Museum of Chocolate

Whether you’re a local or you’re on vacation, we hope our Orlando weekend itinerary gives you some ideas to get out, eat, drink, have fun and connect with your special someone!

A woman in black (left) sits on a lounge chair next to a man in a camo tank (front) poolside under a blue sky.

Our guest bloggers are compensated for their writing contributions and honest opinions.

All information is subject to change. This article is a curated guide and is neither sponsored nor considered an official endorsement. Please be sure to check information directly with any/all tours, guides or companies for the most up-to-date and direct details.

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