48 Hours of Sunshine: Our Orlando Couples Getaway
Escape the winter chill with a sun-filled weekend in Orlando, where resort luxury, delicious cuisine, and outdoor adventures await. From poolside relaxation to lively entertainment at Disney Springs, our journey offers the perfect blueprint for a rejuvenating couples retreat in the Sunshine State.
The winter blues hit us hard and we found ourselves desperately craving sunshine so we decided it was time for a quick escape to Florida. We landed on Orlando because of the flight times available from Cleveland. The trip location was solidified by finding The Hyatt Regency Grand Cypress on points at a great price. We wanted a resort we would not have to leave and this property definitely delivered.
Day 1: Sunshine and First Impressions
We arrived at Orlando airport around noon – I was coming straight from a work trip while Drew flew in from home (on frontier), so we coordinated and met up at the airport. After grabbing our luggage, we headed straight to the Hyatt Regency Grand Cypress. It was SO nice our room was ready for early check-in, allowing us to immediately launch into vacation mode, effectively giving us another day of vacation when coupled with the late checkout we received.
The first order of business was exploring the resort's sprawling grounds before settling in on some pool chairs and ordering from the servers walking by for lunch. With cocktails in hand and the Florida sun warming our skin, we knew we'd made the right decision to escape the cold.
After familiarizing ourselves with all the resort had to offer (spoiler: it's a lot!), we headed back to our room to freshen up for dinner. We had reservations at Four Flamingos, which turned out to be an unexpected highlight when we discovered the owner/restauranteer was in the kitchen that night! The food was spectacular – when in Florida I am absolutely going to order Stone Crab if its on the menu. Drew LOVED the swordfish and it was HUGE. We shared a bottle of wine and got to enjoy dining outside. We had such a nice time connecting over good food.
Wanting to maximize our outdoor time, we decided to grab a Lyft to Disney Springs for the evening. Drew had never been, and I was excited to introduce him to the lively atmosphere. We strolled around people-watching, shopping, and eventually satisfying our sweet tooth with ice cream from Salt & Straw (if you haven't tried their unique flavors, add it to your must-do list!). One particularly special stop was at UNIQLO. I had seen a TikTok that you can do custom embroidery in store and when I spotted the store I had to see if this was true. I was able to customize a super cute travel purse with unique to Florida embroidery options that is a perfect souvenir from our trip.
Day 2: Resort Activities and Disney Springs Crawl
We woke to slightly cooler morning temperatures, making it the perfect time to explore the resort's 1.3-mile walking path. The morning stroll outside was just what we needed before heading to the Lakehouse Restaurant & Bar for breakfast. After breakfast we changed and tried our hand at the resort's pitch and putt golf course, it’s not a Haley and Drew vacation unless it involves some golf!
As the day warmed up, we claimed our spots by the pool for an afternoon of pure relaxation. Despite the pool water being unheated (and quite chilly!), the warm sunshine made lounging poolside with our Kindles absolutely perfect. There's something magical about having nowhere to be and nothing to do except read, nap, and occasionally order another drink from the attentive pool staff.
For dinner, we decided to try something different: a Disney Springs food and drink crawl. We had collected recommendations from friends and followers, and the plan was to hit several spots, sharing appetizers and drinks along the way. Our first stop was Wine Bar George for wine and small plates, followed by appetizers and cocktails at Jock Lindsey's Hangar Bar. The best part? Disney Springs allows to-go drinks, so we could wander between venues with beverages in hand while enjoying the various live music performances scattered throughout the area. We caught an amazing band and spent time just soaking in the atmosphere before catching a Lyft back to our resort.
Day 3: Savoring the Last Moments
For our final day, we prioritized squeezing in every last drop of relaxation before our afternoon flight. We slept in, enjoyed a leisurely breakfast at the Lakehouse again, and then headed straight to the pool to soak up a few more hours of sunshine before reluctantly packing our bags.
I HIGHLY recommend a couples trip like this if you can swing it. The Hyatt Regency Grand Cypress provided the perfect balance of relaxation and activities, and Disney Springs offered just the right amount of entertainment without requiring the commitment of a full theme park day. When winter doldrums hit next year, we know exactly where we'll be heading!
Shop our looks from the weekend:
