Even though Orlando is my hometown of 25+ years, I’m still pleasantly surprised every time I visit. They’re constantly building, constantly growing, and constantly innovating. Plus, moving permanently to Tampa and temporarily to Maine has given me a newfound appreciation for even the most touristy Orlando treasures, like our arsenal of theme parks. When Kyle and I were invited to stay at the Loews Portofino Bay Hotel for the weekend, we accepted immediately. There’s something so romantic about this luxurious Italian-inspired hotel, and for a pre-Valentine’s Day getaway, nothing comes close to a long weekend in Mediterranean paradise. Keep reading for a full recap of our romantic weekend getaway in Orlando a few weekends ago– captured primarily through the lens of my iPhone. 

We left Tampa at dawn (or at least what felt like dawn) to beat Friday’s even nastier than normal I4 traffic, so our romantic weekend getaway in Orlando officially started in the early afternoon. We could’ve easily spent hours finding our way around the stunning Loews Portofino Bay Hotel property, but we settled for a short tour, followed by some much needed R&R before dinner. 

From the get-go, the Portofino Bay staff was even friendlier and more wonderful than we ever could’ve imagined. We were personally greeted by the hotel manager upon check-in, were given a direct line of communication to a private concierge, and were pleasantly surprised to find a sweet welcome gift in our room. Talk about hospitality. 

Since Kyle and I were technically celebrating an early Valentine’s Day, we wanted our romantic weekend getaway in Orlando to be as festive as possible. We graciously accepted invitations to Harbor Nights Romantico, an event held right under the twinkling lights of the Portofino’s picturesque Harbor Piazza. Two of my blogger besties, Ashley Brooke and Mash Elle, were also staying at the Loews Portofino Bay Hotel with their guests, so the entire weekend turned into an intimate group outing that we’ll never forget.

At Harbor Nights Romantico, we were treated to a variety of select red, white, and sparkling wines, plus mouth-watering gourmet food from each of the hotel’s on-site restaurants, live jazz, and a romantic Mediterranean ambiance. Oh, and as a classically-trained singer myself, I was absolutely thrilled when two opera singers emerged from a hotel balcony to put on an Andrea Bocelli-worthy surprise performance. Ah-mazing.

PS- Isn’t this watercolor maxi dress gorgeous? Just looking at the print makes me happy, and it’s one of my all time favorites. Click here for my full outfit details!

Side Note: I wasn’t at all familiar with it before, but Harbor Nights is a regular celebration at the Loews Portofino Bay Hotel! Click here to find out more about their upcoming annual events. Harbor Nights Primavera is April 21st, and my calendar has officially been marked!

We danced and drank until about 9:30 or so, when we finally headed back to our room for some quality alone time. Kyle and I were absolutely blown away to find out that Loews had sent us a tray full of delectable chocolate covered strawberries and bottle of champagne on ice. For an evening that really couldn’t be topped, they found a way to top it. And our entire tray of strawberries was gone in under five minutes. 

After a night in one of their plush king beds, we couldn’t get ourselves up fast enough to get our own breakfast in the morning– so naturally, room service was our only option. You gotta do what you gotta do. 

My lazy Saturday continued by the pool, while Kyle responsibly hit up the gym. The Portofino property has two incredible pools, one for families (complete with an insane water slide) and one strictly for adults. It’s really rare that Ashley, Michelle, and I are together all at once, so we opted for the adult pool to give ourselves the space, plus the peace and quiet, to chat.

In the spirit of togetherness, I ordered an obligatory mojito. Or five.

Before dinner, Kyle and I took some private time to explore more of the Portofino property. Staying at the Portofino really makes you feel like you’re planted in the heart of the Italian countryside. From the rich Mediterranean architecture to the lush and colorful landscaping, it’s literally a slice of European paradise.

You can also check out my resort-inspired outfit details here! This top is versatile enough that I was actually able to wear it twice for the same trip– once with shorts for lounging and once with high waisted flare jeans for dinner. 

And I mean seriously, look at that view!

Our whole group had reservations at The Toothsome Chocolate Emporium & Savory Feast Kitchen, so we took the (very handy) ferry from our hotel to Universal City Walk to walk around and explore before dinner. With the exception of college in Gainesville, Kyle has lived in Tampa his entire life, so he’s never really gotten to experience Orlando City Walk’s nightlife scene before. Ashley and I proudly showed him The Groove, The Hard Rock– where we had our 9th grade homecoming, and the rest of our somewhat embarrassing middle school hangouts.

The Toothsome Chocolate Emporium & Savory Feast Kitchen is still relatively new, so it was all of our first times. Without exaggerating, this place radiates a palpable energy of fun and temptation while spreading the scent of delicious baked goods throughout the entire stretch of City Walk. Also, there will be a line out the door, so be sure to make reservations, especially on the weekends. 

When I say to bring your appetite, I mean to bring your appetite. Between the six of us, we conquered just about every popular item on the menu. For appetizers, we ordered a round of truffle fries, two rounds of roasted brussels sprouts, coffee and chocolate stout chicken wings (which were rich yet shockingly delicious), baked brie, and a loaf of warm chocolate almond bread. It was all incredible, and Kyle was in heaven the entire time. For our entrees, Kyle and I split the Tour de France burger and fire grilled pork chop. My only regret is filling up on baked brie and chocolate bread before our entrees arrived… I was only able to take few bites of the pork chop before stopping myself to make room for dessert. No worries, though; Kyle finished the plate for the both of us. 

In addition to a menu of amazing and unique entrees, Toothsome is known for their outrageously delicious and totally share-able sundaes and milkshakes, served out of keepsake mason jars. As you can see, our table ordered ourselves quite a few to pass around. My personal favorite? The Chocolate X5 milkshake, which is served with chocolate ice cream, chocolate chunks, strawberries, chocolate sauce, fresh whipped cream, and chocolate spirals… with a cherry on top, of course. The Red Velvet and Brownie milkshakes are a close second and third. 

After dinner, we walked off our comatose state in the Toothsome gift shop, which turned out to be a colorful candy shop of sweet treats… on steroids. If you don’t have reservations and find yourself waiting for a table, proceed into the gift shop with caution. You will be tempted to eat everything in sight. 

After sleeping off all 8000 calories from dinner and dessert, we made our way to Universal Studios on Sunday morning to explore the newest additions to the Wizarding World of Harry Pottery. I hadn’t been to Universal in about five years, and since my last visit, they build a scene-for-scene replica of Diagon Alley, which was first on our hit list. 

You can’t have Diagon Alley without the Hogwarts Express, so we rode the train to Islands of Adventure to explore Hogsmead, drink some butter beer, and ride some of IOA’s best rides. My favorites? The Hulk and Dragon Challenge, previously known as Dueling Dragons before Harry Potter World was a thing. 

 A common misconception is that Universal is only good for Harry Potter World. I’ve been going to Universal long before Harry Potter existed, and Islands of Adventure has always been one of my favorites with and without Hogwarts. This may surprise you, but my favorite area has always been Suess Landing, which is a whimsical block of colorful scenery and all of your favorite childhood characters. Plus, a bunch of my high school friends used to work in Suess Landing, and I loved watching them run around in their crazy Dr. Suess-themed uniforms. 

At some point in the middle of our Harry Potter explorations, we stopped for lunch at The Simpson’s Krusty Burger. We ordered two Krusty Burgers with fries, plus a round of strawberry cupcakes… since we didn’t ingest enough sugar during either of the prior evenings. Kyle insisted on ordering Duff’s beer to pair with our Krusty burgers, and I gotta say, Duff beer really hits the spot on a hot Florida day. Another great lunch spot in Universal Studios is the Leaky Cauldron in the Wizarding World of Harry Potter, but it typically has much longer of a wait. 

We had a ways to drive, so we ended up leaving the park around 4PM and ending our romantic weekend getaway in Orlando with a final, first row ride on The Incredible Hulk roller coaster. The picture below pretty much captures how I feel every time I have to leave Universal, except I don’t ever actually lose my keys.

Again, we’re so grateful to the Loews Portofino Bay Hotel for being such gracious hosts. Kyle’s been begging to go back to The Toothsome Chocolate Emporium & Savory Feast Kitchen for another round of milkshakes, so hopefully we can make it back to town in April for the next Harbor Nightsl! If you’ve been planning a romantic weekend getaway in Orlando, be sure to check out the Portofino’s rates and availability here. Plain and simple, there’s no better hotel in the area. Also, if you’re looking for attractions that are a little farther off the tourist beaten path, here are 18 of Central Florida’s lesser known treasures. Happy vacationing!