Universally seen as a great destination for the kids – Orlando and its sister-city Kissimmee offer another side that is just as appealing to us grown-ups.

I’ve had a long, if not regular, relationship with Orlando, and like most of us it started as a child with a visit to Walt Disney World.

Accompanied by both parents, I was the “only” child again (with my diapered and bawling younger siblings thankfully forgotten somewhere back in the cold North with an aunt or two). Disney World was the highlight of a week-long mid-December trip to Florida, a full day and night at the recently-opened theme park, the likes of which the world had never seen. (Quick fact, 51 of Anaheim’s Disneyland could fit inside the massive area that Disney World takes up.)

A shorter, nostalgic return visit to Disney World as a group of late-teen “springbreakers” thanks to a spontaneous side-trip on the drive back to Canada was understandably less magical, perhaps spoiled by the preceding week’s festivities and teenage years spent at a world-class domestic theme park back home.

On a leisurely, month-long road trip in my late 20s with my new wife, a red two-seater convertible with two sets of golf clubs in the trunk we rolled into Orlando on a whim, took in Epcot Center for a few hours, which we loved, and then we were on our way. Once again, it had been a strategic hit focused on a Disney theme park experience. A couple of later visits were very quick, deliberate and all business.

Recently Orlando beckoned again, but this time it was for a major travel industry conference and, thankfully, several extra days to finally get to know the region properly.

Whether it’s romantic getaways for couples, guys/gals trips, group celebrations or business gatherings – Orlando-Kissimmee does it well. It’s safe to say there are 365 days of activities, food & fun that don’t include a theme park.

Kissimmee and Orlando: a quick explainer

Kissimmee and Orlando

The Greater Orlando metropolitan area encompasses a few counties and several municipalities, the largest being the city of Orlando itself and, just to the south, its smaller sister, Kissimmee. The best known attractions of the area are generally found in close proximity to both cities and a stunningly huge selection of accommodations available to visitors are shared between them and their respective counties, Orange and Osceola.

Both are similarly close to the Orlando International Airport (Florida’s busiest), which funnels a large share of the over 75 million annual visitors to the region. If you’re focusing on the many theme parks and other attractions, nature experiences, golf and a generally more relaxing experience, staying outside of Orlando proper and heading towards Kissimmee is a popular choice.

Orlando is a full complement city, with a couple major league sports teams (NBA and MSL), performing art centres, museums, theatres, shopping areas, several excellent pedestrian zones, world-renowned nightlife and a wide and varied restaurant scene (some boasting recently-awarded Michelin stars.) Orlando also hosts the second largest convention centre in the US.

Where to stay

This is a tough subject to tackle, because there are so many options, on a scale that does not seem to be replicated elsewhere in the US, or in the world for that matter. Options run from high-end luxury golf resorts, spa retreats, exquisite 10 bedroom villa rentals to more affordable hotel, townhouse or even camping options. And everything in-between.

As we typically focus on getaways with a significant other, or with an adventurous group of friends (no kids please!) – we have a few suggestions based on our most recent visit. We’ll add more as we discover and vet them.

Rent the vacation home of your dreams, big or small

Feel like avoiding the hotels and resorts and getting a place to call your own, if only for a week? Kissimmee alone boasts over 22,000 vacation homes, and not surprisingly is often called the “Vacation Home Capital of the World.” From a cozy, affordable one-bedroom condo to a jaw-dropping, far less affordable 18-bedroom mansion, you’ll find something that suits your style and budget. Visit the Kissimmee vacation home rental portal or Orlando portal to get started, or just to have fun browsing.

We spent a few days at the Magic Village Yards, in a wonderful 4-bedroom, two-story townhouse located in Kissimmee near many of the attractions. Inside a quiet gated community of similar 3- and 4-bedroom units, with a large community pool (that was peaceful and uncrowded during our stay) and a concierge/reception building at the front of the complex. Each residence was elegantly furnished, with a small patio (with BBQ) out the back. These were great for a few couples or a group of friends looking for a place to call their own during their Florida stay.

Magic Village Yards

If you have a really large group, and a healthy pooled budget, you may want to go really big and look at the large selection of monster villa/mansions. We were wowed by one of them, large enough to comfortably host our travel media party of at least 60 people for the afternoon in its 12 bedrooms and massive common areas inside and out.

vacation home

Reunion Resort & Golf Club

This is a luxury vacation destination that offers a variety of amenities for all types of travelers. The resort features spacious vacation homes and villas, three signature golf courses designed by Arnold Palmer, Tom Watson and Jack Nicklaus, multiple swimming pools, tennis courts, a fitness center, water park, and a variety of dining options. Whether you’re looking for a relaxing golf getaway with the guys or a romantic retreat, Reunion Resort & Golf Club has something for everyone.

Tuscana Resort Orlando by Aston

A Mediterranean-style vacation resort featuring spacious one, two and three-bedroom apartments, all fully-equipped kitchens, private balconies, perfect for couples or groups of friends. The resort’s amenities include a heated outdoor swimming pool, a hot tub, and a fitness center. The Tuscana Resort Orlando offers the nice blend of comfort, convenience and affordability.

Margaritaville Orlando Resort

Margaritaville Orlando Resort

We had a full tour of the property and several suites – and this was a winner (even sent images to my sister as a place to consider buying into at some point in the future). It’s a brand new (2019) tropical-themed resort located in Kissimmee on a massive property. The resort features stylish guest rooms and suites with Caribbean-inspired décor and offers a variety of recreational options and of course, several bar and dining options, including the LandShark Bar & Grill, which serves up classic American fare and tropical drinks, and the 12 Volt Bar, which offers poolside drinks and bites. Within walking distance you’ll find The Promenade at Sunset Walk, a nicely curated main street open to everyone with a nice selection of dining, retail, and entertainment options. The Margaritaville Orlando Resort offers a fun-filled, laid-back vacation experience that is sure to be a hit with anyone.

What to do

Everyone knows about the theme parks, well at least some of them, and for every one you’ve heard of, there’s at least a dozen more you haven’t. While a few are tough to ignore (we love Epcot), Kissimmee has been actively promoting the many nature-based activities that abound in the region. Central Florida is a lush green land of lakes and swamps and waterways and abundant wildlife.

Wild Florida Airboats & Gator Park

Wild Florida Airboats & Gator Park

If you’re in Central Florida you’re definitely in gator country. This nature park offers visitors a chance to explore the Florida wilderness up close. The highlight for us was the airboat ride through the swamps and marshes of the Florida Everglades, particularly Cypress Lake, where you can see a lot of alligators, birds, and other wildlife in their natural habitat. As a long-time birder and nature photographer I really enjoyed the experience and the natural setting.

Wild Florida Airboats & Gator Park great blue heron

There is also a gator park and a small zoo where visitors can see native Florida animals like deer, wild boar, and panthers. In addition to the airboat rides, Wild Florida Airboats & Gator Park also offers visitors the opportunity to take a guided fishing trip, or to see the Florida wilderness from above with the park’s swamp buggy tours.


Should I be doing this?

Celebrating a 75th anniversary next year, Gatorland is a 110-acre theme park and wildlife preserve featuring thousands of alligators and crocodiles, animal shows, a breeding marsh with boardwalk and observation tower, petting zoo, free-flight aviary and nature walk. A highlight was the multi-stage zip-line adventure that has you soaring quite above the park, and the alligator ponds below. It offers an incredible up-close look at these prehistoric beasts, especially at feeding time – with very knowledgeable and passionate park staff, many of them biologists.

Orlando Tree Trek

Orlando Tree Trek

Over the last few years, treetop trekking has really grown in popularity, and Orlando Tree Trek is a great way to give it a shot – an interesting course in a lush Florida forest with good gear, safety rigging and friendly staff to “show you the ropes!” And a couple advanced course if you know what you’re doing. As a bonus there is a separate, and decent length zip line to try.



This region is golfer’s paradise, particularly for Canadian golfers escaping cold weather – there are plenty of courses to play with a range of prices and quality. Here is a link to the Orlando and Kissimmee golf course guides.

Shop a little, shop a lot

With 75 million-plus visitors coming into the 3rd largest metro area in the state, you can count on a fabulous shopping options. Go big with The Florida Mall or The Mall at Millenia, or browse smaller boutiques in ICON Park, Pointe Orlando or free-admission Universal City Walk and Disney Springs.


Take in a game

orlando magic nba

You have your choice of NBA basketball with the Orlando Magic, a Major League Soccer match with Orlando City SC, a women’s soccer team, and a variety of minor league teams. And the Houston Astros have their spring training camp in Kissimmee.

Eat, drink and be merry

With an incredible number of tourists and convention visitors to the region, you can count on “astronomical gastromical” possibilities. We were in town for the official announcement the Michelin was going to be adding a number of star-worthy Orlando restaurants to their new guide. Here are 24 very happy Michelin approved Orlando venues.

immersion fine dining orlando michelin star