City Hall: Center City Philadelphia

Center City is the place to be in Philadelphia during this most festive time of the year. While living in a suburb of the metro, I often visited this area especially around the holidays. There is a gorgeous ice rink and a lot of great restaurants. It’s a bustling center of activity all year-round, especially in the weeks leading up to Christmas. The annual tree lighting ceremony kicks off a long lineup of festive activities. The beautiful tree goes up early December at Wawa Plaza adjacent to City Hall.

The festive event includes live entertainment, a German inspired Christmas market, hot cocoa stands, and Ferris Wheel and holiday train rides. I love that the tree is topped with a Liberty Bell to reflect the city’s historical beginnings. As the “birthplace of our nation” is home to the Liberty Bell, this dazzling topper adds a touch of unique historical charm not found elsewhere.

Christmas tree with Liberty Bell topper in Center City Philly

What to do nearby: Philly is easily one of the best cities to plan a holiday getaway in the US, right up there with NYC in my opinion. There is really so much to do. Honestly, I was surprised that the city does not receive more media coverage. I absolutely love the 2 downtown ice rinks, the German market, and all the festive light shows. You can read more about my experience attending holiday events for the full scoop.

The Rink at PPG Place: Pittsburgh

After moving to a suburb just outside the city, I learned that Pittsburgh is an underrated holiday destination. There is a lot to do here during the month of December including a number of festive holiday light shows, an impressive German holiday market, and more ice rinks than you could imagine (it’s one of the best cities for ice skaters based on my persona experience).

I really love the downtown ice rink although it is crowded and a bit pricey. This 1 million dollar rink is larger than Rockefeller Center. The centerpiece of the rink is a dazzling 60 foot tall, LED lit tree which dances along to holiday music. I really love that you can skate around a big tree, listening to festive music and even enjoy a synchronized show – basically you get to combine multiple activities in the same place.

Beautiful Christmas tree in downtown Pittsburgh

What to do nearby: Shop for handmade German treasures at the People’s Gas Holiday Market. This is a fun time of the year with a lot going on. You have all the regular city attractions (I recommend the wonderful Carnegie museums) plus fun winter and holiday festivities. Check out my winter Burgh guide for more details.

Disney’s Grand Floridian: Orlando, Florida

Another gorgeous Disney resort to visit over the holidays is the impressive Grand Floridian. This is easily Disney’s most romantic, exclusive, and luxurious resort. The decor here is elegant, simple, and timeless. The main lobby tree is classy and gorgeous. I didn’t stay on-site, but I did enjoy strolling around the property. I imagine this would be a gorgeous destination for a couple’s holiday getaway.

Also, their extravagant gingerbread display is a whimsical sight for both the young and young at heart. I saw this spotlighted by the Travel Channel as well as in many other prestigious travel publications. The 2021 display celebrated Disney’s 50th anniversary. Live holiday piano music and gingerbread treats add to the excitement this time of year. If. you are seeking somewhere modern and elegant to stay, I would recommend this property.

Christmas tree at Disney's Grand Floridian in Orlando

What to do nearby: Make reservations for dinner at Victoria & Albert’s. The romantic tourist favorite is one of Orlando’s top rated restaurants.

Disney’s Wilderness Lodge: Orlando, Florida

Yet another gorgeous Disney resort, the Wilderness Lodge is the coziest and most festive of them all. This resort was modeled after National Park Lodges in the Pacific Northwest so it’s super rustic. The vibe is quiet and cozy, making it the perfect escape after a busy day at the parks. When I walk around here, I don’t think Florida at all. So this could be a good staycation choice for locals missing that northern snowy holiday ambiance.

With a grand fireplace and gorgeous decor everywhere, it’s no wonder this is one of the most popular resorts this time of the year – I have seen rates topping $500. It’s definitely the place to stay if you are seeking a cozy mountain-like getaway. While living in Tampa, it was a treat to enjoy a temporary escape from the Florida heat and palms!

Christmas tree at Disney's Wilderness Lodge in Orlando

What to do nearby: Enjoy a drink in the rustic Territory Lounge.

Disney Springs: Orlando, Florida

Disney Springs, the park’s fun shopping and dining oasis, is the place to go when you are not waiting in lines at the parks. In addition to shops, a theater, plenty of dining options, and live entertainment, the complex is totally decked out in holiday cheer.

In addition to seasonal entertainment, there is a year-round holiday shop with the cutest Mickey themed ornaments and souvenirs. I recommend enjoying a special holiday drink at Joffrey’s (they do character art lattes!) and picking up a delicious treat at Erin McKenna’s.

Beautiful Christmas tree at Disney Springs in Orlando, Florida

What to do nearby: Enjoy dinner at Raglan Road, an amazing Irish Pub featuring live step dancing performances