4 Cities to Visit for a Long Weekend

Spring is just around the corner, and this burst of warm weather in Eastern Canada has given me a taste of what’s to come this season. As a young professional, I relish any opportunity for an extra day off, whether it’s to sleep in or to get an extra day for travel. When you only have two or three weeks of vacation time, you have to take advantage of long weekends and holidays to make the most out of the time you have.

In anticipation of future holidays, I’ve come up with four cities that make great long weekend getaways. Whether you’re taking an extra Friday off or heading out first thing Saturday morning, these places have reasonable flights and plenty to see and do.

Orlando, Florida

As I’ve mentioned before, I’m kind of obsessed with Harry Potter, so it’s no surprise that Orlando is at the top of my list. For a long weekend, I’d mix some theme park time with shopping, food and drink, and hanging out by the pool. Sounds like the perfect Easter weekend to me!

There are plenty of reasonably priced Orlando hotels, including many IHG hotels near Universal Studios Orlando. That means lots of Wizarding World of Harry Potter, pool time, and fun in the sun.

New York, New York

In 2016, I headed to New York City for a long weekend, which included driving for 12 hours. We had roughly 48 hours in the city, and were able to pack in a lot.

Whether you’re driving or flying, NYC is the perfect long weekend getaway. Flights are very reasonable from the East Coast, and it’s great to visit during any season. With Victoria Day in Canada and Memorial Day in the U.S. both coming up in May, take in the beauty of NYC in the spring with patio drinks, strolls through Central Park, or one of the many festivals happening throughout the month.

Chicago, Illinois

It’s been a long time since I travelled to Chicago, but it’s high on my list of U.S. cities to visit for a long weekend. Only eight hours away by car or a quick airplane ride from Toronto, Chicago is a fun city, with lots to do and eat, like deep-dish pizza.

Besides eating everything in sight, taking a selfie in front of “The Bean,” and checking out Navy Pier, a long weekend in Chicago wouldn’t be complete without catching a baseball game. I’d love to watch the Toronto Blue Jays play, but I’ll take in a game at Wrigley Field on a beautiful day regardless of who’s playing.

Reykjavik, Iceland

You’re laughing and wondering how you can go to Europe for a long weekend, right? Well, let me tell you, you fly to Iceland. Rowan and I headed to Iceland last November for just five days. Take a few extra days off for an extended long weekend, and explore the beauty of Iceland.

Flying with WOW Air or Icelandair is really reasonable and super chill. If you’re only going for a weekend, you don’t have to worry about crazy baggage fees because you can travel light. There are tons of fabulous things to do all year round, including the Summer Solstice Festival.

What are your favourite long weekend getaways?

  • sofieyah l

    I am seriously considering going to Iceland soon…I really want to visit, but definitely not during winter xD


    • Victoria Stacey

      Do it! Winter is best to see the Northern Lights, but summer would be gorgeous!

  • Anna Hubbard

    Iceland is definitely on my travel list! And I’ll be going to Chicago for a few days this month!
    -Anna | http://www.fivefootandfabulous.com

    • Victoria Stacey

      I hope you enjoy Chicago!

  • I have been dying to go to Harry Potter World. Iceland is also on the list!

    • Victoria Stacey

      My brother was there yesterday and I’m SO JELLY!

  • Oh, so many great places here! I have definitely always wanted to go to Iceland though.

    • Victoria Stacey

      Do it! It was fabulous 🙂

  • Miss ALK

    I’ve been to 3/4! My mom is dying to visit Iceland though so she would love this post haha!

    xoxo A

    • Victoria Stacey

      She will love it!

  • Leeza Smith

    Im from Boston and try to see my BFF who moved to New York every chance I get! its SO much fun, and theres so much to do! I would love to check out Chicago, i went once when I was younger. Awesome city!

    • Victoria Stacey

      I’ve only been the once, but I want to go back! Same with Chicago 🙂

  • I used to think Iceland was a giant landmass of floating ice haha. Great picks!

    Alix | http://www.apintsizedlifeblog.com

    • Victoria Stacey

      It kind of is 😉 Thanks 🙂

  • These are some great destinations! Some friends of mine when to Iceland last May and they absolutely loved it. I definitely want to visit.
    Katie | Millennial on the Move

    • Victoria Stacey

      Do it! So worth it 🙂

  • Chloé Adams

    I’ve done all of these by Iceland on a long weekend! I love that idea.

  • Iceland is amazing! Hard to do in a weekend from the west coast, though. I keep thinking about doing a long weekend in Palm Springs.

  • Rachel Ritlop

    I’ve been to all of these except Iceland and love them all! great suggestions!

  • Ashley Mason

    Great choices! I’d love to go to NYC!

  • I would consider my husband and I pretty serious travelers (we’ve been to nearly 40 countries), but it’s amazing how little of the US I have seen. Take NY, for example. He’s been there a few times, but I haven’t, and we’ve been trying to plan a trip there for what seems like ages.

  • What a great list of places to visit! I’ve been to all but Iceland so that’s next on my list!

  • I was just telling my husband a couple weeks ago that I wanted to drive down to NYC for a weekend! This makes me want to even more!