The Art of the Long Weekend

If you are a 9-5er like me, you are probably limited to a set amount of vacation days per year. This doesn’t mean that you can’t go anywhere though. Most Americans are trained to take their one week-long vacation per year then sit on the rest of their vacation days until they roll over to the next year. Weekends are then spent catching up on chores and errands that they didn’t get to during the week. Sounds pretty depressing if you ask me. I’m here to tell you, that the art of the long weekend is the answer that you’ve been looking for!


Strategically Placed Vacation Days

The stress of using vacation days is real. I get it. But there’s this magic thing called the weekend, where two days off consecutively lineup every week! Throw an extra vacation day on either end of it and you have created a long weekend.

Thanks to Holidays like Memorial Day and Labor Day, we get this “long weekend” treat scattered throughout are year. However these weekends are usually littered with family parties, weddings, or graduation parties. This is why it’s important to create your own long weekend opportunities scattered throughout the year. Adding a third day creates just enough time to get away and make the best of your time off.

Whether you are hopping on a flight or driving a few hours away, getting up early on a Friday morning leaves plenty of time at your destination to enjoy a Friday night, a FULL Saturday and a lazy Sunday morning. This is plenty of time to explore, relax, party or visit with people.


Exploring Your Own Backyard

Obviously the easiest and most affordable option for a long weekend is to travel close to home. If you’re lucky like I am to be from New England, there’s literally hundreds of great destinations just a few short hours away. This might not be as simple for larger states, where cities are much more sparse and spread out. However, you’d be surprised at what you can find near your hometown!

Especially with things like the growing independent craft beer scene, there are an increasing amount of areas worth visiting for the food or drink alone. Websites like Airbnb also are promoting the smaller areas where you won’t necessarily find the large hotels, but plenty to see when you get there. Not only are Airbnb’s typically affordable, but sometimes you’ll get a run-down of what to see, do and eat in the surrounding area from a local. Just because it’s not a big city, doesn’t mean it’s not worth discovering!

There’s so much more to see and do beside NYC and Boston. Burlington, Vermont and Portland, Maine are just a couple of the smaller cities making a name for themselves in New England. Not only have they created a fantastic food and drink scene but they have created cultural draws as well. Besides cities, there’s hiking opportunities all over Western, Mass all the way up through New Hampshire, beach town getaways from the coast of Connecticut right up along the coast of Maine, and plenty of small towns to explore ranging from the outskirts of Boston to the North corner of Massachusetts.

ProTip: Spend some time exploring hashtags on Instagram like #ExploreNewEngland and #VisitNewEngland for some travel inspiration!


Airbnb and Hotel Stays

As I mentioned in the last section, Airbnb is a service that has opened up a lot of options for where to stay on your travels. Because Airbnb’s are run out of people’s homes, this opens up more of a variety for locations to visit and stay at rather than city centers and hotels. Prices may range anywhere from $30 for a private room in someone’s home to $100 and up for full apartments or homes.

(If you book your first Airbnb through my link, you can get a $40 credit towards your first stay! Click Here!)

Another affordable option is camping, which though warm weather is necessary, can be booked last minute for spontaneous getaways. My boyfriend and I chose to camp on Martha’s Vineyard, Massachusetts this summer and were able to book it just two weeks ahead of our travel date! You can typically get a campsite for much less than an Airbnb or a hotel, however camping gear is required, and the initial investment in that can be pricey.

If you are looking for a little more luxury when you travel, there are plenty of travel hacks for booking affordable and/or last minute hotel rooms! Websites like Roomer give you access to all the last minute cancellation rooms for a cheaper price if you’re flexible with where you’re staying. Priceline also is a great option for super last minute travel for cheap prices.

Groupon offers hotel stays in a lot of the major cities across the world. Though they tend to have specific dates that you’re required to travel within, they often are expensive hotels for affordable prices so it’s worth it!

ProTip: One of the best and most old fashioned travel hacks: Call hotels and ask for deals! Never hurts to ask!


Cheap Flights and Spontaneous Travel

If you’re looking a destination a bit farther from home, there are a ton of resources to use to try to score affordable flights. If you’re open to budget airlines and spontaneity, it helps to bring prices down even more.

In America, our options for affordable flights are limited but budget airlines are constantly spreading to more airports, giving us more opportunities than ever. Spirit Airlines, Frontier, and Allegiant are some of the budget airlines offered throughout the country. Spirit just recently began flying to Hartford’s Bradley Airport so I was able to experience a budget airline for the first time this past weekend!

I scored some cheap round-trip tickets to Tampa for my boyfriend and I to visit his Mom before the holidays. People were warning us left and right about this airline so we were a bit hesitant to book at first but it worked out perfectly! I quickly learned that the downside of budget airlines is the crazy amount of fees they sneak in. All in all though, it was still cheaper than a flight through a major airline.

ProTip: If you can opt to fly with only a personal item (backpack or small tote bag) like we did, you can save yourself at least $30.

One of the best travel hacks I have is to sign up for emails from as many cheap flights sites as possible. They may seem like a nuisance when you aren’t actively looking for flights but they will come in handy for those spontaneous getaways!

Here’s a list of just some of the emails I receive daily keeping me posted on all the 48 hour sales and cheap flights to anywhere in the world:

You can choose to either sign up for specific flights to track the prices or just receive alerts for cheap flights out of your chosen local airports. A lot of the deals won’t last long, hence the spontaneity aspect of it but you’ll definitely snag some good deals if you act quick! It also pays to sign up for emails from airlines specifically because they will blast out when they are having flash deals on flights.

If you prefer not to have your inbox inundated with emails, there are a couple apps that will help you as well.

Skyscanner Mostly used to track flights and watch the price changes, however this app has a feature called “Explore” that allows you to find the cheapest flights from your airport to anywhere based on week or month. You can even look for the cheapest flight out this weekend if you’re feeling like running away soon!

Hopper – A great tool for selecting and watching flight prices. Hopper also shows you a monthly view that makes it easy to estimate when prices are going to drop, and if it’s cheaper to shift your flight days by a couple days or couple weeks. You’ll get an alert on your phone telling you to “Buy Now” when the prices drop to the lowest predicted price! I’ve used this app for every trip I’ve taken in the last three years!


Our Long Weekend Getaway to Clearwater, FL

My boyfriend and I just came back from a long weekend down to the Gulf side of Florida. Since he has family there, we were lucky enough to have a place to stay once we arrived. By snagging the cheap tickets on the budget airline, we were able to save even more money.

Our flight took off at 7:30 AM on Friday morning and we arrived in Tampa Airport by 10:30 AM. I highly recommend booking the earliest flight out as possible to take full advantage of your weekend away. We basically had a full day Friday and a full day Saturday in Florida, which made it worth the trip.

ProTip: If you can snag a red eye overnight on a Thursday, even better! (However steer clear of these flights if you can’t sleep on planes. Not worth the fatigue when you only have two days to enjoy in your destination!)

After spending a great weekend with his family, we took a leisurely 12:30 PM flight back on Sunday. We arrived back home early enough to get a load of laundry in before the work week!

That’s about as successful as a long weekend adventure can get 🙂


Let me know if any of you have fun long weekend plans coming up! I’d love to hear about them!

Stay Wild and Adventure on!



  1. I could not agree more, I’m constantly preaching the value of a long weekend–I’ve done 2-3 days in Sweden, Istanbul, and am headed to China as well with just a long weekend and a cheap flight!

  2. This is an amazing post! I love the long weekends and definitely take full advantage of them when I can. I believe in the US we deserve more than a week or two for vacation. I need to look into those websites about flights! Thanks for the helpful tips!

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