Your Guide to Living It up After Tax Season, Part I


Vacations, Flights, and Travel

What’s the best way to get through the long nights, long days, and long forms that tax season brings?

Planning your triumphant celebration when it’s all over.

Don’t worry, though. We’ve done all the legwork to bring you the best options for post-tax season travel and indulgence.

So, whether you’re dreaming of a weeklong trip to Hawaii (WITHOUT your calculator. Sorry, buddy) or just looking forward to a cold beverage and the freedom to binge watch “Unbreakable Kimmy Schmidt,” take a few minutes to bookmark this post.

Consider it your beacon of hope for the stolen moments after you finish a stack of 1099s.

The sheer number of websites claiming to get you the best deals on flights have, ironically, made it hard to know which site REALLY has the best deal.

So, what’s an accountant to do? Take a page from Scott Keyes, the flight guru. He’s gotten so good at flying cheap — or even flying for free — that he’s written countless articles with his top tips. He even has a mailing list of the top cheap flights he finds, which you can subscribe to here.

Scott says, “If I could recommend one website for people who want to get good deals for their flights, it’s”

Why? It’s a hub dedicated to finding “fat-finger discounts,” or incorrectly entered flight prices. You’ll have to jump on them quickly before they’re identified and fixed (most disappear within an hour or two). But if you’re flexible on your destination, you can snag an incredible deal (think a round-trip flight to Italy for $60 instead of $600).

If you have a specific destination in mind, try Skiplagged and ITA Matrix for more incredible deals on flights (Scott-Keyes approved!).

So, where will you make your getaway? We have 10 can’t-miss options for you to consider!

All-Inclusive Options

Let’s tackle this one first. Because after you spend four months in go-mode, a vacation destination where you don’t have to worry about a thing is just the ticket.

Here are your 2017 best bets for all-inclusive vacation destinations:

The Iberostar (Montego Bay, Jamaica)

If you’d like to bring the family with you on your getaway, this resort is a terrific option for traveling all-inclusive with kids. You’ll have access to snacks, food, and room service 24 hours a day, a kids club filled with fun activities for all ages, watersports galore, and, of course, your own private beach in sunny Jamaica.

Royal Hideaway Playacar (Playa del Carmen, Mexico)

If an adults-only adventure sounds more appealing, the Royal Hideaway Playacar is a must-visit. Sip cool drinks all day long on your private terrace, soak in your own hot tub or hammock, and order room service when you get hungry. The resort also includes six pools, massage centers, and lots of dining options. Everything is included, of course!

Secrets Maroma Beach Riviera (Cancun, Mexico)

The rooms at this place are worth the trip alone: Four-poster, canopy king beds, private terraces and hot tubs, and elegant decor with views of the ocean or cultivated gardens. You’ll have access to a private beach, an amazing pool (some rooms even have swim-out access). Along with the typical all-inclusive amenities, Secrets also boasts an impressive golf course and green fees are covered!

Zoëtry Agua Punta Cana, Dominican Republic

White sand, crystal-clear water, and thatched suites that include all the creature comforts you could ask for. The setting is relaxing and indulgent, so get ready to relax like you’ve never relaxed before. Dining is world class, with organic food and beverages, sparkling wine, and fresh fruit delivered to your room daily, a mini bar that’s refreshed twice a day, two infinity pools, and complimentary massages and beach horseback riding.

BodyHoliday at LeSport, St. Lucia

The name says it all: This resort is a holiday for body and soul. Tucked into a secluded sugar-white sand beach right on the edge of a tropical rainforest, BodyHoliday is the epitome of paradise. Dine at five-star restaurants with organic ingredients (grown right on site!), and spend the day sailing, playing golf, scuba diving, or relaxing on the beach. No detail goes overlooked here, so toss the tax returns aside and get ready to relax.

Best Vacation Spots in May

Not interested in an all-inclusive adventure, but want to get away somewhere fabulous right after tax season? These destinations are at the top of their game during the month of May!

Cannes, France

There’s arguably no better time to visit this sunny seaside town in France than in May. The annual Cannes Film Festival takes place here every year. It’s frequented by Hollywood stars and boasts some incredible film achievements. While you’re there, spend some time relaxing on the gorgeous beaches Cannes is famous for!

Louisville, Kentucky

May is a gorgeous month in Kentucky, and it hosts the first leg of the Triple Crown! Find the biggest hat that will fit in your suitcase, and head over to Louisville to sip a mint julep and watch the ponies do the work! While you’re there, enjoy some incredible BBQ and Louisville chili, and visit Waterfront Park.

Charleston, South Carolina

Charleston is not only beautiful during May, it has the benefit of charming beaches (don’t miss Folly Beach!) and a thriving city to explore. Take a relaxing tour through Battery Park to explore the historic mansions. Then tour plantations that have been preserved from the old South, enjoy the city’s hospitality and unique cuisine, and spend an afternoon at Sullivan’s Island.


If you’ve ever wanted to visit Greece, May is one of the best times! It’s less crowded than usual, with lower prices and gorgeous weather, making May the perfect month to enjoy fresh seafood, picturesque beaches, and easy access to tours of the ruins and cities. You’ll obviously want to visit the Acropolis and the Parthenon, but don’t forget gems like pink-sand Elafonissi Beach!

Boise, Idaho

We might be just a TAD biased on this one, but really, Boise is an incredible place to visit. Vogue ranked Boise as one of 2017’s top places to visit! After tax season, enjoy the endless recreation opportunities just a short hop away from the capital city of Boise (like world-class whitewater rafting, fishing, mountain biking, and hiking). May is one of the best times to visit Idaho, with summer activities in full swing.

Tax season is rough, but that just means your celebration, when it’s all over, will be all the more deserved.

Here’s to our savvy, hardworking accountants everywhere. May this year’s post-tax celebration be the best yet!


  1. DIane Aull says:

    Great suggestions! One small point of correction, though. Charleston is in SOUTH Carolina. I know “the Carolinas” get lumped together frequently, but as a native of SC and a current resident of NC, I know the people in BOTH states kinda hate “their” state to be mistaken for “the other one.”


    Myranda Mondry Reply:

    @DIane Aull, good catch! As a native North Dakotan, I totally get it.


  2. Since you went to Greece, I’ve got to add Malaga, Spain to the list. I visited last May for a wedding, and it was AMAZING. Just don’t do what I did, and accidently drive your rental car into town during one of the many nighttime celebrations. The police seem to frown upon tourists driving through large crowds simply because you missed the turn to the garage. :-)


    Myranda Mondry Reply:

    @Jason Spencer, great suggestion! (And great advice!) ;)


  3. Catherine Jude says:

    Amazing post. I will go Mexico in next month I guess there in Mexico are many places for visit. Any suggestions?


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