How to Book a Bad Vacation: A Guide to Doing It All Wrong

Last updated on June 10, 2025

Vacations are supposed to be relaxing, memorable, and rejuvenating. But what if, instead of a dream trip, you end up with a disaster? Booking a terrible vacation is surprisingly easy if you know how to make all the wrong moves. Here’s a tongue-in-cheek guide to ensure your travel plans go completely awry. Or, better yet, learn from these mistakes and let a professional travel advisor save the day.

1. Skip All Research

Why waste time researching destinations, accommodations, or activities? Just pick a place randomly and hope for the best. Book that budget hotel with 1.5-star reviews or the “unbeatable” deal without checking what it includes. Chances are, you’ll find yourself in a noisy, inconvenient, or downright sketchy location.

**Travel Advisor Tip:** Travel advisors know the best neighborhoods, reputable hotels, and hidden gems—saving you from unpleasant surprises.

2. Plan Your Trip Last Minute

Procrastination is the key to chaos. Wait until the night before to book flights, hotels, and tours. You’ll either pay exorbitant prices or find everything sold out. Bonus points if you’re traveling during peak season!

**Travel Advisor Tip:** Advisors can help secure bookings in advance and often have access to exclusive deals or availability.

3. Choose the Cheapest Flights

That $49 flight with three layovers and a total travel time of 27 hours? Perfect! Don’t worry about connections, baggage fees, or seat selection. Arriving exhausted and frustrated will make your vacation all the more “interesting.”

**Travel Advisor Tip:** Advisors consider your budget but also prioritize convenience and comfort, ensuring a smooth travel experience.

4. Ignore Visa and Entry Requirements

Who needs to read up on entry rules? Just assume you can waltz into any country with your passport. Getting turned away at the airport or detained for missing documents will definitely spice up your trip.

**Travel Advisor Tip:** Advisors stay updated on the latest travel regulations and ensure you’re prepared with visas, vaccinations, and other requirements.

5. Overpack Your Itinerary

Book every activity, tour, and experience you can find. Who needs downtime when you can cram 15 attractions into one day? Overextending yourself guarantees exhaustion and plenty of frustration.

**Travel Advisor Tip:** Advisors craft balanced itineraries that allow you to enjoy your trip without burning out.

6. Forget About Travel Insurance

Travel insurance? That’s for worrywarts. Who needs coverage for trip cancellations, medical emergencies, or lost luggage? Wing it and deal with the consequences later.

**Travel Advisor Tip:** Advisors emphasize the importance of travel insurance and help you select the right plan for peace of mind.

7. Ignore Local Customs and Weather

Pack your summer clothes for a winter trip or dress inappropriately for cultural sites. Nothing says “tourist disaster” like being unprepared for the climate or offending locals.

**Travel Advisor Tip:** Advisors provide valuable insights on weather, cultural norms, and packing tips to ensure you’re well-equipped.

8. DIY Everything

Who needs help when you can do it all yourself? Spend countless hours scouring the internet, only to book conflicting reservations or miss critical details. If your accommodation doesn’t match your expectations or your tour was canceled without notice, so be it!

**Travel Advisor Tip:** Advisors take the stress out of planning by handling logistics and curating personalized experiences.

9. Forget to Budget Properly

Blow your budget on the first few days of your trip and spend the rest pinching pennies. Or, better yet, forget to account for currency exchange rates and hidden fees. Running out of money mid-vacation is a guaranteed buzzkill.

**Travel Advisor Tip:** Advisors help you create a realistic budget and ensure there are no surprise expenses.

10. Neglect to Read the Fine Print

Skip over cancellation policies, terms, and conditions when booking. Discovering that your non-refundable room is in a construction zone or your flight can’t be rescheduled will surely add drama to your trip.

**Travel Advisor Tip:** Advisors review all the details to protect you from costly mistakes.

The Solution? Work with a Travel Advisor

While this guide offers plenty of ways to ruin your vacation, it’s best to avoid these pitfalls altogether. Travel advisors are experts at transforming travel dreams into reality. They handle the nitty-gritty details, provide insider knowledge, and offer support before, during, and after your trip. By working with an advisor, you’ll save time, money, and stress—ensuring your vacation is unforgettable for all the right reasons.