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Should I Stay or Should I Go? 8 Things to Consider Before Taking An Extended Vacation

Whether the travel bug has bitten you or you’re just looking to deep-six your nine-to-five for a little while, it’s probably time that you took a vacation. The first question you’ll need to answer is how long you’ll be gone on your stress-melting getaway.

You could go for a few days or a week, but if you’re feeling particularly burned out, you might decide to cash in all of your PTO at once for an extended vacay. No matter which route you choose, there are some things you should consider before you book your tickets.

The extended travel checklist

A checklist is the first thing any traveler needs to keep all of their ducks in a row. Clothes, toiletries, identification, and payment methods are the must-haves of any trip, but for an extended vacation, you’ll need to be more in-depth with your toolkit.

For example, do you receive regular packages or mail? If you don’t make arrangements for your correspondence, you could come back to a mailbox bursting at the seams or worse–an empty, thief-pleasing box. Instead of leaving your post to chance, you should choose a virtual address service like iPostal1 before you go. A virtual address is a physical location that receives mail for you while you’re away, meaning you’ll never have to worry about porch piracy again.

Your checklist should also include things to manage and enjoy your trips, such as a cellphone (and charger), headphones, itinerary and documents, and a travel-sized first aid kit. Extended travelers should also consider different seasons of clothing (summer to winter, for example) and a map of the best hostels and hotels in each new area.

Now that you’ve got a travel toolkit even Gulliver would be jealous of, it’s time to explore the nitty-gritty of your vacation’s length.

Is shorter better?

First, decide if you’re better off with a short break vs. an extended vacation. While sometimes you wish you could stay on vacation forever, other times you need a getaway from your getaway if things drag on for too long.

Knowing your needs might seem easier said than done, but it’s significant when considering vacation length. Will you miss the comforts of home? Are you aimless without a job to keep you busy? While some might enjoy lazing in the sun for weeks at a time, others are sure to go stir-crazy with so much time on their hands.

Another benefit of the shorter vacation is the loved ones left behind. It might be your pet, your friends, or your family. But, unless they’re coming with you, you’re disconnecting from your usual contacts.

That said, sometimes a more extended vacation is what you need to recharge from the stressors of your work-life fully. Investigate your feelings and emotional needs before deciding how much time off to request.

What’s your budget?

Extended vacations can be particularly tricky for budgeting, as you need to plan for more of everything. Of course, that includes more hotel nights or rentals, more tourism, and more amenities. But, it also means budgeting for securing your home too.

Think about your subscription services. Are you taking a break from them, or will you want access during your vacation? What other everyday expenditures might follow you on your trip?

Are you considering insurance options? You might be okay with the basics, but travel insurance can minimize financial loss. Some examples include:

  • Trip cancellation or interruption insurance
  • Medical insurance
  • Theft insurance
  • Evacuati on insurance
  • Baggage insurance
  • Rental insurance

Most tourist destinations and tour groups can be pricey. So you might avoid ticketed events and venues, or you can prioritize them in your budget if seeing the sights is a must for you.

Create a budget that separates what you need and what you want, and be sure to build plenty of flexibility into the fabric of your savings.

Where are you traveling?

Where you’re traveling can dictate budget, pace, and time—for example, visiting a new city versus a new country versus a new continent. In addition, you might need time to travel between locations, time to explore each area thoroughly, and time to relax or enjoy some scenery.

You’ll also need to prepare differently depending on the region you’re exploring. For example, are certain vaccines or tools recommended? Should you learn a new language? Should you enroll with STEP (Smart Traveler Enrollment Program) to inform the nearest embassy of your arrival?

Think about the accommodations and amenities available at your destination. Will you have access to transportation, wi-fi, or electricity? Are you disconnecting from technology and staying closer to nature? Knowing the basics of what to expect will help you swerve past any nasty surprises.

Your home away from home

Where are you staying? Even if you’re the spontaneous type, it’s best to secure a roof over your head somewhere along the way. If you want flexibility, choose lodgings that allow cancellations without significant penalties.

Pick a home base wherever you’re visiting, whether it’s a foreign country or a new state. You might plan to visit every coastal town in a week, but you should have a specific place you plan to rest your head. Then, you can be flexible and proactive.

What accommodations fit your budget? It’s crucial to balance what you can afford and what will make your vacation worthwhile.

Overpacking vs. underpacking

No one enjoys packing, especially when you don’t know when you’ll see your closest again.

Study your destination’s weather and climate for the time of year you’ll be there and make a list of scheduled activities. It’ll help narrow down what you need to pack versus what you can scrap from your suitcase.

Some packing questions you should ask:

  • Can you easily mix and match clothes, or do you need specific outfits for special activities?
  • Is laundry an option?
  • Casual only, or do you have black-tie events?
  • What’s your luggage capacity?
  • Will you bring more than one bag?
  • Does your budget include buying extra baggage for souvenirs?

Making arrangements

Besides pet sitters and arranging with roommates and building managers, you should also arrange for other everyday needs.

If you have plants but no roommate, maybe give a spare key to a neighbor, friend, or family member. Your trusted keyholder might water plants, prevent dust bunnies, and do a general check-in for peace of mind.

Getting the go-ahead from work and other obligations

Now that you’ve made arrangements for your material possessions, it’s time to settle other affairs. Share your impending travel with your book club, bowling team, family, etc. Make sure your acquaintances know you haven’t mysteriously disappeared.

Depending on your work situation, you might negotiate for an approved extended vacation or give notice. Although an extended vacation might be more accessible with travel-friendly jobs that encourage nomadic lifestyles, don’t be discouraged if your boss isn’t on board.

It’s best to be considerate. Make a plan and arrange a meeting with your supervisor to discuss your itinerary. If you’re parting ways with your job entirely, two weeks’ notice is a common courtesy.

Solo vs. group vacation

The factor that impacts all other considerations: solo vs. shared. Budgeting for one or more, choosing activities everyone enjoys, picking travel destinations everyone likes, accommodation that fits the group, etc. Taking a group vacation can slash costs, but it can also complicate the details of even the most straightforward getaway.

The buddy system has its benefits, but it also involves compromise. Decide on ground rules before you go. If possible, plan a mini-vacation or weekend trip to see if your travel partner is a good fit. Discuss your budgets, pacing, and expectations before booking anything.

Wrap up

An extended vacation can breathe new life into your career and mindset, but it’s not without its own considerations. Whether you take off for a month or decide that two days’ worth is plenty for you, enjoy your vacation, and don’t forget the sunscreen.