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How to Pack Long Trips into Weekend Getaways

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The two-week vacation almost seems like a relic you’d find in Sub-Basement D of the Museum of Travel, if such a place were to exist.

Americans on average today only take 13 of their allotted 17 vacation days. The upshot is manifold. Not only does it mean that full two-week vacations, or even one-week trips, are becoming less and less frequent. It also means that when you crunch the numbers, there are more shorter vacations being taken.1

That brings us to weekend getaways, an increasingly popular alternative to one- or two-week trips that often couple the weekend with an extra day on either side: Friday or Monday. (Although there is some benefit to traveling from Thursday to Saturday; we’ll cover that further down.)

And don’t think that 72 hours is a mere sideshow to your traditional four-alarm family vacation. Oh no. With the right planning, itinerary, discipline and travel insurance plan, it’s possible to deflate a 14-day sojourn into a three-day getaway with fewer compromises than you might expect.

In this article, we’ll detail the upside and benefits of weekend getaways vs. traditional, longer vacations, provide some tips on how to pack an itinerary into just three days, and reveal some of the key reasons travel insurance is a must-have for shorter trips.

The Upside of Weekend Getaways

Let’s admit one thing from the get-go: there is still something very appealing about escaping your routine for one or two weeks, whether you’re skiing the slopes of Breckenridge or taming the waves of Tahiti.

But it’s just not always realistic or even possible. And repackaging a traditional long-form vacation into three days comes with plenty of appeal. First, there’s the spontaneity factor. Don’t underestimate the value of booking travel that delivers near instant gratification. You might spend months or more planning and anticipating your big summer family vacation, carefully coordinating where to stay for 10 nights, where to eat 30 meals, as well as plotting out all the other Xs and Os. But planning a weekend getaway is much easier. You can plan and book it over a coffee, waiting only weeks or even days to take off.

Then there is the no-brainer benefit of cost. Yes, traveling over the weekend may come at a bit more of a premium than during the week, in terms of hotel rates and airfare (more on this below.) But the fact that you’re only away from home for three-ish days presents a much more approachable budget. To illustrate this point, let’s do the quick and dirty math, comparing a hypothetical 3-day getaway to a 10-day vacation. Let’s assume that your daily spend per day for the three-day trip per person is $250, including accommodations, meals, and attractions. Let’s then assume that your average daily spend for that 10-day trip is $200, applying a bit of a discount to account for advanced booking discounts, weekday stays and other factors. That adds up to a grand total of $2,000 per person for the 10-day trip and $750 per person for the three-day trip. That’s a savings of $1,250 per person for the shorter trip!

There is also the anxiety of taking all your work vacation days in one big trip, as opposed to sprinkling some here and some there.

With all these factors taken together, it’s not hard to swallow the growing belief that shorter vacations are less stressful, with this peace of mind tied to everything from less time spent packing to lowers costs — and the fact that you’ll have more weekend getaways to look forward to down the road. It’s always a bit of a downer when you return from your one annual vacation in the middle of March — and have 12-months-plus before your next getaway.2

How to Fit a Traditional Trip into a Weekend Getaway

With a weekend getaway, it’s all about maximizing your time. Don’t worry, we have a few tips to get you there…

Choose the right destination

Not every spot fit for week-long itineraries (or longer) can neatly translate into weekend getaways. Take Sydney, which can take at least 22 hours by air to reach from the United States — for each leg. Similarly, some adventure travel, such as deep-woods hiking and camping, may be tougher to pack into a weekend than that 12-person tent. Instead, if you’re on the East Coast, look toward Charleston, which offers an array of attractions from visits to Fort Sumpter for history buffs to Lowcountry foodie stops (try the shrimp and grits at Hominy Grill) and quaint B&Bs aplenty. If you’re looking for something out West you can manage in an extended weekend, you can’t do much better than Austin. The “Live Music Capital of the World” owns its weirdness, and its Tex-Mex heritage runs rich whether you’re dining on “burnt end” tacos or watching the rodeo from the cheap seats.3

Carefully plan your escape

After choosing your destination, the next biggest factor in determining how much time you have to actually enjoy your destination is your method of transportation. If you’re flying, consider leaving on a Thursday and returning Saturday. It’s traditionally much more cost effective than the popular Friday-to-Sunday itinerary. 4 (Pro tip: before booking, also check to see if your flight or selected airport is plagued by delays or cancellations.)

Otherwise, don’t rule out Amtrak, which serves more than 500 destinations in 46 states.5 Traveling by train allows you to skip the time-intensive parking and shuttle routine, TSA checkpoints and more. We crunched the numbers. And, for example, if you’re considering a trip from NYC to Washington, D.C., it can take the same travel time as a flight — under four hours — but potentially cost hundreds of dollars less.6

Don’t get distracted 

If you simply plan on relaxing during your weekend getaway, whether it’s lounging by the beach or rejuvenating at the spa, then you can ignore this next bit of advice. If you have an aggressive itinerary, you need to stay focused. Resist the urge to sleep in, take the scenic route or wander down inviting, unmarked paths. It also means considering bypassing the crowds and long lines that come with the most popular attractions — unless that particular attraction is the top reason why you're making the trip — especially during a destination’s peak season. Also consider choosing accommodations and making meal reservations strategically, mapping locations out to minimize your commute times. (Pro tip: Trip Advisor does a great job of providing traveler ratings and reviews for the top attractions within a specific destination, so that could be an apt starting point for planning weekend getaways. Remember when we recommended Charleston above? They have written up a “Perfect Three-Day Weekend in Charleston.” Just saying…)7

Why Travel Insurance is a Must-Have for Weekend Getaways

Don’t make the mistake of thinking that just because a weekend getaway may be shorter and less expensive that you can forgo travel insurance.

Here are just a few examples of how travel insurance can come up big for small trips

When you need to cancel.

Most trips come with pre-paid, nonrefundable expenses, from attraction tickets to spa treatments. Here is the thing about shorter trips: they’re often planned on shorter notice than longer escapes. That increases your odds of having even more pre-paid, non-refundable expenses. This includes hotel rooms, which you may need to pay for in full vs. simply supplying your credit card number to put a hold on a room when booking further out. A travel insurance plan with a trip cancellation benefit can provide you one streamlined path for obtaining reimbursements in the event that you need to cancel your trip for a covered reason.8

When you make it to the destination. But your bags don’t.

On a week-long trip to Miami, a delayed, lost or damaged bag can be a minor convenience. But when you’re only in a city for a weekend, your wait or rush to replace needed items can critically impact both your itinerary and your budget. Look for a travel insurance plan that includes a baggage loss / damage benefit and a baggage delay benefit, which you’ll find in most Allianz Global Assistance plans. Even better, with the One Trip Prime or One Trip Premier Plan, you may be able to receive a fixed payment of $100 for a covered baggage delay that shows up right in your bank account — no receipt required.9, 10

These are just a few of the benefits that can perform the heavy-lifting to keep your weekend getaways on track. Others include trip interruption and travel delay benefits, 24-Hr. Hotline Assistance to troubleshoot travel issues and more. Now is a good time to find the Allianz Global Assistance travel insurance plan that’s right for your next weekend getaway.

With the right planning and execution, it’s entirely possible to shrink a traditional week (or longer) trip into weekend getaways. Sure, you’ll have to compromise here and there. And maybe even return to the destination to catch everything you missed the first time around. But experiencing a destination in 72 hours is becoming more practical and more popular.

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Mar 21, 2019