6 Tips for Planning the Perfect Overnight Staycation

Published on: November 18, 2013 | Last Updated on October 10, 2019
Apple Store on Fifth Avenue

An overnight staycation can be the perfect antidote for seasonal doldrums. 

Sometimes an overnight staycation can feel like so much more than that. If you choose the right destination, get there early and stay late, you’ll feel like you have been there much longer. It’s a perfect solution for those who don’t have more time to travel.

You can read about our overnight stay at The Pierre, Taj Hotel in New York City, here. But below are some of the lessons we learned about planning an overnight staycation:

1) Think out-of-the-box and do something different 

To make it feel like a real vacation, choose a destination that’s different from the one you’re ordinarily accustomed to. Live in the city? Try the country. Live inland? Try the coast. Spend too much time in the car? Choose a walkable destination.

2) Choose a no-fly destination

You only have two days, so a nearby, easy-to-get-to destination will save you time and money. We could have taken the commuter train (Metro North) New York City but we found a discount coupon for overnight parking that made driving a more economical option.

Tip: If you need to park in New York or any other large city, Google the “name of city” and “parking” and “discount.” You’ll be surprised at all the options for printable discount coupons.

3) One night may be as satisfying as two

To save on hotel costs (or use the money for a more luxurious stay), plan an overnight rather than an entire Friday to Sunday weekend stay. When weekend occupancy rates are low (as they often are in cities), many hotels accommodate early check-ins on Saturday and/or late checkouts on Sunday. (Overnight will feel much longer than that!)

Another advantage of an overnight staycation: You will avoid the hassle of having to stop the mail or of finding someone to water your plants.

4) Pack ultralight 

With an overnight stay, packing is pretty effortless. In fact, all you really need is a toothbrush and change of underwear. You can take a change of clothes but the less you take, the happier you will be when you arrive home without excess laundry.

5) Plan one special event during your stay

Give yourself something to look forward to and something to look back upon—something you really enjoy. We could have opted for a Broadway show but since our plans were last-minute, we made Saturday night dinner reservations at the wonderful restaurant onsite at The Pierre.

6) Don’t over plan

Leave yourself time for spontaneity, unexpected surprises—and even a mid-day nap. We popped into the Apple Store, had lunch at a lovely brasserie on 57th Street, visited a public art exhibit in the park, and ate bagels and French toast for breakfast at Viand, a one-of-kind, hole-in-the-wall coffee shop on Madison Avenue.

Updated 11/18/18

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