How to Plan Your Best Vacation

“One’s destination is never a place but rather a new way of looking at things,” wrote Henry Miller. So, how can you make your vacation feel truly rejuvenating? For the final post of our travel series, six travelers reveal their surprising tips — including the #1 thing to pack — for having the best time on vacation…


Eat a Progressive Dinner

“When I was in my twenties, I took a trip to New Orleans with my sister. One night, instead of committing to a single restaurant, we hopped to three different places, one after another. We asked what their big specials were, ordered one plate at each place and split it. Now whenever I travel, I plan out a progressive dinner. I pinpoint an area with enough spots that are ‘must-try’s, and I find out which dishes they do well. There’s so much good food! And if you think a place is overrated, no worries — you’re trying another place in an hour. I usually eat at the bar, which means I’m more likely to chat with the bartender or local people. Also, explaining what you’re doing is a great conversation starter — everyone wants to offer ideas. It always feels like an adventure, which to me is the goal of any trip.” — Beth Shapouri

Ask for Two Beds

“When my husband and I stay in a hotel, we always request two double beds, instead of one king. It started shortly after our daughter was born — we were in the midst of that sleep-deprived, new-parent haze. We actually booked a king bed at a hotel, but when we showed up to check in, they only had rooms with two doubles remaining (and apologized profusely for the error). That first night in separate beds was an ‘aha’ moment for both of us, and we’ve been requesting them ever since. You can “snuggle” together in one bed, and then you say goodnight and goodbye. I love to stretch out in an X shape, with my arms and legs in no danger of encroaching on someone else’s space. That’s a true vacation and one of the secrets to a happy marriage.” — Nicki Sebastian

Try Something You’ve Never Done

“This year, for my 30th birthday, I took myself on a four-day silent retreat. It was a chance to be by myself in a way that I never had been before, and to quiet my restless mind.

On the first day, everyone went to a big meditation hall to honor ‘noble silence.’ We gave up talking, reading, writing and using our phones. Even eye contact wasn’t allowed. That left eating delicious food, walking, sitting, meditating and sleeping in our own rooms. There was a woman there who was eight months pregnant with her second child and had done the retreat at the same point in her first pregnancy. (I found this out only later, when I could finally talk to her.) She told me it had helped bring her to a really calm place before the intensity of childbirth and new parenthood.

I knew being quiet for four days was going to be difficult, and in some ways it was even harder than I expected. (For example, the time I couldn’t get my room key to work and cursed out loud — my own voice caught me by surprise. You don’t realize how much you talk to yourself!). But while the world has so many amazing places to explore, there is so much that’s interesting going on inside ourselves. I was surprised by the depth of my internal world — so many thoughts about work, family, life and relationships.

When I got home, I felt ready to face things on a very even keel. I was even looking forward to the moments in life when my emotions would run high, so I could see whether I was better able to deal. And for at least two months afterward I was, for sure.” — Hayley Nichols

Pack a Uniform

“Back in the old days, BC (before child), I was a totally haphazard, stuff-a-million-things-into-a-bag-at-the-last-minute kind of packer, but now I like to take away variables and leave head space for enjoying the adventure. So, for trips, everything is navy blue. I have two pairs of pants, a simple stretchy skirt, a long-sleeved cotton shirt and a cardigan — ALL navy blue. I always pack a pair of dark jeans, a bathing suit no matter the season and in the summertime I throw in a pair of denim shorts. When I was a kid, we used to dress up for travel, and I’ve held on to that philosophy. Monochromatic dressing is an easy way to be both comfortable and pulled together, and I gravitate to navy because it’s as sophisticated as black but it’s still a color.” — Brooke Williams

Bring a Soccer Ball

“On a trip to London with our two boys, my husband had the brilliant idea of buying a soccer ball and carrying it around with us as we toured the city mostly by foot. Between the British Museum and the London Tower, we would detour through Hyde or Regent’s Park and kick the ball around with each other, and sometimes with other local kids. I would bring a soccer ball to just about any city that has parks and playgrounds. It’s such an international game, and a perfect way to break up a trip that involves lots of sight seeing and walking for kids.” — Pilar Guzman

Focus on a Few Blocks

“When we travel, my husband and I like to stay in local neighborhoods and inhabit a tiny radius, like just three to five blocks. We go to the same coffee shops and restaurants every day and establish daily rhythms. When we do this, travel becomes less of a vacation, and more like living part our lives somewhere else. It might sound limiting, but it actually feels really exciting, like you temporarily become a different person.

Last spring we stayed in Karakoy, an old Istanbul neighborhood, and everywhere we looked we saw straw baskets dangling from the sides of buildings. We had no idea what they were for. My first instinct was to feel compelled to put something in one of them. I thought, ‘I should put in a banana.’ (I didn’t.)

We talked about the baskets the entire time we were in Turkey. We obsessed over them. What were they for? Why were there so many of them? Often when I’m fascinated by something, I’ll try not to Google it right away, because it’s fun to live with mystery. But we eventually figured out they were simply an old-school way to get items from the street into upper-floor apartments. And because we were there during Ramadan, I could sit on the corner and see a dozen of them descend at dusk all at once and get filled with bread used to break the daily fast. Over time, we saw lots of other things being loaded and unloaded: fruit, sandwiches, bottles, money. We saw a group of kids playing a game by tossing their shoes into one.

Later, a friend from Istanbul told me he hadn’t seen baskets around the city for 15 years, so we’d managed to stumble upon a pocket of random tradition. If you were passing through the neighborhood you might have seen one, but it would have been a fleeting vision; you had to be there every day to really notice them. Experiencing the mystery of the baskets made me fall in love with Istanbul.” — Jennifer Brook


Thoughts? What little things do you do to make a trip feel epic? We’d love to hear…

P.S. 10 tips for traveling with a baby, and the weird thing we do on vacations.

(Illustration by Elizabeth Graeber for Fashion Melange. Soccer ball excerpt via Momfilter.)