The Best Vacation to Take at Every Stage of Your Relationship

Traveling together is one of the best ways to test your relationship—as they say, the experience can make or break it with friends and lovers alike. Taking a trip is often a revealing barometer, showing how your companion handles stress, unfamiliar situations and cohabitation. But the perfect couples’ trip can also really depend on where you are in your journey together. Here are the best ones to take at every single stage of your relationship, from your first anniversary to your 20th, and everything in between.

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best vacations for every relationship stage: a couple sits at a campfire roasting marshmallows
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After a Few Months of Dating: A Local Airbnb

It’s your first trip together—the time to see whether he leaves the toilet seat up and if you can handle being with him for 48 hours straight. Go somewhere stress-free and local, like a cozy ski cabin in Lake Tahoe or sunny beach destination (hello, Miami). Be sure to pepper in some activities as well to see how they handle doing things they’re not jazzed about. (Spoiler: red flag if all they can do is sulk and complain that they hate architecture and will die if you drag them to the Russel Wright Design Center.)

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Once You’ve Made Things Official: A New City

Yay! You’re a legit couple. Time to see how you tackle a new city together for a long weekend getaway. Book a fun hotel like The Graduate Nashville (hit up the Dolly Parton-themed White Limozeen rooftop bar) or go for a classic locale like San Francisco’s Fairmont hotel. Then, the true test comes with the itinerary—especially if you’re a planner and they’re not (or vice versa).

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For Your One-year Anniversary: A Weeklong International Adventure

International trips are challenging any way you slice them. Long-haul flights, culture shock, no more USD. Taking a week to explore a new country together will give you a feel for how cranky your partner gets after a red eye, how they handle foreign currency and customs and how the two of you get along in close quarters for an extended period. And of course, it doesn’t have to be a challenge—be prepared to have fun and celebrate a milestone marker. Make it easy, though, and stick to a country you can navigate (mostly) in English. We see afternoon tea at Fortnum’s and a morning at Fotografiska in your future.

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Before You Move in Together: A Bucket-List Destination

The decision to move in together is serious stuff, so why not do one last litmus test before locking yourself into a year-long lease? Choose a destination where you’ll both feel like fish out of water. That could be somewhere like Morocco, Croatia or Thailand, where you can see how you two do navigating the inevitable challenges of getting around. Doing so together will let you gauge how well you and your future roomie handle conflict.

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The Honeymoon: An Affordable Getaway

Holy crap, planning a wedding is expensive—we're looking at you, $1,500 floral arrangement. Still, you need a vacation, and lucky for you, there are plenty of relatively affordable spots that don’t require a $3,000 (or more) budget for the week. From Jamaica to the Cayman Islands and even sunny San Diego, these destinations offer plenty to see and do, relaxing beaches and prices that won’t break the bank.

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When You Get Pregnant: A Luxurious Spa

Hello, babymoon. If you’re looking to squeeze in one last trip before baby’s imminent arrival, head somewhere super-relaxing and stunning—may we suggest a hotel with an amazing spa? (New York’s Mandarin Oriental and Park City’s Stein Eriksen Lodge are a couple that come to mind.) Then bring on the prenatal’re going to want one.

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After A Year Of Parenthood: A No-Agenda Beach Vacay

Parenting is tough, huh? After a year of changing diapers, you deserve a little slice of paradise. And to go more than five minutes without someone crying or calling for you. Drop off your kiddo with some nice relatives and steal away to a resort where you can do nothing. From Hawaii to Florida and Bermuda, you’re not wanting options. You’ll come back refreshed and ready to handle the next toddler tantrum without batting an eyelash.

best vacations for every relationship stage: diners sit on a patio in trastevere, rome at sunset
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For Your Five-Year Wedding Anniversary: Somewhere Romantic

Five years of marriage calls for a little time to yourselves...and lots of vino. Head somewhere romantic and rekindle the spark—and sip on some of the best wines. Paris and Rome have your name written all over them, but if you want to stay stateside (with a little old-Hollywood glamour), Palm Springs can compete with the best of them.

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When You’ve Got the Kiddos in Tow: An Activity-Friendly Beach

Traveling with kids isn’t necessarily a vacation, but pick the right spot and it can be. One destination that is sure to work with the whole fam? The beach. From Kihei to Amelia Island and a classic New England summer on Cape Cod, you can’t go wrong. Pack the beach towels, a hearty picnic and all the outdoor toys, decamp on the sand and get ready to lay around in the sun. When the little ones are thoroughly entertained all day, you can almost relax and enjoy yourself.

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For Your 20th Wedding Anniversary: Something Majestic

The kids are out of the house! The mortgage is paid off! (Kind of…) You made it! If you can swing and are feeling adventurous, take a month-long journey to part of the world you’ve never been to—and go semi-permanently off the grid while you’re there. From a safari in Kenya to the dazzling lights of Singapore and the sights, smells and sounds of Mumbai, kick off this new life chapter with a spectacular, page-turning trip.

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Freelance PureWow Editor

From 2015-2017 Hannah Loewentheil held the role of Editor covering entertainment, food, travel and all things nyc.

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