The Best Vacation to Take at Every Stage of Your Relationship

• Where to Stay: Hudson Valley Cabin (from $155/night, sleeps 2); Miami Condo (from $106/night, sleeps 6); South Lake Tahoe A-Frame (from $180/night, sleeps 4)
• What to Do: Manitoga/Russel Wright Design Center (Hudson Valley); Vizcaya Museum and Gardens (Miami); Emerald Bay State Park (Lake Tahoe)

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.)

• Where to Stay: The Graduate Nashville (from $229/night); Fairmont San Francisco (from $243/night); The Emily Hotel Chicago (from $239/night)
• What to Do: Country Music Hall of Fame (Nashville); Fisherman’s Wharf (San Francisco); The Art Institute (Chicago)

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).

• Where to Stay: Mama Shelter London (from $185/night); Jaz Amsterdam (from $209/night); Clarion Collection Hotel Kompaniet Stockholm (from $155/night)
• What to Do: afternoon tea at Fortnum’s (London); Anne Frank House (Amsterdam); Fotografiska (Stockholm)

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.

• Where to Stay: Palais Sebban Marrakech (from $179/night); Hotel Antunovic Zagreb (from $142/night); Hilton Sukhumvit Bangkok (from $124/night)
• What to Do: Musée Yves Saint Laurent (Marrakech); Museum of Broken Relationships (Zagreb); The Grand Palace (Bangkok)

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.

• Where to Stay: Seacastles Apartments Montego Bay (from $70/night); Grand Harbour Apartment Cayman Islands (from $150/night, sleeps 2); San Diego Casita (from $159/night, sleeps 2)
• What to Do: Doctor’s Cave Beach (Montego Bay); Starfish Point (Cayman Islands); Balboa Park (San Diego)

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.

• Where to Stay: Mandarin Oriental New York (from $1,095/night); Stein Eriksen Lodge (from $409/night); Carillon Miami Wellness Resort (from $263/night)
• What to Do: Maternity Massage (Mandarin Oriental); Deserving Mothers Massage (Stein Eriksen Lodge); Salt Float Bath Therapy (Carillion Miami)

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 massages...you’re going to want one.

• Where to Stay: Outrigger Waikiki Beach Resort (from $215/night); The Breakers Palm Beach (from $690/night); Bermuda Grotto Bay Beach Resort (from $595)
• What to Do: sunset sail (Waikiki); Flagler Museum (Palm Beach); Bermuda National Gallery (Bermuda)

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.

• Where to Stay: Le Meurice Paris (from $1,909/night); Profumo Maison Ripetta Rome (from $211/night); Renaissance Palm Springs Hotel (from $169/night)
• What to Do: Musée Rodin (Paris); St. Peter’s Basilica (Rome); Palm Springs Aerial Tramway (Palm Springs)

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.

• Where to Stay: Kihei Condo (from $793/night, sleeps 6); Amelia Island Townhome (from $470/night, sleeps 6); Cape Cod Cottage (from $154/night, sleeps 4)
• What to Do: Kama’ole Beach Park (Kihei); Egans Creek Greenway (Amelia Island); Cape Cod Salt Water Taffy (Cape Cod)

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.

• Where to Stay: The Sarova Stanley Nairobi (from $122/night); Sheraton Towers Singapore (from $251/night); The Taj Mahal Palace Mumbai (from $192/night)
• What to Do: Nairobi National Park (Nairobi); Cloud Forest (Singapore); private sightseeing tour (Mumbai)

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.