How to Plan a Honeymoon That Actually Feels Like You

A practical guide to figuring out what you want, what you want to spend, and where in the world that might take you.

There is a point somewhere in wedding planning when people stop asking about the venue, the dress, the flowers and whether you've found a photographer yet and move on to a much more enjoyable question:

“Where are you going for your honeymoon?”

And you may have an answer. Or you may smile confidently while thinking, Excellent question. We have absolutely no idea.

Maybe you've saved an overwater bungalow in Bora Bora, a tiny hotel in Positano, a Japanese ryokan, an African safari and a resort in St. Lucia. One of you keeps sending the other reels of beautiful beaches. The other has a Google search history that suggests you're apparently touring every major city in Europe.

You know you want it to be amazing. You know approximately how much money you're willing to spend. You know this is your honeymoon, so it should feel different from just taking a vacation.

What you may not know is how to turn all of those ideas into an actual trip. That's where I would tell you to stop looking at destinations for a minute. Seriously. Close the 23 browser tabs. We're going to figure out the two of you first.

Before We Decide Where, Tell Me What Tuesday Looks Like

If we were sitting together planning your honeymoon, I wouldn't start by asking you to choose between Italy and Hawaii. I'd ask you to imagine one day of the trip. Not the Instagram version. Your actual day.

• You wake up. What happens next? 
• Are we sleeping until 10 because nobody has anywhere to be?
• Are you already dressed because there's a boat waiting downstairs?
• Are you drinking coffee on a balcony?
• Walking to a bakery?
• Ordering breakfast to the room and refusing to acknowledge the outside world until further notice?

Maybe you're heading out to hike, snorkel, explore ruins or see wildlife. Maybe you're wandering through a market trying things you can't pronounce. Maybe you have dinner reservations you've been looking forward to for six months.

Or maybe the entire plan is:

Pool. Book. Cocktail. Repeat.

Excellent. This is useful information. Because what you're describing isn't a destination. You're describing a feeling. And that's where good honeymoon planning begins.

“We Want to Relax” Is Where Things Get Interesting

Almost every couple wants some version of romance and relaxation on their honeymoon. The problem is that “relaxing” can mean wildly different things.

For one person, relaxation means an all-inclusive resort where someone occasionally appears to ask whether they'd like another drink. For another, it's three hours at a café in Paris with nowhere else to be. Someone else relaxes by hiking through Costa Rica.

And there are people who genuinely relax by waking up at 6:30 a.m. because they have timed-entry tickets to a museum. I know. Those people exist.

The question isn't whether your honeymoon should be relaxing. It's what relaxation looks like to you.

Try this together:

    Finish the sentence:

        Our honeymoon would feel perfect if we had plenty of ________.

    Then:

        We would be disappointed if we came home without ________.

    And finally:

        We absolutely do not want our honeymoon to feel ________.

Those three answers can tell me more than a list of ten destinations.

Now Let's Address the Two Different People Going on This Trip

You love each other. You've decided to get married. You may still have completely different definitions of a good vacation. This is normal. In fact, this is where honeymoon planning starts getting fun.

Maybe one of you is The Planner. The Planner has already researched restaurants and would like everyone to know that reservations open exactly 60 days in advance. The other person is perfectly happy to approve whatever The Planner sends over, provided there is food involved.

Or perhaps you're both planners. Godspeed.

Maybe one of you wants museums and history while the other wants beaches and nightlife. One wants a beautiful hotel. The other says, “Why spend money on the room? We're never going to be there.”

Neither person is wrong. The mistake is trying to solve the disagreement by picking one person's vacation. Instead, we build a honeymoon with rhythm.

Perhaps you spend four nights exploring and three nights doing absolutely nothing.

Maybe we choose a beautiful resort close enough to a town that you can leave when you get restless.

Maybe the person who doesn't care about museums discovers that a private food-and-history tour is considerably more fun than following someone holding an umbrella through six galleries.

Maybe one of you gets the sunrise hike and the other gets the afternoon nap.

The goal isn't compromise in the depressing “neither of us got what we wanted” sense. It's creating a trip where you both get moments that feel designed specifically for you.

Let's Talk About the Honeymoon Budget

Eventually we have to talk about money. And this is where honeymoon searches online can become spectacularly unhelpful. You search “How much does a honeymoon cost?” and get an average.

Great. Except averages don't know you. Two couples can spend exactly the same amount and have completely different trips. Imagine three couples each have $10,000 to spend on accommodations and experiences.

One couple says:

The hotel matters. A lot.

They choose the gorgeous resort and the room with the private plunge pool. They fly economy, eat casual lunches and spend entire afternoons enjoying the property they paid for.

Another says:

Food is basically the reason we travel.

They choose a charming boutique hotel and spend their money on a cooking class, tasting menu, winery, market tour and restaurants they've been dreaming about.

A third says:

We may never do this again. We want the safari.

So that's where the money goes. They stay longer in fewer places, keep other parts of the trip simple and protect the experience that matters most. Same budget. Completely different honeymoons.

So instead of asking:

    “Is $10,000 enough?”

I'd rather ask:

    “What do you want that $10,000 to do for you?”

That's a much more interesting conversation.

Pick Your Splurge

Here's an exercise I love. Separately, each of you chooses the two things you'd be most excited to spend extra money on.

Maybe it's:

• A spectacular hotel.
• The room with the view.
• Upgraded flights.
• An incredible dinner.
• Private tours.
• A boat day.
• Spa treatments.
• Adventure activities.
• More nights away.
• A completely ridiculous once-in-a-lifetime experience.

Then compare answers. You may immediately discover that neither of you cares about flying business class but both of you would happily spend that money on four additional days in Italy. Excellent.

Or one of you cares deeply about the hotel while the other wants experiences. Also excellent. Now we know where we're balancing. A honeymoon doesn't need to be luxurious in every category to feel luxurious. 

Sometimes luxury is a five-star suite. Sometimes it's having a private guide who makes an ancient city come alive. Sometimes it's getting off a twelve-hour flight and seeing someone holding a sign with your name on it. And sometimes luxury is waking up on Wednesday morning and realizing you have absolutely nowhere you need to be.

Okay. NOW We Can Talk About Where.

This is my favorite part.

Because now instead of asking:

    “What are the best honeymoon destinations?”

we can ask:

    “What destinations make sense for the honeymoon you've just described?”

That's how the map gets smaller. You want incredible food, history, beautiful hotels and days spent wandering? Now we're getting somewhere.

You want wildlife, adventure and a few days of serious relaxation afterward? Different map.

You want gorgeous water but know yourselves well enough to admit you'll be climbing the walls after four straight beach days? Great. We're looking for somewhere that gives you both.

You want to fly somewhere, check into one beautiful resort and make approximately zero decisions for seven days? I have no intention of turning you into cultural explorers against your will.

That's the point. The destination should fit you. You shouldn't have to fit the destination.

Then We Make the Checklist

Once we've figured out what you're actually planning, the logistics become much easier. This is when we start thinking about timing, seasonality and how long you can realistically be away. We check passports—preferably before discovering one expires three weeks before departure. We look at flights and accommodations. We talk about travel insurance. We check entry requirements. We figure out transportation. Then we identify the things that need to be reserved ahead of time.

Notice I said the things that need to be reserved, not every waking minute of your honeymoon. There is a dangerous moment in travel planning when enthusiasm turns into an itinerary that reads:

8:00 breakfast
9:00 museum
10:30 tour
12:00 lunch
1:15 transfer
2:00 activity
4:00 other activity
6:00 shower quickly
7:00 dinner

Congratulations. You have created a business trip. Please don't do this to yourselves. Book the experiences you'd be genuinely disappointed to miss. Protect those. Then leave some space.

Because you don't yet know about the café you'll stumble across, the bartender you'll start talking to, the shop you'll wander into, the beach you'll decide not to leave or the afternoon when you both look at the itinerary and say:

    “Do we actually want to do this today?”

You are allowed to say no. It's your honeymoon.

And When You Get There? Stop Planning.

This may be the hardest part for my fellow planners. At some point, the trip you've been researching for months becomes the trip you're actually living. Let it. Take the photos. Then put the phone away.

Order dessert. Take the longer walk back to the hotel. Stay for another drink. Skip something. Change your mind. Sleep late. Laugh when something inevitably doesn't go according to plan.

Especially that last one.

Because ten years from now, you probably won't remember whether you checked every item off the itinerary. You will remember the restaurant you accidentally found. The view from the balcony. The ridiculous taxi ride. The day it rained and you changed everything. The meal you still talk about. The thing one of you convinced the other to try.

Those are the stories that survive the trip.

Please Don't Plan Your Honeymoon for Pinterest

I say this while fully encouraging you to have a honeymoon Pinterest board. Pinterest is wonderful for discovering possibilities. So are Instagram and TikTok. But inspiration can quietly turn into expectation.

Suddenly a honeymoon is supposed to involve an overwater bungalow, champagne breakfast, flowing linen, strategically placed sunhat and two people who apparently never sweat.

That's one kind of honeymoon. It doesn't have to be yours. Maybe yours has hiking boots. Maybe it has street food. Maybe it has museums. Maybe it has roller coasters. Maybe it has a safari jeep. Maybe it has room service and absolutely no alarm clocks.

Maybe you've been dreaming about the same place since your third date. Maybe neither of you has the slightest idea where you want to go. You don't need to know yet. That's the whole point.

Your Wedding Is One Day. Your First Adventure Is a Whole Story.

If you come to me with a perfectly formed honeymoon plan, wonderful. If you come with 47 screenshots, three countries, two completely different travel styles and a sentence that begins with “Okay, this might sound crazy, but…” 

Even better - Bring me the budget. Bring me the wish lists. Bring me the non-negotiables. Bring me the place your friend loved and the hotel you saw once on Instagram. Bring me the thing one of you desperately wants to do and the thing the other has already vetoed. Bring me the “we don't know.”

That's enough. Because figuring out where isn't the first part of planning your honeymoon. Figuring out you is. And once we know that? Then we can start imagining where your first mile might take you.

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The First Mile™

A honeymoon collection by The Curated Mile.

We don't start with where. We start with you.

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