Getting hitched is one of the best reasons to ditch work and undertake your longest, splurge-iest trip ever. But before you dive headfirst into checking off the items on your travel bucket list, take a few minutes to consider the practical stuff—because the trip of your dreams won’t just magically appear by itself.

In fact, lousy hotels, missed flights, lackluster meals and inhospitable weather can significantly hamper a happy holiday, essentially flushing your hard-earned money down the toilet. And while we can’t see the future, we can assure you that proper planning will undoubtedly put the odds in your favor of enjoying the getaway of your dreams.

Here's a handy guide to the best planning tips and advice for your honeymoon. 

Timing is everything

You’ve dutifully set aside your collection of vacation days—now it’s time to work out how to spend them on your honeymoon. It’s important to weigh the time you’ve allotted for your adventure against your destination of choice, and make sure that your trip is spent traveling, not transiting.

With two or three weeks, you’ll have a more generous amount of time to take a crack at a faraway destination and overcome the exhaustion of a long-haul journey and/or jet lag. But a week-long holiday, say, is never well served by spending two full days hoofing it from one continent to another, only to turn around a few days later and repeat the grueling trek back.

Boats next to an idyllic beach backed by tree-lined cliffs in Thailand.
Travel in the right season to get the most out of a trip to Thailand © primeimages / Getty Images

The other major timing consideration has to do with seasonality. Tacking your honeymoon on at the end of your already-set wedding date might preclude travel to certain destinations simply due to the time of year. Large areas of the Caribbean, for example, are prone to hurricanes during the months of September and October. Other destinations have annual monsoons—like Thailand, which has two different curtains of rains that sweep across the kingdom during the latter half of the year.

It’s best to educate yourself on the high and low seasons of your preferred honeymooning locales. Prices, of course, increase with a rise in demand during the months with the most favorable climate and during busy periods such as school holidays (when desirable hotels can also become scarce). Low seasons, on the other hand—or better yet, ’shoulder’ or ‘green’ seasons—can be a worthy option if you want to see more bang for your buck at the expense of rolling the dice weather-wise.

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A couple at window in a hotel room
An extended stay at a hotel or resort can help ease the stress of always being on the go © Jupiterimages / Getty Images

Benefits of DIY

When choosing a destination for your honeymoon, there’s absolutely nothing wrong with sticking to one place, but a protracted vacation—as many honeymoons are—lends itself well to exploring several locales. All-inclusive hotels are going to try to convince you otherwise, and travel agents will try to capitalize on your lack of destination knowledge with tours and templates. 

However, a DIY trip is much easier than you might think, and the rewards are exponentially greater than signing up for a cookie-cutter tour. Hands-on planning is a crucial part of understanding a destination and you’ll arrive in the country with a commendable amount of acquired knowledge that will further guide you to sniff out the top experiences that really speak to you.

Read more: The ultimate guide to having a destination wedding

How to build a multi-stop honeymoon

As the architect of your own multi-stop trip, you might want to think of your honeymoon as a novel; the action on your vacation should swell and ebb accordingly. Think of the beginning of the trip as the initiation phase—you’re adjusting to a new world (maybe getting over jet lag) and want to ease into the action as it gradually builds. The middle section of the honeymoon is where the plot thickens. Your pulse quickens with adventure sports, or late urban nights exploring. Then, with the end of the story in sight, the last section of the holiday is when the jets cool—a denouement of sorts when you once again slow your pace.

It’s the beach in Bahia after Rio and São Paulo, the Amalfi villa at the end of Tuscany and Rome or the ryokan in Hakone when you’re wrapping up Kyoto and Tokyo. You need a chance to unwind at the end of the trip, so you feel revitalized by the holiday, not desperately needing another.

Read more: These 5 islands are the Caribbean’s best-kept secret

A couple in a rooftop pool looking out over a city skyscraper skyline.
Save that show-stopping hotel till the end of your trip © ROSLAN RAHMAN / Getty Images

Picking hotels

Now, with your storybook itinerary you’re going to have to slot in hotels. These should play out in tandem with the pace at each stage of your trip, but you need to slightly trick your future self. Every accommodation option selected should build upon the previous choice. The human mind can’t help but judge, and when you arrive at lodging number two you won’t be able to ignore the instinct to compare it to your accommodation the night before.

So, in order to essentially feel like you’re winning at travel, each hotel must get progressively better—or maintain the quality of the previous stay—culminating in your big splurge at the end, which nicely coincides with your itinerary’s finale. The last slice of the vacation is the happy ever after—just like you and your spouse after the wedding.

Read more: How to plan the perfect wedding abroad

A couple sit looking out over a beautiful canyon.
When it comes to your honeymoon, don't be afraid to dream big © peterotoole / Getty Images

Honeymoon planning timeline

One year before honeymoon: Dream. Think about where you’ve always wanted to go to celebrate your marriage, and get inspired by guidebooks, magazines and websites.

Nine months before your honeymoon: If you’re budgeting your holiday in tandem with your wedding, you’ll likely know at this point what funds you’re hoping to allocate to your trip and can compare your budget against that dream list of destinations.

Six months before your honeymoon: Properly slot in your travel dates after calibrating for personal commitments and taking into account the optimal time–as you deem it–for visiting your destination of choice.

Young lesbian Couple Stop To Take A Selfie At Brandenburg Gate in Berlin
City destinations will always require more planning than beach resorts © Hinterhaus Productions / Getty

Four months before your honeymoon (or earlier): Cement the foundations of your plans, scouting airplane tickets, booking must-have items on your checklist (hotels, visa, park permits) and firming up a version–in very broad strokes–of what your itinerary might look like (which days in which destination for multi-stop trips).

Two months before your wedding (note wedding, and not necessarily honeymoon): If you’ve decided to ask your guests to help you fund your dream trip, now is the time to create an online registry detailing tangible activities to be undertaken at a gradation of price points to suit your wedding guests’ varying budgets.

One month before your honeymoon: The internet enables the world to move a million miles a minute, so once you begin the 30-day countdown you can take to your social platforms to snoop for upcoming events and trending bars, and even find friends that might be crisscrossing your itinerary.

You might also like:
Classic romantic trips with an adventurous twist
How to plan the perfect wedding abroad
How to find - and survive - a holiday romance

This article was first published Jan 11, 2017 and updated Dec 27, 2021.

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