The Honeymoon Guide: Expert Advice from Maddie of Heirloom Travel
After months of planning your wedding, it’s almost time to celebrate! This means putting all your spreadsheets aside, giving your final guest count to caterers, and enjoying your wedding day to the fullest with your family and friends by your side! This ALSO means the honeymoon is right around the corner… but how do you decide where to go? Do you love lounging on the beach and your fiancé wants to climb every mountain and explore the towns nearby?
This could get complicated.
And that’s why Maddie, the owner of Heirloom Travel, is here to help! She understands there’s no set formula for a perfect honeymoon; it’s more about finding compromises to make you both happy (and that’s some marriage advice, too!)

What To Do When Travel Styles Don’t Match
Different travel styles are incredibly common among couples. Maybe one of you loves sleeping in and enjoying a good book by the pool, while the other is bookmarking every hike, food tour, and shop they want to visit!
And neither approach is wrong! Couples don’t have to vacation the same to have a good time –
Her advice:
“ Split the days. Do a couple of “go and do” days together, then build in a day or two where one of you sleeps in and the other goes off to snorkel, hike, or wander through the local market.”
Find a honeymoon location that has both relaxing and exciting elements – think resort town with a quiet beach, but also close to a cool, interesting town.
All-Inclusives vs Immersive Stay

There are pros and cons to both options, but it all depends on the experience you are going for!
All-Inclusive resorts are great if you have a hard time making decisions! With a set of restaurants, bars, and experiences, this is an easy place to relax and have very little decision planning after months and months of planning your wedding. Additionally, it’s paid for upfront! On the other hand, you’re in a bubble. You won’t be able to get that authentic food or see the true location, and it may feel redundant after a few days!
When having an immersive stay, you will be fully able to experience the culture – including food, the people, and the culture. This tends to be the more memorable experience because it’s planned with more intention. With the additional planning, cost can be a bit more unpredictable! Deciding on this option may also require more decision-making, which isn’t always what couples want to do after planning their wedding!
Where To Start
If you’re at the start of planning your honeymoon and don’t know where to start, YOU’RE IN LUCK! Maddie created a honeymoon destination roadmap to start the conversation and get some starting ideas for destinations that would work well for you!
Here’s a new question to consider:
- Are you imagining a calm, relaxing honeymoon or grand adventure together?
- How many days do you plan to spend on your honeymoon?
- Are you up for a long-haul flight?
- Do you want to go on your honeymoon immediately after your wedding, or are you willing to plan a delayed honeymoon? This may open up additional destinations!
- Do you have a rigid budget to stay within? This may rule some places out.

Want to see more? Head to Maddie’s page and download the full PDF!
The “Do Everything” Couple

If you and your fiancé want to do everything and see everything, the destination is more important than usual! Here are a few questions to ask before you pick:
- How long is your honeymoon? Is doing everything realistic for your timeframe?
- Do you want variety within one country, or are you open to combining two?
A few destinations that fit the bill:
- Italy – the Dolomites + Cortina
- Japan – Mt. Kintoki + Hakone
- Switzerland – The Alps + St. Moritz
- New Zealand – The Remarkable + Queenstown
- Wyoming – Grand Teton + Jackson Hole
- Peru – Sacred Valley and Machu Picchu + Cusco
Can You Plan Your Own Honeymoon?
Absolutely. Plenty of people do this. But think about who you hired for your wedding. You didn’t cook the food yourself; you hired a caterer. You didn’t put together a long playlist to play through at your reception; you hired a band or DJ. You probably also hired a planner or coordinator to help make sure your day came together smoothly! Why would your honeymoon, the trip you’ve been looking forward to the whole time, be the one thing you leave to a Tuesday night of tab-hopping between review sites?
You spent months on the wedding getting every detail right: the flowers, the seating chart, the menu tastings, the song you’ll walk down the aisle to. That level of care is exactly what your honeymoon deserves too, and it’s the one part of this whole process where you finally get to hand the details to someone else instead of managing them yourself.
Plus, working with a luxury travel advisor opens doors that Google can’t. Travel Advisors have personal relationships with hotels and suppliers across the globe who help them elevate your entire experience. Think: upgraded rooms, exclusive amenities, reservations at sold out restaurants… all because you know the right person!
Maddie’s Top Picks

There’s no single “best” destination; it really comes down to what the two of you actually want more of: rest, adventure, culture, or some combination. That’s usually the first thing worth figuring out before looking at any specific place. Over the past five years, here are a few honeymoons that have stuck with Maddie:
- 10 days in Italy exploring Tuscany and Puglia
- An elopement + honeymoon in Arizona
- A week at St. Lucia’s most loved all-inclusive resort
- Two weeks in South Africa on safari, in Cape Town and the winelands
- A three-week adventure through Australia’s Gold Coast and New Zealand’s South Island
After years of planning honeymoons, Maddie’s philosophy comes down to one simple idea: the best honeymoon isn’t necessarily the most luxurious, adventurous, popular, or expensive one. It’s the one that feels like the couple.
For couples who want a honeymoon that is thoughtful, seamless, and tailored specifically to them, Maddie and Heirloom Travel can help turn that vision into an itinerary worth remembering long after the wedding day.