Bucket List Travel for Empty Nesters: How to Plan Your First Big Trip Together
Are you ready to plan your first big trip as empty nesters? In this episode, Lisa shares 10 tips for making the most of this exciting new chapter, from creating a dream destination wish list and incorporating both of your interests to traveling during the shoulder season and splurging on a once-in-a-lifetime experience.
Whether you're dreaming of an African safari, an Antarctic cruise, or a relaxing getaway, these tips will help you plan a meaningful trip, make new memories together, and find something exciting to look forward to!
One of my favorite things about travel is having something exciting to look forward to. Planning a big trip together can be a great way to embrace this new season of life and start making memories as a couple.
Whether you're just entering the empty nester stage or your kids have been out of the house for years, here are 10 tips to help you plan your next big adventure!
1. Make a Dream Destination Wish List
One of the best ways to start planning your first big trip is to sit down with your spouse and make a wish list. But here's the catch: do it separately!
Each of you should write down five destinations you've always dreamed of visiting.
Don't share your lists until you've both finished writing them.
Reveal your lists and see where your dreams overlap!
After 20 or 30 years of planning vacations around kids, you might be surprised to discover that your spouse has a dream destination you've never even considered.
Maybe you both have Italy on your list, or perhaps your spouse has secretly been dreaming of an Antarctic cruise. You might discover a destination that excites you both or find yourself inspired by an entirely new idea.
This is a fun way to start brainstorming and discover what you each want from this next chapter of travel!
2. Think About How You Want to Feel
Another great way to narrow down your destination is to think about how you want to feel on your vacation. Instead of starting with a place, start with the experience you're hoping to have.
Ask yourselves what sounds most appealing right now:
Relaxed and rejuvenated: Consider a beautiful beach destination where you can slow down, enjoy the sunshine, and spend time together.
Curious and inspired: Visit a country you've never explored before, like Japan, and immerse yourselves in the local culture, food, and traditions.
Energized and adventurous: Plan a trip around hiking, zip-lining, or another activity that gets you excited.
Ready for something new: Choose an experience you've never tried before and build your trip around it.
There are so many different ways to travel, and this is the perfect opportunity to choose a vacation that fits the season of life you're in now.
3. Include Something Special for Each of You
When planning a trip as a couple, it's important to make sure you're both getting to do things you genuinely love.
For example, I love hiking, while my husband loves music. He's even become a DJ in his 50s and enjoys going to music festivals and experiencing live music. So, why not combine those interests into one vacation? We could spend the morning hiking and the evening at a concert!
Think about the activities that make each of you happy:
Do you love hiking, biking, or spending time outdoors?
Does your spouse love music, art, or trying new restaurants?
Is there a hobby you've wanted to make more time for, like tennis or pickleball?
Is there a special activity you've always wanted to experience together?
You don't have to spend every minute doing the same thing, but incorporating each person's interests makes the trip more meaningful. You can also plan activities you both love and look forward to experiencing together.
The goal is for neither person to feel like they're just tagging along on someone else's vacation!
4. Stay Longer Than You Think You Need To
One of the best parts of being an empty nester is having more flexibility with your travel schedule. You're no longer planning every vacation around school breaks, family schedules, and getting everyone home on time.
So, why not take advantage of it?
Instead of a quick weekend getaway, consider staying for 10 days or even two weeks.
Give yourself time to explore without feeling like you need to rush from one activity to the next.
Build in time to relax and enjoy the destination rather than squeezing everything into a packed itinerary.
I read that the average trip length for couples over 65 is around 15 days, which I think is a wonderful goal to work toward!
Of course, if you're an early empty nester and still working, you might not be able to take two weeks off just yet. But even adding a few extra days can make a big difference.
Longer trips allow you to settle into a destination, experience more of the local culture, and enjoy the vacation without constantly watching the clock.
5. Book Your Big Trip Earlier
If you're planning a bucket list trip, I recommend starting the planning process much earlier than you might be used to.
Some of the most incredible travel experiences require reservations well in advance, especially if you're hoping to stay at a particular lodge, visit a popular destination during a specific season, or book a unique excursion.
For example, my husband and I are already planning a safari for January 2028! We're working with a travel agent and exploring different lodges, hotels, and destinations because some of the best safari accommodations fill up a year or more ahead of time.
Here are a few types of trips where booking early can make a difference:
African safaris: Start researching lodges and safari experiences well in advance.
Antarctic cruises: These are bucket list trips that can require considerable advance planning.
Japan during cherry blossom season: If you want to visit during peak bloom, plan ahead to have more accommodation options.
Popular destinations and unique stays: Special hotels, tours, and experiences can book up quickly.
Booking earlier gives you more choices and helps you secure the experiences you've been dreaming about.
And honestly, one of my favorite parts of traveling is the anticipation! Having a trip on the calendar gives you something exciting to look forward to while you plan, research, and dream about all the memories you're going to make.
6. Travel During the Shoulder Season
One of the biggest perks of being an empty nester is that you no longer have to plan every trip around the school calendar.
Take advantage of that flexibility by traveling during the shoulder season!
The shoulder season is the period just before or after a destination's busiest travel season. Depending on where you're going, it can offer pleasant weather, fewer crowds, and better prices.
For example, Italy can be a wonderful destination in May or October. I've visited in July a few times, and the heat and crowds can make exploring a little more challenging.
Traveling during the shoulder season can mean:
Better accommodation prices and more options.
Fewer crowds at popular attractions.
More flexibility when booking tours and activities.
An easier time getting reservations at restaurants.
More opportunities to enjoy a destination at a relaxed pace.
Of course, the best time to visit depends on the destination and the experiences you want to have. But now that you're not tied to school schedules, you have the freedom to choose dates that work best for you!
7. Visit Fewer Places and Explore Them More Deeply
I love a busy itinerary where you're seeing as much as possible and walking 20,000 steps a day. But when you're planning a longer trip, that pace can get exhausting.
Instead of visiting five cities in 10 days, consider choosing just two or three places and spending more time in each.
Here's why I love this approach:
You can slow down. Enjoy a leisurely breakfast instead of rushing out the door first thing in the morning.
You have room for spontaneous experiences. Your waiter might recommend a favorite museum, or you might stumble upon a local festival you didn't know about.
You can get to know a destination better. Spend time exploring neighborhoods, trying local restaurants, and experiencing everyday life.
You won't feel like you need a vacation from your vacation. A more relaxed pace gives you time to recharge between activities.
You can still see the major attractions on your list, but leaving room for the unexpected often leads to some of the most memorable travel experiences.
Sometimes the best moments are the ones you never planned!
8. Splurge on One Thing That Matters Most
If you've been dreaming about a big bucket list trip, this could be the perfect opportunity to splurge on one special experience.
You don't have to spend a fortune on every part of your vacation. Instead, decide what would make the trip truly memorable for you and prioritize that experience in your budget.
Here are a few ideas:
Stay somewhere extraordinary. Book an overwater villa and spend your days relaxing and enjoying the property.
Hire a private guide. Explore a city you've always wanted to visit with someone who can share its history, culture, and hidden gems.
Book a private chef. We've done this several times in different cities, and it's such a special experience. You can customize the meal to your preferences, and depending on the setting and menu, it may even compare favorably with dining at a high-end restaurant.
Try a once-in-a-lifetime adventure. Think about a hot air balloon ride, river rafting, or another experience you've always wanted to try.
The key is to decide what matters most to you as a couple and spend your money there. You can save on other parts of the trip while still creating an experience that feels extra special.
9. Consider Travel Insurance
Travel insurance is something I'm a little on the fence about, but it's worth considering, especially for longer international trips.
Over the past year, I've purchased travel insurance for most of our trips, primarily because of the medical coverage it can provide.
When it comes to cancellation coverage, I tend to book flights that offer travel credits if I need to cancel. I also look for accommodations with cancellation policies that provide some flexibility. That makes me less concerned about losing the entire cost of a trip if plans change.
However, medical coverage is something I take more seriously, especially when traveling internationally.
Before your next big trip, consider these questions:
Does your current health insurance cover you when traveling internationally?
Would you have coverage for emergency medical treatment abroad?
Does your travel insurance include medical expenses and emergency medical evacuation?
What are the exclusions, coverage limits, and cancellation terms of the policy?
You hope everything goes smoothly on vacation, of course, but unexpected situations can happen. It's worth understanding your coverage before you leave, particularly if you're planning a trip that lasts two weeks or longer.
10. Plan the Trip Together as a Couple
Finally, don't just plan the itinerary. Take some time to talk about how you want the trip itself to feel and what you want your time together to look like.
When you're traveling as a couple, little expectations can make a big difference. Talking about them ahead of time can help you enjoy the experience even more.
Here are a few ideas to discuss:
Downtime: Are you both happy spending a couple of hours on your own in the morning, or would you rather start each day together?
Phone use: Would you enjoy having a phone-free evening each night so you can be more present with each other?
Morning rituals: Maybe you make a point of enjoying breakfast together on the balcony every morning.
Evening traditions: Plan a sunset walk together or find a special place to watch the sun go down each evening.
Shared experiences: Decide which activities are most important to each of you and make sure they're included in the itinerary.
These little traditions don't have to be complicated. Sometimes the simplest moments become the most meaningful parts of a trip.
Taking time to talk about your expectations helps you plan a vacation that feels special for both of you, rather than simply checking destinations off a list.
Start Planning Your Next Adventure!
Entering the empty nester stage of life can bring a lot of changes, but it also opens the door to exciting new experiences. This is your opportunity to revisit those bucket list destinations, try something new, and spend meaningful time together!
Whether you're dreaming of an African safari, an Antarctic cruise, a relaxing beach escape, or an adventure-filled trip to a country you've never visited, there's no better time to start planning.
And remember, you don't have to be newly empty nesters to take advantage of these ideas! Even if your kids have been out of the house for 10 years, you can still plan something exciting and create new memories together.
So grab your spouse, make that wish list, and start dreaming about where you'll go next. The world is waiting, and this next chapter could be one of your most exciting travel seasons yet!