Way-ahead Wednesday: Planning for Big 25th Anniversary Trip

We’re barely into 2026, but would it surprise you that I’m already planning a trip for 2029?

Let me explain. 2029 will be our 25th wedding anniversary. And, it’s also the year that we will become empty nesters, as my youngest will go off to college that fall. Naturally, I want to plan a milestone trip for just me and my husband. Since having kids, we haven’t had hardly any travel with just the two of us, and this is the perfect occasion.

So why do I need to start thinking about this now? Some of my trip ideas require significant savings and planning, so I’ll need time to get my ducks in a row. This year’s travel plans are already booked, and we’re planning going to the Olympics in 2028. That only leaves next year open for other travel. And, if we need to save up a significant amount for the big 2029 anniversary trip, we’ll need to travel lightly/cheaply next year.

I have so many ideas for this big milestone trip! Here are some on our short (err, long) list:

Galápagos Islands Cruise

Our friend went on a cruise around the Galápagos Islands and raved about it. We’ve never been to South America, so this cruise would give us a chance to visit a few places before/after the cruise. The wildlife and scenery look stunning! This would definitely be an epic vacation.

However, due to limits on tourism and cruise ship size, cruises around the Galápagos Islands are quite pricey. We’d be looking at $20k for the cruise for 2 of us. Ouch!

European River Cruise

My parents went on two European river cruises and raved about them.

These ships don’t have all the bells and whistles that big cruise ships have, but the itineraries are appealing. They cost more than a traditional cruise but less than a Galápagos Islands cruise.

South American Cruise

Since we haven’t visited South America, several cruise lines offer itineraries that include Chile, Chilean Fjords, Argentina, the Falkland Islands and more. This would be a great way for us to get a taste of several South American countries.

Switzerland

My family of 5 (+1 niece) visited Switzerland in 2022, and it remains one of our favorite destinations (see my trip report here).. My husband and I would love to return to Switzerland and see more of the countryside, including the Matterhorn.

But…I think our kids would be so upset if we returned to Switzerland without them!

Bora Bora

Then there’s the ultimate romantic destination: Bora Bora. Leana and her husband went there a few years ago, and it looks breathtaking. Costs could add up quickly, though, considering the cost of flights to the island from Tahiti and the high price of resort dining.

Croatia and Greece

A few years ago, my entire family visited Santorini and Mykonos on a cruise. Then, my daughter and I spent a few days in Athens after the cruise, and we loved it! I know my husband would love Athens, too. We could combine a trip to Athens with a few days in Dubrovnik, Croatia and then relax on a new-to-us Greek or Croatian island.

Maui

I’ve been to Hawaii 3 times, and each trip has been well worth the flying time. We haven’t yet been to the island of Maui, and I’d also love to return to the Big Island.

France

My husband and I spent our honeymoon in France, so this country will always have a special place in my heart. While we’ve returned to Paris since our first trip, we haven’t had a chance to return to some of the smaller towns. We’d love to return to Amboise and explore other quaint towns in the countryside.

Are you planning a big milestone trip in the next few years? Which destination would you choose?