Vacation Destination Ideas for Milestone Anniversary Trips

Regardless of the anniversary milestone, and no matter how many years or decades it’s been since you said “I do,” a trip gives you the perfect opportunity to celebrate this important milestone in your relationship as a married couple. A romantic getaway is an ideal opportunity for you to relive your honeymoon 20+ years later or get some much-needed downtime with your spouse for once. It might even be the first trip you take together as a couple since having a family. Here are some of my favorite vacation destinations for milestone anniversaries.

vacation destination anniversary trips

Vacation Destination Ideas for Milestone Anniversary Trips

milestone anniversary trips

Celebrating a milestone anniversary is such a great way to reconnect! One of my favorite tips to travelers is to book a session with a Flytographer in the first few days of your trip. Not only will you get photos to document your travels, but you will also get some insider tips from a local. Take advantage of the session and ask for the best local place to eat and some hidden gems in the area. My husband hates getting his picture taken, but even after our session, he thanked me and looks back on it being one of the best things we did while we were traveling. Check out if your destination has one! You can thank me later! 

Napa Valley, California

What better way to soak up the sunshine and tour some of the most beautiful countryside and vineyards? Making your rounds on your anniversary to various wineries is a fantastic experience and one that you’ll forever remember.

Save up to 30% on hotels for a romantic getaway!!

Aspen, Colorado

Hitting the slopes for your anniversary is excellent for couples who love adventures and nature. Plus, at the end of a long day, you’ll get to snuggle up and warm up by the fire sipping on chocolates and nibbling on sweet treats.

Want to try skiing in BC? Here are the top ski resorts to visit!

All-Inclusive Cancun Resort

After years of being married, sometimes not planning or doing anything is the best “plan” ever. Booking your stay at an all-inclusive resort means that everything is taken care of, and neither of you will have to lift a finger to do anything or plan.

There will be plenty of time to talk, listen, and just relive the past years of your marriage as you reflect on your incredible journey.

As a couple, personally, this is our favorite way to vacation. We have stayed at a handful of resorts in Cancun and continue to come back to the Excellence Playa Mujeres time and time again. It's a beautiful resort, with the most gorgeous grounds, plenty of delicious restaurants to try out, and good live music playing all day long. We also love the flat beach we can walk for miles every day.

We've also spent time at Beaches {all-inclusive for families} and Sandals {all-inclusive for couples} and I'd recommend any of their locations as well.

The Only All-Inclusive Resort Itinerary You Will Need!

vacation destinations for couples

Maui, Hawaii


Is there anything more romantic than snuggling up together on the sugary sand beaches of Hawaii? Those sunsets paired with the atmosphere just scream romance, which is why couples all around the world plan getaways to this area.


You can spend your days soaking up the sun and spend your evenings sipping cocktails by the pool. This type of anniversary trip would be filled with stunning views, sunsets, and fun.

Find the lowest prices on the right Maui hotel for you on TripAdvisor

Sedona, Arizona


There’s just something so mesmerizing about the Red Rocks of Sedona. The way the sun shines off their shape is genuinely remarkable. This part of Arizona is quite stunning to visit and has cute VRBOs and delicious eateries as well. It’s easy to immerse yourself in the community because it’s a place that tourists come to from all over the world.

San Gimignano, Italy


This small town located in Italy is surrounded by walls, creating an immediate romantic ambiance. Spend your days walking hand in hand and looking at the quaint shops, eating at some amazingly delicious restaurants, and stuffing your bellies full of every flavor of gelato that you can. Just on the outskirts of the town, you’ll find family farms that host weddings, events, and other gatherings as well. This is a local Tuscan town that is truly remarkable with all that it has to offer and explore.

anniversary vacation trip

Amalfi Coast, Italy

The postcard-perfect town of Positano also makes a perfect Italian vacation spot as well. If you are considering staying on the Amalfi Coast, check out this post for more information

Safari in Africa

Our 25th wedding anniversary is coming up next summer and for the past few years, we've been planning our trip on safari in Africa. I was able to fulfill a life-long dream of going on safari in the Masai Mara in 2014, but I was solo on that trip and it's been a dream to go visit again. The tent camps are beautiful and there is something magical about driving through untouched lands. 

What to Pack on Safari 

If you are looking for a special way to celebrate your next anniversary, hopefully, this post will inspire you to take a trip or make the most of your next vacation together. Think in the states and outside for some of the best romantic trip ideas! 

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