My husband, Andy, and I will celebrate 25 years together on February 1, 2027, and for months we’ve been trying to figure out where to go. The decision has felt weirdly high-stakes.
Some of that pressure is logistical. I travel for work four to six months a year, often solo or with our four-year-old son, Julian, so trips for just the two of us are rare. Getting away requires syncing two harried work schedules and paying for childcare. When we pull it off, it feels like an event.
An even bigger challenge is finding a trip that can live up to the occasion. A honeymoon, in theory, is simple to plan because there are so many familiar templates: the overwater bungalow, the splurgy beach resort, the grand European hotel. But after 25 years, we want to take a trip that says something about the time we’ve spent together, and also one that takes us on a new adventure, which is tricky, considering that Andy and I have traveled to dozens of countries together and road-tripped across more than 40 U.S. states.
We considered Belmond’s Eastern & Oriental Express in Southeast Asia, then balked at the price. A multicountry tour spanning West Africa sounded promising until we dug into the visa requirements. I suggested Socotra or Iraqi Kurdistan, and Andy noted that a “Level 4: Do Not Travel” State Department warning isn’t the most amorous selling point.
Feeling stumped, I turned to other couples to ask what worked for them.
Alice and Fred Wright, of Atlanta, have been marking big anniversaries with trips for four decades. Their fifth was a camping trip in the Florida Keys; their 40th took them to Norway. Those adventures gave them a chance to step outside work and parenting and remember that they were a couple. “We’re still the person the other one wants to nudge and say, ‘Look at that,’” Alice says.
Beaches Turks and Caicos, which looks out over Grace Bay, makes a point of being both family-friendly and accessible for wheelchair users.
Courtesy of Beaches Resorts
Colorado Springs, Colorado–based Kristy and Ryan Durso celebrated their 25th wedding anniversary at Beaches Turks & Caicos. Kristy is a full-time wheelchair user, though she wasn’t when they met, and says past vacations have meant worrying about whether she could get into the room, reach the beach, or participate in certain activities. “Accessible” sometimes means she is technically present, she observes, but watching everyone else have all the fun. At Beaches, though, she and Ryan swam, sailed, snorkeled, danced, karaoke’d, and renewed their vows. “I wanted to look at the man who has been beside me through every version of our life and say, ‘Yep. Still you,’” Kristy says.
The best anniversary trip, I realized, isn’t about plotting a performatively romantic, honeymoon-style getaway; it’s about choosing a place or experience that says something true about the two of you. Those two couples’ celebrations looked nothing alike, but each was shaped by the life they had built together and what mattered to them at that particular moment. As Andy and I continue to weigh our options, a handful of ideas keep surfacing in my conversations with others, and they might help anyone trying to make a milestone trip feel truly personal.
Return to where it all began
An anniversary can be a good excuse to revisit a place that mattered early in your relationship and see it through a fresh lens. Maybe you first bonded hiking Patagonia’s W Trek, so you decide to return years later to Tierra Patagonia to take in the views of Lake Sarmiento and the Torres del Paine massif. Or maybe you island-hopped on your honeymoon around Sicily or Sardinia, so you retrace some of those stops on a private, crewed catamaran itinerary with Sailuxe.
Round two doesn’t have to be fancier to be meaningful. Tyson and Halie Peveto got married at Thornbury Castle in England and went back for their 10th anniversary. This time, rather than stay at the castle, they booked a more affordable hotel in nearby Bristol and returned to Thornbury for dinner and photos. Halie was pregnant with their first child at the time, and soon after the England trip they moved from their home in Germany to Shanghai. Today, Tyson remembers the vacation as “the closing of so many chapters”: their first decade of marriage, their time in Germany, and life before children.
Going back to the beginning is sometimes the clearest way to see how far you’ve come.
Try something new together
The Ritz-Carlton Bacara, Santa Barbara, looks out over the Pacific Ocean and offers immersive experiences such as a Winemaker for the Day blending session, a Chumash-inspired purification ritual, and a visit to a local organic farm.
Photo by Ron Starr
Couples who think they’ve seen and done it all can still start anew; it just means choosing a destination or activity neither of you has experienced before.
Anya Brudzinska and Matt Pernick, of Manassas, Virginia, went to Africa for the first time to celebrate their 10th anniversary, self-driving through Namibia. Two years later, they returned for another overland adventure through Zambia, Zimbabwe, and Botswana, where a broken 4x4 refrigerator wiped out most of their food early in a 10-day stretch in the bush. The ordeal ended up revealing something useful about their relationship. “When things go sideways, we don’t turn on each other,” Brudzinska says. “We figure out what we can control, deal with what we can’t, and keep going. Botswana showed us how well we work together when circumstances are out of our control.”
Trying something new together can also mean learning a skill closer to home. If you both like wine but have never explored its production, you could stay at the Ritz-Carlton Bacara, Santa Barbara, and do the Winemaker for the Day experience. Hotel partner McKinney Family Vineyards helps couples create a custom blend, then makes either a half or full barrel for them—amounting to around 150 or 300 bottles, respectively—that the winery bottles and finishes with a bespoke label. It’s a fun, collaborative activity that will fuel many anniversary celebrations moving forward.
Andy and I are drawn to the idea of going somewhere neither of us has been before. Adventure operator Wilderness Travel’s new 12-day Algeria itinerary, which launches in November 2027, begins in Algiers and continues through the Roman ruins of Timgad and Djemila before heading south to Djanet for desert hikes and a stay in the Sahara. For us, and plenty of other well-traveled couples, there’s real appeal in finding a place that makes the world feel big again.
Celebrate the life you’ve built
An anniversary doesn’t always have to be just the two of you. Over time, children, relatives, or close friends may be inseparable from the relationship you’re honoring.
For Patty Nasey and David Goldberg of New York City, that meant celebrating their 15th anniversary with their 11- and 12-year-old daughters. The family of four set off on Backroads’ multisport adventure through Yellowstone and Grand Teton national parks. They went biking, hiking, and rafting, and the trip leaders even schlepped a wedding cake down to the shore of Jackson Lake for a vow renewal; Nasey wore the veil from her 1996 wedding. “The girls were, and are, our greatest accomplishment as a married couple,” she says. “It made sense to include them.”
Backroads takes active travelers on itineraries through Yellowstone and Grand Teton national parks that include cycling, rafting, and spotting bison and bears.
Courtesy of Backroads
South Africa is particularly well suited to an anniversary trip that includes your nearest and dearest. Start at Spier, a historic working farm in the Cape Winelands; new three-bedroom private villas sleep six, with heated pools and private chefs. Chase that with a stay at Tswalu Loapi, six standalone safari homes set in a 292,000-acre reserve in the Kalahari. Each micro-camp has a dedicated house manager and chef, plus a private vehicle and a guide-and-tracker team assigned exclusively to your booking. Stanley Safaris can plan the South Africa trip from soup to nuts, handling the flights, transfers, and sequencing so you’re not juggling the needs of a large group all by yourself.
This is one debate Andy and I are still having. He understandably wants some anniversary time that is just the two of us. I keep pointing out that Julian will turn five just before our 25th, meaning he’s already been part of our relationship for 20 percent of it; nothing Andy and I have done together has been more consequential than deciding to have and raise a child. My ideal compromise is to do a shorter adults-only escape, then a bigger family adventure peppered with strategically booked childcare. Best case, it reminds us what a strong little unit we’ve become; worst case, it pushes us to the brink of divorce.
Take the trip you missed the first time
Not every couple gets the honeymoon or anniversary trip they want, when they want it. Money may have been tight, a baby arrived, a parent needed care. Years later, an anniversary can be the perfect excuse to finally make space for the one that got away.
Gloria and Ed Cotton of Elgin, Texas, had to delay their 25th-anniversary celebration. Their planned cruise was canceled, and a later party fell through while they cared for Gloria’s mother after surgery. Once the timing was right, they created a Honeyfund registry to help finance a belated anniversary trip that took them to England, where Ed reunited with British relatives, then on to Portugal, where they boarded a 14-day cruise to Puerto Rico. Gloria says they were just “kids” when they married; after weathering their share of storms, they value their time, health, friendship, commitment, and faith more than ever.
The trip you couldn’t take at 25 might be exactly the one you’re finally ready for at 40, 50, or 60. If India has always been the dream, Micato Safaris can design a custom journey to the Golden Triangle, Varanasi, Ranthambore, the south, or any combination that fits your interests, while handling the guides and logistics.
Andy and I skipped the conventional honeymoon entirely. After more than 20 years together, we had a pop-up wedding with eight guests, then honeymooned the following year in Iceland and the Faroe Islands with our then-16.5-month-old son in tow. The trip was chaotic, rewarding, and very us. Talking to couples like the Cottons reminded me that there’s no expiration date on the trip you meant to take—or any rule saying the version you ultimately plan has to look anything like the one you first imagined.
Create an anniversary tradition
Tu Tu’ Tun Lodge’s glass cabins ensure guests are fully immersed in the forest around southern Oregon’s wild and scenic Rogue River.
Photo by Elizabeth Barclay (L); photo by Elliot Hawkey (R)
There’s something to be said for finding a place you love enough to return to again and again, and letting the history pile up.
Sandy and Brian Oard of Thousand Oaks, California, first visited Naviva, a Four Seasons Resort, in Punta Mita, Mexico, in December 2023. They’ve since returned eight times, most recently for their 33rd wedding anniversary, because they love waking to the sound of ocean waves and chachalaca birds, walking through the jungle, reading together, and befriending the Naviva staff. “Going back feels less like revisiting a resort and more like returning to a place that has become part of our story together,” Sandy says. “At this stage of our marriage, it’s about having the time and space to notice each other again.”
I understood the appeal after a recent kid-free weekend with Andy at Tu Tu’ Tun Lodge on Oregon’s Rogue River. We lounged in Adirondack chairs overlooking the water, feasted on handmade pastas and wood-grilled meats, then drove south to Jedediah Smith Redwoods State Park near Crescent City, California, to wander among the enormous old-growth trees. Back at the lodge, there was no agenda—we could kayak if we felt like it, bake ourselves in the wood-fired sauna, or do absolutely nothing at all. That kind of unstructured time together is almost nonexistent in our everyday lives, and it was a weekend that I could imagine striving to recreate.
Build in time apart
One thing 25 years of traveling together has taught Andy and me: We’re often happier when we don’t spend every waking minute together. We’ve gotten very good at identifying activities one of us will adore and the other will merely tolerate—and occasionally going our separate ways.
For Andy, that often means something food- or drink-driven, like a fermentation or foraging class or a cocktail crawl. I’m usually the one disappearing on the more adventurous outing. On one trip to Hawai‘i, I hiked a volcano while he stayed behind with a book. We reunited later with considerably more to talk about than if one of us had grudgingly tagged along.
Some trips make that divide-and-conquer approach particularly easy. Brush Creek Ranch, a luxury dude ranch set on 30,000 acres near Saratoga, Wyoming, offers enough activities for couples to happily peel off in different directions: One partner might head out for a trail ride or go fly-fishing while the other opts for a llama hike or forest-bathing session.
Cruises are similarly well suited to splitting up for a few hours. On Viking’s Passage to Eastern Europe, for instance, one partner could spend a day in Belgrade e-biking along the Sava River while the other heads to the Nikola Tesla Museum for a privileged-access tour.
A few hours apart can be a shot of adrenaline for a long-term relationship: Split up in the morning, compare notes over dinner, everybody wins. You’re still traveling together; you’re just giving yourselves the chance to miss one another.
So, where will we actually go?
Baja California Sur’s Camp Cecil de la Bahia is sandwiched between the whale-populated waters of Magdalena Bay and a mangrove estuary.
Photo by Uriel Santa Ana Mendoza
After all this research, I’m starting to think the right anniversary trip isn’t necessarily the grandest or most romantic one. It’s the one that reflects who you are now. For us, that means planning two separate celebrations rather than trying to manufacture one trip that checks every box.
We already have the actual anniversary weekend figured out: We’re heading to Camp Cecil de la Bahía, a new seasonal tented camp on a remote spit of sand along Baja California Sur’s Magdalena Bay. Gray whales migrate there to give birth, and during high season they’re known to swim right up to boats, sometimes with calves in tow. (The guides call it “whale soup.”) Neither Andy nor I has ever experienced anything like that. Plus, four days feels long enough to disappear together but short enough to avoid being eaten alive by parental guilt.
Come summer, we’ll plan something longer that includes Julian. We’re still deciding whether to go somewhere new to all three of us (Cyprus, Algeria, or wild-card Timor-Leste are our leading contenders) or revisit a place that already has meaning to our family. Türkiye keeps pulling us back. It’s one of our favorite countries, and the last time Andy and I went together, I was five months pregnant. Taking Julian there now would let us share a place we love with the kid who has changed our lives completely.
Two trips feels right. After all, 25 years is a lot to fit into one itinerary.
