While the world’s ears may still be recovering from the collective Swiftie shrieks — mine included — following Taylor Swift and Travis Kelce’s engagement, we’re already moving on to the next obsession: the honeymoon.
What kind of post-nuptials getaway do you plan for the English teacher and gym teacher of America who have been everywhere — and have a honeymoon budget that rivals the GDP of some countries? We asked top luxury travel advisors how they’d handle the trip of the decade: where to send the high-profile pair, what pitfalls to avoid, and what it really takes to plan happily-ever-after when the whole world is watching.
No, your resort shouldn’t recreate the set of the “Love Story” music video. But a filing cabinet’s worth of NDAs? Non-negotiable.
Privacy First, Paparazzi Never
For advisors who regularly work with celebrity clients, the first step is recognizing that even global icons want their honeymoon to feel like an intimate life milestone.
“Though these are truly celebrities, it is important to remember that they are still people experiencing an important life moment together,” said Kacie Darden, owner of Blue Pineapple Travel — part of the Signature Travel Network. “I think that ensuring that their desires are fully realized rather than what you imagine for them. So, I think even with ultra celebrities, a very open and extensive qualifying conversation is important.”
That intimacy is only possible if security is airtight.
“It would be important to coordinate their personal security team with the aviation and hotel or villa team,” Darden explained. “At this level, all staff interacting with them would certainly be signing their NDA’s and should be well trained on this kind of client.”
Other advisors echoed the need for stealth from the very beginning.
“Typically, the act names of the clients are not given in advance so there’s not a leak of where they are traveling,” said Lia Vincent, owner of Vincent Vacations, also part of the Signature Travel Network. “For TSwift levels, the resort contacts that I am working with would likely need an NDA signed.”
For Jack Ezon, founder of Embark Beyond (a Virtuoso member), the checklist is non-negotiable: aliases, private aviation, NDAs at every turn, and hotels with discreet entries.
“Only fly private (you cannot use an alias with commercial flights),” Ezon said. “Try to avoid public airport terminals… and have every vendor sign an NDA.”
Kate Thompson, SVP of Global Marketing Strategy at Abercrombie & Kent, described her company’s “invisible infrastructure” — a network of over 3,000 staff in 65 offices that can anticipate needs before they arise: “seamless coordination that anticipates needs before they arise.”
Seclusion With Style
For celebrity honeymoons, privacy isn’t just a perk; it’s the whole point.
“For total seclusion and security, properties like private islands or private homes on large amounts of land can provide both luxury and seclusion,” said Darden. “It’s helpful if there is either a helipad or a landing strip so that the entire experience can be fully insular for the celebrity client.”
Vincent pointed to the famous example of Bill Gates renting out the entire Four Seasons Lanai, helicopters and all.
“I don’t think Taylor and Travis will go to this extreme for a honeymoon,” she said, “but celebrities that want privacy can go to that extreme if they want.”
Thompson highlighted A&K’s own Sanctuary portfolio: “Our A&K Sanctuary properties excel in this regard… Gorilla Forest Lodge in Uganda’s Bwindi Impenetrable Forest, for instance, sits within a UNESCO World Heritage Site where the only access is on foot.”
Alexis Berlin, chief growth officer of Travel with Awestruck (also part of Signature), added that Swift’s history favors villas.
“Taylor has had a propensity for villas with privacy in the past, so finding a property with true seclusion without sacrificing world-class culinary, management, and security staff would be first priority,” she added.
(A&K Travel Group)
Artistic Meets Athletic
Balancing Swift’s creative side with Kelce’s athleticism may sound tricky, but advisors see opportunity.
“We might craft a journey that includes private access to intimate cultural experiences, perhaps a dawn visit to Angkor Wat with a leading archaeologist, followed by bespoke athletic pursuits or heli-skiing in untouched powder in Japan,” said Thompson. “Our philosophy of ‘adventure by day, luxury by night’ allows both partners to find their rhythm whilst sharing transformative moments.”
Berlin agreed the couple could go bold: “Imagine a luxury private compound just outside of Kruger National Park or Masai Mara, followed by a resort buyout on Benguerra to tailor to Travis’s athleticism and Taylor’s artistic inspiration.”
Wow Factor Without the Paparazzi Flashbulbs
When it comes to honeymoons, there’s always the temptation to go bigger, flashier, more Instagrammable. But the advisors we spoke to agreed that for Swift and Kelce, the “wow” factor doesn’t need fireworks or over-the-top theatrics. It needs to feel authentic.
“Wow moments are all about tailoring an experience to a client,” said Darden. “When a moment is curated and special to their desires, it will not feel staged to them and instead will feel personal and special.”
That element of surprise is key. Thompson argued that the best memories are engineered to feel spontaneous, even if every detail was meticulously planned in advance.
“The most memorable moments feel serendipitous and thoughtful whilst being meticulously orchestrated,” she said. “True luxury today lies in hyper-personalization. It’s rarely about grand gestures, but rather the deeply personal touches that resonate.”
For Berlin, the real “wow” is giving the couple room to breathe.
“The wow moment is no one shoving a camera in your face, asking for your autograph, or ‘discretely’ recording you from across the table,” she said. “The secret would be in creating moments for the couple that allow them to fully relax, grow closer, and soak into a natural environment.”
The magic might not be in sweeping gestures but in deeply personal details.
“Maybe it is their wedding song on a record with their wedding picture in it playing when they arrive,” Ezon suggested. “Maybe it is coasters with the night sky and constellation on the night he proposed.”
One Honeymoon to Rule Them All — Or “The Eras Tour” of Getaways?
Swift and Kelce have already perfected the art of the “mini-moon” — those quick escapes between tour stops and NFL games. But their advisors are split on whether this particular milestone deserves a single grand gesture or a series of carefully planned retreats.
“I would recommend a single honeymoon,” said Vincent. “They already do take a lot of mini-moons as a couple. This is going to be a big deal where they decide to honeymoon and the destination they choose will see a huge increase in business from the exposure. I’m excited to hear where they go.”
Others argue that the couple’s demanding schedules call for more flexibility. Thompson suggested that one trip won’t be enough to capture both romance and recovery.
“For couples with such demanding calendars, we often recommend a hybrid approach: an immediate post-wedding sanctuary of seven to ten days for true disconnection, followed by carefully planned luxury escapes throughout their first year,” she said.
And then there’s the question of timing. Ezon pointed out that athletes, unlike pop stars, don’t always have the luxury of working around their own calendar.
“The idea of a multi-moon continues to grow in the real world,” he said. “It really depends on when they get married. Most Sports celebrities plan their wedding at the end of their season, so they have time to prepare and go away without pressure.”
From gorilla trekking in Uganda to Amanzoe in Greece, from heli-skiing in Japan to French Polynesian island buyouts, the options are limitless. But advisors agree that Swift and Kelce’s honeymoon will hinge on two things: privacy and personal meaning.
“Though these are truly celebrities, it is important to remember that they are still people experiencing an important life moment together,” said Darden.
“The art lies in understanding that true luxury today is about authentic connection rather than ostentatious display,” Thompson added.
Wherever they go, one thing’s certain: The honeymoon will be as closely tracked as Taylor’s jet — only this time, hopefully, with better reviews.
Related Stories
Editor’s Note: The Timeless are Trending
Inside Europe’s Newest Luxury Hotel Suites
The Plaza NY & Lacoste Team Up for Tennis-Themed Afternoon Tea
