These Are the Celebratory Trips Travel Advisors Are Planning for 2026

From high school graduation to retirement and everything in between, people are more inclined than ever to celebrate life’s major milestones with the trip of a lifetime – and travel advisors are often the ones making those memories happen. 

Celebratory trips are typically long-haul, bucket list travel that present advisors with an opportunity to build a stronger relationship with their clients by both discussing life together and planning the perfect way to celebrate.  

As travelers continue to mark milestones around the world, here are some exciting celebratory trips that travel advisors are planning for 2026. 

Dubai and Maldives Honeymoon

Michelle McAllister, a travel advisor at MCM Travels, is planning a honeymoon vacation to Dubai and the Maldives in spring of next year. She had previously booked the bachelor and bachelorette trips for the same couple to Punta Cana and Los Cabos, respectively, and they have placed their trust in her again for their next adventure. 

“I have planned this trip for a few families in the past, but this is my first honeymoon to Maldives,” McAllister told Travel Market Report. “I’m excited to find new options for them that are truly romantic and unforgettable.” 

First, the newlyweds will fly to Dubai and spend two nights at a hotel on Jumeirah Beach. They’ll then fly to the Maldives, including a seaplane to Conrad Maldives Rangali Island, where they’ll spend the bulk of their trip – about six or seven nights.  

The clients will stay in an overwater villa at the Conrad property, which offers “beautiful waters, all-inclusive dining, and even an underwater restaurant,” McAllister said, adding that the couple will likely also enjoy excursions such as snorkeling, a catamaran tour, and other water activities. She is booking the honeymoon with Funjet Vacations, Viator, and Allianz Insurance.  

Greek Island Honeymoon 

Kathy Kadlec, marketing manager and travel advisor at Cary Travel Express, a storefront agency in Illinois, is also planning a 2026 honeymoon, a multi-island trip to Greece. The Millennial-aged clients came to her via a referral; though they’d done some of their own destination research, they quickly realized an expert was needed to make the trip truly come together. 

“Especially with a couple going on their honeymoon, they don’t want to have to worry about all these little pieces,” Kadlec told TMR. “It shows our value for what we do in the industry.” 

At the end of May 2026, the couple will fly into Athens and spend one night there. Then, they’ll take a mix of private transfers, ferries, and flights to navigate to Mykonos for two nights, Paros for three nights, and Santorini for three nights. 

Because the clients came to her with a budget, Kadlec booked them in 3- and 4-star hotels in Mykonos and Paros and completed the trip with a 5-star in Santorini for a “wow” factor. She is booking the entire trip through Avanti Destinations, and activities will include a Santorini sunset cruise, free time exploring on their own, water activities, and a winery tour and lunch. 

“They’re going to get the romance and the relaxation but the history and the culture as well,” Kadlec said. ” I went with some of the recommendations from other travel advisors in our office; that is the advantage to [working in-person] because there’s 20 of us that are out traveling and going to these destinations. We also get testimonials from clients who have come back and look to our relationships with tour operators.” 

Greek Island Graduation 

Travel advisors say that Italy and Greece continue to be hot destinations as bucket list vacations for couples and families. Sonia Bhagwan, owner of Dream Vacations, is planning a multi-destination Greek vacation – this one to Athens, Naxos, and Santorini – for a family who has been saving up for almost five years. 

The family – two adults and their two teenagers – is celebrating the oldest child’s high school graduation. They are splurging on First Class round-trip flights to Athens, where they’ll stay for a few days. They’ll then take ferries to Naxos and Santorini, spending four days on each island in top-tier hotels. 

“I love to hear the excitement in my clients’ voices when we are on the phone discussing various aspects of the vacation,” Bhagwan told TMR. “I am happy that I can be a part of this lifelong dream for this family and can help them create unforgettable memories.” 

Bhagwan booked the trip through FunJet for accommodations, Centrav for the air, and SeaJets for the ferry transfers. 

Scottish Retirement Celebration 

Four recent retirees have decided to forgo a retirement party in favor of a grand, 23-day trip through Scotland and several other parts of Europe in July 2026. The fine details are important for such a long trip, where they will be bouncing from country to country. That’s where their travel advisor, Jackie Ceren, president of Travel Consultation & Mediation Inc. In Florida, comes in. 

“I love planning all the logistics and making sure everything is smooth and right,” Ceren told TMR. “I go through it like, five more times to make sure it all lines up. Sometimes you don’t catch it the first time.”   

The clients will fly into Scotland and embark on Tauck’s “A Week in Scotland” tour. Then, the friend group will spend four nights at a golf club in Scotland before saying goodbye to the country and heading to new ones. 

Next, they voyage on a Regent Seven Seas Cruise that sails from London to Stockholm. Once in Stockholm, they’ll take a heritage tour, then fly to Brussels and tour there before returning home. 

“I’m constantly going in and re-evaluating what I booked, and that’s what I love to do,” she said, “besides making the client feel like they’re the only one going on a trip and they’re special. Their trip has a lot of meaning for them and me.” 

Sri Lankan 50^th Anniversary 

While she’s crafted Sri Lankan itineraries before, including for herself, this one is “radically different,” she told TMR, “with deep cultural immersion, village exploration and engaging experiences that help the local communities. 

“They are skipping most of the ‘tourist’ sites in favor of naturalist and anthropologist designed experiences, and they are going to some of the more remote and less visited national parks to see wildlife.” 

Davis is working with a tour operator called Ayu in the Wild to piece together the 16-day trip, which will include a lot of time meeting with locals, such as a tsunami survivor, dance teacher, farmer, chef, and family for a home-cooked meal. 

“I’ve been to Sri Lanka multiple times, and it is probably one of my three favorite destinations in the world,” Davis said. “Their trip is unlike anything I have seen or designed before, and it makes me want to go back so I can travel their itinerary.”