When people think of a weekend getaway, a road trip to a nearby town likely comes to mind. But a short timeframe doesn’t have to make for a humdrum, “are we there yet” type of car ride. With a little creativity, a weekend excursion can be the trip of a lifetime.
Not only can these tiny treks delight travelers, they can also help advisors build and maintain client relationships. Though these shorter trips come with smaller commissions, there is a solid business case for booking weekend travel. Two travel planning pros — who are weekend travel warriors themselves — shared their strategies for making the most of these bookings and offered tips for enticing, repeatable journeys.
The Overbooked Are Not Unbookable
Busy is an understatement for many Americans right now. With return-to-office policies sending formerly remote workers back to the office and packed extracurricular calendars after the workday, finding a moment of peace, let alone two weeks for a vacation, can seem impossible. But don’t assume these overbooked people can’t be booked for travel. That’s exactly where the weekend trip — coupled with a bit of creative magic — comes in.
“A lot of my clients are in the throes of raising children, and I personally feel children’s schedules right now are more demanding than ever,” said Casey Ferkingstad of Magical Vacation Planner, a TRAVELSAVERS affiliate. “They’re involved year-round in sports. There’s no offseason; there’s no downtime. Parents are often forced to take these mini getaways, whether it is with kids in tow or without. A three- to four-night vacation is all that a lot of families really can put on the calendar, and we’re not even talking about budget, just taking time away.”
Given those constraints, advisors must make the trip as seamless as possible. Ferkingstad recommended all-inclusive options with nonstop flights and easy ground transport to the destination after landing.
“I think it’s really important to not rule out these types of trips just for busy clients,” she explained.
Similarly, Jonathan Alder, CEO of Jonathan’s Travels, sees the value in a shorter sojourn. “There’s no less value we bring as an agent to a two-day trip,” he said. “It’s always about valuing your client’s business and having them value you. Every trip is an important trip. The secret is never say no unless there’s a reason why and you can explain. ‘This isn’t big enough for me’ is not a [reason] why.”
The weekend getaway can offer a chance to showcase your knowledge and build a relationship — even when the budget is particularly tough. “You could steer people to places that show your wealth of knowledge instead of either insulting them or losing them entirely,” he explained.
On the other hand, when a client does have more money to work with, a short trip can offer a chance for an even more pampered experience.
“Time is money,” Alder said. “Sometimes you don’t have the time to spend on a long trip. So if you’re not going to have the time, wouldn’t you rather have the most amazing three days? Maybe that’s all the time you have between work, school and family stuff.”
Plus, as Ferkingstad said, “You never know what their budget might be next time; it keeps you on your toes.” Booking a variety of different travel experiences makes for a fun workday, she added.
Finding that weekend niche, whether it’s a luxurious retreat, a quick cruise or a bucket list destination, can bring in new clients and help build relationships with existing clients between their bigger trips. Plus, Ferkingstad advised, when the economy is tough, people are still likely to book weekend getaways, even if they’re pausing bigger excursions.
“No matter what might be going on in the world, you can do three- or four-night stays for an affordable budget for most people,” she explained. “We can’t always market the $10,000 to $20,000 trip, but the $2,000 to $5,000 trip, those are pretty much always available. They really can add up over time and kind of pad you.”
Where To Weekend
The destination really matters for a weekend trip, Ferkingstad explained. In this case, it’s not quite an open book to go anywhere. You’ll need to suggest places with nonstop flight options available from your client’s home airport, or near enough to access. If you have a client located somewhere like rural Indiana, for example, perhaps they’d be willing to drive to Chicago to find more nonstop flight options without the hassle and risk of a layover.
Speaking of flights, a client who is willing to splurge on upgraded seating options can make a longer trip possible.
“I’m a firm believer that a weekend trip can be so much more,” Alder noted. “If you’re flying business or first, why can’t it be Tokyo? If you’ve got a flat bed, why not go out on a Friday and come back on Monday? Go there for Saturday, Sunday, go home Monday. Have a blast. A lot of times a short trip is great because you don’t have time to even have the jet lag set in and you’re already home.”
For an adventure closer to home, Ferkingstad recommended Cancun because it’s one of the most cost-effective destinations. It’s home to many resorts, so the supply and demand works in travelers’ favor. Plus, it has a larger airport with enough flights that pricing doesn’t creep too high.
“From a travel agent perspective, Cancún is always going to be one of the most affordable spots,” she said.
She also recommended cruises for travelers on a tight timeline who want to get away and make the most of the experience onboard the ship. Guests can relax poolside, climb rock walls, try surf simulators, see theater performances and enjoy upgraded dining.
“There’s a lot to do, and you don’t have to worry about running around or leaving for an excursion,” she explained. “You come back to the same place every night.”
When it comes to resorts, it’s important to know the distance of each option from the airport, so you’re not wasting any precious time. In Jamaica, for example, a handful of resorts are within a 10-minute drive of the airport, but others are more than an hour away, and those latter options would cut down on the traveler’s time actually enjoying the trip.
Though it’s integral for advisors to learn as much about as many resorts as possible, Ferkingstad acknowledged that it’s impossible to know everything about every resort. For a weekend trip, she relies on her favorites — the places she knows so well that she has their spa menus saved on her computer. She refers back to places other clients have loved in the past. Then, she always looks for ways to maximize the trip given her relationships with destination partners. Maybe she can help her clients score a coveted dining reservation, for instance.
No matter which option piques your client’s interest, make sure to help them feel special and find ways to enhance the trip even on a compressed timeline. “Clients really want to feel relaxed and taken care of,” Ferkingstad said. “Try to remember that we want to actually sell the experience.”
She keeps that in mind when arranging the little details, too. Sure, a shuttle that stops at multiple resorts might be cheaper option for a ground transfer from the airport, but when time is short, your client is better off with their own, air-conditioned private transfer.
“It might cost $100 or $200 more, but you’re selling that experience of getting them to that destination quicker,” she explained.
When helping clients decide on room categories, she often encourages room types with club, concierge or butler level services. Those staffers can help make a quick stay worthwhile by unpacking and packing suitcases or reserving pool or beach chairs, allowing your guests to sleep in.
Though these options cost more, once travelers understand the value, “you’d be surprised how many times people can find the money for that,” she added.
In addition to sorting out the room type, find time to hammer out the other details with your client to make the most of their time. When possible, lock in cabana rentals, spa appointments and meal reservations well in advance. “Plan everything we possibly can,” she explained. “And that doesn’t mean fill up every moment of their day.”
Embracing the Weekend
Both advisors live the ethos of making the most of every trip, even shorter ones.
Alder has even traveled to the Czech Republic for a weekend trip, and he once did a whirlwind New York City trip for 24 hours on New Year’s Eve, packed with a spa visit, a show, a speakeasy and the Times Square ball drop. “If you have the budget but not the time, why not spend the money on the most amazing day of your life,” he said.
When Ferkingstad got married at Hyatt Ziva Cancun recently, many of her guests attended for a four-night stay at the property, which she said is perfect for multigenerational groups.
“If you’re sitting here waiting for the ideal time to go, there’s never a perfect time,” Ferkingstad said. “If a weekend trip satisfies the itch to go experience somewhere on your bucket list that’s new, do it even if you can’t do a full in-depth trip. Waiting to make memories is the No. 1 mistake we make.”
Originally appeared in the Summer 2026 issue of The Compass magazine
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