How to Take Your First Luxury Vacation

  • Tips from luxury travel experts on the best ways to step your trip up a notch
  • Take honeymoons, often travelers’ first introductions to luxury

Claire Ballentine (with inputs from Bloomberg)
Updated24 Jul 2019
Vacationers enjoy the beach near Ginostra.
Vacationers enjoy the beach near Ginostra.(AFP )

Backpacking through Europe or road-tripping across the U.S. may be fun when you’re young, but when the thought of shoving your carry-on into a crowded overhead compartment or staying in a no-name motel makes you want to reconsider your vacation altogether, you know it’s time for a luxury trip. (That and when looking at your bank account inspires more pride than dread.)

But how to define “luxury” exactly?

To Lindsey Epperly, founder and chief executive officer of Atlanta-based Epperly Travel, it’s a four- or five-star getaway that’s catered to your personal preferences. “What people should look for is a major difference in terms of service,” she says. “Luxury is about anticipating needs. It’s walking to the hotel bathroom realizing you forgot your toothpaste, and it’s already there.”

New York’s David Prior, founder of members-only travel club Prior LLC, adds that it can be a mix of high and low amenities. It’s more about convenience (time is the ultimate luxury, after all) and personalization. “It’s not necessarily infinity pools or fancy cocktails. We’ve noticed people want to splurge on a really special experience,” he says.

In the interest of helping you maximize your money and take your next trip up a notch, we talked to more than a dozen travel experts for the best ways to splurge (and save) on a luxury vacation.

Set Your Intentions

Almost every travel adviser we spoke with stressed the importance of taking time before the trip to consider your goals for the vacation.

“When we work with clients, you don’t lead with where they want to go, you lead with why they want to go there and what they want to get out of it,” says Todd Bliwise, founder of travel company An Avenue Apart.

Do you want to come back relaxed? Maybe a beach or countryside locale would be best. Interested in adventure and experiences that leave you exhausted? That calls for mountains or jungle or a busy city. Have no idea where you want to go? Bliwise says the greatest gift you can give a travel agent is telling them your budget, length of time off, and desired takeaways from the trip—and let them work their magic.

Take honeymoons, often travelers’ first introductions to luxury. But even a big trip celebrating a career milestone or a substantial raise is no less fraught as the internal logic is the same: “This is a once-in-a-lifetime experience, I don’t want to penny-pinch, I want to really go for it,” says Bliwise. “When you approach your first luxury trip, you should always lead with emotional variables.”

Setting your intentions clearly and specifically is the best way to make sure the cost/value ratio of luxury traveling is in sync with your values, and it will minimize disappointment on not seeing value in your “investment” with the greater outlay of cash. If you’re new to high-end traveling, learning that “luxury” is more of a feeling than a price point takes some figuring out—and is different for everyone.

Strategize Like a Financial Adviser

David Kolner, senior vice president at Virtuoso Ltd., a network of top-shelf advisers, says to consider currency exchange rates when planning your trip. Visiting the U.K. right now is a better deal for American travelers than it has been in years, since the dollar is strong against the pound. Similarly, the lira’s drop has made Turkey a much less expensive luxury option.

Kolner also recommends strategizing your long-term travel bucket list like you would your financial plan, going so far as to map out how much you can spend on trips in the next five or 10 years. While this sort of advising is a growing niche for family travel, even those without kids can benefit from advance planning.

“People plan their retirement all the time, but on travel, people literally just make it up every trip, every single time,” he says. That kind of willy-nilly-ness is a surefire way to open yourself up to disappointment and waste money.

Think About Seasonality

Visiting destinations in shoulder season is common travel advice, but at the luxury level, planning around the peak can significantly boost your access to high-end amenities.

Melissa Biggs Bradley, founder of Indagare Travel Inc., recommends St. Barts in July, for instance, calling it a hidden secret and the perfect way to avoid the throngs of winter sun-seekers in December and January. Our own data-crunching suggests you think a bit earlier even, May and June, to get the best bang for your buck.

It’s also worth considering what it is you want—say, rugged Mediterranean or Atlantic coast—and transferring that desire to an emerging destination. If you’re interested in the south of France and Italy, try Croatia or Portugal instead. “Having a similar vacation on the Mediterranean is much less expensive, and you’re not losing out in terms of the quality of food or property,” she says.

One caution: If your bucket list includes places such as Machu Picchu, there’s no cheaper time than the present (even if there are worthy alternatives). As governments consider visitation limits due to overtourism concerns, Bradley’s advice is to go now, before it’s too late.

Consider a Safari

Almost every travel expert said that safaris were especially popular for first-time luxury trips—and for good reason.

It’s difficult to do a safari on a tight budget, explains Jack Ezon, founder of Embark Beyond, a luxury lifestyle partnership specializing in bespoke travel. “To do it right, it’s really expensive, but it’s also very transformational.”

Bliwise likes to combine safaris with an island destination or time in India and Nepal for a hiking experience. That’s especially popular for couples who have split interests—one desires a relaxing beach trip while the other wants adventure.

For safaris in particular, cutting corners cedes control on a ton of underlying variables, he says. Some travel companies shove too many people into the safari vehicles, for instance, which can lead to a miserable experience of straining over fellow passengers’ shoulders for three hours. That dissatisfaction is magnified because even a “cheap” safari is still a hefty proposition.

Traveling to Africa also means you’re avoiding the masses vacationing in Europe—the No. 1 place Bliwise says Americans should skip for their first luxury trip. “I don’t say that out of disrespect, but it’s incredibly accessible,” he says. “You’re not going to go only once in your life.”

Airport Add-Ons Offer Outsize Results

Splurging on an airport greeter that can welcome you to your destination and help you through customs and immigration is a great way to start your trip on a high note, says Anna Hawley, a custom travel consultant at TCS World Travel.

Ezon recommends airport VIP service Isroyal. “If you have a flight connection, you can get picked up by a golf cart and driven to your connecting flight. Those are small luxuries that cost $400 or $500 and can make a huge difference.”

He also uses Luggage Free, a company that ships luggage to your destination (and back home) so you don’t have to lug around a heavy suitcase or worry about airlines losing your bags.

Invest in a Private Guide ...

One big differentiating factor between a luxury trip and a regular one is the ability to do things privately and on your own schedule—no cramming into a tour bus with 50 other people.

For instance, Hawley from TCS World Travel has booked clients a shopping expert to take them through the markets in Marrakesh, and in Rome she’s coordinating a Da Vinci Code-inspired scavenger hunt for kids to explore the city. “The private guide aspect is obviously an added expense, but it’s something that takes the level up,” she says. “You really get in-depth and get to know the culture, and you see some off-the-beaten-path areas.”

This is also a way to make a hectic destination less intimidating, says Elisabeth Nelson, a managing director at TCS.

She recommends taking this approach in India where heavy traffic and linguistic differences can overwhelm even an experienced traveler. “You will still be in a crowded road, but with a private car and air conditioning, it makes things much less scary,” she says.

… But Save on a Private Driver

While a private guide is useful in helping you explore a new location, having a private car and driver throughout the entire trip isn’t always worth the extra expense, says Kathy Sudeikis, who’s been a travel adviser for almost 50 years (and yes, mom to actor Jason Sudeikis, too).

Indagare’s Bradley agrees drivers are a simple area to economize, if needed. Maybe that means booking a hotel in the middle of the city or a beach villa that’s within walking distance of a nearby town. “We have a lot of people who will choose one central destination, so they don’t have to move around a lot,” she says.

If you really want a private driver, TCS’s Hawley recommends booking one for the first day to introduce you to the new location. After that, you may feel more comfortable taking public transportation or walking the streets on your own.

For Lodging, Splurge at the Beach, Save in the City

If you’re visiting a beach destination where you’ll spend the majority of your time in your resort, paying extra for luxury lodging is a must, says Sarah Fazendin, an adviser at the family-focused Videre Travel. Think of it like a cost-per-use rationale when buying clothing; you’re getting much more for your money given the time utilized. She recommends booking a villa in the Cayman Islands or Costa Rica, which are less crowded than other beach destinations in the region and as a result may feel more “authentic.”

By the same logic, Ashley Diamond, travel adviser for Ovation Travel Group, suggests spending less on hotel rooms in a city where you’ll spend the majority of your time outside exploring.

“It is entirely fine to stay in an entry-level room at some of the finest hotels in the world, especially since you will have access to all the amenities on the property,” she says. “Not everyone needs a lot of square footage.”

Prior recommends splitting the difference and booking a fancy hotel for the first and last night of your trip—and economizing on the rest. He says to think of these stays as “punctuation notes” for your trip. You’ll appreciate everything all the more.

“The French say luxury should be taken in small does,” says Prior, “and I kind of believe that, too.”

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