8 Trip Upgrades That Are Always Worth the Splurge, According to Travel Pros

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Whether you’re strolling through Savannah, jetting off to Lake Como to sip spritzes or making another one of your dream vacations a reality, investing in a handful of small travel upgrades can make a big difference and move a great trip into ultra-luxurious territory.

As we mentioned in our guide to 2023 vacation trends, the overall experience trumps the price for many luxury travelers. The average jetsetter booking with the global travel agency network Virtuoso says they’re willing to ante up about $7,000 more in terms of total travel dollars invested per person in 2023 compared to 2022.

Now that you’ve budgeted more to travel well—without an ounce of guilt—we tapped a handful of travel experts from across the country to help you know where to invest that money to maximize your experience. Prepare to book your least stressful and most unforgettable excursion yet. Now that’s priceless.

8 Travel Upgrades That Are Worth the Splurge, According to Pros

Hiring a travel agent or advisor.

Many people skimp on—or go without—travel agents and travel management companies, thinking that they'll save money, explains Simone Collins, the Audubon, Pennsylvania-based CEO of Travelmax. In the long run, this strategy rarely pays off.

“They end up spending more money than they otherwise would have, or waste valuable time on hold with airlines or troubleshooting problems when things go wrong. Investing in a good travel agent or agency is like having a good insurance plan or lawyer: When things go wrong, you're glad to be covered and it's really helpful to have experts advocating on your behalf,” Collins says.

A travel agent or advisor is a real person whose job is to handle your entire trip—headaches included, says Samantha Brown, the New York City-based host of the Emmy Award-winning PBS show, Samantha Brown's Places to Love.

In addition to booking every aspect and smoothing out any unexpected speed bumps or hurdles along the way, a travel agent or advisor brings their strong relationships and ample experience to the table to secure access to value-added extras and experiences you may not ever discover or have access to on your own.

“A travel agent’s fee varies from a percentage of the trip or a flat fee,” Brown says. If you’re trying to determine how much to set aside, a rough estimate is about 5 to 15 percent of the trip cost, or about $500 or so as a flat rate. “Whatever it is, when something goes wrong (and lately something always seems to be going wrong), the agent will pick up the phone and go to bat for you. Very well worth it!”

VIP arrival at international airports.

Many airports offer VIP arrival services that whisk those who are willing to pay through private or semi-private security lines.

“Often, $200 or so can save you so much time and hassle in the immigration, customs and baggage claim process that's required for all international travel,” explains Whitney Shindelar, an Iowa-based travel advisor and owner of the trip design company Undiscovered Sunsets. “All airports handle this differently and at a different price point, and it's not always available. But at least ask, and definitely keep it in the itinerary when your travel pro recommends it—as it's often recommended for good reason!”

High-quality luggage and sneakers.

Speaking of baggage claim, no one wants to fight with pesky wheels, flimsy luggage or struggling to smash everything into a too-small carry-on bag. Since you’ll have it in hand longer than your checked bags, Collins says it’s especially worth it to splurge on luxe luggage that’s durable, long-lasting and offers features that meet your needs. Brands like Away, Monos and July are industry pro favorites.

As you’re commuting and when you get to your destination, you might want to think twice about wearing your fashion-forward pumps or that pair of brand-new boots (who knows if they'll lead to blisters?). Instead, splurge on a chic pair of walking shoes. Allbirds, Kizik and Rothy’s all offer stylish and sturdy models.

“Good walking shoes cost more than people expect, say, in the $200 dollar range, but they are worth the spend. There is nothing worse than being in painful or uncomfortable shoes while traveling,” Brown says.

Private transfer services.

Navigating public transportation, taxis or Ubers upon arrival in a brand new destination does not provide a stress-free start to a vacation, Shindelar confirms.

“Even if you never have a private transfer during the rest of your trip, make the beginning and endas seamless as possible. I highly recommend to my clients that they don’t skimp on private arrival and departure transfers to and from the airport,” she says.

Private transportation can also come in clutch at other points of your vacation, whether it’s a car service that takes you from city stop one to city stop two via a route that allows you to stop for a scenic lunch, or for a safe ride that allows you to imbibe.

“Here in Wine Country, one of the biggest mistakes we see guests make is not arranging transportation for their wine tastings. People often overestimate their tolerance, so getting a driver to take you around is a worthwhile splurge that allows you to have fun, relax and know you’re in safe hands,” says Jeff Wielgopolan, the service director at Meadowood Napa Valley in Napa, California.

Hotel rooms with certain amenities.

If you’re unsure what’s available, reach out to the property (or, better yet, have your agent or advisor do so). Whether you’re craving an open floor plan, separate seating areas, a fireplace, or otherwise, articulate what you like and chances are high that you’ll enjoy your home away from home much more than if you simply booked the basic option, Wielgopolan says.

You might not need the penthouse suite or other most lavish hotel room option at every stop, but if your travel agent or advisor tells you to upgrade at a certain point, “you better listen! When working with travel pros, a hotel is never just a hotel. It's always part of the experience. The location matters. The room category matters. The view from the room matters,” Shindelar says.

For Brown, the upgrade she’s looking for is a junior suite instead of a standard room. It’s always larger than a basic bedroom, and it comes complete with a separate seating area. When Brown is traveling with her family, the cost of that extra room is so worth it: “It’s a must for keeping everyone’s nerves a little more calm.”

Keep in mind that certain hotel loyalty programs might help you “unlock” other perks, access and opportunities to earn future rewards or free stays, adds Brad Anderson, the McLean, Virginia-based vice president of the Hilton Honors Program.

Private tours with local guides.

“Many of our wealthiest and highest-profile clients skip tours because they associate them with crowds, tourist traps and inauthentic experiences. This is a shame, since private tours—led by locals—can lead to amazing experiences,” Collins says.

Splurge on private tours whenever possible, especially those which involve access to private property and behind-the-scenes views of local life, culture and historical sites. This can really bring a destination to life and add context that you might otherwise miss while roaming around by yourself.

“My heart is very sad when travelers remove the majority of guided experiences and prefer to explore on their own,” Shindelar admits. “The experience is incomparable!”

You have a couple different options here: Local guides focused on a specific theme throughout certain parts of the experience (Shindelar often taps on-site pros who are part of Context Travel) or one guide to assist with the trip from start to finish.

In Egypt, for example, you can have one guide travel with you and guide you through Cairo, Luxor, Aswan and Abu Simbel or you can have one guide in Cairo, one guide in Luxor, one guide in Aswan and a final one in Abu Simbel. Having one guide from start to finish is more expensive, as there are more costs to be covered, but as they get to know you—and your preferences—they can customize the itinerary even more to suit your needs.

An airport security lane “fast pass.”

Score access to a separate—and often, far shorter—line that makes the check-in and customs process much smoother. Not only will this save you stress, but during busy travel seasons, it might also be the difference between you missing or making your flight. Brown adores her CLEAR membership, which now also links up to security checks used at some concerts, offices and other large events or venues around the country.

For CLEAR, “biometrics are used for your face to go through security, and then you are personally escorted by a CLEAR employee to the TSA agent where they wave you through,” she explains. “I can’t say enough about how smooth this makes the airport experience for me and my family, and kids under 18 can join your membership for free!”

Other options include TSA PreCheck, which is terrific for stateside travel, and Global Entry, which is like PreCheck with international perks. Before you pay full price, check with your credit card company; many reimburse some or all of the enrollment fee.

Travel insurance.

You can’t put a dollar amount on peace of mind, so it’s very much worth it to invest in travel insurance, especially if you’re booking a big international trip.

“One illness could totally undo all the money and time you’ve contributed,” Brown says. If you’re going overseas, it’s wise to also consider purchasing a separate travel medical insurance, “as no plan in the U.S. covers you when you are abroad. Medjet and companies like them will transport you on a private plane anywhere you’ve traveled back to your home so you can seek emergency care with your own hospital and doctors.”

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