Vacation Upgrades Worth It (and Not): Avoid A Shining Sequel
Family travel is a luxury and a privilege many people never get to enjoy, but anyone who has done it for any length of time can relate to Clark Griswold. The stress gets amplified the second conditions stop being ideal. The fix is knowing which vacation upgrades are actually worth it and which ones are just resorts charging you extra to feel fancy. Spend in the right places and you decrease your odds of an unplanned police chase.
Quick verdict: Pay up for legroom, assigned seats, a real airline, TSA PreCheck, a bigger room at a decent property, a roomier rental car, a cruise verandah, and a front-of-line pass when it covers what you actually want to ride. Skip full-price first class, day lounge passes, hotel rooms “with a view,” club level, luxury rental cars, park hoppers, and cruise-line shore excursions. The rest of this post is the math behind those calls.
What Are the Vacation Upgrades That Are Worth it?
1. Air Travel
1a. Extra Legroom Seats or Discounted First Class
1b. Flight Upgrade Seats Selection
1c. Choose Carriers That Are Not of the Budget Variety
1d. Priority Pass Lounges
1e. TSA Precheck Boarding Passes
2. Hotel Travel Class Upgrades
2a. Get a Larger Room
2b. Stay at a Nice Property
3. Ground Transportation
3a. Reserve Larger Rental Cars
3b. Use Private Transportation
4. Cruises
4a. Book Staterooms with Verandahs
5. Theme Parks
5a. Most Front of the Line Passes
5b. Cost Effective Dining Plans
5c. Some Dessert Parties and Dining Plans with VIP Seating for Fireworks
What Vacation Upgrades Are Not Worth it?
1. Air Travel Flight Upgrade
1a. Full Price First Class Tickets
1b. Day Lounge Passes
2. Hotels
2a. Rooms with a View
2b. Hotel Upgrade Packages That Include Things About Which You Don’t Care
2c. Club Level Access
3. Ground Transportation
3a. Luxury Rental Cars
4. Cruises
4a. Cruise Excursion Tours Booked Directly Through the Cruise Line
5. Theme Parks
5a. Dining Plans That Are Not Cost Effective
5b. Park Hopper Add Ons
5c. VIP Packages for Fireworks That Do Not Make Sense
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Vacation Upgrades That Are Worth it
1. Air Travel – Vacation Upgrades That Are Worth it
1a. Extra Legroom on Flights or Discounted First Class
When should you upgrade your flight seats? Anytime you have your kids with you.
Kids come with a lot of baggage, and not just emotional. They also have this inconvenient adorable habit of ending up in your lap halfway through the flight. Diaper bags, plane snacks, and a tablet running on 4% battery are fun to wedge your feet around, sure, but what if you didn’t have to? Extra legroom goes a long way.
I’m not telling you to buy a cash first-class ticket for a five year old unless it makes you genuinely happy or you found a great deal. Our first-class seats are booked almost entirely with miles and points, which you can earn just by signing up for the airlines’ free loyalty programs. If you haven’t started earning travel points yet, you’re leaving the best upgrades on the table.
Pro tip: If you’re having trouble finding award availability, try ExpertFlyer. You can set up alerts that ping you the moment seats open up. There’s a free version and a paid one.
No points stash yet? Just buy the extra legroom. It’s far cheaper than first class, it often comes with a much-needed cocktail, and it’s not a necessity so much as the difference between arriving human and arriving feral.
1b. Seat Selection
Most airlines sell a basic fare that won’t let you pick seats ahead of time. Why should you care where you sit? We’re all going to the same place, right? Sure, but will you get there without having to throw yourself on the mercy of a stranger so you can sit next to your own child?
Air travel is hectic enough. Don’t add another stressor to the pile. Paying a little extra to lock in your seats at booking is one of the cheapest sanity upgrades there is. Just do it.
Heads up if you fly Southwest: the famous cattle call open-seating free-for-all is gone. As of January 27, 2026, Southwest moved to assigned seating, so you now choose your seat when you book (except on the cheapest Basic fare) instead of lining up and duking it out in the aisle. Boarding is split into Groups 1-8 instead of the old A/B/C lineup, and everyone on the same reservation gets the same boarding group, so families board together by default. If you want to know how the airline still stacks up for families, I broke that down in seven reasons to fly Southwest with kids.
1c. Carriers That Are Not of the Budget Variety
There’s a reason budget airlines undercut the major carriers. There’s no legroom, and they will get you at every turn. That’s fine if you’re flying solo and ready to throw down. The kids don’t need to watch mommy go all Lindsay Lohan over a $65 carry-on fee.
The usual greatest hits: charging extra for a carry-on, canceling nonstop flights and rebooking you onto something with a five-hour layover in a city you didn’t want to see, and customer service that ranges from indifferent to openly hostile. A few have earned reputations for being outright dishonest.
You’re not guaranteed a perfect trip on any airline, but your odds of disaster go way up when the base fare was $19. The upgrade to a real carrier looks reasonable the moment you’ve paid for bags, seats, and a missed connection that ate the first day of your vacation. If you don’t want to pay the premium, start racking up miles and points to cover it.
1d. Priority Pass Membership
Airports are crowded. On a good day you can find seats at the gate together. Best of luck during the holidays. Airport lounge access is priceless (except it does, in fact, come with a price). The fancy lounges have showers and hot buffets; even the bare-bones ones have food, drinks, real seats, and quiet, which is plenty when you’ve got toddlers melting down by the window.
Lounges know how much people love them, so they charge a small fortune for one-off day passes. Those rarely pencil out. A membership is the smarter buy.
Priority Pass is a membership that gets you into lounges all over the world. Is Priority Pass worth it? If you fly often, absolutely. It pays for itself.
A heads up if you’re chasing lounge access through a credit card: this perk moves around a lot. Some premium travel cards with hefty annual fees still bundle in a Priority Pass Select membership, but card lounge benefits get cut and reshuffled constantly (Hilton’s Amex cards, for example, dropped their complimentary Priority Pass visits a while back). Don’t pick a card for a lounge perk without confirming it still exists. If you want help thinking that through, start with my guide to the best miles and points credit cards for beginners.
1e. TSA Precheck Enrollment
Waiting in line is fun. Like a root canal. Airport security lines are some of the worst, and at the end of this one you don’t get Space Mountain. You get to remove half of what you’re wearing and get probed. Fortunately, you can enter a much shorter line and keep your dignity (and your shoes) with the TSA PreCheck known traveler program.
A new PreCheck enrollment runs roughly $76 to $85 depending on which approved provider you pick, down from the old flat $85, and it’s good for five years. Renewals online are cheaper still. Children can typically go through the PreCheck lane with an enrolled parent or guardian, but the age cutoff changes, so confirm the current rule on the TSA’s PreCheck page before you assume your teenager rides free. This is money well spent, and a number of travel credit cards reimburse the application fee as a perk, so you may not pay for it at all.
2. Hotel Upgrades – Vacation Upgrades That Are Worth it
2a. Hotel Suite Upgrade
Remember how the McCallisters started out in that motel in Miami, then switched to the suite at The Plaza? The trip improved substantially, and it wasn’t just because they found Kevin. More space changes everything.
A room with two real spaces, like a one bedroom, holds all the kids’ stuff without turning the floor into a tripping hazard. It lets children on different nap schedules exist in different areas. Best of all, parents can shut an actual door on their children without a Madeleine McCann situation.
Sign up for the loyalty programs at the major hotel chains before you book. Points are free, and elite status can land you a complimentary upgrade at check-in. If you’re not slated for a free one, ask the price to bump up at the desk; sometimes a one bedroom costs barely more than a studio, and the front desk would rather sell it than leave it empty.
2b. Nice Property
A bigger room is great, but even a suite wouldn’t stop the cash in your wallet from getting lifted at the Braidwood Inn. You don’t need the Waldorf Astoria when you’re traveling with kids, but don’t book a dump either.
A nice resort usually comes with perks like kids’ clubs and childcare. Some of those save you money; more importantly, they save your sanity, which at a certain point in the trip is worth more than money.
A good property is easy to book on points if you’ve got a balance with the chain. You can earn those several ways, but the fastest route runs straight through credit cards.
You can often find a deal on a nice property if you go looking. Check Groupon and sites like Booking.com, Travelocity, Hotellook, Tripadvisor, Hotels.com, and Expedia to scout the rates. If the price matches, book directly through the hotel so you still earn points, but these sites tell you what’s out there.
For Disney properties, consider renting Disney Vacation Club points to score a deluxe resort for a deep discount.
3. Ground Transportation – Vacation Upgrades That Are Worth it
3a. Larger Vehicles
I get the urge to grab the cheapest rental car to get you from Point A to Point B, but on vacation you’re hauling around even more stuff than usual. Will your luggage, car seats, and stroller actually fit in that economy box with Bozo and Cookie?
If you need an SUV to get through life at home, rent one on vacation too. The bump in price is often small, and you’ll be far happier than you would be playing luggage Tetris in a parking garage at 11 p.m.
Compare options on a site like Orbitz, then book directly through the rental car company so you can grab any membership perks. You can also book free rental days with miles and points through a credit card travel portal.
3b. Private Transportation
If you’re skipping the rental car and your resort doesn’t run a free shuttle, book private airport transportation. Shared shuttles and buses are slow, crowded, inconvenient, and yet another chance to drag your luggage around a parking lot. Is saving a few bucks really worth it after you’ve been traveling all day?
With a few people in your party, a private car or van can actually come out cheaper than everyone buying shuttle seats, whether that’s a town car, an Uber XL, or a booked transfer service. Price it out before you travel instead of deciding curbside while a kid wails about a dropped pretzel.
4. Cruises – Vacation Upgrades That Are Worth it
4a. Verandah Staterooms
Cruise staterooms are small. Cruise lines are infamous for cramming people into the most modest of quarters, anywhere from the size of a refrigerator box to that of a studio apartment. Unlike a hotel room, you’re not even guaranteed a window.
You might figure you don’t care about the room because you won’t be in it much, but that’s short sighted. Even if you don’t need the square footage, you’ll love having a verandah cruise balcony.
Common areas on a cruise ship get packed. There is nothing better than sitting on your own private verandah with the ocean going by and no one else in sight. A balcony also gives the adults somewhere to hang out (and pour a drink) once the kids are asleep. And if anyone in your party gets seasick, the fresh air cannot be beat.
On some itineraries, like Alaska, the verandah cabins carry a hefty premium. On a lot of Caribbean sailings you can move up to a larger room with a balcony for a relatively small bump. If you’re weighing a family sailing in general, I went deep on the value question in are Disney cruises worth it.
5. Theme Parks – Vacation Upgrades That Are Worth it
5a. Front of the Line Passes
Theme parks have a lot to offer, but the obvious downside is the constant waiting. A solid touring plan trims some of it, but on a crowded day you can’t make it disappear without a front-of-line pass.
These passes go by different names depending on the park. At Walt Disney World and Disneyland, the paid line-skipping service is now called Lightning Lane: a Multi Pass lets you pre-book a set of attractions, a Single Pass covers the headliner rides individually, and there’s a top-tier Premier Pass too (the old “Genie+” and “FastPass+” names are retired). At Universal Orlando it’s the Express Pass, which now covers the brand-new Epic Universe park that opened in May 2025 (it skips nearly every ride there). Whatever the brand calls it, the value math is the same.
Expect to pay real money, but a good pass will improve your day tenfold. It’s almost always worth it to me when the pass is effectively unlimited (like Universal’s Express) and covers what my family actually wants to ride. If you only visit a park once in a blue moon, take it seriously. For more on which Disney add-ons earn their keep, see my breakdown of which Magic Kingdom extras are worth it.
5b. Cost Effective Dining Plans
Most theme parks sell some kind of dining plan. Most of them only pay off if you intend to spend the whole day stuffing your face with mediocre food. But there are a few genuine gems that save you money on food you’d have bought anyway, so don’t write every plan off on reflex.
Some regional parks, like Six Flags, let you bolt an inexpensive all-season dining plan onto a season pass so you eat all year. If you go even a handful of times, that one usually wins. One catch since the Six Flags and Cedar Fair merger: the dining add-ons aren’t interchangeable between legacy Six Flags and legacy Cedar Fair parks, so buy the plan for the chain you’ll actually visit.
The Disney World Dining Plan is back (the Quick-Service and standard Table-Service plans are bookable again; the Deluxe plan is sitting out for now). It has never been cheap. You know what else isn’t cheap? Every single thing you eat at Disney World.
Here’s the angle that can flip it from rip-off to bargain: for 2026, Disney is running a “kids eat free” promotion, where children roughly ages 3 to 9 get a free dining plan all year when you book a qualifying package (room plus dining for the older guests) at a Disney-owned resort. If you’ve got little kids who love a character meal, run the numbers, because a free child plan changes the math fast. For the full toolkit, see my guide to saving money on Disney trips.
5c. Some Dessert Parties and Dining Plans with VIP Seating for Fireworks
There is a real risk that I will choke a stranger who tries to slide in front of my kids, who have already been holding a spot for an hour waiting for the show to start. I love the idea of these packages purely because they keep me out of handcuffs, but they aren’t always worthwhile.
Some of them barely cost more than just eating at the restaurant on its own, and occasionally you can fold one into your regular dining plan. Those are the ones to grab.
Before you book, check three things: how crowded the free public viewing area gets, how early you’d have to stake out a spot without the package, and exactly which reserved section your money buys. Weigh those, and decide if skipping the scrum is worth the price to you.
Vacation Upgrades That Are Not Worth it
A vacation upgrade is worth it for three reasons:
- It saves you money.
- It substantially improves your experience.
- It makes you really happy.
If anything on the list below hits one of those three for you, go for it. If it doesn’t, here’s why I’d keep my wallet shut.
1. Air Travel
1a. Full Price First Class Tickets
First class is lovely, but is paying thousands of dollars apiece for children to sit in it lovely? The wider seat and the warm nuts do not begin to cover the added cost of the ticket. If you can’t get it at a real discount or with miles and points, buy the extra legroom and call it a day.
1b. Day Lounge Passes
A membership like Priority Pass can absolutely earn its keep if you fly enough. One-off day passes are a different story. They’re steep and almost never worth it. If you just need to escape the crowd, go grab a table at a sit-down restaurant or hunt down an empty gate instead.
2. Hotels
2a. Rooms with a View
I’ll happily pay up for a balcony on a cruise, but a hotel view rarely earns the upcharge unless it’s something genuinely once-in-a-lifetime. Ask yourself:
- Will you actually be in the room enough to enjoy it?
- Will the view do you any good in the dark while your kids sleep?
- Do you really want to pay extra for a front-row look at kids dyeing the pool water yellow?
If not, save your money.
2b. Hotel Packages That Include Things About Which You Don’t Care
Hotel packages can save you money, especially the ones tied to a theme park, so it’s always worth checking the current offers. But when an “upgrade” package comes at an inflated rate and bundles in a spa credit, a wine tasting, and a champagne breakfast you’d never use, take a hard pass and book the room on its own.
2c. Hotel Concierge Upgrade
Some packages buy you into a concierge or club-level lounge stocked with light food and a few alcoholic drinks. Sounds nice. It’s almost never worth the cost. A hotel lounge doesn’t do what an airport lounge does, because you already have somewhere private to escape to: your room. If the crowd downstairs gets to you, just go upstairs.
The one time to reconsider: if you can genuinely eat enough meals in the lounge to skip a restaurant or two, the math can tip. Add up what you’d actually eat there. If it doesn’t clear the upcharge, skip it.
3. Ground Transportation
3a. Luxury Car Rental Upgrade
I’m all for upgrading a rental car to fit your family. I’m not for upgrading it to fit your midlife crisis. A family trip is not the time for the convertible. That Ferrari was not built for car seats, and you will spend the whole week terrified of a juice-box spill.
4. Cruises
4a. Cruise Excursion Bookings Directly Through the Cruise Line
Do not book your shore excursions directly through the cruise line. Cruise-line excursion prices are wildly inflated. You can usually book the exact same tour, with the exact same local operator, for substantially less by going straight to the shore-excursion provider. The cruise line already has plenty of your money. Cut out the middleman.
One honest caveat: book a third-party tour with enough buffer to get back to the ship on time, because the cruise line will wait for its own excursions and will absolutely leave you standing on the dock if you booked outside. A reputable independent operator builds in that cushion. Read the reviews before you commit.
5. Theme Parks
5a. Dining Plans That Are Not Cost Effective
A theme park dining plan only makes sense if it saves you money on food you’d have bought anyway. Several parks push all-you-can-eat plans, and to come out ahead on those you’d have to eat more than the Nutty Professor’s entire family. The last thing you want to feel in 95-degree heat between roller coasters is uncomfortably full.
You may also be boxed in on where you can use it, since some plans don’t cover every restaurant in the park. Run the math on your actual eating habits. If it doesn’t clearly come out ahead, skip it.
5b. Park Hopper Tickets
This is probably the most controversial pick on the “not worth it” list. The park hopper add-on costs more and lets you bounce between parks in a single day. Some people adore it and get real use out of it. Unless the parks are within walking distance of each other, I don’t think it’s a good investment for families with little kids.
Are park hopper tickets worth it for you? Ask yourself:
- Can your young kids happily fill a whole day at one park?
- Is hopping between the parks a genuine time suck?
- Would you rather skip a pointless midday bus ride with a stroller and a melting toddler?
If you answered yes to any of those, you probably don’t need to upgrade to park hopper passes.
5c. VIP Packages for Fireworks and Shows That Do Not Make Sense
A dining package that drops you into a reserved section away from the general-public scrum can be worth it. Plenty of the others are a rip-off. It is not worth hundreds of dollars if you still have to show up an hour before showtime and elbow strangers for a sightline. Look up exactly what the package guarantees before you go.
Frequently Asked Questions About Vacation Upgrades
How much does TSA PreCheck cost, and is it worth it?
A new enrollment runs roughly $76 to $85 depending on the approved provider you choose, and membership lasts five years. For a family that flies even a couple of times a year, the shorter line is well worth it, and plenty of travel credit cards reimburse the fee outright. Confirm the current price and the rules for children on the TSA’s PreCheck page before you enroll.
Is a Priority Pass membership worth it?
If you fly often, yes, a lounge membership pays for itself in food, drinks, and quiet alone. If you barely fly, it probably doesn’t, and you should not buy a credit card purely for lounge access without confirming the perk still exists, because card lounge benefits change constantly. One-off day passes are the worst value of all.
Is the Disney World Dining Plan worth it?
It depends on how your family eats, but it’s worth a real look for 2026 because Disney is running a kids-eat-free promotion that gives children roughly ages 3 to 9 a free dining plan when you book a qualifying package at a Disney resort. If you’ve got little kids who love character meals, that can swing the plan from overpriced to a genuine deal. Always do the math against what you’d actually order.
Is a front-of-line pass worth it at theme parks?
Usually, if it covers the rides you care about and you’re only visiting once or twice. Universal’s Express Pass (now valid at the new Epic Universe park too) and Disney’s Lightning Lane options can turn a day of waiting into a day of riding. The catch is the price and the fine print, so check exactly which attractions are included before you buy.
Final Thoughts – Vacation Upgrades That Are Worth it
I love a luxurious vacation as much as the next person. It’s great when things are easy, and even better when I know I got a good deal and didn’t throw money away. There are plenty of vacation upgrades that are genuinely worth it, and a handful that absolutely are not. Spend the extra cash when it’ll make you happy or save your sanity. Don’t spend it on autopilot just because the checkout page suggested it.
Weigh your choices, do what makes sense for your family, and upgrade the parts of the trip that actually move the needle. You won’t regret it.
You gave some great travel tips. I always pay extra for a hotel room with balcony and ocean views. But you are ‚úÖ i spend 95% of my time outdoor when i am on vacation. So the balcony = extra $$$ that could go towards food cost.
Great piece! The hotel upgrades… this was a game changer when we really started spending time at far away places. Having a comfortable ‚Äúhome base‚Äù makes recovering from a day having fun, all the better.
Very detailed post. Thanks for sharing these information
What an excellent detailed list on getting upgrades when traveling. For many, I’ve learned that having a friendly smile and word can make a big difference when trying to get upgrades most anywhere. We always use our credit card air miles for either Premium Economy or Business Class Upgrades on long haul flights. Great post & Pinned for others to see! 🙂
Such excellent informative suggestions! Thank-you!
As a former Shore Excursions Assistant Manager on cruise ships I don’t know what to say about “booking excursions through the cruise line” part, but I agree to the rest of your pointers!:))
You are so right about the importance of paying extra for a good airline! I can’t count the number of times my life was made easier by a better flight! These suggestions are all great; thanks for the useful information!
This is such a great list. I miss traveling so much and can’t wait to get back at it someday!
Family trips are so memorable! Im looking forward to our small addition in our family in April 2021. What a beautiful post!
This is some wonderful information! I always fail to leave enough room in my budget for what I’ll be eating on my trip so the dining package plan was some great advice for someone like me.
This is an excellent article helping people decide how to balance their travel budget versus their travel wishes. As you rightly said, one still needs to make the decision of his/her personal preferences.
I loved this article making family travels easier. I don’t have kids but as guide I offer private tours especially designed for family, so I take very serious the argument and I hope I’m doing my part to grow nice good travellers
Thank you. There is so much good information here. And I will never cruise without a veranda again 🙂 It made our cruise so much better!
I agree on most of these, particularly the cruise ship balcony. We’ve done several different cabin configurations, but I really love that balcony and I USE it. I just find it so peaceful to just sit there and watch the ocean. Bonus tip – be careful with the flights you pick. We ended up on a flight from Orlando to Salt Lake. Since both destinations are especially jam-packed with KIDS, it was a miserable flight. There had to have been at least a dozen kids under 4 on that flight. We were really wishing we’d taken the option that routed us through New York instead.
Great post! Signing up for TSA precheck was one of the best decisions ever! I only wish I had paid extra for Global Entry.
This is so detailed and helpful thank you! I always get extra legroom not because I’m tall but because I get anxiety being so near to lots of people and find it makes such a huge difference.
Getting TSA precheck was the best money I ever spent on traveling! I used to hate the airport part of traveling, now I only mildly dislike it haha – great post!!