When you’re planning a trip and have a little extra room in the budget, where should that money actually go? Not all splurges are created equal. In fact, in nearly every category of travel planning, the cheapest option and the best-value option are not the same thing at all.
Here are five categories where spending a bit more can make a huge difference in how your trip actually feels.
1. Flight Splurges
The flight that doesn’t start your trip off on the wrong foot.
A few small upgrades here can save you a lot of stress:
- Seat selection. Many basic economy fares don’t include seat selection, which means you might not sit with the people you’re traveling with. You could get lucky, but you might not.
- Checked luggage. If you’ve ever tried to do carry-on only and ended up stressed about fitting everything in (or worse, had to buy an extra suitcase mid-trip), you know checking a bag can be worth every dollar.
- Better flight times. Think about your sleep schedule, your overall travel plans, and whether you really want to be driving to the airport in the dark.
- Nonstop flights. Skipping a connection means one less chance of a delay causing you to miss your next flight, and fewer opportunities for your luggage to go missing.
My number one tip: fly in a day early, especially for cruises, international trips, or group trips. This protects the first day of your trip from being ruined if something goes wrong with your flight. This is especially critical for cruises — if you miss your flight and the ship has already left, you may end up having to catch up with it at the next port, which can get expensive fast. Travel insurance may help if the delay is a covered reason, but personally, I’d always rather just go in a day early than risk it.
2. Arrival and Transportation Splurges
The arrival that doesn’t start with stress.
How you get from the airport to your destination matters more than people often think:
- Prearranged transportation means you’re not standing at baggage claim trying to figure out your next move. You simply follow the directions provided by your travel professional.
- A hotel near your activity, cruise port, or main area can sometimes cost more upfront, but it’s worth weighing against the time and hassle of longer transfers.
- The right size vehicle for your group and luggage. Nothing ruins an arrival faster than everyone piling extra suitcases onto their laps in the back seat.
My number one pick: private airport transfers. They’re easy to book, and they make all the difference between feeling lost and confused after a long flight versus having someone simply waiting for you.
3. Room, Resort, and Cruise Splurges
The room that works for real life, not just the booking screen.
This category affects your entire trip and applies whether you’re traveling as a couple, a family, or a multigenerational group — and it doesn’t necessarily mean going for the most luxurious option available.
- Room location or view. At an all-inclusive resort, that might mean choosing between a tropical (greenery) view or an ocean view — and within ocean views, a partial side view versus a full oceanfront view. Tip: book early if you want the best locations.
- Cabin category on a cruise. Balcony, window, or interior (where you can’t see — or feel — the weather at all). I personally always recommend at least a balcony, since being able to step outside and check the weather adds so much to the experience.
- The ship or resort itself. What it offers in terms of entertainment, dining, and itinerary — and for cruises, which ports it can actually fit into, since smaller ships can access destinations larger ones can’t.
My top tip: choose the room category that actually fits how you travel, whether that’s on a cruise, at an all-inclusive, or elsewhere.
4. Experience Splurges
The experience they’ll still talk about later.
These are the moments that turn a good trip into an unforgettable one:
- Private or small-group tours for a more interesting, educational, or exclusive experience.
- Specialty dining — especially on cruises. Steakhouses, in my experience, are always worth it.
- A photo shoot or special celebration moment, like a private balcony or beachfront dinner.
- Spa days, cabanas, or adults-only experiences — some resorts and ships are adults-only entirely, while others have designated adults-only areas.
My number one tip: book one truly special excursion. This is about making memories — and memories, not souvenirs, are what you’ll actually take home with you and talk about for years.
5. Peace of Mind Splurges
The breathing room that keeps one problem from becoming the whole trip.
- Flexible booking options, which usually don’t cost much more and let you cancel or change your trip without losing money or needing to prove a reason.
- Professional planning help. This varies by advisor — some charge a planning fee, some don’t.
- Built-in downtime. Trips like Disney World can leave you needing a vacation from your vacation. Adding an extra night, or a full extra day with nothing planned, can help you come home actually feeling rested.
- Pre- or post-trip extensions. If you’re sailing out of a city like Rome, consider spending an extra two or three nights there before or after your cruise — you’ve already invested the time and money to get there, so why not see more of it?
My number one peace of mind splurge: travel protection. I don’t really think of it as a splurge — to me, it’s a necessity. A flexible booking policy can offer flexibility, but it typically doesn’t cover airfare. And things like sickness, accidents, missed connections, or delays are out of your control. Nobody plans for them, but they happen — and I’ve seen them happen to people. I don’t want that to happen to you.
Ready to Plan a Trip Where the Splurges Actually Pay Off?
If you’re not sure which of these upgrades make sense for your specific trip and budget, that’s exactly what I’m here for. Reach out today and let’s put together a travel plan that protects your time, your money, and your peace of mind, so you can focus on the part that matters: making memories.