How to Find Luxury Travel Bargains for Boomer Travelers

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Man and woman hold glasses of champagne on the deck of a luxury cruise ship.
Luxury travel is our favorite way to go!

Updated 07.20.2019: Luxury travel is the way that Alan and I like to explore the world. We’ve clinked champagne glasses more times than we can count as a luxury cruise ship leaves port. In Shanghai, we sat in the bed of our luxury hotel room at The Peninsula Hotel and pointed the remote control toward the window to raise the automatic shades on another day of exotic adventure. And there’s nothing better than waking up in a private cabin at Triple Creek Ranch—voted the world’s best hotel—knowing that a gourmet breakfast is waiting for us in the dining room followed by a day of adventure.

Even though Alan and I enjoy luxury travel, neither of us is a frivolous spender. We’ve worked hard through the years, including being responsible when it comes to savings and investments. Like all the other luxury travelers that we know, Alan and I look for luxury travel bargains to make our travel dollar work as hard as it can for us.

How to find luxury travel bargains

Looking out on the green grounds and two pools of a luxury hotel on Maui.
Montage Kapalua Bay is our favorite luxury travel experience on Maui.

Finding the best values in luxury travel is a matter of staying educated. Here’s how we stay in the know:

Know when to go on a luxury trip

Traveling during shoulder season offers the best luxury travel deals. Timing a trip immediately before or after prime travel season at a destination brings the cost down, sometimes dramatically. Enjoying luxury without the crowds is an added bonus.

For luxury cruises, repositioning itineraries offer the best deal. Fares are often priced at 2 for 1—be prepared for plenty of sea days.

A flexible schedule allows us to take advantage of last minute luxury travel specials. How do we find them? By signing up for emails from our favorite travel companies, including hotels and cruise lines. Our inbox sees a steady stream of offers.

Read more luxury travel tips before planning your next trip.

Know where to look for the best value in luxury travel

Beige stone spires of the Cologne Cathedral on a snowy day with blue skies.
Enjoying a walking tour of Cologne, Germany, on a Rhine River Christmas Markets cruise.

Before booking a mainline cruise with add-on charges for water, alcohol, tips and more, compare the fare to those of all-inclusive luxury cruises that fold those amenities into one price. You’ll also want to compare the size of the cabin and if a balcony is included. If the cost is still too steep, look for a shorter itinerary on the luxury line. Or book a premium cabin on the mainline cruise that offers additional perks.

Save money on international business class fares by purchasing tickets from gateway cities (we always consult Skyscanner to determine the best price and route). After arranging our international flight, Alan and I purchase a domestic ticket to arrive at the gateway city a day ahead of the international flight just in case there are routing problems. This is especially helpful if, like us, you travel from a second or third tier airport. And you’ll also avoid those extra-long travel days that will zap any boomer’s energy.

Treat yourself to luxury close to home by learning about resorts, boutique hotels and guest lodges in your area. Apply the money you saved on transportation costs, to a luxury lodging experience. Don’t forget to sign up for emails to learn about special offers. And many resorts offer special pricing to locals during the off season.

Know whom to ask for luxury travel advice

Guide opens a bottle of champagne during a stop on a luxury safari.
Our travel agent knew that we would love Ivory Lodge in South Africa. She was right.

We wouldn’t plan a luxury trip without using the services of a travel advisor who is an expert—and top seller—in the type of travel or destination that we’re seeking. Their advice, and clout with the company, will save us money as well as keep us from making expensive mistakes like choosing a cruise cabin in a bad location on the ship. An agent who belongs to Virtuoso or another luxury travel network can also offer access to upgrades, unannounced sales and other perks.

When booking accommodations, go to the source. Reserve directly through the hotel rather than a third party booking company. Call the hotel’s local number (not the chain’s customer service line), to inquire about special pricing. This is also the time to ask if upgrades are available. If you don’t score when making the reservation, ask again at check-in. 

And, as I mentioned earlier, to be the first to know about luxury travel bargains, sign up for email notifications from hotel, cruise and airline loyalty programs.

No traveler likes to pay more than necessary. Even if you’re not a luxury traveler, these strategies will help you find the best value for your trip.

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