7 Places the Upper Middle Class Spend Summer Holidays — How You Can Visit for Cheap, Too

Summer is almost here, and you might be thinking about heading somewhere new. You’ve heard about many of the chic vacation destinations of the upper middle class, but you may not think a trip like that is in your budget this year.

What you might not realize is you can visit these swanky destinations without breaking the bank. Planning travel through a budget-minded lens can allow you to experience these breathtaking locales without breaking the bank.

Prepare to be amazed that the posh places that can actually be affordable. Here’s a look at seven locations the upper middle class spends their summers that you can also visit on a relatively modest budget.

Jaw-dropping coastal scenery, quaint towns and opulent resorts make the Amalfi Coast of Italy popular with tourists, said Sushant Yadav, a travel agent with Travelosei.

The upper middle class might visit the area in June and stay in a five-star hotel like the Hotel Villa Franca Positano, which can easily cost $1,300 per night or more.

Luckily, that’s not the only way to visit the area.

Yadav recommended traveling during the off-peak season, which runs from December to March. However, he said you might still be able to avoid high-season prices by traveling in the warmer, more desirable months of May or September.

He said it’s also best to avoid staying in the busiest, most popular towns.

“Salerno or Praiano towns have cheaper accommodations but still allow one easy access to famous sites,” he said.

To save money getting around the area, he recommended using public transportation.

“Along the coast, one can take advantage of this cost-effective method of traveling by bus operated by SITA Company,” he said.

This bus company offers several routes that connect Amalfi Coast towns, as well as those to other areas such as Sorrento, Salerno and Naples.

For many, Maui is a dream vacation. According to Yadav, the upper middle class really enjoy the pristine beaches, lush rainforests and top-tier resorts Maui has to offer.

When booking a room, wealthy travelers might choose a resort like the Grand Wailea, a Waldorf Astoria Resort, which starts at around $1,000 per night.

To visit this city on a budget, Yadav recommended booking early to secure competitive rates on flights and accommodations.

He advised staying in an Airbnb or VRBO rental, so you can save money on food by cooking many of your meals.

Famous sunsets, beautiful white buildings and deluxe hotels make Santorini a beloved destination among the upper middle class, Yadav said.

To save money on a trip, he suggested visiting in the spring or autumn.

“Low-season prices are available between late April to early June or September to October,” said Yadav.

As for affordable accommodations, he advised seeking out hostels or budget hotels around Perissa or Kamari.

Also, “Skip eating in touristy restaurants and instead try local bakeries and tavernas.”

Yadav calls Lake Como a “celebrity hotspot.” As he explained, the beautiful lakeside views, grand villas and tranquil surroundings make it a popular vacation destination for the upper class.

While there’s many different Lake Como towns to visit, including Bellagio and Como, but Yadav advised staying in less touristy towns.

“The cost of accommodation is generally lower in places like Menaggio or Varenna,” said Yadav. “You can also take advantage of the ferry network as an economical way to get around the lake with its towns.”

Instead of an expensive meal out, he suggested purchasing fresh produce from local markets and having a picnic by the lake.

The upper middle class can’t get enough of the Napa Valley, said Yadav. That’s all due to its famous wineries, picturesque vineyards and fine dining.

To make the trip more affordable, Yadav recommended visiting during the week.

“Weekdays usually have cheaper hotel rates than weekends do,” he added.

Wine tastings — a popular napa valley activity — can easily cost $30-$40 or more per person, but Yadav said you can save money by getting discounted passes.

For example, you might buy the Napa Priority Wine Pass tasting card, priced at $49-69, which gives you access to over 300 wine tasting deals.

“Several wineries give discounts on wine tasting passes, which can be used as many times as you want,” continued Yadav.

As for accommodations, he recommended staying outside the Napa Valley in Sonoma or Santa Rosa.

Another popular vacation spot, the Hampton’s seaside communities on Long Island see a lot of the rich and wealthy every summer.

But, Justin Crabbe, the CEO and founder of Jettly, said, “You can enjoy the Hamptons atmosphere without renting an expensive beach house.”

If you’re on a budget, Crabbe recommended seeking out affordable motels, renting Airbnbs or camping in the area.

“Pack picnics to eat on public beaches instead of splurging at pricey restaurants,” added Crabbe.

For entertainment, he suggested avoiding the paid attractions, and instead taking advantage of free outdoor concerts, festivals and winery events.

He said, “Hike trail networks instead of paying for tours and activities.”

If you’re local to the New York City area, Crabbe said you can take the train or bus from there, instead of paying pricey parking rates.

According to Crabbe, the upper middle class view the picturesque New England island as a summer playground.

“It features luxurious stores, dune-backed beaches and imposing houses,” said Crabbe.

To save money, he recommended camping at public sites or seeking out Airbnbs located away from the more expensive downtown area.

“Picnic at scenic spots like Madaket Beach, instead of dining out constantly,” he added.

To save money on transportation around the island, he advised renting bikes, instead of taking taxis. Additionally, he said you can take public shuttles from the ferries, instead of expensive private transports.