The Favorite Travel Destinations of Old Hollywood Icons

Want to travel like Audrey Hepburn and dress the part? In this post, you’ll uncover 3 favorite A-lister travel destinations and styled outfits to match. Caution: After reading about Old Hollywood glam icons' vacation destinations, you may rearrange your schedule, purchase a travel wardrobe, and book a flight!

Hollywood celebrities escape to some of the most luxurious destinations to unwind and get away from the camera. A-listers like Audrey Hepburn, Marilyn Monroe, and Humphrey Bogart have their favorite travel destinations and escape getaways.

Today's superstars are equally enthusiastic about visiting these glamorous places, relaxing, partying, or spending time with friends and family.


#1. Saint-Tropez, France

Have you never been told that Saint-Tropez is paradise? Then, just like Karl Lagerfeld, you miss out on a lot!

Brigitte Bardot’s film, "And God Created a Woman," was primarily shot in Saint-Tropez and the French Riviera. The film's success made Bardot an international sensation, and Saint-Tropez became the next chic destination, which it remains to this day.

“Tropez-Today” My friend, Tenley, enjoying her vacation. Saint-Tropez — July 2022.

What was once a humble fishing village is now a go-to destination for celebrities and the world's wealthiest and most influential people.

The popularity and glamorization of Saint-Tropez are all thanks to Brigitte Bardot, a French actress, and a Golden Era Hollywood icon.

Saint-Tropez is more than the turquoise beaches of Moorea, Plage de Pampelonne, and Tahiti because the entire area was designed for relaxation and recreation.

What To Do?

You can stroll around the old town of La Ponche and Place des Lices and explore the narrow streets lined with small, charming shops and dainty cafés. If you are fond of the outdoors, then go for a half a day hike around Sentier du Littoral so you can go around the peninsula and admire it from a different point of view.

 

Dress like Brigitte Bardot with high-waisted washed jeans, a white cropped blouse, and “chunky heeled” sandals.

And, if you have the luxury of time (of course you do, you're on vacation!), head to Cap Camarat, the second-tallest lighthouse in France.

A trip to Saint-Tropez wouldn't be complete without a boat tour so you can see the Gulf of Saint-Tropez, the Maritime Museum, and Baie de Canebiers up close.

You might even bump into celebrities like Leonardo DiCaprio, Jennifer Lopez, and Kate Moss, who have made the peninsula their private playground.

What to Wear?

It is best to pack a suitcase full of lightweight linen or cotton outfits for your holiday in Saint-Tropez. Pack staples that you can mix and match, like a basic white tee and several tops in neutral colors, because you can easily team these with shorts, striped pants, and wrap-around skirts.

Casual Tees

High-Waisted Pants

Saint-Swim

One-piece swimsuits can also double as tops, and with the right accessories, you can transition smoothly from the beach to an evening party.

The Little Black Dress Reimagined Hailey Feldman Style Blog - Travel Destinations of Old Hollywood A-Listers

LBD, Reimagined

Pack your LBD for any surprise gathering that requires you to dress up nicely. A pair of sandals or ballet flats can complete your OOTD.

Little White Bikini

 

Wedge Sandals

Chic Flats

Natural-Tone Handbags

Dainty Jewelry


#2. Cabo San Lucas, Mexico

Cabo San Lucas is another celebrity favorite in Los Cabos, Mexico. Jennifer Aniston, for example, is such a regular visitor that the locals have nicknamed her "Queen of Cabo." As it is conveniently located about 2.5 hours from Los Angeles, the rich and the famous find Cabo is ideal for a quick weekend getaway.

What to Do?

Cabo San Lucas offers a silent promise of indulging you with a "getting away from it all" feeling, which is why most celebrities visit. Beautiful Cabo has everything a vacationer could want.

Cabo has something for everyone to enjoy, whether fishing, lounging by the beach, shopping, or indulging in delicious food. Of course, it has the standard tourist destinations that you can explore, like the El Arco and a camel outback adventure.

If you want to holiday like a celebrity, go luxury sailing, snorkeling, explore the Fin de la Tierra aboard a transparent boat, or laze around in a private yacht. As the sunset paints your backdrop a magnificent orange hue, sip your cocktails and party the night away.

 

What to Wear?

Laid-back and comfortable outfits are a must when vacationing in Cabo. You will need several swimsuits and cover-ups since you will likely spend plenty of time in the water. You will also need a stash of lightweight dresses, breathable tops, and linen pants for your casual dining escapades.

Turquoise Jewelry

Mini Turquoise Cuff

Dina Mackney 18-karat yellow gold plated bracelet in Sleeping beauty turquoise. One size fits most. Made in USA. — $290

Mini Hoop Earrings with Half Enamel & Pave

Mini Hoop Earrings with Half Enamel and Pave, Blue by Joanna Laura Constantine. Blue 18 karat gold plated brass. Cubic zirconia pavé. — $225

Make sure you also have a couple of dresses for evenings at resorts, as they often treat guests to a posh night. Let's get you styled!

Maxi Dresses

Mini Dresses

Pack Machine Wash Pieces

This festive piece by Farm Rio's Pineapple Garden romper is crafted of a printed linen blend. It is stylish and easy to travel with. I love packing pieces that I can easily toss in the washing machine.

Sporty, Sexy, Versatile

Black Halo always does a great job designing pieces that can go from sunrise to sunset. This sporty, chic, and classic look is one of my favorite pieces in The Old Hollywood Travel Destinations Collection.

 

Chic Sets


#3. St. Barts, Caribbean Island

Princess Paradise

Old Hollywood icons like Greta Garbo and A-listers like Sir Paul McCartney and Princess Diana valued the exclusivity St. Barts offers. This French-speaking island is considered one of the most expensive getaways and has become the center of billionaires and influencers.

Saint Barthélémy, or St. Barts, is a small Caribbean island popular with the rich and famous because of its white-sand beaches and luxurious shops. It has been dubbed "Hollywood South" because of how frequently Hollywood celebrities visit this island. This island is home to beach clubs, rugged cliffs, cruise ships, and hotels with a perfect postcard setting.

This is a hotspot for celebrities where they can extravagantly spend their money yet enjoy privacy—an indulgence they won't get in the US.

What to Do?

Aside from sailing around the islands on your superyacht, there are a variety of water activities to try while at St. Barts. Kite surfing, fishing, kayaking, sailing, and surfing are all great ways to test your adrenaline and get closer to nature, mainly because St. Barks is a surfing paradise in its own right. You can also dive or snorkel to glimpse the shipwrecks and the fish-rich reefs.

After soaking up in the sun, treat yourself to some retail therapy in both high-fashion labels and smaller local outlets in the alleys and lanes of Gustavia, the undisputed shopping capital of the Caribbean. While strolling around, breathe in and admire the capital's stunning architecture.

What to Wear?

Most of your vacation itinerary is tropical, so you'll be tempted only to pack sets of swimsuits, cover-ups, and flip-flops. With temperatures reaching 82°, you'll need airy, light, and loose-fitting apparel to wear in St. Barts.

Feminine Lace

Maxi Dress by Free People. The feminine lace trim & billowy tiered silhouette gives a relaxed + elegant look, from brunch to beach!

Embroidered Corset Top by Charo Ruiz Styled by Hailey Feldman Palm Beach Style Blog

Embroidered Corset Top

Charo Ruiz designed this Ibiza-inspired top with a corset-like construction.

Travel Packing Tip:

Bring a few additional items such as kaftans and loose-fitted cropped blouses to match the island's smart-casual style. Versatile pieces are essential to pack so you can wear the same dress when relaxing by the beach or shopping in town.

Evening Dresses

Ladies, make sure you have a dressy outfit with you, too, because one of the highlights of a St. Barts vacation is the glitz and glamor of a night party.

Styling Tip:

Purchase a dress in black or white to maintain a neutral background. Add a pop of color with champagne or gold-tone accessories, like the champagne box clutch below. Neutral pieces are essential for traveling. Shop neutrals and never wait at baggage claim again!


Before You Go Beauty

Of course, skin essentials and body care are also a must, so you can feel good and smell good as you explore the cape. You can't go wrong with Chanel body lotion and fragrance.


I Almost Forgot…

Puerto Vallarta, Mexico

Old Hollywood giants like Richard Burton and Elizabeth Taylor lived here in the 1960s at their home, Puente del Amor. Today, you can fall in love as Richard Burton and Elizabeth Taylor did in their home!

Book the grand and luxurious Elizabeth Taylor Suite, which was her personal quarters at the former homes of Elizabeth Taylor and Richard Burton, Casa Kimberly.


Vacation Mode On!

It's time to get lost in this magnificent paradise and discover why legendary Hollywood icons and today's celebrities flock to these islands! Bring your social media-worthy OOTDs, plenty of sunscreen, and positive vibes for a vacation to remember.

Hailey Feldman Style Blog Palm Beach Signature Logo

Do any of these three Old Hollywood glam icons' vacation destinations pique your interest? And if they do, consider it a sign to rearrange your schedule and book that flight. After all, as the Asian Proverb goes, it's better to see something once than to hear about it a thousand times.


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