Have a Romantic Retro Weekend in Palm Springs

Updated on Sep 17, 2023

Palm Springs is a great place for a fun and romantic weekend getaway with a vintage twist. With streets named after Frank Sinatra, Bob Hope, and other stars from the 50s and 60s, the atmosphere there oozes midcentury style and charm. I used to think Palm Springs was just a place to play golf and lounge by a pool, but it’s a hip getaway with great restaurants and lots to do!

When to Go

You’ll find the most pleasant weather in Palm Springs from October through April. We’ve gone at the end of March, as well as on Halloween weekend. In both cases, the weather was ideal: warm enough to swim during the day but not too hot.

Summer (May through September) is the low season due to the brutal heat. A good number of restaurants and businesses even close for the summer. But, you’ll get better hotel deals and smaller crowds during this off-season, if you can tolerate the heat.

Where to Stay

If you want to stay “near the action,” I would recommend finding a hotel on or near Palm Canyon Drive, which has a ton of nice shops and restaurants and is easily walkable. For a quiet romantic weekend, you’ll want to steer clear of the more rowdy hotels that cater to singles though.

We picked the Ingleside Inn, a small Spanish-style boutique hotel with a more classic vibe and home to Melvyn’s restaurant, famous for its Rat-Pack and Hollywood clientele in the 50s and 60s. It also has a nice pool and nightly entertainment at the bar, but it’s not a singles meat market. It’s ideally located, close to the main drag, but not too close. We found the staff to be friendly. Other than a few minor deficiencies in the room (no full-length mirror, only one luggage rack, and no real table), it was a good hotel for a romantic weekend getaway close to the action on South Palm Canyon Drive.

Pool at the Ingleside Inn, Palm Springs
Pool at the Ingleside Inn, Palm Springs

If you’re more of a resort type of person, there are many mega-resorts 30 minutes south of Palm Springs in Palm Desert. Most are centered on golfing, but many have huge swimming pools and spas for non-golfers.

I would say, wherever you decide, make sure it has a nice pool because you’ll need it to escape from the heat.

Getting Oriented

As you drive into Palm Springs on highway 118, you may want to make a quick stop at the Palm Springs Visitors’ Center to get a taste of everything Palm Springs has to offer. You can’t miss it; it’s under the huge Palm Springs Aerial Tramway sign. Among other things, you can get a mobile app that takes you on an architectural tour of Palm Springs. They also have restrooms if you need them after the drive.

The Best Date Activities in Palm Springs

Palm Springs has a wonderful retro vibe and tons of things to do. Surprisingly, I also found a lot of interesting history to take in. Here are some of our favorite things to do!

1. Palm Canyon Drive / Village Fest

Any trip to Palm Springs should probably include a walk down Palm Canyon Drive (North and South), with its wonderful assortment of restaurants with outdoor dining and interesting shops. We found it buzzing with outdoor diners and other activity throughout the day and into the evening.

It’s very walkable, and in fact, nearly every Thursday they close the street off to traffic for Village Fest, a street fair with crafts, food, and entertainment. It has a great night-market type of vibe!

2. The Palm Springs Aerial Tramway

The Aerial Tramway is one of the most famous attractions in Palm Springs. The “world’s largest tram car” takes you 8,516 feet up Mt. San Jacinto, where there are two restaurants, an observation deck, a small museum, and over 50 miles of hiking trails. Be sure to watch the video which explains the history of the tram. And of course, the views are spectacular.

The temperature at the top is typically 30 to 40 degrees cooler than at the base, so bring a jacket even if it’s 90 degrees in the valley. Sometimes there is even snow up there!

Unless you’re doing a hike, you don’t really need to linger up there for long. But it’s worth a visit!

3. Sunnylands

I didn’t know what Sunnylands was until we went to Palm Springs. Basically, when U.S. Presidents want to work or relax on the West Coast, many have done it at Sunnylands. Every President from Eisenhower to Obama has stayed here, in many cases conducting historic business with foreign leaders, or just to rest.

Sunnylands was the winter home of Walter and Leonore Annenberg. Walter was a publishing mogul most famous for popularizing TV Guide magazine, and later selling it for billions of dollars. He and his wife were friends with many politicians, as well as celebrities like Frank Sinatra, and they hosted parties at Sunnylands often.

Today, Sunnylands has a free visitor center that screens a 30-minute film explaining the history and significance of Sunnylands, which I highly recommend. They also have an art gallery, gift shop, and small cafe. But what I enjoyed the most was walking through the desert gardens in front of the visitor’s center. There are also gardens in the back.

Check the website for free events such as Yoga, Friday bird walks, Sunday outdoor concerts, and Tai Chi.

There are also guided tours which are somewhat expensive. We did the Historic House Tour which I would recommend if you are into Mid-century Modern architecture or art in general. We also did the Open-Air Experience grounds tour, but I would skip that since much of it is just the golf course. Note these tours sell out and often require advance purchase.

Even if you just stop in Sunnylands for an hour to watch the video and walk the gardens, I think it’s a worthy and fun destination that helps you understand the history of the area. All for zero dollars (unless you do a tour). Just note, there are times when Sunnylands is closed for events, so check their website first.

4. Brunch

I would say that the unofficial meal of Palm Springs is brunch, with many restaurants highlighting it.

If you drive into Palm Springs on Highway 111 (which becomes North Palm Canyon Drive) in the morning ready for a good meal, a great first stop is brunch at 1501 Uptown Gastropub. We were drawn here by the crab Benedict and were not disappointed. Note that reservations may be required for brunch.

1501 Uptown Gastropub
1501 Uptown Gastropub

For an amazing ambiance that will transport you to southern France, check out Farm right in the center of town off of South Palm Canyon Drive. The food and charming outdoor patio make this the best brunch date location that I’ve found in Palm Springs!

For a great home-style brunch, check out Elmer’s Restaurant. Forget about the glue, people sometimes wait over an hour for a meal there. The place has a diner atmosphere, but you come here for the food, not the ambiance.

If you just want a smoothie, we highly recommend Fruit Wonders right in the center of town. It gets 4.5 stars on Yelp! and their date shake was amazing!

I know I have left out a TON of great brunch places. Explore and let me know which ones you like!

5. The Palm Springs Air Museum

As a military history geek, of course I loved the Palm Springs Air Museum, which features one of the largest collections of military aircraft from WWII, the Korean War, and the Vietnam War in the world, as well as some more modern aircraft like the F-117A Nighthawk. It was named one of the 14 Best Air Museums in the world by CNN Travel.

These photos capture only a tiny fraction of the planes at the museum:

My wife is definitely not a military history geek, but even she enjoyed the visit! Maybe not as much as I did, but I do think it’s a “must-do” activity for everyone who visits Palm Springs. Admission is only $22, which I think is a bargain. Be sure to take time to read about the history of these planes as well as the wars in which they flew and the pilots who flew them. That makes the experience much richer.

6. Fine Dining

Palm Springs has a thriving culinary scene with some great restaurants. Check out this list of The 19 Essential Palm Springs Restaurants (mostly on or near Palm Canyon Drive), by EaterLA.

We enjoyed dinner at one restaurant on that list, Workshop Kitchen + Bar. With its concrete walls and trendy farm-to-table New American cuisine, Workshop Kitchen + Bar seems like a restaurant you’d find in Los Angeles, New York, or San Francisco (and in fact it does have a Los Angeles location).

7. Hole-in-the-Wall Hidden Gem Restaurants

If you’re on more of a budget, or just want something more casual, Palm Springs has some great hole-in-the-wall restaurants that are not so big on ambiance, but have amazing food.

Hands down, the best restaurant in this category in Palm Springs is Rooster and the Pig, featuring Vietnamese American cuisine with the perfect amount of spiciness to challenge your tongue but not overwhelm it. Located in an unassuming mini-mall, they don’t take reservations, so you may have to wait an hour or more during peak periods (thus I recommend going for an early dinner there). If you do find yourself faced with a long wait, just pop in next door to their adjoining lounge bar, decorated with lanterns on the ceiling, for a drink. The food is so worth the wait! We loved this place so much that we did something unprecedented for us – we had dinner there two nights in a row.

Gabino’s Creperie is literally just a window in a narrow alley but they serve the best crepes I’ve ever had. There’s no indoor seating; just a few outdoor tables. The crepes are kind of rolled up into a cone and wrapped in paper so you can have them on the go. This is a “must” while you’re in Palm springs.

Just next door, you can get hand-crafted ice cream at Kreem, which features some of the best flavors in town.

Pumpkin and blueberry Ice cream with postcard from Kreem
Ice cream and postcard from Kreem

8. The Palm Springs Art Museum

The Palm Springs Art Museum has an impressive collection of modern and contemporary art and is well worth stopping by if you or your date have any interest in art, or if you just want to escape from the heat for a while. It’s conveniently located just a short walk from the main drag, Palm Canyon Drive. Be aware that the museum is only open Thursdays through Sundays.

Outdoor sculptures at the Palm Springs Art Museum
Outdoor sculptures at the Palm Springs Art Museum

Even if you don’t want to pay for admission, you should still stroll the grounds and the free Faye Sarkowsky Sculpture Garden, a four-acre garden with 14 sculptures open during daylight hours.

Of course, it’s impossible to miss the 26-foot-tall “Forever, Marilyn” statue in front of the museum. It’s a big selfie stop for many. However, it’s not affiliated with the museum, which loathes it for several reasons. One of which is that she’s basically mooning the front of the museum. It was put up by the city to spur tourism. You can make up your own mind about what you think about it.

"Forever, Marilyn" with the Palm Springs Art Museum in the background
“Forever, Marilyn” with the Palm Springs Art Museum in the background

9. Hiking

When you think of Palm Springs, hiking is probably not the first thing that comes to mind, mainly because of the searing heat. But, don’t count it out if you can find a not-so-hot time of day, because Palm Springs does have some wonderful trails.

My top pick is Andreas Canyon, with its shady palm trees along a stream and huge rock formations. This is a really short and easy trail, only one mile, so it’s great if you’re not really that into hiking, but want to get outside for a bit.

If you want a more challenging hike, here are some other trails to try out!

10. The Living Desert Zoo and Gardens

Rated one of the top ten zoos in the United States by Conde Nast Traveler, the Palm Springs Living Desert Zoo and Gardens is a very worthy destination during your Palm Springs visit. Yes, kids will love it, but adults on Yelp! love it as well, giving it 4.5 star rating. The word you most often see on reviews is “underrated”. This zoo is a hidden gem!

The Living Desert Zoo and Gardens in Palm Desert
The Living Desert Zoo and Gardens in Palm Desert

Just go early or late in the day to avoid the heat. The Zoo is not in Palm Springs proper but just a short distance away in Palm Desert.

11. The Shag Store

Some might disagree, but I believe the Shag Store is a “must” for any first-time Palm Springs visitor because it helps you understand the vibe and aesthetic of the city so well. Plus, the playful artwork will put anyone in a good mood.

The Shag store in Palm Springs
The Shag store in Palm Springs

Artist Josh Agle, known as “Shag” (look at the middle four letters in his first and last name) creates 50s retro-styled illustrations based on his experiences of going to parties in midcentury modern residences in Palm Springs.

The store is at the north end of the busy area of Palm Canyon Drive, so it’s convenient to drop in before or after dinner somewhere on that main street.

12. Your Hotel’s Pool and Spa

You should definitely allocate some of your time in Palm Springs to just hanging out by the pool with a drink in your hand.

If you’re into spas, be sure to reserve ahead of time!

And don’t forget to do the hot tub at night!

13. Vintage Clothing Shopping

If you enjoy shopping for vintage clothing, you’re in luck because Palm Springs has a fantastic vintage shopping scene. In downtown, notable vintage shops include The Frippery, Iconic Atomic, and Mitchells. If you don’t mind a 20-minute drive to Palm Desert check out The Fine Art of Design. Check out this article for more details!

14. The Palm Springs Windmill Tour

As you drive to Palm Springs you can’t miss the hundreds of imposing and beautiful white wind turbines covering the landscape. This might not be for everyone, but if you’re into engineering or renewable energy, the Palm Springs Windmill Tour should be on your list. They have a self-driving tour that starts at their tour center, where you first watch a 15-minute video before proceeding in your car. The tour gets 4.5 stars on Yelp!

Wind turbines on the way to Palm Springs
Wind turbines on the way to Palm Springs


I’ve been blown away by the number of really fun things there are to do in Palm Springs, whether you are into military aircraft, animals, hiking, presidential history, or just lounging by a pool. It’s definitely a great weekend date idea if you’re looking for relaxation and cool things to do. – Brian

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