Palm Springs November 2023

Palm Springs on a Timeshare Deal

So, I’m a sucker who got roped into one of those timeshare presentations for a “free” 3-day trip—and I decided to use it for a quick getaway to Palm Springs. I dragged my boyfriend along for the ride, and we each scored a $100 Visa gift card, so at least there was that.

We kicked off our little road trip with a stop in Yermo at one of my favorite roadside diners: Peggy Sue’s 50’s Diner. If you’ve never been, it’s a total throwback—classic diner food, quick service, and waitresses rocking retro 1950s outfits. It’s one of those places where you have to stop at least once; it’s practically a rite of passage if you’re driving that route. They also have a fun little gift shop filled with nostalgic lunch boxes, old-school candy, and quirky vintage-style souvenirs.

We rolled into Palm Springs in the early evening, checked in, and kept it pretty low-key that first night.

Peggy Sues

Finally Riding the Tram

One of my bucket list items for Palm Springs has always been riding the Palm Springs Aerial Tramway. Fun fact: I actually lived in Palm Springs for nine months in a condo directly across from the tram—but somehow, I never went up. I’ve regretted it ever since, so you better believe we weren’t skipping it this time.

The price is what had kept me from going before: $34.95 per person (and yes, it stings a little), but we bit the bullet and headed up. Parking is an extra $15, and there are multiple lots, so prepare to walk a little if it’s busy.

The tram itself is huge and offers incredible views of Chino Canyon and the desert below. On the way up, it was absolutely packed—standing room only—but the ride back down was much less crowded, which made it way easier to snag photos without someone’s elbow in the frame.

Once at the top, there are several overlooks and hiking trails, ranging from quick strolls to longer treks if you’re feeling ambitious. There were rock climbers, meet-ups, and plenty of activities going on when we were there—you could easily spend most of the day exploring. There’s also a restaurant and a coffee shop at the summit if you want to grab a snack or just sit and soak up the view.

We couldn’t stay too long, though—we had our timeshare presentation scheduled that afternoon (ugh), so we left enough time to head back down and make it on time.

The tram view going up

View from the top

Another view from the top

Timeshare Presentation & Dinner

The hotel itself was… fine. Nothing special, nothing terrible—just okay. As for the timeshare presentation, it took about 90 minutes, which honestly wasn’t as painful as I expected. We had a nice older gentleman leading our session, and I think he figured out pretty quickly that I was not his target audience.

I just couldn’t wrap my head around the numbers they were throwing at us. Why would I commit to years of payments when I can find my own hotel for way less per night—and not be locked into anything? Still, my curiosity about how these things work was satisfied, and we walked away with our Visa gift cards and zero regrets.

That evening, we treated ourselves to dinner at Alps Village, a cozy spot with a German-inspired menu. The food was solid, but the giant soft pretzel stole the show—I have zero self-control when it comes to those. The service was excellent, the atmosphere was warm and welcoming, and overall, we left happy and very full.

A Quick Detour: Skydive San Diego

The next morning, we were up early and on the road to Skydive San Diego. My boyfriend is a skydiver and was working on earning his coaching status, so he had a scheduled session with one of the instructors there.

I set up camp under the shady canopy of some trees and spent the morning hanging out while he jumped… several times. It turned into a full-day thing—most of the morning and part of the afternoon—but it was fun to watch the parachutes floating down against the clear blue sky.

On the way back to the hotel, we grabbed some tacos, and let me just say… they were amazing. Honestly, if you’re anywhere near San Diego, do yourself a favor and get some Mexican food—it’s on a whole different level down there.

Breakfast in Redlands & Heading Home

On our last morning, we hit the road and stopped in the Redlands area at a spot called Cheliz Restaurant. I ordered a crispy chicken sandwich with onion rings, and honestly, the chicken was amazing—juicy, crunchy, perfectly done. The onion rings looked incredible but were just… okay. Edible, but nothing mind-blowing. My boyfriend went for a classic pancake breakfast and had no complaints.

The service was great, the food hit the spot, and from there, we made the rest of the drive home.

The trip was a success in every way that mattered:

  • I didn’t get talked into buying a timeshare 🙌

  • My boyfriend achieved his skydiving coaching goal 🪂

  • And we squeezed in great food, fun adventures, and plenty of little wins along the way.

Tips for Visiting Palm Springs & Beyond

Whether you’re visiting Palm Springs on a timeshare deal like we did or planning your own weekend getaway, here are a few tips to help you make the most of your trip:

🛎️ Where to Stay

  • Timeshare Promo Stays → If you’re doing one of these, prepare for the 90-minute presentation—but honestly, it wasn’t that bad, and we scored $100 Visa gift cards each.

  • Hotels & Resorts → Palm Springs is packed with options, from chic boutique hotels to bigger resorts and vacation rentals.

  • If you want to stay outside the hustle, nearby towns like Cathedral City and Palm Desert often have cheaper rates.

🚠 Palm Springs Aerial Tramway (Bucket List Must!)

  • Cost: $34.95 per person + $15 parking

  • Go early or late → The tram gets crowded fast, so aim for off-peak hours for fewer people and better photos.

  • Bring a jacket → The temperature at the top is much cooler than on the desert floor.

  • Plan for at least 2–3 hours up top to enjoy:

    • Scenic overlooks

    • Hiking trails

    • Rock climbing areas

    • A restaurant & coffee shop

🍴 Food & Drink Recommendations

  • Peggy Sue’s 50’s Diner (Yermo) → Retro vibes, quick service, fun gift shop.

  • Alps Village (Palm Springs) → German-inspired menu + the giant soft pretzel is a must.

  • Cheliz Restaurant (Redlands) → Get the crispy chicken sandwich, skip the onion rings.

  • San Diego Mexican Food → If you venture south, grab tacos. Trust me, you won’t regret it.

🪂 Skydive San Diego (For Thrill Seekers)

  • Great spot for training, coaching sessions, or just watching skydivers land.

  • There’s plenty of shaded space for spectators to relax while waiting.

  • If you’re into extreme sports, this is a fun detour that breaks up your trip.

🛍️ Quirky Stops Along the Way

  • Peggy Sue’s Gift Shop → Vintage-style souvenirs and old-school candy.

  • Downtown Palm Springs → Cute boutiques, retro shops, and unique finds.

  • Redlands → A good halfway stop between Palm Springs and home for food and coffee.

🕶️ Best Time to Visit Palm Springs

  • Spring & Fall → Perfect weather, fewer crowds, and better hiking conditions.

  • Winter → Mild and beautiful, especially around the holidays.

  • Summer → Expect triple-digit temps but enjoy lower hotel rates and quieter attractions.