As Empty Nesters start to think about downsizing, some choose to stay in the same town or city. For others, it may mean relocating to a different city, a new state, or even another country.

If you want to move, but you’re wondering where the best place to retire might be, start by looking at places you’ve already visited—just through a different lense.

When you were younger, travel was about experiences—what to see, where to eat, what to do. But now? It becomes more about lifestyle. Could you actually live there day-to-day? Would it feel like home?

For example, when we went to San Francisco (aka, “City by the Bay”) years ago, we thought it was a fun place to visit—but never once considered living there. At that stage of life, retirement wasn’t even on our radar. We were way too young to even think about where we’ll retire.

Now that we’re older, it’s top of mind. In fact, I can’t stop thinking about it, and have pretty much made a project out of it!

With a new phase of life, shifting priorities, and a different financial picture, we’d approach the next visit very differently. Instead of just sightseeing, we’d be paying attention to things like cost of living, neighborhoods, healthcare access, and overall pace of life.

Is San Francisco A Good Place To Retire?

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When evaluating a potential place to retire, it helps to look beyond the highlights and consider both the perks and the challenges. Some you’ll be able to see while you’re there, and some can be further researched online.

Pros

Some good things about living in San Francisco:

• Mild Climate Cooler summers; moderate winters.
• Quality Healthcare San Francisco has some of the best medical centers in the nation.
• Rich Cultural Scene Symphony, ballet, museums, theaters.
• Natural Beauty Forests, parks, hiking trails, coastal views.
• Diverse Dining From fine dining to casual neighborhood cafes—a food lover’s paradise!
• Inclusive Community A very welcoming and accepting environment for all residents.
• Good Public Transportation Various systems for those without a car.

Cons

Some challenges to living in San Francisco:

• Mild Climate Is it too similar to your current climate—are you looking for something different?
• Limited Housing Options Long waitlists, high prices.
• High Cost Of Living One of the most expensive cities in the nation—a strain on retirement budgets.
• Traffic/Parking Problems Very high.
• Urban Density Noise, crowded streets, lack of privacy.
• Homelessness Crisis Ongoing problem, may be distressing to see.
• Earthquake Risk Retirees will want to ensure that their homes are earthquake-prepared.
• Fog/Weather Variability Frequent fog and cool temperatures may not appeal to everyone.

Aside from doing your own research, the only way to know if San Francisco is right for you is to see it for yourselves—it’s time to pack your bags!

Things To Do

Fisherman’s Wharf and Pier 39

Start your visit by hanging out at Fisherman’s Wharf and Pier 39—the most visited destination in San Francisco—where there are street performers, musicians, souvenir shops, great places to eat, and lots of people-watching to keep things lively. Don’t miss the sea lions basking in the sun—it’s a classic San Francisco experience.

Ghiradelli Square

Next, stroll over to Ghirardelli Square for some boutique shopping and delicious chocolate treats, while enjoying the waterfront.

Aquarium Of The Bay

Then, visit the nearby Aquarium of the Bay where you can walk through clear tunnels surrounded by sharks, rays, and local marine life from the San Francisco Bay. It’s a fun way to experience marine life up close, and a nice break from the crowds outside.

Alcatraz

If you have time, you also might want to take the Alcatraz Tour of a small, rocky island with an old maximum-security federal prison that housed some of the most notorious criminals in U.S. history.

Wrap up the day by relaxing with good food/drink, while planning adventures for the remainder of your trip—exploring San Francisco’s many neighborhoods, heading across the iconic landmark, Golden Gate Bridge to Napa Valley for a wine tasting tour, and so much more!

There are so many things to do while visiting San Francisco, and would take numerous visits to see/do them all! This website has a Digital Visitor’s Guide filled with beautiful photos and information to help you plan your visit.

Would We Live In San Francisco?

Our next trip to San Francisco will focus on retirement potential. After city adventures, we’ll definitely head to wine country to enjoy our love of red wine, and explore more affordable properties nearby. Despite the city’s vibrant culture and scenery, we wouldn’t choose to live in the city—mainly due to affordability, but also because moving to a dense urban environment, after living in the country for decades, would be quite a shock!

Is San Francisco—or a nearby town—on your retirement list?

Conclusion

Deciding where to downsize or retire is a mix of practical considerations and personal preferences. Visiting places with fresh eyes, imagining daily life there, and weighing costs, climate, and community can make a huge difference in your choice. Whether you stay close to home or relocate far away, the key is finding a place that fits your lifestyle, your budget, and your vision for this next chapter.

By exploring cities like San Francisco (or anywhere else you’ve dreamed of), you’ll have a clearer sense of where your “forever home” could be, without the guesswork.

Happy exploring!

Travel Accessories

After making your travel plans, start thinking about the essentials you need to make your trip smoother, more comfortable, and a little more fun.

Many of these are perfect for short getaways or longer adventures, and I’ve included links to make it easy if you want to grab them.

• Apple AirPods—For music, podcasts, or hands-free calls on the go.
• Blanket—Stay warm on flights and road trips.
• Carry-on Luggage—Compact, durable, and easy to roll.
• Duffle Bag—Ideal for weekend trips, or for extra items.
• Jewelry Case—Keeps jewelry organized, tangle-free, and secure.
• Neck Pillow—Reduces neck pain by keeping your head upright.
• Sleep Mask—Blocks out light for better rest.
• Travel Size Containers—Perfect for toiletries, without taking up too much space.
• Noise Cancelling Headphones—Ideal for flights or hotel noise.
• Crossword Puzzle Book—Fun for downtime.

Cool😎Gear

Empty Nester Merch, including Traveling—for you, or for gifts—COMING SOON!

Related

Empty Nester Traveling: Time For A Vacation For Two

Reconnect With Your Spouse: 9 Helpful Ways To Survive The Empty Nest

How To Move Beyond The Empty Nest: 8 Tips For Moms

It’s Your Turn To Fly, Mama!