A Surprise Retirement Contender: Coastal Delaware

For a long time, I’ve talked about Panama City Beach or Santa Rosa Beach in the Florida Panhandle as my ideal place to retire.

And for good reason. I already love that part of Florida. The beaches, the outdoor lifestyle, the wildlife, and the ability to kayak, bike, photograph, and explore almost year-round all line up almost perfectly with the kind of retirement I imagine.

But retirement is a long-term decision, and the more seriously I think about it, the more a different question keeps coming up:

Is there a place that gives me most of what I love about the Florida Panhandle—but with less hurricane risk, more predictable long-term costs, and better access to the rest of the country?

That question is what led me somewhere I honestly didn’t expect to be considering at all:

Milton, Delaware.

At first glance, it doesn’t seem like a natural comparison. The Florida Panhandle is warm, familiar, and already part of my mental map. Milton, Delaware is new, unfamiliar, and sits in a completely different region of the country.

But when I started comparing them side by side—not just on weather, but on risk, access, lifestyle, and long-term livability—the trade-offs became a lot more interesting than I expected.

And the first place that really stands out in that comparison is hurricane risk.

Hurricane Risk

This is probably the biggest reason I continue looking outside Florida.

I’m not talking about whether the remnants of a hurricane can bring rain or flooding hundreds of miles inland. That can happen almost anywhere.

I’m talking about the kind of direct coastal hit that destroys piers, damages bridges, tears roofs off houses, and changes an entire community overnight.

That is a very different level of risk.

And the historical difference between coastal Delaware and the Florida Panhandle is hard to ignore.

Delaware has not had a direct hurricane strike in well over a century.

Northwest Florida, on the other hand, has experienced major hurricanes within very recent memory.

The most obvious example is Hurricane Michael, which came ashore near Mexico Beach in 2018 as a Category 5 hurricane and devastated parts of the Panama City area.

That is not some distant historical event.

It happened eight years ago.

When I think about buying a retirement home that I may own for the next 20 or 30 years, that matters to me.

I’ve also experienced how that recent history changes the way you react when another hurricane starts moving in your direction.

I was staying on the beach in Panama City Beach during Hurricane Sally in 2020. Sally was expected to hit farther west, so Panama City Beach wasn’t originally looking like the main target.

Then the storm began shifting east.

PCB never took the direct hit, but sitting there watching that change was a little different when Hurricane Michael had devastated the Panama City area only two years earlier.

I stayed up most of the night monitoring the local news. Sirens were going off, and the station was tracking funnel clouds and tornado warnings around the area. Every update had me wondering how much farther east Sally might move.

The next morning, I went down to check on my Jeep.

Luckily, the parking garage sat above ground level.

The driveway didn’t.

It was under several feet of water.

What sticks with me now isn’t simply the flooding.

It’s how I reacted to the storm.

Recent history had already shown me what could happen if a major hurricane came directly into that area. Michael was still fresh enough that when Sally unexpectedly began moving toward PCB, I wasn’t looking at it as just another rainy night.

I was awake.

I was watching.

And I was wondering what the next update would say.

In Delaware, I suspect I would react differently.

I would still watch the forecast and take tropical weather seriously. But with more than a century separating the area from the kind of direct hurricane strike I’m concerned about, I might look at the forecast, see tropical weather moving through, and go to bed.

That difference in mindset comes from a difference in history.

And if I have a choice between two places I genuinely enjoy, that becomes a real factor.

Insurance Risk

This goes hand in hand with hurricanes.

Florida homeowners insurance has become one of the biggest question marks in my retirement planning.

I may be able to afford the house.

The bigger question is what it costs to keep owning that house 10 or 20 years later.

A major hurricane doesn’t just affect the houses directly in its path. It can affect the entire insurance market.

That means premiums can rise even if my particular house escapes damage.

Delaware doesn’t eliminate insurance costs or coastal risk, but the historical hurricane exposure is simply not comparable to the Florida Panhandle.

For someone trying to make retirement expenses more predictable, that matters.

Taxes

Florida has one obvious advantage here.

There is no state income tax.

Delaware does have a state income tax, so I’m not pretending this is a clean win.

But Delaware’s system is more nuanced than it first appears.

Social Security income is not taxed in Delaware, and there are exclusions available for qualifying retirement income. That means the actual tax burden in retirement can look quite different from simply looking at the state's top income-tax rate.

On top of that, Delaware has no state or local sales tax.

And one thing I recently came across that is worth noting: Delaware is often cited as having among the lowest property tax burdens in the mainland United States. While rates vary by county and assessment, the overall effective property tax cost is generally low compared with most states.

So instead of a simple “tax versus no tax” comparison, it becomes a more realistic question of how actual retirement income, spending, and homeownership costs line up.

When I retire, I’ll care less about one headline tax rate and more about my total cost of living.

Being Stuck at the Bottom of the Map

This is another thing I hadn’t really thought about until recently.

Florida gives me warm weather.

What it doesn’t give me is easy access to much of the rest of the country.

From the Panhandle, most major destinations involve a long drive or a flight.

Delaware changes that completely.

And this may be one of the biggest differences between the two locations.

Within roughly an hour and a half of Milton is Wilmington, Delaware, and an Amtrak station sitting directly on the Northeast Corridor.

From there, I can reach Philadelphia, Baltimore, Washington, New York, and plenty of other places without ever driving into those cities.

And these are not necessarily “weekend trips.”

That is what makes this so interesting to me.

I could leave the house around 8:00 in the morning, take the train into a major city, spend the day seeing museums, eating somewhere interesting, taking photographs, or simply exploring, and still sleep in my own bed that night.

That adds an entirely different layer to retirement life.

And Yes — Alligators

Call me irrational if you want.

Alligators concern me.

Not so much for myself.

I’m thinking more about my dogs.

A lot of the things I want to do in Florida overlap with alligator habitat.

Kayaking. Fishing. Wetland walks. Photography. Exploring places like Point Washington.

With two small dogs, that means I would always have to be paying attention around the water.

In Delaware, that concern basically disappears.

And for the kind of outdoor life I want, that is another plus.

What I Actually Want From Retirement

All of those things explain why I’m still looking.

But they don’t explain why Milton works.

For that, I have to go back to what I actually want retirement to look like.

I’m not simply searching for warm weather or a house near the beach.

I’m trying to build a lifestyle.

And there are five things that keep showing up in that picture.

1. Beaches

This is still non-negotiable.

I love being around the ocean.

Morning walks.

Sunrise and sunset.

Ocean breezes.

Taking a chair to the beach and realizing three hours later that we really haven’t done anything.

That sounds pretty close to perfect.

One reason Panama City Beach has remained at the top of my list for so long is that the beach can become part of everyday life rather than something reserved for vacations.

Milton surprisingly keeps much of that.

Lewes, Cape Henlopen, and the Delaware beaches are nearby. Depending on exactly where we lived, some destinations could even be realistic e-bike trips.

So while I would be trading the Gulf of Mexico for the Delaware coast, I wouldn’t be trading away coastal life.

That distinction matters.

2. Photography

I also want retirement to give me more time behind a camera.

Not necessarily because I need to come home with a masterpiece every morning.

I just like the process.

Morning mist over a pond.

Birds moving through a marsh.

A marina before everyone wakes up.

An old building in a coastal town.

A forest trail.

Boats.

Wildlife.

Sunrise at the beach.

I want to be somewhere that gives me a reason to grab a camera and leave the house.

Coastal Delaware has far more variety than I expected.

There are beaches, wetlands, rivers, ponds, forests, wildlife refuges, farms, historic towns, and working waterfronts all relatively close together.

And then there is something Florida can’t give me in quite the same way:

four different seasons.

I could photograph the same location in spring, summer, fall, and winter and end up with four completely different versions of it.

For someone who enjoys photography, that isn’t a small advantage.

3. The Along the Sound YouTube Channel

Photography also ties directly into another part of my retirement plan.

Along the Sound will be a YouTube channel, in addition to this website.

My idea isn’t to retire and immediately become someone constantly searching for “content.”

I want the opposite.

I want the videos to grow naturally out of the life I’m already living.

If I’m heading out before sunrise to photograph birds, bring the video camera.

If I’m kayaking somewhere new, film some of it.

If my wife and I are exploring a coastal town, tell that story.

If I take the Subaru into the mountains for an overnight trip, that can become a video.

If I’m sitting beside the water making coffee while Obi conducts a full security inspection of every squirrel in the vicinity, that probably deserves documentation too.

The channel would be about coastal living, nature, photography, travel, outdoor adventures, retirement, and all of the smaller experiences that come along with this next chapter.

And this is another place where Delaware becomes unexpectedly interesting.

The variety is enormous.

Beach one week.

Salt marsh the next.

A historic town.

A bike trail.

Kayaking.

Fall foliage.

A train ride into Philadelphia.

A mountain stream in Pennsylvania.

Snow falling on the same trail I filmed in July.

For Along the Sound, four seasons could actually be an advantage rather than a drawback.

4. Kayaking

I definitely want a kayak to become part of normal retirement life.

Sometimes I may fish.

Sometimes I’ll take a camera.

Sometimes I may paddle around for absolutely no useful reason whatsoever.

That last one may become my specialty.

Milton sits along the Broadkill River, and the surrounding area has an abundance of water.

Rivers.

Ponds.

Bays.

Marshes.

Coastal waterways.

Some of the neighborhoods I have looked at even have kayak launch points nearby.

That is exactly the kind of access I want.

I don’t want kayaking to become an expedition that requires an hour of driving every time I decide to go.

I want to be able to look outside on a nice morning and think:

I believe I’ll go paddle somewhere.

Then go.

5. Biking

The same thing applies to biking.

I want an e-bike partly for recreation, but I also like the idea of using it as actual transportation.

Give me a good trail and I would much rather ride ten miles for coffee than load the bike onto the back of the Subaru and drive somewhere simply to ride it.

The Delaware coast has an impressive collection of bike trails and connections around Lewes, Rehoboth, Cape Henlopen, and the surrounding communities.

That changes the bike from another recreational toy into something I could genuinely use as part of everyday life.

And that is much closer to what I have in mind.

Delaware’s Huge Wild Card: Amtrak

Then there is something I really wasn’t considering when I started this search.

The train.

Milton itself doesn’t have Amtrak service, but Wilmington is roughly an hour and a half away.

Once I reach Wilmington, I can park the car and suddenly have access to the Northeast Corridor.

This is where the comparison with Panama City Beach starts getting really interesting.

Because I’m not talking about destinations I might visit once every five years.

Several of these places are close enough by train that I could leave Milton in the morning, have an entirely different experience for the day, and still sleep in my own bed that night.

That is a remarkable amount of variety for someone who technically lives near the beach.

Philadelphia

Philadelphia would be almost ridiculously accessible once I reached Wilmington.

Museums.

Architecture.

Rittenhouse Square.

Reading Terminal Market.

Historic neighborhoods.

Restaurants.

Street photography.

My wife could spend time looking at art while I wander around photographing buildings and people, and somehow we could both claim the other person was tagging along on our trip.

Then we have dinner and take the train back.

That isn’t a vacation.

That can simply be a Tuesday in retirement.

Baltimore

Baltimore gives me another completely different environment.

Fells Point.

The Inner Harbor.

Historic brick neighborhoods.

Waterfront photography.

Seafood.

The George Peabody Library.

It has enough to do for repeated trips, but it’s close enough that every visit doesn’t have to become an overnight stay.

Go up.

Explore.

Eat something good.

Come home.

Washington, D.C.

Washington may be the best example of what I mean.

The Smithsonian museums alone could occupy countless trips.

Then there is the National Mall.

The Capitol.

The Tidal Basin.

Georgetown.

Architecture.

Restaurants.

Photography.

And I can do all of that without driving a car through Washington traffic.

That may deserve its own line on the retirement spreadsheet.

Again, I could leave home in the morning, spend the day at a museum or walking around Washington, and come back to Milton that night.

The ability to combine quiet coastal living with that level of cultural access is something I hadn’t considered before.

Princeton

Princeton gives me a completely different kind of day.

Gothic architecture.

A beautiful university campus.

Museums.

Tree-lined streets.

Shops and restaurants around Palmer Square.

It sounds like the kind of place that could be especially good in fall, when I’m already looking for something different to photograph.

Old Town Alexandria

Alexandria may be another perfect compromise for my wife and me.

Historic streets.

The Potomac waterfront.

Restaurants.

Shops.

Architecture.

And the Torpedo Factory Art Center.

She gets the art.

I get the cameras.

Then we both find somewhere to eat.

That seems fair.

New York City

And then there is New York.

This one still sounds a little ridiculous when I think about it.

Instead of driving into Manhattan, dealing with traffic, and paying what amounts to a ransom to park a car, I can take a train into Midtown.

Chelsea galleries.

The High Line.

Central Park.

Museums.

Restaurants.

Street photography.

Broadway.

New York might sometimes make more sense as an overnight trip, depending on what we wanted to do.

But that isn’t really the important part.

The important part is access.

From a quiet coastal town in Delaware, I could have one of the biggest cities in the world sitting within easy rail reach.

That dramatically changes what “living near the beach” can mean.

And I Still Get Mountains

One reason I initially liked the idea of places farther north than Florida was mountain access.

I love the coast, but I also like forests, mountain streams, waterfalls, and the idea of eventually doing some fly fishing.

From Panama City Beach, reaching genuine mountain country takes some commitment.

From Delaware, the Appalachians suddenly become much more accessible.

Within roughly a half-day drive are several completely different environments.

Michaux State Forest and South Mountain

Pennsylvania’s Michaux State Forest gives me dense forest, mountain roads, hiking, Appalachian Trail access, and cold-water streams.

That sounds like an ideal place for a Subaru Wilderness overnight trip.

Drive up.

Find a trail.

Take some photographs.

Try some fly fishing.

Make coffee in the morning.

Come home.

That is almost exactly the kind of small retirement adventure I picture.

Catoctin Mountain and Western Maryland

Western Maryland offers wooded ridges, waterfalls, streams, mountain trails, and cooler temperatures.

Again, it gives me a completely different environment without requiring a major vacation.

One morning I could be photographing shorebirds along the Delaware coast.

The next weekend I could be standing beside a mountain stream.

That is the kind of variety I didn’t realize Delaware could offer.

The Poconos and Delaware Water Gap

Go north and things change again.

Lakes.

Waterfalls.

Hemlock forests.

Rocky trails.

Cold streams.

Mountain scenery.

And in fall, the entire place changes color.

For photography and for the Along the Sound YouTube channel, that opens up a completely different visual world.

Shenandoah and the Blue Ridge

A little farther away and Shenandoah National Park enters the picture.

Skyline Drive.

Blue Ridge overlooks.

Forest trails.

Waterfalls.

Mountain streams.

Fog rolling through the valleys.

Fall color.

Golden-hour light from an overlook.

I love the beach enough that I could probably photograph it forever and not get bored.

But having this kind of scenery within a long-weekend drive gives me even more variety.

So What Do I Give Up?

There is no perfect place.

If there were, somebody would have already moved there and doubled the home prices before I discovered it.

Delaware’s most obvious disadvantage compared with Panama City Beach is winter.

There is no getting around that.

I would lose the almost year-round warmth of the Florida Panhandle.

There will be cold mornings.

There will be gray days.

There will occasionally be snow.

January at a Delaware beach will definitely not feel like January in Panama City Beach.

But I’m starting to wonder whether that bothers me as much as I once thought it would.

I don’t need every retirement day to be 75 degrees.

Sometimes a cold day sounds pretty good.

Light a fire.

Make coffee.

Put a record on.

Edit photographs.

Work on a video.

Write something for the website.

The occasional cold day may actually make those things more enjoyable.

Then spring arrives and actually feels like spring.

Fall becomes something special instead of simply a slightly cooler version of summer.

And summer still gives me the beach.

For someone interested in photography and video, I’m starting to think four seasons might add more than they take away.

Why Milton Has Moved Up the List

This is what surprised me most.

When I first started looking at Delaware, I assumed I would find an interesting compromise.

Something safer or cheaper, perhaps, but clearly less appealing than Panama City Beach.

That isn’t what happened.

Instead, I found another version of the retirement lifestyle I want.

I still get:

• Beaches.

• Coastal living.

• Kayaking.

• E-biking.

• Photography.

• Wildlife.

• Fishing.

• Marshes and waterways.

• Small coastal towns.

• Plenty of material for the Along the Sound YouTube channel.

But I also gain things that Panama City Beach simply can’t offer in the same way.

A dramatically lower history of direct hurricane strikes.

Potentially less long-term insurance uncertainty.

No state or local sales tax.

Low property taxes compared with much of the country.

No normal concern about alligators while walking the dogs near the water.

Four distinct seasons.

Easy access to Amtrak and the Northeast Corridor.

Philadelphia.

Baltimore.

Washington.

New York.

Mountain country within a few hours.

That is a surprisingly strong list.

Then I checked the houses.

That may be what officially moved Delaware from “interesting” to “serious contender.”

The homes I’m finding around Milton are in roughly the same price range as many of the homes I’ve been following around Panama City Beach.

So this isn’t a situation where I’m comparing the lifestyle I really want with somewhere cheaper that I could tolerate.

I’m increasingly comparing two places where I could genuinely picture us being happy.

And that makes the decision much more interesting.

Florida Still Has One Huge Advantage

Panama City Beach has something Delaware can’t duplicate on a spreadsheet.

I already love it.

I’ve spent enough time there that it feels familiar.

I know what it feels like to wake up there.

I know the beaches.

I know the general rhythm of the area.

When I picture retirement, it is very easy for me to insert myself into that environment because I have already experienced it.

Delaware is still theoretical.

I can research Milton for months.

I can look at houses.

Study maps.

Find bike trails.

Look at beaches.

Plan kayaking trips.

Find restaurants.

Research train schedules.

None of that replaces actually standing there.

Maybe my wife and I visit coastal Delaware and immediately love it.

Maybe we spend three days there and both say:

This is nice, but it isn’t Florida.

Either answer would be useful.

That is what scouting trips are for.

But there is one thing this entire exercise has already changed for me.

When I first started thinking seriously about retirement, my question was basically:

Where in the Florida Panhandle do I want to live?

Now the question is broader.

What kind of life do I want to live in retirement—and where can I build it while avoiding risks I don’t necessarily need to take?

Panama City Beach may still win.

In fact, if I had to choose today, familiarity alone would probably keep it in front.

But for the first time, another place has given me a version of retirement that looks genuinely competitive.

Coastal Delaware wasn’t supposed to be on the list.

Now Milton may be one of the places I most want to see for myself.

And I definitely didn’t see that coming.