• Casie Dionne

Our First Family Road Trip | Top 5 Spots in Dewey Beach, Delaware


Mommy, Daddy and Story on our first family vacation

There is no better time than now for a getaway. Sometimes just a quick weekend away from your usual surroundings is all you need to recharge.

Last month my family and I took advantage of a 4 day weekend, rented a car and drove 2.5 hours away from New York City to Dewey Beach, Delaware.


Roadtripping in style with our Cadillac SUV

We wanted a low key destination not too far from New York, yet nearby the water, where we could stay safe but still have some family fun.

Dewey Beach checked all these boxes and more and now I’m sharing with you the top 5 spots that we visited that should be on your itinerary too.

Rehoboth Boardwalk

Stopping for a sweet treat at the Rehoboth Boardwalk

This is your classic boardwalk experience.

You have the beach on one side and shops, games, restaurants and sweet treats on the other. You’ll see young and old people alike enjoying themselves.

Penny Lane Mall in Rehoboth Boardwalk

An entire day can be spent there and you would not get bored. We chose to come here after dinner to get dessert and take a nice sunset stroll.


Rita’s Italian Ice

Happy I got my Rita's Italian Ice fix

If you know, you know...

I first got turned on to Rita’s when I was living in Baltimore years ago. Rita’s is synonymous with summer, everyone flocks there to get their delicious Italian ices and custards. They have so many flavors to choose from. I picked up the Italian ice and custard combo in cherry and vanilla for the first time and it Did. Not. Disappoint.

There are a few different locations around Dewey Beach and there is one located on the Rehoboth Boardwalk, so you can hit two spots on this list in one shot.


Famous Chaps Pit Beef BBQ

I wouldn’t call Dewey Beach a foodies destination BUT there are plenty of classic comfort, seafood and bar food options. And BBQ!


We stumbled upon this award-winning Maryland based restaurant and decided to give it a go. My husband and I are BBQ lovers and the pickings in NYC are slim (yep, I said it) so seeing the sign for BBQ was like seeing an oasis in the desert.

And it was good y’all!



I’ll have to link pictures to their site because we had no time to take pictures of our plates, we were too busy getting our grub on.


Dewey Beach

Mommy, Daddy and Story at the beach

There are quite a few beach options, one to suit whatever vibe you’re looking for, from low-key to lively. We opted for a low key atmosphere.


This was Story’s very first trip to the beach and we had high hopes but as you can see from the look on his face, Story was not having it.

Daddy and Story not so happy after his first dip in the ocean

Oh well, we’ll try again next year.


Tanger Outlets


Did I mention that Delaware has no sales tax? No? Oh, then I probably should have lead with that.

You‘re going to want to save room in your budget for shopping at the nearby Rehoboth Beach outlet malls. All your favorite stores are there. There is always a sale and again, I say No Sales Tax!

And that's it!


Delaware was a beautiful surprise, I never imagined that I would be vacationing there. It's a well-kept secret, definitely a secret from my social circles, but no more. If you have the opportunity to check this beach location out, put this at the top of your list. You will not regret it.


With Love,


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