Chincoteague, Virginia is Perfect for Multi-generational Vacations

Photo Credit: Dana Arnold Photography

Chincoteague, VA was the perfect spot for our multi-generational getaway.  It is a peaceful beach town without all the craziness of a crowded boardwalk or wall-to-wall people.  There were tons of family-friendly attractions perfect for our little ones and Grammy alike.  Most importantly, Chincoteague is a great location to relax and unwind as a family.

Photo Credit: Dana Arnold Photography


We wanted to stay in a central location so our home base hotel was right on Main Street.

We booked two adjoining rooms on the first floor with balconies that looked over the Chesapeake Bay.  We enjoyed a hot breakfast every morning, snacks in the evening, and a heated indoor pool with the kids.  The entire hotel was spotless, and the staff was super friendly.  We booked an extra night because we were having such a great time.

Chincoteague Virginia
Lady B enjoying the gorgeous view


The location was perfect for us.  We were less than 10 minutes away from Assateague Island National Seashore.  We were blessed to spend a lazy morning on the sand listening to the sound of the waves.  We had the beach to ourselves, another reason why we love off-season travel.  We even spotted some of the famous wild ponies.

Chincoteague Virginia
Assateague Island National Seashore

Just a short ride up Main Street and we found our third LOVEwork sign.  These big LOVE signs are all over Virginia, and we’ve set out on a mission to find as many as we can.

Chincoteague Virginia
LOVEwork: 4083 Main St. Chincoteague Island, VA 23336

So, when you travel with a toddler, or three, it is so important to find places they’ll truly enjoy.  For us, that means we always search for the nearest park with a big playground.  In Chincoteague, that meant Veteran’s Memorial Park.  It is a lovely waterfront park with tennis and basketball courts, pier, ball field, boat ramp, skate park, pavilion, restroom, and the all-important playground

Photo credit: Dana Arnold Photography

And, it has the perfect view of the Assateague lighthouse.

Photo Credit: Dana Arnold Photography

The Bites

Quite a few of the local restaurants are closed during the off-season, but we were still able to find great local seafood and family-friendly spots.  Our favorite restaurant was Don’s Seafood.  Being from Annapolis, I crave really good seafood when we travel to beach towns.  The cream of crab soup was fantastic.  We all had fish or crab dishes, and they were so fantastic.  Don’t forget to take home a slice of Smith Island Cake too.

We didn’t get to enjoy their outdoor dining, but it looked like a great spot for a family meal.

Chincoteague Virgina
The outdoor dining area at Don’s Seafood

Another local favorite we enjoyed was Island Creamery.  The ice cream is heaven, and it is a really cute family-friendly spot.

Chincoteague Virginia
Yummy goodness at Island Creamery

Growing up just 3 hours from Chincoteague, I can’t believe we never visited this beautiful island.

Assateague Island National Seashore
Assateague Island National Seashore: Our first National Park

We created wonderful family memories on this trip, and we’re already planning to visit again this summer.  If you are looking for the perfect East Coast multi-generational beach vacation, Chincoteague, Virginia is for you.

Let’s continue the conversation on Instagram:

Thank you, Dana Arnold Photography for capturing our family time in Veteran’s Memorial Park.  We’ll cherish these photos forever.  Reach out to Dana for your next vacation.  She’s an amazing travel photographer.

Angelica Kajiwara
Angelica Kajiwara
Powered by Dealspotr



  1. This is the first time i heard about this place, and it looks amazing, family-friendly and i think pet-friendly too. Taking a vacation with keeps could be hard, and it is nice to stay in a place where is it condusive for the little ones. Ohh the beach looks gorgeous too!

    • It is pet-friendly, for sure, and the beach was so relaxing. We had the best morning enjoying the ocean and sand. Thanks for stopping by!

  2. Chincoteaque?!? How do we pronounce that? I am glad I stumbled upon your post because I love reading about place I never knew existed! I can imagine this beach town when the sun is shining, when having a sunset dinner at Don’s seafood slurping down creamy crab soup…thats life! Such a great family you have there!❤️

    • SHINK-uh-teeg (I think). Thank you for your kind words. We love exploring together. Chinoteague is a beautiful spot.

  3. I have never heard of Chincoteague before. Your photos are beautiful. Also, I did not realise that Virginia has LOVE signs all over, what a fun thing to do is to photo everyone in each location. I would enjoy the outdoor dining at Don’s Seafood and the Ice Creamery – my favourite type of food. A destination that is perfect for all ages.

    • The LOVE signs are such a fun find. We love when we stumble upon them. Thanks so much for stopping by!

  4. Chincoteague Island looks blissfully remote and laid back. I love places like that, where you can have some fun away from the crowds. I’ve been in several places in Virginia, but didn’t make it to the beaches there, so I don’t have a comparison. I’m sure however that they are not as peaceful as the ones on Chincoteague Island. Would love to visit this place someday and maybe try some ice cream from the island creamery.

    • It is a wonderful town and so peaceful. We’re already planning our next trip. Thanks for stopping by!

  5. I must say I woukd have not even known about this place if it was not for pists like thesethat show is less promoted places. Chincoteague, VA Is surely a great place for a family holiday and I can see it in your photos that you all had a great holiday. I love the small town with its offerings like the ice cream place. Great to know that the beaches are not to far and you can e hour some sun sea and sand as well. Overall a great destination

  6. I will start with saying that your kids are so cute. Love the pictures specially “Yummy goodness at Island Creamery” one. Chincoteague looks so peaceful, laid back and lovely. Looks like you had the place only to yourselves. Looks like a great holiday place and as you said for multi-generation.

    • Yes, she loves her ice cream! Having the place to ourselves is part of why I love travelling in the off-season. Thanks for stopping by

  7. I love quaint and laidback seaside towns. Chincoteague looks fantastic, and for someone who enjoys places that have a slow pace to them, it’s perfect. I like how there is something for everyone here, and the beach and boardwalk are not crowded. Adore the LOVE chairs.

    • My little ones love the big chairs and letters so much. And yes, it is such a quiet little town in the off-season. A great find!

  8. I’ve never heard of Chincoteague before, so thank you for introducing it to me! It looks like the perfectly quaint beach town, and I’d have a field day with all the seafood there. Living in an inland city (Chicago), I go nuts with the seafood whenever I travel to a coastal city. Looks like you all had a great time!

  9. This looks like the perfect vacation for you and your family. The photo of everyone sitting in the oversized Adirondack chairs is darling! I think blog posts that talk about multi-generational travel are so important and need to be covered more often. I read your other post about Chincoteague, and I’m itching to go there more than ever!

    • We love living and travelling with my mom, and I think a lot of families travel like us. It’s fun to hear from them, and see who takes the Grands along. Thank you for reading my posts. I can’t wait to read about your future trip to Chincoteague.

Leave a Reply

Your email address will not be published. Required fields are marked *