40 for 40-Island #20: Assateague Island, VA



The Island: Assateague Island, VA 38.0933° N, 75.2071° W

Where: Eastern Shore of Virginia…across the bridge from Chincoteague

How: Passing through Chincoteague, you go over a bridge and into Assateague, a beautiful uninhabited state park island.


Why: We planned to explore the beach and hiking trails on the island but the wind and mosquitoes made this impossible. Apparently, the island is known for having TERRIBLE mosquitos and it lived up to its name. We didn’t even get past our Jeep without being inundated with the little pests. And YES, we had bug spray. 


What: A gorgeous, uninhabited island, we loved the calmness and beautiful scenery. (We had a lovely driving tour :)) This island is also where the infamous Chincoteague ponies live and graze most of the year. Every spring, approximately 70 fouls are born and later swim to Chincoteague for the annual Pony Penning and auction.

40 for 40-Island #19: Chincoteague Island, VA



The Island: Chincoteague Island, VA

Where: Chincoteague is located on the Eastern Shore of VA.  If you take the well known Chesapeake Bay Bridge tunnel and head north to the northern tip of Virginia you land in Chincoteague. (The eastern shore is very sleepy and lovely in general)

How: We headed north from Cape Charles up the Eastern Shore passing many little, sleepy fishing and crabbing towns. As seafood lovers, this was our kind of area. Chincoteague is a town ive wanted to visit for years and I knew it needed to be a stop on our island tour. 


Why: Ever since I was a little girl, I wanted to see the infamous Chincoteague ponies swim in their annual pony swim. Our daughter has become very interested in horses and it just so happened the annual swim was during the time we were nearby. We awoke at about 5AM drove then took a bus then walked to the marshy area that ponies are known to swim to. After about 3 hours standing in the muck and grass we got word it was time for the swim! We were awestruck watching these little ponies swim in a large pack across teh water while being guided by the Saltwater Cowboys. It was mesmerizing!


What: For hundreds of years, wild ponies have inhabited neighboring Assateague Island. Its believed these ponies originate from a wrecked Spanish galleon from the 1800’s. Pony Penning and auctions date back to the 1800’s and in the early 1900’s after a string of disastrous fires, the Volunteer Fire Dept. turned the pony penning into a national event drawing thousands of people and fundraising dollars. In 1947, a book called Misty of Chincoteague was published and that along with the herd leaders, the Saltwater Cowboys, the event drew international attention. To this day, every year in July thousands come to the small town of Chincoteague to witness and often bid on the ponies. They are well known to be a strong breed and very sought after.


40 for 40-Island #18: Isla de Lindsey, Cape Charles, VA



The Island: Isla De Lindsey, Cape Charles, VA 37.2679° N, 76.0174° W

Where: Okay this one we kinda made up! While vacationing in Cape Charles, we were sitting on the beach with all the other vacationers and marveled at the shallow water that went on for what seemed like forever. We decided to move our chairs to a little spit of sand that we could call all our own. 


How: While sitting there, over time we kept losing more and more island. It was the perfect little private island in shallow water while it lasted!

Why: This was one of the many reasons we LOVED Cape Charles. The beach is shallow for as far as the eye can see and is perfect for kids and adults alike who want their own space in the water and dont wanna get too deep. 

What: This beach is part of the Chesapeake Bay and goes on all along the western side of town. Cape Charles is an adorable little town with restaurants, shops and plenty of seafood. We really enjoyed biking, walking and golf carting as we explored the entire town. 


40 for 40-Island #17: Jamestowne Island, VA

The Island: Jamestowne Island, VA 37.2035° N, 76.7588° W


Where: On the Eastern Shore of Virginia near Williamsburg

How: Rich in History and connected to Virginia by causeway, this island is easily accessible since its a major historic site and National Park. The park offers vehicle tours of the marshlands and walking tours of the settlement.


Why: We were in the area and wanted to show and teach our daughter a bit about the history of the first settlement and where the settlers first came to America.


What: Short on time, we took the scenic driving tour thru the island’s beautiful marshes and wetlands. We will definitely be back to visit more when we have the time!

40 for 40-Island #16: Party Island, SML, VA

The Island: Party Island/ Betty’s Island, SML 37.0497° N, 79.6394° W

Screenshot 2023-02-06 102149

Where: Betty’s Island, nicknamed Party Island, is a small little island on Smith Mountain Lake in Virginia where you will almost always see several pontoon boats (and an occasional cruiser) up on the beach.

How: We recommend hopping on your jet ski or your friends boat for this spot. Kayaking, swimming etc, to the island isnt recommended. 


Why: This is a great spot for boaters who are social butterflies and want to make new friends while enjoying to sand, water and sun of SML. If you love sharing space and making new friends then this is the perfect place for you. Bigger boats CAN anchor but its hard. This spot is best for smaller boats and pontoons. 


What: While the island is surrounded by nice swimming water, there is an obvious spot where people tend to beach their boats. There are also some fun swings over the water and some primitive camping.

40 for 40-Island #15: Cape San Blas, Fl

The Island: Cape San Blas, Fl 29.6675° N, 85.3525° W


Where: Located in the southernmost part of the Gulf, i like to say as you are about to head south there is the most quiet, quaint and gorgeous area of Florida called Cape San Blas. If you own an RV its the PERFECT place for you as you can find plenty of parking right on the white sand beaches. 

How: Since we have a rented RV in tow, we found a great little spot in someone’s side yard that offered a comfortable, flat place to stop for a few days with only a few steps to the beach. 


Why: Admittedly, this wasn’t an area I had really heard of but know of friends who venture here all the time. It’s a beach and it’s not as crowded as some areas so we knew it would be a great spot for us. 

What: We soaked up all Cape San Blas had to offer: the quiet, white sandy beaches, local fare and a must stop was Indian Pass Raw Bar. Anything that has raw bar in the name is bound to be delicious. We were delighted with this little country store, seat yourself type restaurant and even more delighted when a couple starting belting out Garth and Trisha songs like pros.


40 for 40 – Island #14: Destin/Sandestin, Fl

The Island: Destin/Sandestin, Fl 30.3935° N, 86.4958° W


Where:  Destin sits in the middle of the Florida panhandle 

How: Our next stop in the RV tour brought us to the most delightful beach going spot in the middle of a bustling vacation destination. We parked for two days at Camping on the Gulf and its EXACTLY how it sounds. If you book early, your RV can be parked literally on the gorgeous sandy beach. We were about 5 spots in and it was still gorgeous. While the weather was a bit chilly for too much beach going, we really enjoyed using the wind to our advantage with kite flying and other fun activities. 


Why: Driving and parking RIGHT on the beach is our idea of fun!

What: Camping on the Gulf offered plenty to do with the beach, a pool and plenty nearby. We ventured into the town of Destin to play tourist and always found the Blue Chair Bay Rum bus that was on tour.


40 for 40 – Island #13: Crab Island, Destin, Fl


The Island: Crab Island, Destin, FL 30.3939° N, 86.5050° W

Where: on the north side of Destin Bridge at the entrance to Choctawhatchee Bay


How: Isn’t the shifting sand and tides so fascinating? Crab island was once an actual island but with shifting sands and erosion, crabs island is now a sandbar with water levels from 1-4ft. The only way to get there is by boat, PWC or if you are feeling extra adventurous maybe a kayak or SUP. (This method is NOT recommended based on the current coming our of the inlet.)

Why: Any island/sandbar that requires a boat ride too and we are ALL IN! We were in the Destin area and looking for a fun day on the water. 


What: After a short ride aboard the Crab Island Shuttle Boat we dropped an anchor and jumped in the water, and EVERYONE immediately got out! The weather on this day ended up being a bit chilly but by the middle of the trip everyone was in the water enjoying water toys, games, paddle boarding and swimming. There were even some takers for the ice cream boat and the BBQ pontoon boat was a big hit for lunch!

40 for 40 – Island #12: Okaloosa Island, Fl


The Island: Okaloosa Island, Fl  30.3980° N, 86.5977° W

Where: Between the Florida/Alabama border and Destin in the Florida Panhandle

How: We took a pit stop during our RV tour to stop and play on the massive dunes on this island. 


Why: We were in awe of the gorgeous white sand dunes that seemed to go on forever. The pictures don’t do it justice, they were huge!


What: While this island seems to be a great family vacation spot, we were just passing thru. If you plan to stay there are restaurants, adventure parks, dolphin trips and plenty of family friendly adventures!

40 for 40 – Island #11: Perdido Key, Fl


The Island: Peridido Key, Fl 30.3035° N, 87.4273° W

Where: Florida Panhandle next to the infamous Florida/ Alabama line.

How: We took a break from our typical boating/sailing and decided to rent an RV and run south to the Florida panhandle. 

Why: With a trailer in tow, we camped in Perdido Key and enjoyed all it had to offer. We camped in a state park that offered a playground, lots of outdoor exploring and hiking trails. They also had a beach perfect for swimming and kayaking but it was closed from previous hurricane damage. 


What: Perdido Key is a perfect mix of action and relaxation. Flora Bama alone has several restaurants, bars, the yacht club (our fave) and several other options all within walking distance. We had the pleasure of experiencing Easter morning church on the beach right in front of Florabama.


We then hit the yacht club for lunch and watched with envy while boat after boat beached themselves right next to the yacht club stage.