Chincoteague Island, VA: Where to Stay, Where to Play, What to Eat. A 5-Day Itinerary

Chincoteague is one of the best summer getaways in Virginia for outdoor lovers and families. This coastal island on Virginia's Eastern Shore is packed with adventure—from spotting wild horses to sunset cruises, biking scenic trails, kayaking through Tom’s Cove, and eating fresh seafood straight off the boat. Whether you're looking for family fun, quiet beach moments, or unique water-based lodging, this guide has everything you need. We even included our personal 5-day itinerary—tested and family-approved—to help you plan your own trip to Chincoteague Island.

1. Where to Stay

2. Where to Play

3. Best Hikes

4. Where to Eat

5. Homeschooling/Learning Resources

6. 3 Day Itinerary
   

Where to stay:

1. Stay in a Unique Floating Bungalow- Bluefin Bungalows & Marina. Choose a floating bungalow or a waterfront standard, both with full kitchens. Palm trees, pool, island vibes, grills, fire pits, and direct access to the water. Sleeps 2–6 guests, with some dog-friendly units. On-site marina where you can dock your boat or rent jet skis, kayaks, or a double-decker party boat with a slide!

Where to play:

1. Daisey’s Island Cruises – Take a guided boat tour to see wild ponies and learn about Misty’s descendants. Tip: Sunset tours are the most magical time to go.

2. Sea Rocket – Rent kayaks or book a double-decker party boat with a slide. You can launch right from the dock at Bluefin!

3. Chincoteague National Wildlife Refuge – Visit the Visitor Center, complete a Junior Ranger badge, and visit Wildlife Loop.

4. Assateague Lighthouse – Climb the 175‑step historic lighthouse for panoramic views of marsh, bay, and wild ponies. Open weekends (April–Nov).

5. Tom’s Cove Beach – Protected swimming cove, great for families; gentle waves and wide sand.

6. Museum of Chincoteague Island – Learn about local maritime history, pony legends, and island culture.

   
   

Best Outdoor Activities:

1. Kayak or paddleboard Tom’s Cove – Calm waters and scenic views. Launch directly from Bluefin or Veterans Memorial Park.

2. Bike the Wildlife Loop – 3-mile flat loop through the Chincoteague National Wildlife Refuge. Look out for wild ponies, egrets, and more. Bring bug spray!

3. Beach walk to Tom’s Cove Hook – A quiet, sandy stretch perfect for shorebird spotting and sunset views.

4. Veterans Memorial Park – Playground, fishing dock, and paddle boarding with views of Assateague Lighthouse. Great spot for active kids.

Where to eat:

1. Blackfin Island Grill – Coastal American menu. Try the Crabby Patty (soft shell crab burger)—a 9/10 from our kid burger expert. That’s basically a Michelin star.

2. Gary Howard Seafood – Best spot for fresh seafood. Some of the best oysters, blue crabs, and shrimp on the Eastern Shore.

3. Famous Pizza and Sub Shop – Great for an easy family dinner. Don’t miss the crab pizza.

4. Ropewalk – Best spot to eat dinner and watch the sunset. Huge selection of crushes, sandy patio, games, and a playground for kids.

5. The Village Restaurant – Fresh seafood, upscale but casual, with waterfront views. Great spot for a nicer family dinner or sunset date night.

6. Etta’s Channel Side Restaurant – One of the island’s oldest eateries with local charm, crab cakes, and water views. Ask about the pony cookies for kids!

7. Sea Star Café – Hidden gem for sandwiches, salads, and daily specials. Try the Cowboy Panini and enjoy the outdoor picnic tables.

8. Mr. Whippy – The island’s classic soft serve stand. Huge cones, sundaes, and milkshakes perfect after a hot day. Bonus: it’s been family-run for over 30 years.

9.  Island Creamery – Voted Best Ice Cream in America by TripAdvisor. Small batch, homemade flavors using local dairy. Try the Pony Tracks or Wallops Rocket Fuel.

10. BYOC (Build Your Own Cookie) – Custom cookie sandwiches, local ice cream, and fun toppings. A newer addition, but already loved by kids and adults alike.

    
    

Homeschooling/Learning Resources:

1. Barrier Island Ecosystems

Online Resources: barrierislandcenter.org – Explore ecology, history, and wildlife of Virginia’s barrier islands.

Field Trip Ideas: Chincoteague National Wildlife Refuge Visitor Center

Suggested Books:

• "Life in a Salt Marsh" (grades 3–6)

• "The Secret Life of the Beach: Understanding the Natural History of Sandy Shores" (ages 12+)

2. Wild Ponies & Conservation

Online Resources: assateagueisland.com

Field Trip Ideas:

• Daisey’s Island Cruises

• Assateague Lighthouse

Suggested Books:

• "Misty of Chincoteague" (all ages)

• "Stormy, Misty’s Foal" by Marguerite Henry (ages 9–12)

• "True Stories of Animal Heroes: Ponies of Chincoteague" by Kelly Milner Halls (ages 10–13)

Our 5 Day Itinerary:

Day 1

• Midday: Check into Bluefin Bungalows & Marina and settle into your floating bungalow.

• Evening: Grab an easy dinner from Famous Pizza and Sub Shop—don’t skip their crab pizza.

Day 2

• Morning: Enjoy coffee on your deck and take in the view. Start the day slow, then head to the pool or paddleboard from Veterans Memorial Park, where you’ll get a view of the Assateague Lighthouse.

• Lunch: Take advantage of the kitchen in your bungalow—there’s a local grocery nearby.

• Afternoon: Head to Blackfin Island Grill for an early dinner. Order the Crabby Patty (soft shell crab on a burger)—our 9-year-old burger expert gave it a 9/10, which is basically a Michelin star.

• Evening: After dinner, take a sunset wildlife cruise with Daisey’s Island Cruises. We saw ponies and dolphins and it was one of the most beautiful evenings of our trip.

Day 3

• Morning: Enjoy a morning on the water and rent a kayak from Sea Rocket—launch right from the dock at your stay.

• Lunch: Enjoy tacos or bowls at Pico Taqueria, a local favorite with island flair—quick, casual, family-friendly.

• Afternoon: Rent the double-decker party boat with a slide from Sea Rocket for a half-day. Perfect for swimming, fishing, and exploring—this was a huge hit with the whole family.

• Evening: Watch the sunset and eat dinner at Ropewalk. Huge crush menu, sandy patio, playground, and outdoor games for the kids.

Day 4

• Morning: Explore the Chincoteague National Wildlife Refuge Visitor Center and hike the nature trail. Earn your Junior Ranger badge!

• Lunch: Grab sandwiches at Sea Star Café – A popular, locally owned spot serving fresh sandwiches, salads, and soups made to order. Vegetarian and vegan friendly.

• Afternoon: Go swimming in the ocean at Assateague Beach.

• Evening: Get fresh steamed seafood from Gary Howards Seafood. Chincoteague is known for its oysters.

• Late evening: Bring your bikes and ride the 3 miles wildlife loop trail in Chincoteague National Wildlife Refuge. Bring bug spray! Stop by Island Creamery or Mr. Whippy for ice cream on the way home.

Day 5

• Check out of Bluefin Bungalows—but don’t hit the road just yet. Stroll the shops along Main Street, pick up a souvenir, and grab coffee at Main Street Shop & Coffeehouse or the Village Bean.

• Before leaving town, make one last stop at Sandy Pony Donuts for a warm donut and say goodbye to the ponies on your way out!

Want to make it into a road trip? Add these nearby spots:

• Janes Island State Park, MD – 1 hr; island state park known for kayaking and paddleboarding

• Kiptopeke State Park, VA – 1 hr 45 min; see the WWII-era concrete ships

• Maryland Assateague – 30 min; beach trails, wild horses, and the Rackliffe House history center

Ready to Plan Your Adventure?

For more family-friendly road trips and info on our favorite destinations for adventurous families check out our adventures at We Chose Adventures. Join us as we explore more family-friendly trails, scenic drives, and outdoor getaways in the Mid-Atlantic and beyond!

Check out some of our videos of our trip here: