For me, there’s no better place in the world than the Chesapeake Bay at sunset. It’s truly magical watching the sun slowly dip below the horizon while the sounds of gently lapping waves lull you into a state of peace. I’ve seen my fair share of sunsets on the Chesapeake, and the most magical were on a sunset paddle. In this post, I’ll share my personal experiences, my favorite kayak guided sunset tours and public kayak launches.
The Chesapeake Bay is a majestic body of water that stretches over 6 states in the Atlantic region. It has more than 100 estuaries and has over 11,000 miles of shoreline. The Bay is a huge attraction for outdoor recreation, but it’s also a refuge for abundant wildlife. This water is not just a bay; it’s an ecosystem brimming with life and history. The bay is home to over 3,600 species of plants and animals, making it one of the most diverse ecosystems in the world. It’s also an important body of water for the area, providing a vital source of food, recreation, and transportation to the millions of residents in the watershed. In recent years, the bay has faced challenges such as pollution and habitat loss, but there have been significant restoration efforts to protect and preserve this natural treasure. Visit CBF for more information on Bay restoration.
To plan your trip to the Chesapeake, may I suggest reading How to Plan a Trip to Maryland’s Chesapeake Country first.

Important Safety Notes
- Check tides before you go
- In warmer months, wear insect repellent.
- Certain types of mud and marsh appear to be safe to cross on foot, but they can be deceiving. Use caution
- Beware of stinging sea nettles and jellyfish in the water in the summer months.
- Plan ahead. Leave your route and return time with a relative or friend.
- Check weather conditions before you leave.
- Always wear a life jacket.
- In an emergency, stay with your vessel. Marshes cannot be crossed on foot.
- Cell phone service is not always reliable. Don’t count on it for rescues.
- Bring a spare paddle or pole, rain gear, water, sunscreen, insect repellant, a hat, and snacks.
- If your canoe/kayak gets stuck, stay put. Try shifting your weight carefully as you push off with your paddle or pole.
Paddler’s Guide to Wildlife Encounters
The Bay is known for its pristine landscapes and waterscapes. As you paddle, keep your eyes open for wildlife including bald eagles, osprey, egrets, and great blue herons. During migration times in spring and fall, you might also see a wide range of ducks and geese and other waterbirds. Beneath your kayak, you can expect to see blue crab, rays, and lots of species of fish.
Guided Sunset Paddles on the Chesapeake Bay

The Chesapeake Bay is home to numerous outfitters and organizations that offer expert-led tours during sunset. I personally love taking a guided tour of different areas of the bay. You can often learn about wildlife, history and the ecosystem on these tours, as well as seeing beautiful scenery. Ive seen bald eagles, osprey nests, and huge stingrays on these tours.
Capital SUP (Annapolis, MD)
Join a guided sunset paddle event on the South River in Annapolis, MD. This expertly guided paddle tour is so fun! This is the perfect way to see Annapolis and one of my favorite kayak tours in Maryland. Paddle along the shoreline through the river and coves. You may even catch some live music from Quiet Waters Park as you pass by! What a perfect evening, right?
Blackwater Adventures(Cambridge, MD)
Experience the sunset on the iconic Choptank River. Join this guided sunset paddle tour as it leaves from the Hyatt in Cambridge. Watch as the sun dips below the horizon behind the Route 50 Bridge. This is a unique way to experience the bay, and one of the best kayak tours in Maryland.
Janes Island State Park (Crisfield, MD)
This is my personal favorite- A guided sunset paddle to a remote island. This tour leaves from Janes Island State Park in Crisfield, MD. The tour arrives at a remote island just before sunset. You can dock your kayak and stroll along the pristine shoreline, or bring a blanket to watch the daylight fade. Here is a pro tip- don’t forget bug spray! You need to add this Maryland kayak tour to your list!

Public Kayak Launches on the Chesapeake Bay
The Chesapeake Bay offers a ton of public kayak launches and put-ins that are perfect for launching your own kayak as the sun sets. You can choose to seek a tranquil cove setting or the open waters of the Bay- there’s something for everyone. Here are my insider tips for some of the best kayak put-ins for sunset paddles on the Chesapeake Bay.
Matapeake State Park (Stevensville, MD)

https://www.qac.org/facilities/facility/details/matapeakefishingpierandramp-127
If you’re looking for an awesome spot to kayak near the Bay Bridge, check out Matapeake State Park in Stevensville, Maryland. This public kayak launch is a gem for paddlers of all levels. The park offers stunning views of the bay and the iconic Chesapeake Bay Bridge. Plus, with easy access to launch sites, picnic tables, restrooms and plenty of parking, getting out on the water couldn’t be easier. Keep in mind, this kayak launch is on the open Bay and the water won’t be as calm as other places. Paddling in the open waters of the Bay at sunset is a picture perfect moment you won’t soon forget.
Kiptopeke State Park (Cape Charles, VA)
https://www.dcr.virginia.gov/state-parks/kiptopeke
Kiptopeke State Park, located in Cape Charles, Virginia, is an incredibly unique park along the Chesapeake Bay. Known for its beautiful beaches, diverse wildlife, and stunning views of the bay, this park offers something for everyone. The public kayak launch is easy to find from the parking lot. Paddlers can explore the park’s unique concrete ships by water, which were used as part of a ferry service during World War II. This park will be the perfect setting for a sunset paddle on the Chesapeake.
St Michaels Harbor, MD

This charming Eastern Shore town is a perfect launching point for exploring the Miles River and the Chesapeake Bay. The town has a picturesque harbor and historic architecture to explore. I love gliding through the calm waters and taking in the stunning views of homes (ehem, mansions) on the water. There is a public kayak launch on both sides of town- one at the St. Michaels boat ramp, and another at the waterfront park on San Domingo Creek. Plus, with plenty of rental options nearby and guided tours available, getting out on the water couldn’t be easier in this waterfront town.
Sunset Adventures Await
Sunset kayaking on the Chesapeake Bay is a magical experience that offers tranquility and natural beauty. Whether you’re paddling solo or joining a guided tour, the bay’s serene waters and stunning sunsets are sure to captivate your heart. I encourage you to embark on your own sunset kayaking adventure and experience the magic for yourself.


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