Life on the water. Shared.
There are places on the Chesapeake most people never experience — quiet creeks, remote beaches, working waterfronts shaped by generations, and stretches of shoreline where the pace of the water still sets the rhythm of the day.
Backwater Expeditions was built to share that side of the Bay through shallow-draft skiff rentals, captained trips, guided ecotours, kayak adventures, and custom experiences designed around authentic access to Virginia’s coastal backwaters.
Whether exploring at your own pace or stepping aboard for a guided experience, every trip is shaped by the water, the weather, and the character of the Chesapeake itself.
Services
17' Skiff Rental
The Skiff
Built for the Backwaters
The 17’ York River Skiff is a locally built shallow-draft boat designed for exploring the creeks, marshes, rivers, beaches, and backwaters that define Virginia’s Chesapeake Bay region.
Simple, stable, and easy to operate, these skiffs are built for relaxed days on the water rather than speed or crowded marina hopping. Their shallow draft allows access to quiet shoreline areas and hidden corners often inaccessible to larger vessels.
Ideal for couples, families, fishermen, photographers, and anyone looking to slow down and experience the water at a different pace.
Perfect For
Fun on the Water
• Exploring marsh creeks and shoreline backwaters
• Fishing and crabbing
• Wildlife viewing and birding
• Remote beaches and sandbars
• Lighthouse and sightseeing trips
• Relaxed family outings
• Photography and sunset cruising
• Slow days on the Chesapeake without a fixed agenda
These boats are best suited for guests looking for a simple and authentic experience on the water rather than high-speed recreation.
Delivery & Access
Convenient Dockside Service
Skiffs are available for pickup or delivery to select waterfront homes, marinas, and launch locations throughout Mathews and surrounding areas.
Delivery options are designed to make getting on the water simple and convenient, especially for guests visiting the region or staying along the shoreline.
Because conditions, tides, ramp access, and travel distances vary throughout the Chesapeake Bay region, delivery availability may differ by location.
If you are unsure whether delivery is available to your rental property or preferred launch location, feel free to reach out before booking.
On The Water
Your Safety First
Every rental includes a walkthrough covering operation of the vessel, local conditions, required safety equipment, and basic navigation considerations before departure.
These boats are intentionally simple and approachable, but guests should still expect changing weather, wind, tides, shallow areas, and typical Chesapeake Bay boating conditions.
Backwater Expeditions is built around relaxed and responsible experiences on the water, with safety, local knowledge, and respect for the waterways remaining part of every trip.
Delivered Kayak Rentals
The Kayaks
Simple Exploration
Backwater Expeditions uses Ocean Kayak Scrambler 11 Series sit-on-top kayaks designed for exploring the quieter and more hidden side of the Chesapeake Bay region.
At 11’6” long, these kayaks offer a stable, approachable, and easy-to-paddle platform ideal for both first-time paddlers and experienced kayakers alike. Their sit-on-top design makes getting on and off simple from shorelines, docks, beaches, and shallow marsh edges while remaining well suited for calm coastal waters, protected creeks, and shoreline exploration.
Perfect for relaxed paddling, wildlife viewing, photography, fishing, family outings, and slow exploration of marsh creeks and backwaters, the Scrambler 11’s are built around comfort, simplicity, and spending meaningful time on the water rather than speed or technical paddling.
Whether launching from a waterfront rental home or slipping quietly through the marsh at sunset, kayaking offers one of the closest connections to the landscape and rhythm of the Chesapeake itself.
Delivery & Access
Easy Access to the Water
Kayaks are available for delivery to waterfront homes, vacation rentals, campgrounds, and select launch locations throughout Mathews and the surrounding Chesapeake Bay region.
Delivery options are designed to make getting on the water simple and convenient, especially for guests visiting the area or staying along the shoreline.
For guests not staying directly on the water, launch and delivery options may vary depending on travel distance, conditions, and access availability.
If you are unsure about delivery to your location, feel free to reach out before booking.
Perfect For
Quiet Chesapeake Adventures
• Exploring marsh creeks and shoreline backwaters
• Wildlife viewing and birding
• Photography and sunset paddles
• Waterfront vacation stays
• Family-friendly outings
• Fishing and crabbing access
• Relaxed solo paddles
• Quiet exploration away from crowds
• Experiencing the Chesapeake at a slower pace
Kayak rentals are best suited for guests looking for a simple, immersive, and authentic experience on the water rather than fast-paced recreation or guided group tours.
On The Water
Relaxed & Approachable
Every rental includes a quick overview covering launching, paddling basics, local conditions, safety equipment, and considerations for tides, weather, and shoreline conditions before departure.
These kayaks are intentionally stable, approachable, and easy to use, but guests should still expect changing Chesapeake Bay conditions including wind, current, shallow areas, boat traffic, and shifting weather.
Backwater Expeditions is built around relaxed and responsible experiences on the water, with safety, local knowledge, and respect for the waterways remaining part of every trip.
Life on the water. Shared.
The Experience
The Experience
Guided Chesapeake Exploration
Backwater Expeditions offers captained trips aboard a 23’ Carolina Skiff and guided kayak ecotours built around exploring the quieter and more authentic side of the Chesapeake Bay.
Whether cruising shoreline waters by skiff or paddling quietly through marsh creeks by kayak, these experiences are designed around wildlife, working waterfronts, lighthouse views, marsh ecology, photography, local history, and the constantly changing character of Virginia’s coastal backwaters.
The 23’ Carolina Skiff provides a comfortable platform for relaxed exploration with greater range and access to a wide variety of waterways throughout the region, while guided kayak trips offer a closer and quieter connection to the marsh and shoreline environment.
Every trip is shaped around the guests onboard, the conditions that day, and the natural rhythm of the Chesapeake itself rather than a fixed route or scripted attraction.
Trip Style & Access
Flexible & Personalized
Guided experiences may take place aboard the 23’ Carolina Skiff, by kayak, or a combination of both depending on the goals, pace, comfort level, and interests of the group.
Skiff-based trips allow greater range, comfort, and access to larger stretches of shoreline and Bay waters, while kayak ecotours focus on quiet exploration close to the marsh, shoreline, and shallow backwaters.
Launch locations, trip timing, and routes may vary depending on weather, tides, wildlife activity, and seasonal conditions throughout the Chesapeake Bay region.
Private trips are ideal for couples, families, photographers, visitors to the area, and anyone looking for a more personal and authentic experience on the water.
Perfect For
Experiences Worth Slowing Down For
• Lighthouse and sightseeing trips
• Wildlife viewing and birding
• Marsh ecology exploration
• Working waterfront experiences
• Photography outings
• Family-friendly adventures
• Sunset cruises and paddles
• Remote beaches and shoreline exploration
• Quiet time on the water away from crowds
• Learning about the Chesapeake from a local perspective
Some guests want a hands-on experience exploring marshes and shoreline ecosystems, while others simply want to relax and spend meaningful time on the water with family and friends.
No two trips are exactly alike because no two days on the Chesapeake are exactly alike.
Local Knowledge
Rooted in the Chesapeake
Backwater Expeditions experiences are led by a licensed captain and Certified Virginia Ecotour Guide with professional experience spanning marine emergency response, Chesapeake Bay shoreline systems, coastal resilience, and years navigating local waterways throughout the region.
Trips are intentionally designed to feel approachable, relaxed, and authentic while maintaining a strong focus on safety, changing conditions, local knowledge, and respect for the waterways and ecosystems being explored.
Life on the water. Shared.
Guided Trips
Backwater Expeditions offers guided Chesapeake Bay experiences by kayak and aboard a 23’ Carolina Skiff designed around exploring the quieter and more hidden side of the water.
Whether paddling quietly through marsh creeks or cruising farther stretches of shoreline by skiff, these trips are built around wildlife, working waterfronts, lighthouse views, remote beaches, marsh ecology, local history, and the constantly changing character of Virginia’s coastal backwaters.
Some experiences focus on birdlife, photography, and hands-on exploration for families and kids. Others are simply about slowing down, getting away from crowded destinations, and spending meaningful time on the water with family and friends.
The kayak experiences offer a closer, quieter connection to the marsh and shoreline, while the 23’ skiff allows access to larger areas of the Bay with greater comfort and range. Every trip is shaped around the guests onboard, the conditions that day, and the unique rhythm of the Chesapeake itself rather than a fixed route or scripted tour.
No two days on the water are exactly alike here, and that is part of what makes these experiences worth sharing.
Life on the water. Shared.
Delivered Kayak Rentals
Backwater Expeditions offers delivered sit-on-top kayak rentals designed around a slower and more personal way to experience the Chesapeake.
These are not crowded river trips or commercial paddle tours. They are opportunities to quietly explore marsh creeks, shoreline backwaters, hidden coves, working waterfronts, and calm stretches of water that are best experienced close to the surface and at your own pace.
For some guests, that means an early morning paddle through the marsh watching osprey and herons work the shoreline. For others, it is a sunset drift through still water with family and friends, letting the pace of the tide and wind shape the experience. Kids often turn every shoreline into an adventure, while photographers and nature lovers find themselves slowing down to notice details larger boats pass right by.
The kayaks are simple, stable, and approachable for both first-time paddlers and experienced explorers alike. Delivered directly to waterfront homes throughout Mathews and the surrounding Chesapeake Bay region, they offer an easy way to step straight from your stay into the landscape that makes this part of Virginia special. For guests not staying on the water, select launch and delivery locations are also available.
Like everything at Backwater Expeditions, the goal is not to rush people from stop to stop. It is to share a more authentic side of life on the water and the quiet corners of the Chesapeake that continue to shape the people who live here.
Life on the water. Shared.