Dewey Beach isn’t just about sunbathing and beachside bars; it’s also a fantastic spot for water-based adventures. Whether you want to paddle quietly through calm waters or try something a bit more challenging like windsurfing, Dewey Beach offers options that suit nearly every type of traveler. We especially enjoyed the Windsurfing Lesson on Rehoboth Bay — it’s perfect if you’re looking to try a new skill with expert guidance. But if you prefer relaxing on the water, kayaking and paddleboarding are both affordable and flexible choices. With so many options, it’s worth considering what kind of experience matches your interests, budget, and energy level.
In this guide, we’ll review the four best tours in Dewey Beach. We’ll cover everything from beginner-friendly kayak rentals to more skilled windsurfing lessons. Our goal is to help you pick the adventure that best fits your style and make your visit even more memorable.
1. Dewey Beach: 2 HR Kayak Rental Rehoboth Bay
Paddle through the peaceful, shallow waters of Rehoboth Bay with this flexible kayak rental — perfect for first-timers or those looking for a relaxed afternoon on the water. For just $50 per person, you get two hours of paddling with options for single or tandem kayaks. The rental includes basic tips and guidance, making it an ideal choice if you’re new to kayaking. You can choose to paddle at your own pace, exploring the tranquil waterways and enjoying sightings of wildlife like ospreys, herons, and even bald eagles.
One of the key advantages is the flexibility — you can book a time that suits your schedule and decide whether you want to go solo or with a partner. The shallow waters of Rehoboth Bay are calm enough for beginners, but still offer enough interest with bird-watching and scenic views. This tour offers excellent value, giving you two hours of independence without the hassle of guided groups or crowded tours.
Bottom line: If you want an affordable, easy way to explore Dewey Beach’s waters while soaking in nature, this kayak rental is a top pick. It’s especially suited for families, couples, or anyone wanting a peaceful paddle with plenty of wildlife sightings.
$50 per person
2. Dewey Beach: Paddleboard Rental
For those who prefer standing on the water, a paddleboard rental in Dewey Beach offers a fun, active way to enjoy Rehoboth Bay. At just $35 per person for two hours, it’s a budget-friendly option that puts you directly in control. The rental includes all taxes and fees, so what you see is what you pay — making it straightforward for independent travelers.
Paddleboarding is great for a variety of skill levels; you can sit, kneel, or stand, depending on your confidence. The calm waters make it easy to explore at your own pace, and the sights of local wildlife — from herons to ducks — are right there as you glide along. Whether you’re looking for a relaxing activity or a bit of a workout, paddleboarding offers both in a single package.
If you’re new to paddleboarding, the stability of the boards and the straightforward rental process help you feel confident right away. Plus, the freedom to explore without a guide means you can customize your experience based on your mood and energy level.
Bottom line: A paddleboard rental is perfect for independent travelers wanting a straightforward, enjoyable water activity with minimal fuss and maximum fun.
$35 per person
3. Windsurfing Lesson on Rehoboth Bay
If you’re craving a challenge or want to learn a new water sport, the windsurfing lesson at Dewey Beach is an excellent choice. For $175 per person, you get a two-hour beginner lesson that covers the basics of windsurfing, from balancing on the board to harnessing the wind. The lesson includes all necessary equipment — no need to bring your own gear — and is conducted in small groups, which means personalized attention.
What makes this experience special is the opportunity to learn a skill that combines balance, strength, and wind awareness. The instructor’s expertise ensures you’ll get a gentle, clear introduction to windsurfing, even if you’ve never tried it before. Post-lesson, many find themselves eager to practice on their own or with friends. The views of Rehoboth Bay during the lesson are a bonus, providing a stunning backdrop for your new skill.
While the price is higher than simple rentals, this is an experience that offers real value for those wanting a memorable and active day. It’s perfect for adventure seekers, water sports enthusiasts, or anyone ready to step out of their comfort zone.
Bottom line: A windsurfing lesson is a memorable way to add excitement to your visit, especially if you’re interested in trying something different and challenging on your trip.
$175 per person
4. Ocean City Tandem Kayak Rental
Last on our list is a tandem kayak rental in Ocean City, Maryland, which offers a different but equally relaxing experience. For $47 per person, you can explore the Assawoman Bay from behind the beach of the Aloft Hotel. The rental lasts between 1 and 2 hours, giving plenty of flexibility to fit into your schedule.
What sets this tour apart is the scenic setting and the ease of launching right from the beach. The calm waters and open views make it a great choice for couples, families, or groups of friends. Wildlife sightings are common here, from shorebirds to occasional dolphins. The experience is about enjoying the peaceful environment and taking in the views at your own pace — no guided group required.
While it’s a shorter experience than the Dewey Beach options, the advantage is the opportunity to explore a different bay with fewer crowds and more coastline to discover. The scenic waters of Ocean City combined with the relaxed pace make this a solid choice for a quick but engaging water adventure.
Bottom line: For a laid-back, scenic paddle in Ocean City, this tandem kayak rental provides a simple way to enjoy the water and wildlife without breaking the bank.
$47 per person
How to Choose the Best Tour in Dewey Beach
When deciding which water adventure to try, consider your budget, physical activity level, and what kind of experience you seek. If you want a simple, peaceful paddle with wildlife sightings, the 2-hour kayak rental or the paddleboard rental are excellent. For those eager to learn something new and active, the windsurfing lesson offers a memorable challenge. If your plans include exploring nearby Ocean City, the tandem kayak rental provides a scenic, relaxed experience.
Booking early is advisable, especially for windsurfing lessons and rentals during busy weekends or holidays. Also, think about the weather — calm, sunny days will make your water adventure far more enjoyable.
Final Thoughts
Dewey Beach offers a variety of water-based tours suited for different interests and skill levels. For a tranquil experience and wildlife watching, the kayak rental is hard to beat. If you’re looking for a straightforward, independent paddle, the paddleboard rental delivers fun and flexibility. The windsurfing lesson stands out if you’re ready for a physical challenge and want to learn a new skill, while the Ocean City tandem kayak provides a scenic day trip with friends or family.
No matter your choice, booking ahead will ensure you get the time slot that fits your schedule. These experiences can turn a regular beach trip into a memorable aquatic adventure. So, pack your sense of adventure and enjoy all that Dewey Beach’s waters have to offer.