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Premium Gwynn's Island Sunset Cruise | Class Act

  • Published Date: July 16, 2025
  • Fishing
  • Mathews County
  • $500 - $1,500 price range

Summary

Picture yourself sailing on calm waters as the sun dips below the horizon, painting the sky in soft hues. That's what you'll experience on our 5-hour evening cruise around Gwynn's Island in the Chesapeake Bay. Our boat comfortably fits up to 6 guests, making it perfect for a family outing, a get-together with friends, or a romantic evening for two. Feel free to bring your favorite drinks and snacks to enjoy on board as we navigate the scenic tributaries. We've got safety covered with our experienced crew, so you can relax and soak in the peaceful atmosphere. It's a great way to unwind and create lasting memories in this beautiful coastal setting. For those looking for something extra special, we even offer intimate wedding ceremonies on the water. Whether you're celebrating or just want a unique evening out, our tour gives you a personal, laid-back experience of the bay's natural beauty.
Premium Gwynn's Island Sunset Cruise | Class Act

Sunset on the Bay

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Two people enjoying fishing on Gwynn Island

Catch of the day: Chesapeake Bay style

2 small fish caught by a person on Gwynn Island

Chesapeake Bay: A fisherman's paradise

6 anglers fishing on the shores of Gwynn Island

Bay adventures: Fish, fun, and friends

Group of 5 people enjoying a fishing trip on Gwynn Island

Epic fishing on Chesapeake Bay

4 people enjoying fishing trip in VA

Nice lil cruise with these ladies today!!

Two people fishing in Virginia

Hooked on Chesapeake Bay adventures!

Fishing on Gwynn Island

Chesapeake Bay: Where big fish await

Three people fishing in Virginia

Reeling in memories on Chesapeake Bay.

Person fishing on Gwynn Island

Fishing fun under the Chesapeake sun

Six people fishing in Virginia

Casting lines, catching dreams in the Bay

Two people enjoying fishing on Gwynn Island

Catch of the day: Chesapeake Bay style

2 small fish caught by a person on Gwynn Island

Chesapeake Bay: A fisherman's paradise

6 anglers fishing on the shores of Gwynn Island

Bay adventures: Fish, fun, and friends

Group of 5 people enjoying a fishing trip on Gwynn Island

Epic fishing on Chesapeake Bay

4 people enjoying fishing trip in VA

Nice lil cruise with these ladies today!!

Two people fishing in Virginia

Hooked on Chesapeake Bay adventures!

Fishing on Gwynn Island

Chesapeake Bay: Where big fish await

Three people fishing in Virginia

Reeling in memories on Chesapeake Bay.

Person fishing on Gwynn Island

Fishing fun under the Chesapeake sun

Six people fishing in Virginia

Casting lines, catching dreams in the Bay

Two people enjoying fishing on Gwynn Island

Catch of the day: Chesapeake Bay style

2 small fish caught by a person on Gwynn Island

Chesapeake Bay: A fisherman's paradise

6 anglers fishing on the shores of Gwynn Island

Bay adventures: Fish, fun, and friends

Group of 5 people enjoying a fishing trip on Gwynn Island

Epic fishing on Chesapeake Bay

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Sunset Serenity: Gwynn's Island Boat Tours

Get ready for a laid-back evening on the water with Class Act Charters. Our 5-hour Chesapeake Bay boat tours around Gwynn's Island are the perfect way to unwind and soak in the coastal beauty. Whether you're looking for a chill night out with friends, some quality family time, or a romantic date, we've got you covered. And hey, if you're thinking about tying the knot, we even do small weddings right on the boat – talk about a unique "I do" with a view!

Evening on the Bay

Picture this: You and up to five of your favorite people, kicking back on a comfy boat as we cruise around Gwynn's Island and its scenic creeks. Bring along your favorite drinks and snacks – it's BYOB and picnic-style out here. As the sun starts to dip, you'll get front-row seats to one of the best shows on the bay – a Chesapeake sunset painting the sky. Our crew knows these waters like the back of their hand, so you can just relax and enjoy the ride. It's the kind of easy-going trip that turns into those "remember when" stories you'll be telling for years.

Cruising the Coastline

We'll motor along at a nice, easy pace, giving you plenty of time to take in the sights. Gwynn's Island's got a mix of pristine shorelines and cozy waterfront homes that'll have you daydreaming about island life. Keep your eyes peeled for ospreys diving for fish or herons wading in the shallows. If you're into photography, bring your camera – the golden hour light out here is something else. And don't worry if you're not a seasoned boater; our stable, spacious vessel is perfect for first-timers and old salts alike.

Why Folks Love Our Tours

There's something special about being out on the water as day turns to night. It's like hitting the pause button on life for a while. Our guests tell us it's the perfect mix of adventure and relaxation. Families love how it brings everyone together without the distractions of screens and schedules. Couples rave about the romantic vibes – nothing like cuddling up under a blanket as the stars come out. And for those thinking about popping the question or saying "I do," well, let's just say we've seen our fair share of happy tears out here on the bay.

Chesapeake Bay Wildlife

While we're not targeting any specific fish on this tour, the Chesapeake Bay is teeming with life. You might spot striped bass (we call 'em rockfish around here) breaking the surface as they chase bait. Keep an eye out for blue crabs scuttling along the bottom in shallow areas – they're the local delicacy and the backbone of many watermen's livelihoods. In the air, you could see bald eagles soaring overhead or pelicans doing their dive-bomb fishing routine. And if you're lucky, you might even catch a glimpse of a pod of dolphins making their way up the bay. Each season brings different critters, so there's always something new to see.

Time to Set Sail

Ready to trade the hustle and bustle for some bay breezes? Our Chesapeake Bay boat tours from Gwynn's Island are calling your name. Whether you're a local looking for a new way to appreciate your backyard or a visitor wanting to experience the real Chesapeake, we've got you covered. Remember, we can only take up to 6 guests, so these trips tend to fill up fast – especially during peak sunset season. And if you're thinking about a waterfront wedding, let's chat about making your big day extra special out on the water. Don't forget, your deposit locks in your spot, so give us a shout and let's get you booked for an evening you won't forget. The bay's waiting – come on out and see what all the fuss is about!

About the Deltaville Motorboat

Company vehicle

Vehicle Guest Capacity: 6

Manufacturer Name: John Deere

Maximum Cruising Speed: 28

Number of Engines: 1

Horsepower per Engine: 550

Step aboard our comfortable boat for a laid-back 5-hour tour around the picturesque Gwynn's Island and Chesapeake Bay. With room for up to 6 guests, it's ideal for small groups looking to unwind on the water. Bring your favorite snacks and drinks to enjoy as we cruise along the shoreline and scenic inlets. Whether you're gathering with family, friends, or that special someone, our experienced crew will ensure a smooth and enjoyable ride from start to finish. As evening approaches, take in the changing colors of the sky reflected on the calm waters - it's a sight that never gets old. We can even host intimate weddings aboard for couples seeking a unique bayside ceremony. Whatever the occasion, our tours offer a peaceful escape and the chance to make lasting memories in this beautiful coastal setting. Remember, your deposit secures your spot for this relaxing time on the bay.
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