Sunset Cruise

100% (1) Southold, NY 1 - 6 People 3 Hours From $950 Trip #9141
Fishing in Destin
Fishing in Destin
Fishing in Destin
Fishing in Destin
Fishing in Destin
Fishing in Destin
Fishing in Destin
Fishing in Destin
Fishing in Destin
Fishing in Destin
Fishing in Destin

About Your Trip

Type

Boat Cruise, Sunset Cruise

Skill Levels

Beginner, Intermediate, Advanced

Weather

You won’t lose your deposit if the trip is canceled due to weather.

Set Sail into the Sunset with Captain Dave on Long Island’s East End

Climb aboard with Captain Dave and treat yourself to the ultimate East End escape—a luxury sunset cruise through some of the most scenic waters in all of New York. Departing from Brick Cove Marina, this experience is your ticket to golden skies, gentle sea breezes, and an unforgettable evening on the water.

As the sun begins to set, you’ll cruise past the...

About Your Trip

Set Sail into the Sunset with Captain Dave on Long Island’s East End

Climb aboard with Captain Dave and treat yourself to the ultimate East End escape—a luxury sunset cruise through some of the most scenic waters in all of New York. Departing from Brick Cove Marina, this experience is your ticket to golden skies, gentle sea breezes, and an unforgettable evening on the water.

As the sun begins to set, you’ll cruise past the charming shops of Greenport, the upscale shoreline of Shelter Island, or the storied beauty of Sag Harbor. If you’d rather skip the scene, let Captain Dave take you off the beaten path into the quiet, secluded coves that make this part of the coast so magical. Whether you're looking for romance, relaxation, or a memorable evening with close friends, there's no better backdrop than the calm waters of the East End at dusk.

You'll be riding in style aboard a Sabre 36 Express—a classic, New England-built yacht that blends timeless craftsmanship with modern comfort. With spacious seating, smooth performance, and wide-open views, this vessel is designed for maximum comfort as you cruise into the sunset.

Captain Dave offers a variety of flexible options to match your mood and vision—from short sunset cruises to half- or full-day outings. Don’t see the perfect fit? Just ask, and he’ll help create a custom trip to suit your style.

Whether you're toasting the day with a glass of wine, celebrating something special, or just soaking in the peaceful beauty of the coast, a sunset cruise with Captain Dave promises an evening of laid-back luxury and coastal charm. All you need to bring is your favorite snacks, drinks, and a sense of adventure.
Amenities

Type

Boat Cruise, Sunset Cruise

Skill Levels

Beginner, Intermediate, Advanced

Beer

Feel free to enjoy responsibly, but please no glass.

Music

You can play your own bluetooth music.

Weather

You won’t lose your deposit if the trip is canceled due to weather.

Flexible Cancelation

This trip can be canceled up to 14 days before the trip.

Lunch

Lunch / light snacks are included.

Physicality

This trip requires an easy level of physical activity.

Kid Friendly

This trip is not suited for small children.

Disability Friendly

This trip is not suited for those with disabilities.

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Pricing Matrix

3 hours
1 Person
$950.00
2 People
$950.00
3 People
$950.00
4 People
$950.00
5 People
$950.00
6 People
$950.00
Pay 15% of the price as a deposit today, with the balance due on the day of the trip.
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About Your Guide

Profile photo of Captain Experiences guide Dave

Dave M.

Independent Guide
US Veteran Veteran
Quiet
Laid-back
Beginner Oriented
Comfortable
Quality
Instructional
Captain Dave is the owner, operator, and captain. He is a United States Coast Guard Certified Master Captain earning his credential from the Maritime Institute in San Diego, California.

A North Fork native, Captain Dave has been operating in the waters surrounding the East End of Long Island for over 20 years. With experience operating all over the country - from the Pacific Ocean off the coast of Southern California, to the Gulf of America...

About Your Guide

Profile photo of Captain Experiences guide Dave

Dave M.

Independent Guide
Captain Dave is the owner, operator, and captain. He is a United States Coast Guard Certified Master Captain earning his credential from the Maritime Institute in San Diego, California.

A North Fork native, Captain Dave has been operating in the waters surrounding the East End of Long Island for over 20 years. With experience operating all over the country - from the Pacific Ocean off the coast of Southern California, to the Gulf of America off the coast of Alabama and Florida – he knew there was no place like home.

After completing his time in the United States Marine Corps, it was a dream to start a charter business back on the North Fork. With a passion for fishing and a love of the water, he spends his free time reeling in anything that swims and spending time with his family.
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Rapid Fire Guide Q & A

What’s the biggest fish you’ve caught?
50 lb Tarpon on a fly
If you were cooking for all your friends what would you cook?
Burgers or steak

Rapid Fire Guide Q & A

What’s the biggest fish you’ve caught?
50 lb Tarpon on a fly
If you were cooking for all your friends what would you cook?
Burgers or steak
What’s your favorite band?
Anything Country
What’s your favorite movie?
The Patriot
What’s your favorite sports team?
NY Jets
What’s your drink of choice?
Celsius
What was your last halloween costume?
Coach Mike Ditka
What do you want for Christmas this year?
A puppy
How did you get started guiding?
As an outdoorsman, some of my favorite memories are from when I helped other hunters or anglers harvest a trophy of a lifetime.
What makes you different from other guides?
I am easy to work with and flexible when it comes to customer needs, I will do almost anything to ensure your charter is satisfactory.
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Start Location & Lodging Options

Southold, New York

About Your Boat

Boat photo for Sunset Cruise
Boat photo for Sunset Cruise
Boat photo for Sunset Cruise
Boat photo for Sunset Cruise
Boat photo for Sunset Cruise
Boat photo for Sunset Cruise
Boat Type
Down East Cruiser
Boat Manufacturer
Sabre Express
Boat Length
36'
Boat Restroom
Yes

About Your Boat

Boat Type
Down East Cruiser
Boat Manufacturer
Sabre Express
Boat Length
36'
Boat Restroom
Yes
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Trip Details & Amenities

Type

Boat Cruise, Sunset Cruise

Skill Levels

Beginner, Intermediate, Advanced

Beer

Feel free to enjoy responsibly, but please no glass.

Music

You can play your own bluetooth music.

Weather

You won't lose your deposit if the trip is canceled due to weather.

Flexible Cancelation

This trip can be canceled up to 14 days before the trip.

Lunch

Lunch / light snacks are included.

Physicality

This trip requires an easy level of physical activity.

Kid Friendly

This trip is not suited for small children.

Disability Friendly

This trip is not suited for those with disabilities.

Everything Else to Know

All gear is included, but we also recommend bringing sunglasses, sunscreen, weather-appropriate clothing, and anything else you might want on the trip.
We use a cashless autopay system. We'll send you a boarding pass, and on the day of the trip, your guide will scan your boarding pass to automatically transfer the remaining balance. The only cash needed is to tip your guide (we recommend 20%).
Cancel for free up to 14 days before the trip and receive credit back to your account. Cancelling within 14 of the trip will forfeit your deposit to the guide. Day-of cancellations and no-shows will be charged the full balance of the trip to their card.
In the event of inclement weather you'll be covered by out 100% Weather Guarantee and will not lose your deposit.

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First Time Booking with Us?

Captain Experiences is home to thousands of quality, vetted fishing, hunting, and other outdoor sports guides across the US and beyond. Our mission is to Unlock the Outdoors by making it quick and easy to book the trip of a lifetime every time with our Damn Good Guides.
We vet our guides and only partner with the best of the best. Our guides do their very best to keep you safe, show you a great time, and send you home with a memorable experience shared with family and friends.
Once you've paid your deposit at checkout, we'll send you a QR Code boarding pass. Just show your guide your boarding pass on the day of the trip, they'll scan it, the remaining balance will transfer automatically, and you'll be all set to get out there. Just make sure you bring a cash tip for the guide!
In the event of inclement weather, our guides will check the conditions and make the final call on whether its safe to go on the trip. If they decide the trip needs to be postponed, we'll work closely with you to reschedule or provide a credit for the full deposit, which can be applied to any of our trips in the US and beyond.
Each trip's price is determined by the guide and reflects all associated costs. A significant factor in pricing is often the type of boat and the corresponding fuel expenses. Additional costs may include leases, marina or slip fees, and the expenses involved in providing and maintaining the necessary gear for your trip.
After booking your trip, we'll connect you directly with your guide to discuss additional details. In the meantime, our team is here to answer any questions via email, text, or phone.
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