Pleasure Cruises

100% (1) Southold, NY 1 - 6 People 4 - 8 Hours From $1,500 Trip #9142
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

Skill Levels

Beginner, Intermediate, Advanced

Weather

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

Discover Long Island’s Coastal Gems on a Half-Day or Full-Day Cruise with Captain Dave

Looking to spend the day unwinding in style along Long Island’s East End? Join Captain Dave for a half-day or full-day pleasure cruise and explore one of the most picturesque and peaceful stretches of water in New York—all aboard a beautifully outfitted Sabre 36 Express.

Departing from Brick Cove Marina, these cruises are the perfect blend of luxury and laid-back coastal...

About Your Trip

Discover Long Island’s Coastal Gems on a Half-Day or Full-Day Cruise with Captain Dave

Looking to spend the day unwinding in style along Long Island’s East End? Join Captain Dave for a half-day or full-day pleasure cruise and explore one of the most picturesque and peaceful stretches of water in New York—all aboard a beautifully outfitted Sabre 36 Express.

Departing from Brick Cove Marina, these cruises are the perfect blend of luxury and laid-back coastal charm. Choose from a variety of stunning destinations—drift through the quiet backwaters of Shelter Island, dock for lunch in Greenport’s lively harbor, or soak in the rich maritime history of Sag Harbor. Whether you want to explore, relax, or a little of both, Captain Dave will tailor your cruise to fit your ideal day on the water.

The Sabre 36 Express is your floating oasis—offering top-tier comfort, ample seating, and smooth, quiet cruising. It's ideal for couples, small groups, and families looking to escape the hustle and reconnect with the beauty of the open water. Spend the day lounging on deck with a drink in hand, diving in for a swim, or hopping ashore to browse local shops and waterfront dining spots.

A half-day cruise is great for a relaxed morning or afternoon outing, while a full-day charter gives you time to fully immerse yourself in all the East End has to offer. Either way, Captain Dave ensures every detail is handled with care and flexibility. Don’t see a pre-set itinerary that suits your style? No problem—custom cruises are welcome!

Just bring along your favorite food, drinks, and weather-appropriate gear. Ice and water are provided on board, so you can settle in and focus on enjoying your perfect day at sea.

From sightseeing and swimming to sunbathing and sipping, a pleasure cruise with Captain Dave is your ticket to effortless coastal adventure—and memories that last long after you’re back on land.
Amenities

Type

Boat Cruise

Skill Levels

Beginner, Intermediate, Advanced

Beer

Feel free to enjoy responsibly, but please no glass.

Weather

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

Kid Friendly

This trip is not suited for small children.

Disability Friendly

This trip is not suited for those with disabilities.

Flexible Cancelation

The deposit for this trip is non-refundable.

Lunch

Please provide your own food / snacks.

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Pricing Matrix

4 hours 8 hours
1 Person
$1,500.00
$2,400.00
2 People
$1,500.00
$2,400.00
3 People
$1,500.00
$2,400.00
4 People
$1,500.00
$2,400.00
5 People
$1,500.00
$2,400.00
6 People
$1,500.00
$2,400.00
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 Pleasure Cruises
Boat photo for Pleasure Cruises
Boat photo for Pleasure Cruises
Boat Type
Jet Boat
Boat Manufacturer
Sabre Express
Boat Length
36'
Boat Restroom
No

About Your Boat

Boat Type
Jet Boat
Boat Manufacturer
Sabre Express
Boat Length
36'
Boat Restroom
No
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Trip Details & Amenities

Type

Boat Cruise

Skill Levels

Beginner, Intermediate, Advanced

Beer

Feel free to enjoy responsibly, but please no glass.

Weather

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

Kid Friendly

This trip is not suited for small children.

Disability Friendly

This trip is not suited for those with disabilities.

Flexible Cancelation

The deposit for this trip is non-refundable.

Lunch

Please provide your own food / snacks.

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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Unbelievable pleasureful experience, best guided trip we have EVER had.

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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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