Damn Good Southold Tour Guides

Check real-time availability and compare rates on private Southold guides. Boat Cruise, Sunset Cruise, and Whale Watching trips available.

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Damn Good Guides

You will only find quality, vetted guides on Captain Experiences, and we know them all on a first-name basis

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Recently Booked Guides In Southold, Ny

Veteran Operated
This trip is managed by a veteran of the US armed forces.
Fishing in Destin
Fishing in Destin
Fishing in Destin

Boat Cruise in Southold

Pleasure Cruises

100% (1)
36 ft 1 - 6 People From $1,500
Veteran Operated
This trip is managed by a veteran of the US armed forces.
Fishing in Destin
Fishing in Destin
Fishing in Destin

Boat Cruise, Sunset Cruise in Southold

Sunset Cruise

100% (1)
36 ft 1 - 6 People From $950
Fishing in Destin
Fishing in Destin
Fishing in Destin

Boat Cruise, Sunset Cruise in Freeport

Sunset Cruise

NEW
34 ft 1 - 4 People From $975
Fishing in Destin
Fishing in Destin
Fishing in Destin

Whale Watching in Freeport

Whale Watching

NEW
34 ft 1 - 4 People From $975
Fishing in Destin
Fishing in Destin
Fishing in Destin

Boat Cruise in Freeport

Half Day Cruise

NEW
34 ft 1 - 4 People From $865
Fishing in Destin
Fishing in Destin
Fishing in Destin

Boat Cruise in Freeport

Full Day Cruise

NEW
34 ft 1 - 4 People From $1,610

“Our Damn Good Guides go above and beyond, and we’ve handpicked every single one. We’re passionate about the outdoors and look forward to getting you out on the trip of a lifetime, every time.”

Jonathan and Attison   |   Co-founders   |   Austin, Texas

More Guides In Southold, Ny

Fishing in Destin
Fishing in Destin
Fishing in Destin

Boat Cruise in Freeport

Full Day Cruise

NEW
34 ft 1 - 4 People From $1,610
Fishing in Destin
Fishing in Destin
Fishing in Destin

Boat Cruise in Freeport

Half Day Cruise

NEW
34 ft 1 - 4 People From $865
Fishing in Destin
Fishing in Destin
Fishing in Destin

Whale Watching in Freeport

Whale Watching

NEW
34 ft 1 - 4 People From $975
Fishing in Destin
Fishing in Destin
Fishing in Destin

Boat Cruise, Sunset Cruise in Freeport

Sunset Cruise

NEW
34 ft 1 - 4 People From $975
Veteran Operated
This trip is managed by a veteran of the US armed forces.
Fishing in Destin
Fishing in Destin
Fishing in Destin

Boat Cruise, Sunset Cruise in Southold

Sunset Cruise

100% (1)
36 ft 1 - 6 People From $950
Veteran Operated
This trip is managed by a veteran of the US armed forces.
Fishing in Destin
Fishing in Destin
Fishing in Destin

Boat Cruise in Southold

Pleasure Cruises

100% (1)
36 ft 1 - 6 People From $1,500
See All Trips in Southold

Other Captain Experiences Trips in Southold

Fishing in Destin
Fishing in Destin
Fishing in Destin

Inshore, Nearshore Fishing in Hampton Bays

Shinnecock Inshore Slam

100% (1)
40 ft 1 - 6 People From $775
Fishing in Destin
Fishing in Destin
Fishing in Destin

Deep Sea Fishing in Hampton Bays

Overnight Northeast Canyons

100% (1)
40 ft 1 - 3 People From $4,900
Hot Trip
people are viewing this trip.
Fishing in Destin
Fishing in Destin
Fishing in Destin

Deep Sea Fishing in Hampton Bays

Offshore Tuna / Marlin / Mahi Mahi

100% (1)
40 ft 1 - 6 People From $3,000
Fishing in Destin
Fishing in Destin
Fishing in Destin

Inshore, Deep Sea Fishing in Hampton Bays

3 Hour Inshore Special

NEW
26 ft 1 - 6 People From $550
Fishing in Destin
Fishing in Destin
Fishing in Destin

Inshore, Nearshore Fishing in Hampton Bays

Hampton Bays Hour Inshore Trip

100% (1)
27 ft 1 - 8 People From $550
Fishing in Destin
Fishing in Destin
Fishing in Destin

Inshore, Deep Sea, Nearshore in Hampton Bays

12 Hour Offshore Trip

100% (1)
27 ft 1 - 4 People From $2,200
Fishing in Destin
Fishing in Destin
Fishing in Destin

Inshore, Deep Sea Fishing in Hampton Bays

3 Hour Special

100% (1)
27 ft 1 - 5 People From $600
Fishing in Destin
Fishing in Destin
Fishing in Destin

Inshore, Nearshore Fishing in Hampton Bays

5 Hr Half Day Inshore Fishing Trip

NEW
26 ft 1 - 6 People From $750
Fishing in Destin
Fishing in Destin
Fishing in Destin

Inshore Fishing in Hampton Bays

4 Hour Inshore Fishing Trip

NEW
26 ft 1 - 6 People From $650
Fishing in Destin
Fishing in Destin
Fishing in Destin

Inshore, Nearshore Fishing in Hampton Bays

6 HR Inshore Fishing Trip

NEW
26 ft 1 - 6 People From $850
Fishing in Destin
Fishing in Destin
Fishing in Destin

Inshore, Nearshore Fishing in Hampton Bays

8 HR Full Day Inshore Trip

NEW
26 ft 1 - 5 People From $1,100
Fishing in Destin
Fishing in Destin
Fishing in Destin

Deep Sea, Nearshore Fishing in Shelter Island

Overnight Canyon Tuna

100% (1)
34 ft 1 - 3 People From $3,000

Need a Place to Stay?

Everything to Know About Booking a Hunting Guide in Southold

Why should I book a tour in Southold with Captain Experiences?

Our Damn Good Guides currently offer 6 private trips in Southold, and the most popular trips in the area are Pleasure Cruises guided by Dave, Sunset Cruise guided by Dave, and Sunset Cruise guided by Adam.

All guides on Captain Experiences are vetted by our team. You can access their reviews, click through trip photos, read bios to get to know them, and preview trip details like species, techniques, group sizes, boat specs and more.

Looking for private kid friendly trips in Southold? Check out our beginner and family friendly trips in Southold.

What types of tours are common in Southold?

Boat Cruise hunting is the most popular type of fishing in Southold as well as sunset cruise hunting and whale watching hunting.

The most commonly sought after species in Southold are: 1. humpback whale, 2. minke whale, and 3. fin whale.

How much does a Southold private trip cost?

Prices in Southold can range anywhere from about $916 to $1,926, but the average price for a half day trip in Southold is $1,053. The average price for a full day trip in Southold is $2,005.

Is booking a guide worth the money?

Hiring a guide provides a number of benefits and many choose to book a guide for a combination of experience, local knowledge, convenience, and cost-effectiveness.

Working with experienced guides who know the best local spots and techniques can dramatically increase your odds of a great day. Having someone who is in the wild every day and knows the area like the back of their hand is going to give you the best chances of having a great trip.

Booking a guide is also more cost effective, especially if you only get out a handful of times per year. When you consider all of the costs you would incur on your own such as the price of a boat, maintenance, insurance, gas, high-quality gear and tackle, repairs, and more, you’ll find that DIY is sometimes not worth the expense.

Even if you’ve got a great setup already in your home waters, booking a guide also provides a great opportunity to experience new techniques, new locations, or even a chance at a new target species to knock off the bucket list.

What month is best for tours in Southold?

The most popular season for tours in Southold is summer, and most people book their trips 38 days in advance.

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Our guides are Damn Good Guides, which means they’re vetted by our team of outdoor experts who know them on a first-name basis. We hand pick each and every one of them, and our network spans all across the US and beyond.

The proof is in the pudding, and we’re incredibly proud of our 4.9 / 5 average review score. Hit the button below to see more trip options:

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