Damn Good Boat Cruise Guides In Freeport

Check real-time availability and compare rates on private Freeport boat cruise guides. Confidently book your next trip.

Choose a Date
5/5 Average Rating

Damn Good Guides

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

Experts Available 24/7

Our US-based team is available 24/7 to help you with any questions or concerns

100% Weather Guarantee

We want to keep everyone safe, so in the case of inclement weather we'll work with you to reschedule at no cost

Recently Booked Boat Cruise Guides In Freeport, 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

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
Fishing in Destin
Fishing in Destin
Fishing in Destin

Boat Cruise, Sunset Cruise in Point Pleasant Beach

Yacht Rock Sunset Cruise

100% (2)
23 ft 1 - 5 People From $375

“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 Boat Cruise Guides In Freeport, Ny

Fishing in Destin
Fishing in Destin
Fishing in Destin

Boat Cruise, Sunset Cruise in Point Pleasant Beach

Yacht Rock Sunset Cruise

100% (2)
23 ft 1 - 5 People From $375
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

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
See All Boat Cruise Trips in Freeport

Other Captain Experiences Trips in Freeport

Fishing in Destin
Fishing in Destin
Fishing in Destin

Inshore, Nearshore Fishing in Port Washington

Striper Trolling Trip

100% (1)
31 ft 1 - 6 People From $800
Fishing in Destin
Fishing in Destin
Fishing in Destin

Inshore Fishing in Port Washington

Big Fish With Your Big Group

NEW
46 ft 1 - 40 People From $3,600
Fishing in Destin
Fishing in Destin
Fishing in Destin

Inshore Fishing in Port Washington

15-Person Private Charter

NEW
60 ft 1 - 15 People From $1,750
Fishing in Destin
Fishing in Destin
Fishing in Destin

Inshore, Nearshore, Flats in New York

Full Day NYC Charter

100% (1)
22 ft 1 - 3 People From $750
Fishing in Destin
Fishing in Destin
Fishing in Destin

Deep Sea Fishing in Freeport

Offshore Monster Sharking!!

NEW
31 ft 1 - 4 People From $2,000
Fishing in Destin
Fishing in Destin
Fishing in Destin

Deep Sea Fishing in Freeport

Striper Extravaganza!

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

Deep Sea Fishing in Freeport

New York Sea Bass Thriller!

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

Inshore, Nearshore Fishing in Freeport

Thresher Shark Fishing Fun!

NEW
31 ft 1 - 4 People From $1,200
Fishing in Destin
Fishing in Destin
Fishing in Destin

Deep Sea Fishing in Howard Beach

Bluefin Tuna / Shark Trip

NEW
29 ft 1 - 4 People From $2,500
Fishing in Destin
Fishing in Destin
Fishing in Destin

Inshore, Flats Fishing in Howard Beach

Inshore Fishing NY/NJ/NYC

NEW
29 ft 1 - 6 People From $700
Fishing in Destin
Fishing in Destin
Fishing in Destin

Inshore, Nearshore Fishing in New York

Shark Boss Special

100% (1)
36 ft 1 - 6 People From $1,500
Fishing in Destin
Fishing in Destin
Fishing in Destin

Inshore, Nearshore Fishing in New York

Bass And Blues

100% (1)
36 ft 1 - 6 People From $700

Need a Place to Stay?

Everything to Know About Booking a tours trip in Freeport

What are the best boat cruise trips in Freeport?

What do I need to know about Boat Cruises in Freeport?

Freeport feels like a place that’s held onto its wild side, where boat cruises aren’t about racing the clock but about slipping into the natural rhythm of the water. Out here, the coastline is a mosaic of sandy beaches, marshy inlets, and quiet coves—perfect for slow rides that let you catch every splash of a dolphin or glimpse of a heron stalking the shallows. Whether you’re cutting through the bay or drifting along the Intracoastal Waterway, Freeport’s waters invite you to breathe deep and take it easy.

The captains who know these parts well bring more than just skill—they bring stories, too. They’ll guide you to tucked-away spots where the water stays clear and the world feels a little smaller. Expect stops at hidden sandbars, chances to jump in and cool off, and maybe even a glimpse of a sea turtle cruising by. There’s an old-school vibe here, like a day on the water is less about the checklist and more about feeling alive.

Boat cruises in Freeport are for those who want to unplug without losing the sense of adventure. The sun overhead, the breeze carrying salt and pine, and the steady hum of the engine all combine into a simple kind of freedom. Out here, the world slows down, and the kind of quiet you don’t get anywhere else settles in. It’s a reminder that sometimes the best journeys happen at the pace of the tide.

What are the most popular months for Boat Cruises in Freeport?

Spring in Freeport is a quiet awakening. The marsh grasses freshen up, the air warms just enough to invite you out, and the waterways begin to hum with life. Boat cruises this season feel like slipping into a well-kept secret—gliding past mangroves heavy with bird nests and spotting dolphins teasing the surface. It’s the perfect time to catch the water before the summer crowds arrive, with every ripple telling a story of renewal and calm.

Summer turns up the heat, but the water remains your cool refuge. Early morning cruises are best—when the sun is just rising and the breeze is still fresh. Afternoons might bring quick tropical showers, sharp and sudden, but those only add to the drama of the coast. As the day cools into evening, boat rides become golden-hour rituals, with the sky lighting up in fiery oranges and pinks, making each trip feel like a private celebration of the Gulf’s wild beauty.

Fall and winter bring a softer, quieter pace to Freeport’s waterways. The air cools, the crowds thin, and the water takes on a glassy stillness that invites reflection. Migratory birds pass through in flocks, and the shoreline’s colors shift into warm, muted tones. It’s the kind of season that slows time down—a perfect chance for longer, slower cruises that soak up the raw, untamed spirit of this coastal gem.

Recent Reviews

Other Featured Cities

Didn't Find What You Were Looking For?

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:

See All Boat Cruise Trips in Freeport