Damn Good Boat Cruise Guides In Westport

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Recently Booked Boat Cruise Guides In Westport, Ma

Fishing in Destin
Fishing in Destin
Fishing in Destin

Boat Cruise in Westport

River Cruising With Capt Ray

100% (1)
25 ft 1 - 6 People From $375
Fishing in Destin
Fishing in Destin
Fishing in Destin

Boat Cruise in Westport

Boat Cruise - Elizabeth Islands

100% (1)
25 ft 1 - 6 People From $600

“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

Other Captain Experiences Trips in Westport

Fishing in Destin
Fishing in Destin
Fishing in Destin

Inshore, Nearshore Fishing in North Kingstown

Kayak Fishing

100% (1)
12 ft 1 - 3 People From $300
Veteran Operated
This trip is managed by a veteran of the US armed forces.
Fishing in Destin
Fishing in Destin
Fishing in Destin

Deep Sea Fishing in Falmouth

Offshore- 3 Minutes From Seacrest

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

Inshore, Nearshore Fishing in Portsmouth

Newport, RI Fishing Trip

NEW
30 ft 1 - 4 People From $700
Fishing in Destin
Fishing in Destin
Fishing in Destin

Nearshore Fishing in Westport

Ocean Charter (1/2 To 5 Miles Out)

NEW
31 ft 1 - 12 People From $600
Fishing in Destin
Fishing in Destin
Fishing in Destin

Inshore, Nearshore Fishing in Fairhaven

6-8 Hours Day Trip – Buzzards Bay

NEW
26 ft 1 - 6 People From $675
Fishing in Destin
Fishing in Destin
Fishing in Destin

Inshore Fishing in Westport

Buzzards Bay Inshore

100% (1)
25 ft 1 - 6 People From $700
Fishing in Destin
Fishing in Destin
Fishing in Destin

Deep Sea Fishing in Westport

Tuna Trip

100% (1)
25 ft 1 - 4 People From $1,700
Fishing in Destin
Fishing in Destin
Fishing in Destin

Inshore, Deep Sea, Nearshore in Fairhaven

Massachusetts Inshore/Nearshore

NEW
25 ft 1 - 12 People From $550
Fishing in Destin
Fishing in Destin
Fishing in Destin

Deep Sea, Nearshore Fishing in Fairhaven

10 Hour Trip – Shark Fishing

NEW
25 ft 1 - 8 People From $1,500
Fishing in Destin
Fishing in Destin
Fishing in Destin

Inshore Fishing in Westport

Buzzards Bay Inshore - Seacraft

100% (1)
20 ft 1 - 2 People From $550
Fishing in Destin
Fishing in Destin
Fishing in Destin

Inshore Fishing in Westport

Full Day Shark Trip

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

Inshore Fishing in Warwick

Family-Friendly 4hr Inshore Fishing

100% (1)
21 ft 1 - 4 People From $500

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Everything to Know About Booking a tours trip in Westport

What are the best boat cruise trips in Westport?

The best boat cruise trips in Westport are:

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

In Westport, the sea’s never just scenery—it’s a way of life. Tucked into Washington’s rugged coastline, this small harbor town delivers boat cruises with salt, soul, and a working-class edge that makes every trip feel earned. Whether you're heading out past the breakwater on a deep-water tour or cruising the quieter inland routes, there’s a rawness to the experience that’s hard to find elsewhere. You’re not just along for the ride—you’re part of something real.

The beauty of cruising here is in the contrast. One moment you're weaving past fishing vessels and weathered docks, and the next you're wide open on the Pacific, with gray whales surfacing off the bow and seabirds dancing overhead. Local captains run these waters like seasoned trail guides—equal parts storyteller and seafarer. They'll show you the hidden pockets of the coast, where tide meets timber and every rock has a name, a story, or both.

And the best part? It’s never polished or packaged. Westport boat cruises are straightforward, salt-washed, and built for folks who’d rather trade a five-star deck chair for a little grit and open sky. You’ll come back windblown, maybe a little sunburned, and totally clear on why the water here isn’t just something to look at—it’s something to be part of.

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

Westport’s boat cruises shift with the seasons, each one bringing a fresh rhythm to the water. Winter’s a rugged affair—cold, bracing air and rougher seas that test your grit and reward you with raw, untamed views. It’s the season for serious sea life spotting: migrating gray whales, seals hauled out on rocky ledges, and the occasional bald eagle cruising the winds. Dress warmly, hold tight, and savor the kind of salty solitude you won’t find anywhere else.

Spring is the thawing point, when the coast starts to come alive with new energy. The water calms down, the skies clear, and the wildflowers bloom along the cliffs. Boat tours shift into gear for whale watching, birding, and exploring tide pools exposed by low tides. It’s a season of discovery, where every turn reveals something fresh—whether that’s a harbor seal pup or a hidden cove with glassy water perfect for a quiet paddle.

Summer and early fall are Westport’s glory days on the water. The weather warms, the ocean settles, and the harbor fills with boats of every shape and size. This is prime cruising season—long, sunlit days that stretch late into the evening, with sunsets that hit like a punch of color against the Pacific. It’s when you can really unwind, kick back with a cold drink, and let the coast work its slow magic. Come fall, the crowds thin, but the warmth lingers—perfect for those who want to savor the coast without the fuss.

Recent Reviews

  • ★★★★★
    Ray was an awesome captain and guide. Very easy going and flexible on what we wanted to do and where to go. Glad we booked.

    Michael J. | June 23, 2025

    Trip: River Cruising With Capt Ray

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