About Your Guide

Profile photo of Captain Experiences guide Zak Smith

Zak Smith

Independent Guide
Comfortable
Laid-back
Talkative
Hands-off
Quality
Captain Zak has been cruising the waters of the Florida Keys for years—so saying he knows his way around is putting it lightly. After spending some time cruising around on “Raven” his 36′ sailboat, he dropped anchor in Key West and never looked back.

He’s spent plenty of time exploring coastal Florida, The Everglades and the Lower Keys, getting to know the local waters, wildlife, and hidden spots. Zak’s a big nature lover, and he enjoys sharing cool facts about the unique plants and animals you’ll see out on the water.

He’s also a bit of a history buff and loves swapping stories about Key West’s colorful past. When he’s not out on the boat, you’ll probably find him diving, sailing, growing bananas, or kicking back with some good rum and a cigar.

About Your Guide

Profile photo of Captain Experiences guide Zak Smith

Zak Smith

Independent Guide
Captain Zak has been cruising the waters of the Florida Keys for years—so saying he knows his way around is putting it lightly. After spending some time cruising around on “Raven” his 36′ sailboat, he dropped anchor in Key West and never looked back.

He’s spent plenty of time exploring coastal Florida, The Everglades and the Lower Keys, getting to know the local waters, wildlife, and hidden spots. Zak’s a big nature lover, and he enjoys sharing cool facts about the unique plants and animals you’ll see out on the water.

He’s also a bit of a history buff and loves swapping stories about Key West’s colorful past. When he’s not out on the boat, you’ll probably find him diving, sailing, growing bananas, or kicking back with some good rum and a cigar.
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Casual Monday Charters Trips

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Fishing in Destin
Fishing in Destin
Fishing in Destin

Sunset Cruise in Key West

Luxury Sunset Cruise

100% (1)
32 ft 1 - 24 People From $600
Fishing in Destin
Fishing in Destin
Fishing in Destin

Boat Cruise, Booze Cruise in Key West

Luxury Sandbar Charter

100% (1)
32 ft 1 - 6 People From $1,200
Fishing in Destin
Fishing in Destin
Fishing in Destin

Eco Tour, Boat Cruise, Snorkeling in Key West

Luxury Sandbar & Snorkel Trip

100% (1)
32 ft 1 - 6 People From $1,200

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Recent Reviews of Casual Monday Charters

5.0
based on 1 review

Kari

Verified Review

Zak was an excellent captain and guide! He kept us safe and comfortable for the ride and took us to the perfect sandbar location. We’ll be booking him again next girls trip to Key West!

Kari

Verified Review

Zak was an excellent captain and guide! He kept us safe and comfortable for the ride and took us to the perfect sandbar location. We’ll be booking him again next girls trip to Key West!
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Casual Monday Charters Photo Gallery

Luxury Sandbar Charter
July 23rd, 2026
Key West, Florida
Luxury Sunset Cruise
July 23rd, 2026
Key West, Florida
Luxury Sandbar Charter
July 22nd, 2026
Key West, Florida
Luxury Sunset Cruise
December 18th, 2025
Key West, Florida
Luxury Sandbar & Snorkel Trip
December 26th, 2025
Key West, Florida
Luxury Sunset Cruise
December 18th, 2025
Key West, Florida
Luxury Sandbar & Snorkel Trip
December 18th, 2025
Key West, Florida
Luxury Sandbar & Snorkel Trip
December 18th, 2025
Key West, Florida
Luxury Sandbar Charter
July 23rd, 2026
Key West, Florida
Luxury Sunset Cruise
July 23rd, 2026
Key West, Florida
Luxury Sandbar Charter
July 22nd, 2026
Key West, Florida
Luxury Sandbar Charter
July 22nd, 2026
Key West, Florida
Luxury Sandbar Charter
December 26th, 2025
Key West, Florida
Luxury Sandbar & Snorkel Trip
December 26th, 2025
Key West, Florida
Luxury Sunset Cruise
December 18th, 2025
Key West, Florida
Luxury Sandbar & Snorkel Trip
December 18th, 2025
Key West, Florida
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