14 Trips Available

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$500

Guides > Captain Paul Peter

Calypso Cowboy Charters

Big Pine Key FL

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Your Captain

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Paul Peter

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Territory

Calypso Cowboy Charters Fishing Territory
Guides > Captain Paul Peter

Calypso Cowboy Charters

locationBig Pine Key FL

Guidesly Guarantee

Your Captain

guide pic

Paul Peter

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Paul Peter, Captain at Calypso Cowboy Charters

Calypso Cowboy Charters offers private boat charters in the Florida Keys designed for anglers, families, and groups looking for a personalized day on the water. Operated by a Florida native with over 13 years of professional guiding experience and 25 years of service in the U.S. Coast Guard, this charter blends local knowledge, safety, and a hands-on approach that welcomes both beginners and experienced guests.


Trips depart from Big Pine Key and explore the clear, shallow waters of the Florida Keys, targeting popular local species such as snapper, grouper, trout, and mackerel. Fishing trips are structured as private 5- or 6-hour charters and include rods, reels, bait, and gear. Captain Mike is known for his patient teaching style and enjoys helping adults and kids learn techniques, understand local conditions, and gain confidence on the water.


In addition to fishing, Calypso Cowboy Charters offers private sandbar tours and nature eco tours. Sandbar trips are perfect for families, couples, and small groups who want to relax, swim, and enjoy the Keys’ shallow flats. Eco and nature tours focus on the unique backcountry, mangroves, and wildlife that make this region special, providing a calm and educational experience suitable for all ages.


All trips are run aboard a spacious 26’ Twin Vee center console powered by twin 150 Suzuki engines. The boat offers a smooth, stable ride with plenty of room to move, a trolling motor for shallow water access, and onboard radio for safety. While the vessel can accommodate up to eight passengers, private trips are limited to smaller groups for comfort and quality.


Calypso Cowboy Charters runs year-round, making it easy to plan a Florida Keys fishing charter, private boat tour, or eco experience any time of year. Whether you’re booking a family-friendly fishing charter, a private sandbar tour, or a guided nature cruise, every trip is customized to your group’s goals, pace, and experience level.

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Upcoming Availability

December 2025
January 2026

Expertise & Attributes

fishing

fishing

Master GuideMaster GuideGood with New AnglersGood with New AnglersGood with FamiliesGood with FamiliesGood with KidsGood with KidsNature / Wildlife ViewsNature / Wildlife ViewsSaltwater FishingSaltwater FishingI Tie My Own FliesI Tie My Own Flies

What's Included

Good to Knows

Good to Knows

Your Guide has some important details about your trip with them.

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Cancellation Policy

Cancellation Policy

When you book your fishing trip, you will need to first put down a deposit to hold the reservation.

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What's Included

Good to Knows

Good to Knows

Your Guide has some important details about your trip with them.

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Cancellation Policy

Cancellation Policy

When you book your fishing trip, you will need to first put down a deposit to hold the reservation.

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Trips Available with Calypso Cowboy Charters

Half Day Sandbar Tour in Florida KeysTop-Rated
Half Day Sandbar Tour in Florida KeysInstant Booking
Half Day Sandbar Tour in Florida KeysTour - Adventure

Half Day Sandbar Tour in Florida Keys

Relax and enjoy a private half-day sandbar tour in the Florida Keys with a local captain who knows the area well. Choose a 5- or 6-hour private boat trip perfect for families, couples, and small groups looking to unwind on the water. Visit shallow sandbars ideal for swimming, wading, and soaking in the Florida Keys scenery at a comfortable pace. Departing from Big Pine Key, this personalized sandbar tour offers flexible timing, plenty of space, and a laid-back atmosphere tailored to your group’s preferences, making it a great option for sightseeing, social time, and coastal relaxation.

Morning Trip

Half Day Sandbar Tour in Florida KeysMaximum 8 persons allowed
(base trip price includes 8 guests)
Half Day Sandbar Tour in Florida Keys5 Hours
Half Day Sandbar Tour in Florida Keys8:00 AM
$500

Morning Trip

Half Day Sandbar Tour in Florida KeysMaximum 8 persons allowed
(base trip price includes 8 guests)
Half Day Sandbar Tour in Florida Keys6 Hours
Half Day Sandbar Tour in Florida Keys8:00 AM
$600

Pick Your Date

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Half Day Guided Mackerel Fishing Trip in Florida KeysTop-Rated
Half Day Guided Mackerel Fishing Trip in Florida KeysInstant Booking
Half Day Guided Mackerel Fishing Trip in Florida KeysFishing - Inshore
Half Day Guided Mackerel Fishing Trip in Florida Keys

26' Twin Vee Center Console26'Twin Vee Max 8 guests (base trip price includes 8 guests)

Half Day Guided Mackerel Fishing Trip in Florida Keys

Join Capt. Paul for a private half-day mackerel fishing trip in the Florida Keys, perfect for families, beginners, and experienced anglers. Choose a 5- or 6-hour inshore adventure targeting king and Spanish mackerel, with all rods, reels, bait, and tackle provided. Fishing licenses are included, so you can focus on learning techniques and catching fish. Departing from Big Pine Key, trips take place aboard a 26’ Twin Vee center console with plenty of space and a smooth ride. Each private charter is tailored to your group’s pace, ensuring an enjoyable, educational, and memorable fishing experience.

Morning Trip

Half Day Guided Mackerel Fishing Trip in Florida KeysMaximum 8 persons allowed
(base trip price includes 8 guests)
Half Day Guided Mackerel Fishing Trip in Florida Keys5 Hours
Half Day Guided Mackerel Fishing Trip in Florida Keys8:00 AM
$700

Morning Trip

Half Day Guided Mackerel Fishing Trip in Florida KeysMaximum 8 persons allowed
(base trip price includes 8 guests)
Half Day Guided Mackerel Fishing Trip in Florida Keys6 Hours
Half Day Guided Mackerel Fishing Trip in Florida Keys8:00 AM
$800

Pick Your Date

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Half Day Grouper Fishing Trip in Florida KeysTop-Rated
Half Day Grouper Fishing Trip in Florida KeysInstant Booking
Half Day Grouper Fishing Trip in Florida KeysFishing - Inshore
Half Day Grouper Fishing Trip in Florida Keys

26' Twin Vee Center Console26'Twin Vee Max 8 guests (base trip price includes 8 guests)

Half Day Grouper Fishing Trip in Florida Keys

Enjoy a private half-day grouper fishing trip in the Florida Keys with Capt. Paul, perfect for families, beginners, and experienced anglers. Choose a 5- or 6-hour inshore fishing adventure targeting gag grouper, with all rods, reels, bait, and tackle provided. Fishing licenses are included, so guests can focus on catching fish and learning techniques. Trips depart from Big Pine Key aboard a comfortable 26’ Twin Vee center console, offering plenty of space and a smooth ride. Each private charter is tailored to your group’s pace, ensuring a fun, educational, and memorable fishing experience.

Morning Trip

Half Day Grouper Fishing Trip in Florida KeysMaximum 8 persons allowed
(base trip price includes 8 guests)
Half Day Grouper Fishing Trip in Florida Keys5 Hours
Half Day Grouper Fishing Trip in Florida Keys8:00 AM
$700

Morning Trip

Half Day Grouper Fishing Trip in Florida KeysMaximum 8 persons allowed
(base trip price includes 8 guests)
Half Day Grouper Fishing Trip in Florida Keys6 Hours
Half Day Grouper Fishing Trip in Florida Keys8:00 AM
$800

Pick Your Date

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Half Day Trout Fishing Trip in Florida KeysTop-Rated
Half Day Trout Fishing Trip in Florida KeysInstant Booking
Half Day Trout Fishing Trip in Florida KeysFishing - Inshore
Half Day Trout Fishing Trip in Florida Keys

26' Twin Vee Center Console26'Twin Vee Max 8 guests (base trip price includes 8 guests)

Half Day Trout Fishing Trip in Florida Keys

Experience a private half-day sea trout fishing trip in the Florida Keys with Capt. Paul, ideal for beginners, families, and experienced anglers. Choose a 5- or 6-hour inshore fishing adventure targeting sea trout, with all rods, reels, bait, and tackle provided. Fishing licenses are included, so you can focus on learning techniques and catching fish. Departing from Big Pine Key, trips take place aboard a comfortable 26’ Twin Vee center console with ample space and a smooth ride. Each private charter is customized to your group’s pace, ensuring an educational, fun, and memorable fishing experience.

Morning Trip

Half Day Trout Fishing Trip in Florida KeysMaximum 8 persons allowed
(base trip price includes 8 guests)
Half Day Trout Fishing Trip in Florida Keys5 Hours
Half Day Trout Fishing Trip in Florida Keys8:00 AM
$700

Morning Trip

Half Day Trout Fishing Trip in Florida KeysMaximum 8 persons allowed
(base trip price includes 8 guests)
Half Day Trout Fishing Trip in Florida Keys6 Hours
Half Day Trout Fishing Trip in Florida Keys8:00 AM
$800

Pick Your Date

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Half Day Snapper Fishing Trip in Florida KeysTop-Rated
Half Day Snapper Fishing Trip in Florida KeysInstant Booking
Half Day Snapper Fishing Trip in Florida KeysFishing - Inshore
Half Day Snapper Fishing Trip in Florida Keys

26' Twin Vee Center Console26'Twin Vee Max 8 guests (base trip price includes 8 guests)

Half Day Snapper Fishing Trip in Florida Keys

Target red snapper on a private half-day fishing trip in the Florida Keys with an experienced local captain. Choose a 5- or 6-hour inshore snapper fishing charter designed for beginners, families, and seasoned anglers. All rods, reels, bait, and tackle are provided, and fishing licenses are included. You’ll fish aboard a comfortable 26’ Twin Vee center console with plenty of room for your group. Departing from Big Pine Key, this private snapper fishing trip focuses on hands-on guidance, relaxed pacing, and a customized approach to help your group enjoy a productive and enjoyable day on the water.

Morning Trip

Half Day Snapper Fishing Trip in Florida KeysMaximum 8 persons allowed
(base trip price includes 8 guests)
Half Day Snapper Fishing Trip in Florida Keys5 Hours
Half Day Snapper Fishing Trip in Florida Keys8:00 AM
$700

Morning Trip

Half Day Snapper Fishing Trip in Florida KeysMaximum 8 persons allowed
(base trip price includes 8 guests)
Half Day Snapper Fishing Trip in Florida Keys6 Hours
Half Day Snapper Fishing Trip in Florida Keys8:00 AM
$800

Pick Your Date

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Half Day Eco Tour in Florida KeysTop-Rated
Half Day Eco Tour in Florida KeysInstant Booking
Half Day Eco Tour in Florida KeysTour - Wildlife

Half Day Eco Tour in Florida Keys

Explore the natural beauty of the Florida Keys on a private half-day eco tour led by an experienced local captain. Choose a 5- or 6-hour wildlife-focused boat tour designed for families, couples, and small groups. Cruise calm backcountry waters, mangroves, and shallow flats while learning about the Keys’ unique ecosystem and local wildlife. This relaxed nature tour offers flexible pacing, comfortable seating, and a personalized experience tailored to your group’s interests. Departing from Big Pine Key, each private tour provides a peaceful way to enjoy sightseeing, wildlife viewing, and quality time on the water with a knowledgeable guide.

Morning Trip

Half Day Eco Tour in Florida KeysMaximum 8 persons allowed
(base trip price includes 8 guests)
Half Day Eco Tour in Florida Keys5 Hours
Half Day Eco Tour in Florida Keys8:00 AM
$500

Morning Trip

Half Day Eco Tour in Florida KeysMaximum 8 persons allowed
(base trip price includes 8 guests)
Half Day Eco Tour in Florida Keys6 Hours
Half Day Eco Tour in Florida Keys8:00 AM
$600

Pick Your Date

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Half Day Guided Fishing Trip in Florida KeysTop-Rated
Half Day Guided Fishing Trip in Florida KeysInstant Booking
Half Day Guided Fishing Trip in Florida KeysFishing - Inshore
Half Day Guided Fishing Trip in Florida Keys

26' Twin Vee Center Console26'Twin Vee Max 8 guests (base trip price includes 8 guests)

Half Day Guided Fishing Trip in Florida Keys

Enjoy a private half-day guided fishing trip in the Florida Keys with an experienced local captain. Choose a 5- or 6-hour inshore fishing charter designed for families, beginners, and seasoned anglers alike. Trips target popular species such as gag grouper, red snapper, sea trout, and Spanish mackerel. All rods, reels, bait, and gear are provided, and fishing licenses are included. You’ll fish aboard a 26’ Twin Vee center console with plenty of space and a smooth ride. Departing from Big Pine Key, this private charter focuses on hands-on instruction, relaxed pacing, and a customized experience tailored to your group’s goals.

Morning Trip

Half Day Guided Fishing Trip in Florida KeysMaximum 8 persons allowed
(base trip price includes 8 guests)
Half Day Guided Fishing Trip in Florida Keys5 Hours
Half Day Guided Fishing Trip in Florida Keys8:00 AM
$700

Morning Trip

Half Day Guided Fishing Trip in Florida KeysMaximum 8 persons allowed
(base trip price includes 8 guests)
Half Day Guided Fishing Trip in Florida Keys6 Hours
Half Day Guided Fishing Trip in Florida Keys8:00 AM
$800

Pick Your Date

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Vehicle

26' Twin Vee Center Console

Boat Type:

Boat Guest Capacity:

8

Boat Length:

26 ft

Manufacturer Name:

Twin Vee

Model Year:

2006

Engine Manufacturer Name:

Suzuki

# of Engines:

2

Horsepower Per Engine:

150

Maximum Cruising Speed:

32

Features: Trolling Motor VHF Radio

Calypso Cowboy Charters Twin Vee Boat

This 26’ Twin Vee center console delivers a smooth, stable ride powered by twin 150HP Suzuki engines. Built for versatility and comfort, it features a wireless trolling motor and VHF radio, making it well-suited for fishing trips, sandbar outings, and eco tours throughout the Florida Keys.

Boat

Calypso Cowboy Charters Twin Vee Boat image 0

26' Twin Vee Center Console

Boat Type:

Boat Guest Capacity:

8

Boat Length:

26 ft

Vehicle Details

FAQs about Calypso Cowboy Charters

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