Two Anchors FL 

 Baillies Bluff Road 1029, Holiday, FL 34691, United States

Two Anchors FL 

Holiday, FL, United States
21 feet
6

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Welcome aboard Two Anchors FL, where your day on the water is private, relaxed, and built around what you want to do.

Captain Kasey offers private charters along Florida’s beautiful Gulf Coast, departing from the Tarpon Springs area. Whether you want to spend the day at a secluded sandbar, search for dolphins, snorkel, collect shells, explore local islands, stop for waterfront dining, or catch an unforgettable Gulf Coast sunset, your trip can be customized for your group.

Unlike crowded tour boats, the entire boat is reserved just for you and your party. Sit back and enjoy the ride while your licensed captain handles the boat and helps you make the most of your time on the water.

Your charter includes:

* Private boat and licensed captain
* Fuel included
* Cooler stocked with ice and bottled water
* Free private parking
* Easy marina pickup
* Sandbar and island-hopping options
* Dolphin and wildlife viewing
* Snorkeling and shelling opportunities
* Waterfront restaurant stops upon request

Trips are family-friendly and great for couples, families, birthdays, celebrations, visitors, or locals who simply want a day on the Gulf without the hassle of renting and operating a boat themselves.

No crowded tour. No complicated planning. Just your group, your captain, and a day on the water.

Book your private Two Anchors FL charter and experience the Gulf Coast like a local

Welcome aboard Two Anchors FL, where your day on the water is private, relaxed, and built around what you want to do.

Captain Kasey offers private charters along Florida’s beautiful Gulf Coast, departing from the Tarpon Springs area. Whether you want to spend the day at a secluded sandbar, search for dolphins, snorkel, collect shells, explore local islands, stop for waterfront dining, or catch an unforgettable Gulf Coast sunset, your trip can be customized for your group.

Unlike crowded tour boats, the entire boat is reserved just for you and your party. Sit back and enjoy the ride while your licensed captain handles the boat and helps you make the most of your time on the water.

Your charter includes:

* Private boat and licensed captain
* Fuel included
* Cooler stocked with ice and bottled water
* Free private parking
* Easy marina pickup
* Sandbar and island-hopping options
* Dolphin and wildlife viewing
* Snorkeling and shelling opportunities
* Waterfront restaurant stops upon request

Trips are family-friendly and great for couples, families, birthdays, celebrations, visitors, or locals who simply want a day on the Gulf without the hassle of renting and operating a boat themselves.

No crowded tour. No complicated planning. Just your group, your captain, and a day on the water.

Book your private Two Anchors FL charter and experience the Gulf Coast like a local

Two Anchors FL
Captain
Two Anchors FL
ID & credentials verified
responds within an hour

Trip availability and prices

Trip Date:
Group Size:
Select date to see availability
September 2026
SuMoTuWeThFrSa
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Number of days
1
Group Size
2 adults • 0 children
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4 Hour – Island & Sandbar Escape
FREE Cancellation 3 days notice
4 hour trip multiple starting times (9:00 AM, 10:00 AM, 2:30 PM)
Seasonal trip
(Fri, Sat, Sun)
+1
US $450
Private tour: up to 6 people
6hr Mid-day Trip
FREE Cancellation 3 days notice
6 hour trip multiple starting times (10:00 AM, 11:00 AM)
Seasonal trip
(Fri, Sat, Sun)
+5
US $650
Private tour: up to 6 people
8 Hour – Premium Custom
FREE Cancellation 3 days notice
8 hour trip multiple starting times (9:00 AM, 10:00 AM)
Seasonal trip
(Fri, Sat, Sun)
+5
US $795
Private tour: up to 6 people
There are 2 people looking at this charter.

Customer reviews

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FAQs about Two Anchors FL

Two Anchors FL offers the following trips to customers:
  • US $450 per group - 4 Hour – Island & Sandbar Escape (4 hours)
  • US $450 per group - 4 Hour – Island & Sandbar Escape - 10:00 AM (4 hours)
  • US $450 per group - 4 Hour – Island & Sandbar Escape - 2:30 PM (4 hours)
  • US $650 per group - 6hr Mid-day Trip (6 hours)
  • US $650 per group - 6hr Mid-day Trip - 11:00 AM (6 hours)
  • US $795 per group - 8 Hour – Premium Custom (8 hours)
  • US $795 per group - 8 Hour – Premium Custom - 10:00 AM (8 hours)
When you book a trip with Two Anchors FL, you can expect the following amenities onboard:
  • GPS
  • Chart Plotter
  • Depth Finder
  • Anchor
  • Life Jackets
  • Bimini
  • Bow Sundeck
  • Audio System
  • Ice Box
  • Baitwell
  • Rod Holders
Trips booked with Two Anchors FL include:
  • Snorkeling Equipment
  • Drinks
Two Anchors FL offers the following activities:
  • Boat & Yacht Tours
  • Sunset Dinner Cruises
  • Island Hopping
  • Booze Cruises
  • Snorkeling & Diving Tours
  • Whale & Dolphin Watching
  • Eco-Tours
  • Sandbar Tours
  • Birthday Celebrations
  • Bachelorette & Bachelor Parties
  • Corporate & Group Events

Your operator

Two Anchors FL
Two Anchors FL
Two Anchors FL

Holiday, Florida, United States

ID & license verified
Member since March 2026

Captain Two Anchors FL is based in Holiday, Florida, and expertly operates a 2016 Hurricane 21CC Center Console. Specializing in snorkeling, island hopping, scenic boat and yacht tours, lively booze cruises, and unforgettable sandbar trips, the captain ensures every adventure is safe, fun, and unforgettable.

Our Team
Kasey J.

Kasey J.

Captain

ID & license verified
Member since March 2026

Captain Two Anchors FL is based in Holiday, Florida, and expertly operates a 2016 Hurricane 21CC Center Console. Specializing in snorkeling, island hopping, scenic boat and yacht tours, lively booze cruises, and unforgettable sandbar trips, the captain ensures every adventure is safe, fun, and unforgettable.

Our Team
Kasey J.

Kasey J.

Captain

What the boat is like

Boat category
Center console boats
Boat type
Center console
Boat manufacturer
Hurricane
Boat Model
21CC
Year built
2016
Boat length
21 ft
Capacity
6 persons
Engine model
Yamaha
Max crusing speed
40 knots
Powered by
1 x 150HP
Engine Type
Outboard
Fuel Type
Gas
Boat category
Center console boats
Boat type
Center console
Boat manufacturer
Hurricane
Boat Model
21CC
Year built
2016
Boat length
21 ft
Capacity
6 persons

Which kind of activities are offered

Boat & Yacht Tours
Sunset & Dinner Cruise
Island Hopping
Booze Cruises
Snorkeling & Diving Tours
Whale & Dolphin Watching
Eco-Tours
Sandbar Tours
Birthday Celebrations
Bachelorette & Bachelor Parties
Corporate & Group Events

Which amenities are available onboard

GPS
Chart Plotter
Depth Finder
Anchor
Life Jackets
Bimini
Bow Sundeck
Audio System
Ice Box
Baitwell
Rod Holders

What's included in the trip price

Snorkeling Equipment
Drinks
Cooler with ice and water included.

What’s allowed on the boat

Child Friendly
No age limits, children and families welcomed.
Smoking
Alcohol
BYOB for guests 21+
Swimming

What additional terms you should be aware of

Security deposit of US $100 per tour is required

A refundable deposit of US $100 per tour is required at boat pick-up and will be returned to you when the boat is returned without damage. Security deposit is to be paid directly to the charter operator.


Fuel is included

Fuel is included in the price of the rental.

How cancellations work

Free cancellation up to 3 days prior to trip

You can cancel or modify your booking up to 3 days before the trip date, free of charge. If you cancel or modify your booking later, or fail to show up, you'll forfeit 100% of what you've paid.

More details

How you can pay

Reserve with a 30% booking deposit, pay the captain the rest

When the captain confirms your trip, BoatBooker charges your credit card a 30% booking deposit to guarantee your reservation.

The remaining balance is to be paid directly to the charter operator on or prior to your trip date in one of the following payment methods:

 Cash

 Visa

 Mastercard

 PayPal

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