Our Key West Boat Charters

See the real Key West on a private charter with a local captain!

Captained Combo Charters Base Pricing

1.5 Hours Private Charter - Sunsets and Scenic Cruise $395

BOAT CHARTER WITH CAPTAIN FOR UP TO 6 GUESTS - PLEASE CALL FOR PARTIES OF 7 - 12 GUESTS
2.5 Hours Private Charter $495

BOAT CHARTER WITH CAPTAIN FOR UP TO 6 GUESTS - PLEASE CALL FOR PARTIES OF 7 - 12 GUESTS
Half-Day: 4 Hour Private Charter $595

BOAT CHARTER WITH CAPTAIN FOR UP TO 6 GUESTS- PLEASE CALL FOR PARTIES OF 7 - 12 GUESTS
3/4 Day 6 Hour Private Charter $895

BOAT CHARTER WITH CAPTAIN FOR UP TO 6 GUESTS- PLEASE CALL FOR PARTIES OF 7 - 12 GUESTS

FISHING or LOBSTERING +$100

UPGRADE YOUR CHARTER BY CHOOSING OUR DOUBLE DECKER SLIDE BOAT FOR AN ADDITIONAL $200 OR RIDE IN COMFORT ON OUR 33FT CENTER CONSOLE FOR AN ADDITIONAL $100.

We are by appointment only, so please do not arrive to our location without contacting us.

CALL US NOW TO BOOK YOUR TRIP

(305)-587-3499

Get Inspired, Check Out Our Gallery!

We Provide: Bottled water and Ice -Snorkel gear, fishing rods, lobster equipment, licenses, and bait.

You Bring: Any other drinks than bottled water, food, sunscreen, towel, protective clothing for the sun, swim wear, and warm clothes during the winter months.

Departure Times Departure times are normally 9am, 2pm or 4pm(2.5hr afternoon option), Sunset trips are also available.

Number of Passengers 6 people maximum per captained charter boat. Groups with 7-12 passengers please navigate to our bareboat charter page or book two captained charter boats.

Maximum Weight Limit 325 LBS. maximum for any passenger. For groups with a combined weight of over 1400lbs., the double decker pontoon boat, tritoon, or panga center console must be used.

Book direct and save!

Let The Fun Begin!

Book directly with Fun In The Sun and save on third-party fees! We’re here to make your boat charter experience as enjoyable and cost-effective as possible. Call us today to secure your spot and keep more of your money for the fun and sun! Why pay extra fees when you can book directly and save? Call Fun In The Sun now to secure your unforgettable boat charter experience and keep your money where it belongs—right in your pocket. Skip the third-party booking fees and enjoy more adventure for less!

(305)-587-3499

Our Charter Boat Fleet

With Fun In The Sun there's a boat for everyone!

26ft Century Deck Boat

Our main charter boat is the 26ft Century deck boat, powered by a 250hp Yamaha four stroke. Equipped with sound system, fresh water rinse down, shaded area, cushioned seating, fishing license, and swim ladder.

26ft Century Deck Boat Charter Pricing

BOAT CHARTER WITH CAPTAIN FOR UP TO 6 GUESTS - PLEASE CALL FOR PARTIES OF 7 - 12 GUESTS

23ft Tritoon

23ft Tritoon Powered by a 150 Yamaha four stroke. Equipped with stereo, vhf, GPS, and coolers.

23ft Tritoon Charter Pricing

BOAT CHARTER WITH CAPTAIN FOR UP TO 6 GUESTS - PLEASE CALL FOR PARTIES OF 7 - 12 GUESTS

30ft Double Decker Pontoon

30ft Double Decker Saltwater Pontoon Boat with slide. Powered by a 150hp Yamaha four stroke. Equipped with stereo, vhf, GPS, changing room, and two coolers.

30ft Double Decker Pontoon Charter Pricing

BOAT CHARTER WITH CAPTAIN FOR UP TO 6 GUESTS - PLEASE CALL FOR PARTIES OF 7 - 12 GUESTS

33ft Center Console

33ft Center console Powered by a Yamaha four stroke. Equipped with stereo, vhf, GPS, and coolers.

33ft Center Console Charter Pricing

BOAT CHARTER WITH CAPTAIN FOR UP TO 6 GUESTS - PLEASE CALL FOR PARTIES OF 7 - 12 GUESTS

36ft Invincible

Fun In The Sun’s 36′ Invincible delivers power, comfort, and versatility— a premium center console designed for guests who want performance without compromise. .

36ft Invincible Charter Pricing

BOAT CHARTER WITH CAPTAIN FOR UP TO 6 GUESTS - PLEASE CALL FOR PARTIES OF 7 - 12 GUESTS

40ft Intrepid

Fun In The Sun proudly introduces our 40′ Intrepid— a high-performance luxury center console powered by triple engines for a smooth, exhilarating ride. Perfect for discerning guests, this premium vessel offers comfort and style for private charters, and custom adventures. With plenty of room, it’s the ideal choice for a fast, luxurious, and elevated day on the water.

40ft Intrepid Charter Pricing

BOAT CHARTER WITH CAPTAIN FOR UP TO 6 GUESTS - PLEASE CALL FOR PARTIES OF 7 - 12 GUESTS

43ft Lisa Lynn

The Lisa Lynn is a beautiful 43′ Luxury Charter Boat with 4 staterooms and 2 baths. Lisa Lynn can comfortably sleep up to 6 passengers (for 7-12 passengers day trips navigate to our bareboat charter page). This is the perfect boat to take on a private luxury snorkeling trip to one of our amazing reefs, or a sunset cruise to entertain friends and family. The yacht is available for custom charters, including a variety of Sunset & Day Cruises and Multi-day Trips to the islands. The Lisa Lynn is also available as a stay-aboard vacation rental at an exquisite yacht club. For more Info navigate to our Yacht Charters page.

43ft luxury yacht Charter Pricing

BOAT CHARTER WITH CAPTAIN FOR UP TO 6 GUESTS - PLEASE CALL FOR PARTIES OF 7 - 12 GUESTS

Cancelation Policy

View Cancelation Policy

Please call +1 (305) 587-3499 ASAP if you would like to cancel your trip. If the trip is cancelled by the customer, and FITSKW can rebook the trip your credit card will be refunded the full amount.

Our Locations:

MOST CAPTAINED CHARTER BOATS

Stock Island Yacht Club
6000 Peninsular Ave, Key West, FL 33040
Get Directions

SOME RENTAL BOATS (call/text to confirm)

Oceans Edge Key West
5950 Peninsular Ave, Key West, FL 33040
Get Directions

Cancelation Policy

View Cancelation Policy

Please call +1 (305) 587-3499 ASAP if you would like to cancel your trip. If the trip is cancelled by the customer, and FITSKW can rebook the trip your credit card will be refunded the full amount.

Our Key West Boat Charters

See the real Key West on a private charter with a local captain!

Captained Combo Charters Base Pricing

FISHING or LOBSTERING +$100

UPGRADE YOUR CHARTER BY CHOOSING OUR DOUBLE DECKER SLIDE BOAT FOR AN ADDITIONAL $200 OR RIDE IN COMFORT ON OUR 33FT CENTER CONSOLE FOR AN ADDITIONAL $100.

We are by appointment only, so please do not arrive to our location without contacting us.

(305)-587-3499

Get Inspired, Check Out Our Gallery!

Book direct and save!

Let The Fun Begin!

(305)-587-3499

Our Charter Boat Fleet

With Fun In The Sun there's a boat for everyone!

26ft Century Deck Boat

Our main charter boat is the 26ft Century deck boat, powered by a 250hp Yamaha four stroke. Equipped with sound system, fresh water rinse down, shaded area, cushioned seating, fishing license, and swim ladder.

26ft Century Deck Boat Charter Pricing

BOAT CHARTER WITH CAPTAIN FOR UP TO 6 GUESTS - PLEASE CALL FOR PARTIES OF 7 - 12 GUESTS

23ft Tritoon

23ft Tritoon Powered by a 150 Yamaha four stroke. Equipped with stereo, vhf, GPS, and coolers.

23ft Tritoon Charter Pricing

BOAT CHARTER WITH CAPTAIN FOR UP TO 6 GUESTS - PLEASE CALL FOR PARTIES OF 7 - 12 GUESTS

30ft Double Decker Pontoon

30ft Double Decker Saltwater Pontoon Boat with slide. Powered by a 150hp Yamaha four stroke. Equipped with stereo, vhf, GPS, changing room, and two coolers.

30ft Double Decker Pontoon Charter Pricing

BOAT CHARTER WITH CAPTAIN FOR UP TO 6 GUESTS - PLEASE CALL FOR PARTIES OF 7 - 12 GUESTS

33ft Center Console

33ft Center console Powered by a Yamaha four stroke. Equipped with stereo, vhf, GPS, and coolers.

33ft Center Console Charter Pricing

BOAT CHARTER WITH CAPTAIN FOR UP TO 6 GUESTS - PLEASE CALL FOR PARTIES OF 7 - 12 GUESTS

36ft Invincible

Fun In The Sun’s 36′ Invincible delivers power, comfort, and versatility— a premium center console designed for guests who want performance without compromise. .

36ft Invincible Charter Pricing

BOAT CHARTER WITH CAPTAIN FOR UP TO 6 GUESTS - PLEASE CALL FOR PARTIES OF 7 - 12 GUESTS

40ft Intrepid

40ft Intrepid Charter Pricing

BOAT CHARTER WITH CAPTAIN FOR UP TO 6 GUESTS - PLEASE CALL FOR PARTIES OF 7 - 12 GUESTS

43ft Lisa Lynn

43ft luxury yacht Charter Pricing

BOAT CHARTER WITH CAPTAIN FOR UP TO 6 GUESTS - PLEASE CALL FOR PARTIES OF 7 - 12 GUESTS

View Cancelation Policy

Our Locations:

MOST CAPTAINED CHARTER BOATS

SOME RENTAL BOATS (call/text to confirm)

View Cancelation Policy

Our Locations:

ALL CAPTAINED CHARTER BOATS

RENTAL BOATS (CALL TO CONFIRM LOCATION)