This reservation qualifies for a full refund because of the incident affecting %locationTitle%. If you've confirmed with your captain that your trip is affected, we can help you change or cancel the reservation now.

COVID-19

We are now offering customers full refunds and captains penalty-free cancellations for reservations booked on or before March 14 with a trip date of June 15 or earlier in affected areas. Please note this policy will not cover any new bookings.

Southwest Florida is boating again! Hurricane Ian has passed, and captains are back in action.

Need a boat rental? Search, read reviews & book the best deals online with us! More than %numCharters% boats in %numCountries% countries.

Need a boat rental? Search, book & review the best deals online on BoatBooker.com

BoatBooker.com - Search, Compare & Book Boat Rentals Worldwide. Book your boating trip now!

Search, Compare & Book Boat Rentals Worldwide - BoatBooker

BoatBooker – the world's largest boat rental travel company

Securing your account gives you full control over your data, trips, and payments.

Are you sure you want to skip securing your account?

We've sent your password-free login link to %email%. Open the email and click the link to sign in.

We will send you a confirmation email once you register. This will give you access to all the benefits BoatBooker has to offer.

Choose a unique but memorable password to give you access to your BoatBooker account.

To have full control over your data, trips and payments, set up your account by linking one of your social accounts.

Successfully created password

A verification code has been sent to %email%

Enter verification code

Try logging in with a different email address or go back to view all login options.

%email% was not recognized

This captain has been rated highly by customers.

When you plan to go boating, read messages from your captain here.

Filters are loading...

Finding the best local boat rentals for you...

Looking for boating charters nearby? Compare & book boating charters and open sea boating trips!

In %p1% this listing was one of our most booked in %p2%!

This is a shared trip. There will be up to %p% people on the boat, including children

This listing participates in our Preferred Listings Programme. Preferred listings offer excellent service and quality in relation to the best available rates. Based on this, and on feedback received from previous guests, we highly recommend this listing.

You will have the entire boat privately chartered and can bring up to %p% people, including children

This captain has published boating reports in the last 15 days.

Your dates are popular – we've run out of trips with this boat rental! Check out more below.

When you book with BoatBooker you&rsquo;re getting the lowest rate &bull; If you find a better price for your trip we'll refund the difference!

Wanna go boating tomorrow? Book a trip with instant confirmation and you're all set.

We also have great deals available in the following cities that match your search criteria.

Please check if you filled out all information correctly.

Error occured

Send an email

Contact our booking specialists.

You should get a response from our booking specialist within 24h.

%destination%: No results for your search criteria

%destination%: No results on your selected date

%destination%: No results that match your group size

No results for your search criteria

We also have great deals in the following cities that match your search criteria.

Tip: To get the most out of your trip, choose a date with low to moderate wind.

Boating conditions for %month%%destinationTitle%%state%%country%

Weather forecast for %destinationTitle%%state%%country%

The top boating charters in Big Pine Key

Big Pine Key

Departure Time

Duration

Package Types

Discounts

Price per Day

Review Score

Activities

Policies

Allowed On Board

Boat Types

Boat Categories

Set sail for an unforgettable adventure with Flatzlife Charters, a beautifully restored 1996 Maverick MA Flats Boat, based in Summerland Key. 

Flatzlife Charters

Key West Sailing Center teaches sailing on Hobie Wave's based out of Key West. 

Key West Sailing Center

Meet Captain Craig, a fishy dude who’s been fishing his whole life. 

Goliath Charters

Climb aboard Livin’ the Dream Charters LLC, a beautifully restored 1987 Downeaster Tunnel Hull Center Console, based out of scenic Little Torch Key. 

Livin’ the Dream Charters LLC

Rated #1 on TripAdvisor, Keys Boat Tours operates a 2016 Bulls Bay 2300 Center console based out of Big Pine Key. 

Keys Boat Tours

Sandbar Somewhere Charter is a sleek 2023 Sundance Dx22 Center Console, based out of Summerland Key, offering an unforgettable adventure on the water for up to five guests. 

Sandbar Somewhere Charter

TNT Charters is a 1982 SeaCraft Potter Hull center console (restored in 2018), based out of Little Torch Key. 

TNT Charters

Join Captain Billy Romano and Something Fishy Charters for an unforgettable adventure in the beautiful waters of Key West. 

Something Fishy Charters

Good Times Key West LLC is a 2011 Sailfish 2360 Center console based out of Key West. 

Good Times Key West 24’ Center Console.

Discover the ultimate adventure with Outta Line Charters, a sleek 2024 Contender 21 Open Center Console based in Stock Island. 

Big Pine Key: 58 boats available

Sort by