Pine Island to Cabbage Key & Cayo Costa

5.0

(8 reviews)

Stringfellow Road 16501, Bokeelia, FL 33922, United States–

Pine Island to Cabbage Key & Cayo Costa

Bokeelia, FL, United States

–

21 feet

5.0

(8 reviews)

Trips & prices Boat info What's included Contact captain Activities

Trips & prices What's included Boat info Reviews Contact captain Activities

Set off on a private island adventure with Captain Randi – Island Tours, departing from Four Winds Marina on Pine Island. This isn’t just a boat ride—it’s your VIP pass to the best of Southwest Florida.

Cruise in style on a sleek 22’ NauticStar center console, perfect for up to 6 guests. Powered by a 200HP Yamaha, this boat is fast, smooth, and built for exploring hidden beaches, spotting dolphins, and hopping between iconic island destinations.

Your day is completely customizable, but most guests love the perfect combo:
Cayo Costa – untouched beaches, shelling, swimming, and that “no roads, no crowds” vibe
Cabbage Key – a legendary island restaurant only accessible by boat (cheeseburgers + dollar bills included)

Whether you want to relax on the beach, hunt for shells, grab lunch, or just cruise and take in the views, Captain Randi has you covered with local knowledge, great energy, and a fun, laid-back vibe.

Onboard you’ll enjoy a Bluetooth sound system, cooler for your drinks, and plenty of space to kick back. Snorkel gear is available as an add-on if you want to explore below the surface.

Private tour (just your group—no strangers)
Alcohol, kids, and swimming all welcome
Fully equipped with all required safety gear for peace of mind

If you’re looking for a fun, effortless, and unforgettable day on the water—this is it.

Spots fill fast—book your private charter with Captain Randi now.

Customer reviews

5.0

(8 reviews)

4.9

Boat & equipment

5.0

Captain & crew

5.0

Boating Experience

Customers' gallery (13)

All reviews (8)

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Showing 1 – 5 of 8 reviews

Landau Kristin

5.0

Verified

Randi is fantastic!

3 Hr – Private Shelling Cayo Costa - 9:00 AM on March 31, 2026 • 2 adults

Randi took myself, my daughter and my 3 year old granddaughter out to Cayo Costa for an afternoon of shelling and beach time. When deciding on which captain to book I read all of the reviews and decided Randi seemed like the perfect match for us. I was not disappointed, Randi was not only a very capable boat captain but very knowledgeable about the area. She even helped my granddaughter make a sandcastle! We highly recommend her and would use her services again. Thank you Randi for a perfect trip!

Response from Captain

April 1, 2026

Thank you SO much! It was my pleasure 💜⚓️🧜‍♀️

Anastasia Wesseln

5.0

Verified

Perfect day!

3 Hr – Cayo Costa Island Beach on August 25, 2025 • 2 adults

Booked a few months in advanced- Captain Randi immediately reached out to confirm what we wanted to do! She was also extremely responsive to any questions we had leading up to the charter - including adding on people and questions for some nervous passengers! She was incredibly kind and understanding! Leading up to the charter the weather looked terrible - Randi communicated that she was looking and seeing when the ideal window was and we talked about alternative times and days! By some miracle the weather turned out perfectly - it’s was really windy so the first choice beach didn’t work but Randi always had a backup plan! She had fun stories about the local area and knew where the wildlife was! When we spotted dolphins she was able to get them to chase our boat and it was so cool! I absolutely recommend Captain Randi - you won’t regret it!

Michael Bevill

5.0

Verified

New

Beautiful trip and fabulous captain!

3 Hr – Private Shelling Cayo Costa on April 16, 2026 • 2 adults

Had a great time! Randi is super fun and accommodating. The island is beautiful and you can truly tell she has so much experience there and has great respect for not only the land, but also her guests. Highly recommend!

Response from Captain

April 16, 2026

Awwww thank you so much!! That really means alot to me 🧜‍♀️

Pamela Troxel

5.0

Verified

New

Cabbage Key - Cayo Costa tour

4 Hr – Cabbage Key & Cayo Costa on April 14, 2026 • 6 adults

We had a wonderful trip with Captain Randi! Her boat is beautiful and she was very friendly and informative. definitely would recommend

Response from Captain

April 14, 2026

Thank you so much for the lovely review 💜🧜‍♀️

Sharon Maddux

5.0

Verified

Best Day of our Trip!

4 Hr – Cabbage Key & Cayo Costa on April 3, 2026 • 3 adults

Trip availability and prices

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May 2026

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2 adults • 0 children

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3 Hr – Cayo Costa Island Beach - 8:00 AM

FREE Cancellation 3 days notice

3 Hour Trip

starts at 8:00 AM

US $375