Pine Island to Cabbage Key & Cayo Costa
Pine Island to Cabbage Key & Cayo Costa
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 21’ 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.
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 21’ 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.
Trip availability and prices
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Customer reviews
Rating
Customers' gallery (13)
All reviews (8)
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!
Thank you SO much! It was my pleasure 💜⚓️🧜♀️
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!
Awwww thank you so much!! That really means alot to me 🧜♀️
We had a wonderful trip with Captain Randi! Her boat is beautiful and she was very friendly and informative. definitely would recommend
Thank you so much for the lovely review 💜🧜♀️
Captain Randi provided a great trip to Cabbage Key and Cayo Costa! Our group had great time and would highly recommend.
Thank you so much for the kind words!! Hope to see you all again one day soon 🥰
FAQs about Pine Island to Cabbage Key & Cayo Costa
What are the trip rates for Pine Island to Cabbage Key & Cayo Costa?
- US $375 per group - 3 Hr – Cabbage Key Lunch (3 hours)
- US $375 per group - 3 Hr – Cayo Costa Island Beach (3 hours)
- US $375 per group - 3 Hr – Cayo Costa Island Beach - 1:00 PM (3 hours)
- US $375 per group - 3 Hr – Cayo Costa Island Beach - 11:00 AM (3 hours)
- US $375 per group - 3 Hr – Cayo Costa Island Beach - 12:00 PM (3 hours)
- US $375 per group - 3 Hr – Cayo Costa Island Beach - 8:00 AM (3 hours)
- US $375 per group - 3 Hr – Cayo Costa Island Beach - 9:00 AM (3 hours)
- US $375 per group - 3 Hr – Private Shelling Cayo Costa (3 hours)
- US $375 per group - 3 Hr – Private Shelling Cayo Costa - 10:00 AM (3 hours)
- US $375 per group - 3 Hr – Private Shelling Cayo Costa - 11:00 AM (3 hours)
- US $375 per group - 3 Hr – Private Shelling Cayo Costa - 9:00 AM (3 hours)
- US $460 per group - 4 Hr – Cabbage Key & Cayo Costa (4 hours)
- US $460 per group - 4 Hr – Cabbage Key & Cayo Costa - 8:00 AM (4 hours)
- US $460 per group - 4 Hr – Cabbage Key & Cayo Costa - 8:30 AM (4 hours)
- US $460 per group - 4 Hr – Cabbage Key & Cayo Costa - 9:00 AM (4 hours)
Which amenities are available onboard with Pine Island to Cabbage Key & Cayo Costa?
- GPS
- VHF Radio
- Chart Plotter
- Depth Finder
- Anchor
- Wheel Steering
- Life Jackets
- Audio System
- Outside Speakers
- Ice Box
- Rod Holders
What add-ons can be available with Pine Island to Cabbage Key & Cayo Costa?
- Drinks
Which kinds of activities does Pine Island to Cabbage Key & Cayo Costa offer?
- Boat & Yacht Tours
- Island Hopping
- Whale & Dolphin Watching
- Eco-Tours
Your operator
Hi, I'm Captain Randi — your local guide to the hidden gems of Southwest Florida. I specialize in private, personalized boat charters to some of the most beautiful spots in the area, including Cayo Costa, Cabbage Key, and the surrounding barrier islands. Whether you're looking for world-class shelling, dolphin encounters, or a relaxing day on secluded beaches, I create easygoing, fun experiences for couples, families, and small groups. My goal is simple: give you a day on the water you'll never forget. As a USCG-licensed captain with a passion for these waters, I know where to find the best shells, the calmest beaches, and the most active wildlife — without the crowds. You'll be cruising on a clean, comfortable boat designed for both relaxation and adventure. Every trip is private, flexible, and tailored to what you want to do. Shelling, Dolphin watching, Cayo Costa beach time, Cabbage Key lunch trips, and Sunset cruises If you're ready for a laid-back, memorable day on the water — I've got you covered.
Hi, I'm Captain Randi — your local guide to the hidden gems of Southwest Florida. I specialize in private, personalized boat charters to some of the most beautiful spots in the area, including Cayo Costa, Cabbage Key, and the surrounding barrier islands. Whether you're looking for world-class shelling, dolphin encounters, or a relaxing day on secluded beaches, I create easygoing, fun experiences for couples, families, and small groups. My goal is simple: give you a day on the water you'll never forget. As a USCG-licensed captain with a passion for these waters, I know where to find the best shells, the calmest beaches, and the most active wildlife — without the crowds. You'll be cruising on a clean, comfortable boat designed for both relaxation and adventure. Every trip is private, flexible, and tailored to what you want to do. Shelling, Dolphin watching, Cayo Costa beach time, Cabbage Key lunch trips, and Sunset cruises If you're ready for a laid-back, memorable day on the water — I've got you covered.
What the boat is like
Which kind of activities are offered
Which amenities are available onboard
What's included in the trip price
What’s allowed on the boat
What additional terms you should be aware of
Security deposit is not required
A refundable deposit is not required by 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.
How you can pay
Reserve with a 10% booking deposit, pay the captain the rest
When the captain confirms your trip, BoatBooker charges your credit card a 10% 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
When paying the remaining balance with a credit card, an additional 2.5% charge will apply.
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