Captain
Randi Hess

Member since January 2025 Bokeelia, United States
Background
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.
Techniques
Cayo Costa Shelling, Island Hopping, Dolphin Watching, Cabbage Key lunch, Manatee Watching, Cayo Costa Beach Time

Hey, I'm Captain Randi Hess

Bokeelia, United States
Background
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.
Techniques
Cayo Costa Shelling, Island Hopping, Dolphin Watching, Cabbage Key lunch, Manatee Watching, Cayo Costa Beach Time
Verified

My Listing

Excellent
5.0 / 5
(8 reviews)
Bokeelia
 Instant Confirmation
trips from US $375

Customer reviews

Rating summary
Excellent
5.0 / 5
out of 5 stars from 8 reviews
Boat
Excellent
4.9 / 5
Crew
Excellent
5.0 / 5
Experience
Excellent
5.0 / 5
Photos & videos by reviewers (13)
Beautiful trip and fabulous captain!
Beautiful trip and fabulous captain!
Beautiful trip and fabulous captain!
+10
Customer rating
8
0
0
0
0
Customers claimed
Good experience
100%
Friendly captain
100%
Recommend this charter
100%
Appropriate for children
100%
Satisfied with the boat
100%
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Showing:
5 of 8 reviews
Nicholas D.
Excellent
5.0 / 5
Experience:
Excellent
5.0 / 5
Boat
Excellent
5.0 / 5
Crew
Excellent
5.0 / 5
Overall

Captain Randi Rocks!

VERIFIED   4 Hr โ€“ Cabbage Key & Cayo Costa on November 14, 2025
Captain Randi provided a great trip to Cabbage Key and Cayo Costa! Our group had great time and would highly recommend.
Nicholas D. recommends Pine Island to Cabbage Key & Cayo Costa
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Steven L.
Excellent
4.7 / 5
Experience:
Very good
4.0 / 5
Boat
Excellent
5.0 / 5
Crew
Excellent
5.0 / 5
Overall

Boating with Randi

VERIFIED   3 Hr โ€“ Cabbage Key Lunch on February 20, 2026
Steven L. recommends Pine Island to Cabbage Key & Cayo Costa
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Steven L. recommends Pine Island to Cabbage Key & Cayo Costa
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Heath J.
Excellent
5.0 / 5
Experience:
Excellent
5.0 / 5
Boat
Excellent
5.0 / 5
Crew
Excellent
5.0 / 5
Overall

Go with Randi - Thank Me Later

VERIFIED   4 Hr โ€“ Cabbage Key & Cayo Costa on April 18, 2025
Took the family (wife and two kids, 17 and 23) on 4-hr island hop starting at Cabbage Key for lunch and then on to Cayo Costa...
Heath J. recommends Pine Island to Cabbage Key & Cayo Costa
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