Captain Randi - Island Tours 

4.9
/5
(4 reviews)
 Stringfellow Road 16501, Bokeelia, FL 33922, United States

Captain Randi - Island Tours 

4.9
/5
(4 reviews)
map-thumbnail
Stringfellow Road 16501
Bokeelia, FL, United States

Captain Randi - Island Tours offers private charters to Cayo Costa and Cabbage Keys Islands aboard a 22ft Nauticstar Legacy Center Console based out of Bokeelia on Pine Island. It can take up to 6 guests. The boat is powered by one 200 HP gasoline outboard Yamaha engine, offering a maximum cruising speed of 45 knots. The vessel comes equipped with an ice box and outside speakers.

The captain, Randi Hess specializes in local barrier island tours. Cruise to historic Cabbage Key for lunch, followed by beach time and shelling on beautiful Cayo Costa. Dolphins are often encountered on this trip.

You will find all the necessary safety features onboard, the boat features an anchor, GPS, life jackets (infant, child, and adult), VHF radio, and wheel steering.

Reserve your spot now and get ready for a day of adventure and comfort aboard Captain Randi - Island Tours!

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Customer reviews

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Rating summary

4.9/5
out of 5 stars from 4 reviews
Boat
4.8/5
Crew
5.0/5
Experience
5.0/5

Photos & videos by reviewers (7)

Captain Randi Rocks!
Captain Randi Rocks!
Perfect day!
+4

Customer rating

4
0
0
0
0

Customers claimed

Good experience

100%

Appropriate for children

100%

Friendly captain

100%

Satisfied with the boat

100%

Recommend this charter

100%

Showing 1 - 4 of 4 reviews
Showing: 4 of 4 reviews
Anastasia W.
Anastasia W.
5.0/5

Aug 25, 2025

3 Hr – Cayo Costa Island Beach

Perfect day!

VERIFIED

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!

Booked a few months in advanced- Captain Randi immediately reached out to confirm what we wanted to do! She was also extremely...  

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 Anastasia W. recommends Captain Randi - Island Tours
 Anastasia W. recommends Captain Randi - Island Tours

Heath J.
Heath J.
5.0/5

Apr 18, 2025

4 Hr – Cabbage Key & Cayo Costa

Go with Randi - Thank Me Later

VERIFIED

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 for secluded beach time. Randi has a warm and engaging personality, and obviously really enjoys her work, sharing local facts and history with a personal touch and great sense of humor. Took extra time at the end of the tour to find dolphins for us. Couldn’t have been happier with the day, made fantastic memories with the family. Thank you Randi, 10/10!

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...  

Review media 0
Captain replied
 Heath J. recommends Captain Randi - Island Tours
 Heath J. recommends Captain Randi - Island Tours
undefined (The Captain)
Replied on April 19, 2025
Thank you SO much for the lovely review!! I really appreciate it 🙂🌴☀️

Nicholas D.
Nicholas D.
5.0/5

Nov 14, 2025

4 Hr – Cabbage Key & Cayo Costa

Captain Randi Rocks!

VERIFIED

Captain Randi provided a great trip to Cabbage Key and Cayo Costa! Our group had great time and would highly recommend.

Captain Randi provided a great trip to Cabbage Key and Cayo Costa! Our group had great time and would highly recommend.  

Review media 0
Review media 1
Captain replied
 Nicholas D. recommends Captain Randi - Island Tours
 Nicholas D. recommends Captain Randi - Island Tours
undefined (The Captain)
Replied on November 15, 2025
Thank you so much for the kind words!! Hope to see you all again one day soon 🥰

Steven L.
Steven L.
4.7/5

Feb 20, 2026

3 Hr – Cabbage Key Lunch

Boating with Randi

VERIFIED
NEW

 

 Steven L. recommends Captain Randi - Island Tours
 Steven L. recommends Captain Randi - Island Tours

Trip availability and prices

Trip Date:
Days:
Group Size:
Select date to see availability
March 2026
SuMoTuWeThFrSa
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Number of days
1
Group Size
2 adults • 0 children
Change
Almost there...
3 Hr – Cayo Costa Island Beach - 8:00 AM
FREE Cancellation 3 days notice
3 Hour Trip, starts at 8:00 AM
Price for up to 6 people
US $375 
3 Hr – Private Shelling Cayo Costa
FREE Cancellation 3 days notice
3 Hour Trip, starts at 8:00 AM
Price for up to 6 people
US $375 
3 Hr – Cayo Costa Island Beach - 9:00 AM
FREE Cancellation 3 days notice
3 Hour Trip, starts at 9:00 AM
Price for up to 6 people
US $375 
3 Hr – Private Shelling Cayo Costa - 9:00 AM
FREE Cancellation 3 days notice
3 Hour Trip, starts at 9:00 AM
Price for up to 6 people
US $375 
3 Hr – Cabbage Key Lunch
FREE Cancellation 3 days notice
3 Hour Trip, starts at 10:00 AM
Price for up to 6 people
US $375 
3 Hr – Cayo Costa Island Beach
FREE Cancellation 3 days notice
3 Hour Trip, starts at 10:00 AM
Price for up to 6 people
US $375 
3 Hr – Private Shelling Cayo Costa - 10:00 AM
FREE Cancellation 3 days notice
3 Hour Trip, starts at 10:00 AM
Price for up to 6 people
US $375 
3 Hr – Cayo Costa Island Beach - 11:00 AM
FREE Cancellation 3 days notice
3 Hour Trip, starts at 11:00 AM
Price for up to 6 people
US $375 
3 Hr – Private Shelling Cayo Costa - 11:00 AM
FREE Cancellation 3 days notice
3 Hour Trip, starts at 11:00 AM
Price for up to 6 people
US $375 
3 Hr – Cayo Costa Island Beach - 12:00 PM
FREE Cancellation 3 days notice
3 Hour Trip, starts at 12:00 PM
Price for up to 6 people
US $375 
3 Hr – Cayo Costa Island Beach - 1:00 PM
FREE Cancellation 3 days notice
3 Hour Trip, starts at 1:00 PM
Price for up to 6 people
US $375 
4 Hr – Cabbage Key & Cayo Costa - 8:00 AM
FREE Cancellation 3 days notice
4 Hour Trip, starts at 8:00 AM
Price for up to 6 people
US $460 
4 Hr – Cabbage Key & Cayo Costa - 8:30 AM
FREE Cancellation 3 days notice
4 Hour Trip, starts at 8:30 AM
Price for up to 6 people
US $460 
4 Hr – Cabbage Key & Cayo Costa - 9:00 AM
FREE Cancellation 3 days notice
4 Hour Trip, starts at 9:00 AM
Price for up to 6 people
US $460 
4 Hr – Cabbage Key & Cayo Costa
FREE Cancellation 3 days notice
4 Hour Trip, starts at 10:00 AM
Price for up to 6 people
US $460 
There are 4 people looking at this listing.

Customer reviews

Loading...

Rating summary

4.9/5
out of 5 stars from 4 reviews
Boat
4.8/5
Crew
5.0/5
Experience
5.0/5

Photos & videos by reviewers (7)

Captain Randi Rocks!
Captain Randi Rocks!
Perfect day!
+4

Customer rating

4
0
0
0
0

Customers claimed

Good experience

100%

Appropriate for children

100%

Friendly captain

100%

Satisfied with the boat

100%

Recommend this charter

100%

Showing 1 - 4 of 4 reviews
Showing: 4 of 4 reviews
Anastasia W.
Anastasia W.
5.0/5

Experience:

5.0/5

Equipment

5.0/5

Crew

5.0/5

Overall

Perfect day!

VERIFIED

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

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!

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...  

Review media 0
Review media 1
Review media 2
Review media 3
 Anastasia W. recommends Captain Randi - Island Tours

Heath J.
Heath J.
5.0/5

Experience:

5.0/5

Equipment

5.0/5

Crew

5.0/5

Overall

Go with Randi - Thank Me Later

VERIFIED

4 Hr – 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 for secluded beach time. Randi has a warm and engaging personality, and obviously really enjoys her work, sharing local facts and history with a personal touch and great sense of humor. Took extra time at the end of the tour to find dolphins for us. Couldn’t have been happier with the day, made fantastic memories with the family. Thank you Randi, 10/10!

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 for secluded beach time. Randi has a warm and engaging personality, and obviously really enjoys her work, sharing local facts and history with a personal touch and great sense of humor. Took extra time at the end of the tour to find dolphins for us. Couldn’t have been happier with the day, made fantastic memories with the family. Thank you Randi, 10/10!  

Review media 0
 Heath J. recommends Captain Randi - Island Tours
undefined (The Captain)
Replied on April 19, 2025
Thank you SO much for the lovely review!! I really appreciate it 🙂🌴☀️

Nicholas D.
Nicholas D.
5.0/5

Experience:

5.0/5

Equipment

5.0/5

Crew

5.0/5

Overall

Captain Randi Rocks!

VERIFIED

4 Hr – 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.

Captain Randi provided a great trip to Cabbage Key and Cayo Costa! Our group had great time and would highly recommend.  

Review media 0
Review media 1
 Nicholas D. recommends Captain Randi - Island Tours
undefined (The Captain)
Replied on November 15, 2025
Thank you so much for the kind words!! Hope to see you all again one day soon 🥰

Steven L.
Steven L.
4.7/5

Experience:

4.0/5

Equipment

5.0/5

Crew

5.0/5

Overall

Boating with Randi

VERIFIED
NEW

3 Hr – Cabbage Key Lunch on February 20, 2026

 

 Steven L. recommends Captain Randi - Island Tours

FAQs about Captain Randi - Island Tours

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What the boat is like

Boat category
Center console boats
Boat type
Center console
Boat manufacturer
Nauticstar
Boat Model
Legacy Center Console
Year built
2015
Boat length
22 ft
Capacity
6 persons
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