Capt. Rob and Rachel were customers before purchasing Island Sailing in 2015. They have enjoyed taking care of customers, sharing our local waters and taking guests all of the way to the Bahamas.
Capt. Rob has a deep passion for sailing and being out on the water. He learned to sail on dinghies and a 27' Catalina before living on board
Capt. Rob and Rachel were customers before purchasing Island Sailing in 2015. They have enjoyed taking care of customers, sharing our local waters and taking guests all of the way to the Bahamas.
Capt. Rob has a deep passion for sailing and being out on the water. He learned to sail on dinghies and a 27' Catalina before living on board a 45' Island Trader ketch with his father in the Bahamas. At least every other summer you will find Capt. Rob sailing Bahamian waters again!
Rachel helps to ensure that our guests have a better experience than most other charters - she add the luxury and high expectations to Island Sailing - and keeps Capt. Rob focused!

Captain Mark, whose hometown is Colorado Springs, Co., has spent many years on the water. As a 50T Master USCG licensed Captain, photographer, and as a certified scuba instructor, Captain Mark will gladly provide charter guests with diving excursions on their sailing trips. He enjoys extended day and overnight trips, and sailing up/dow
Captain Mark, whose hometown is Colorado Springs, Co., has spent many years on the water. As a 50T Master USCG licensed Captain, photographer, and as a certified scuba instructor, Captain Mark will gladly provide charter guests with diving excursions on their sailing trips. He enjoys extended day and overnight trips, and sailing up/down the FL coast, including the Keys. Captain Mark is also a veteran of the United States Army.

Captain Marty started sailing a long time ago, 1966, in Puerto Rico, on his dad's 25' cutter. Since then, he has sailed in a variety of places like Puget Sound in the Northwest, Grenada in the Caribbean, Cazumel, Mexico, Tom's River, New Jersey, and much more. Until 2014, he was employed as a mortgage banker, but his undergraduate degree
Captain Marty started sailing a long time ago, 1966, in Puerto Rico, on his dad's 25' cutter. Since then, he has sailed in a variety of places like Puget Sound in the Northwest, Grenada in the Caribbean, Cazumel, Mexico, Tom's River, New Jersey, and much more. Until 2014, he was employed as a mortgage banker, but his undergraduate degree is in Limnology, so he worked at MSU's research lab on Lake Michigan for a season before completing his MBA at Northern Michigan University. Since 2014, he has taken his trawler from Naples into Canada twice and completed the Great Loop and the Triangle Loop. He enjoys meeting the people who charter with us at Island Sailing and he has experience in the Everglades which helps to explain the local wildlife. Most of all, he enjoys sailing and helps his passengers get enjoyment from it as well.

Island Dreams, our 31' Catalina, built in 2007, is easy-to-sail and fun. She has many essential features, making her the perfect vessel for captained charters and bareboaters. She also has all of the latest toys and conveniences, including:

She is safe, stable and really easy to sail. She is equipped with 2 cabins and a head, with a galley, stove/oven, and refrigeration. With a shoal draft wing keel, she allows access to cruising waters unreachable by other sailboats.


We have a stocked refrigerator with water and soda on each sail. You can bring food and/or drinks with you. We have all the cups, plates, cutlery and supplies that you will need for your sail!

Island Time, our 47' Beneteau, is a 2004 beauty. She is extremely spacious and perfect for those extended trips and family outings, or perfect for a sunset or day sail. She has all the latest toys and conveniences, including:

She adds a little more space and comfort for you sails. The perfect vessel to take on the wind and seas or to relax on the bow with friends and family.


She is equipped with 3 cabins, 2 heads (one of which is electric), as well as a very spacious salon to eat or relax down below when you need a break. A large swim platform with shower and grill can turn this vessel into your floating backyard barbecue. Island Time is available for captained charter only.

Ensuite forward cabin with electric head and shower allow you some time to yourself on overnights and sleep on a high-quality mattress.

This cabin sleeps two people and is connected to the aft head. Enough space to relax after a day of sailing and store all of your belongings in the hanging locker and storage areas.

This cabin sleeps two people and is next to the galley. Enough space to relax after a day of sailing and store all of your belongings in the hanging locker and storage areas.

Our cockpit has a wooden folding table that opens up to ensure that you and your guests can enjoy a proper meal while sailing - living the life!

We take Island Time for our local overnights, the Florida Keys, Dry Tortugas and Bahamas. Check out the Trips and Specials page for more information
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