Naples' Premier Sailing Charter Company

Island Sailing - Naples, FL​​

Island Sailing Naples | 800 12th Avenue South, Naples, FL | islandsailingnaples@gmail.com | 239.398.1483

*per person* sails

​​*Per person* sails allow for smaller groups/individuals the opportunity to join others on a sunset sail, rather than secure the entire vessel.  

Sunset per person sails

  • Join us any Wednesday OR Saturday during the months of December thru May, on our 3-hour *per person* sunset sails.
  • Cost:  $75/person​
  • Up to 6 guests.


Fullmoon / Sunset per person sails

  • Please join us for a Full Moon / Sunset Sail, which includes both a sunset and a full moon rise on your sail!  
  • Tuesday, March 19, 7-10 p.m.
  • Cost is $75/person
  • ​Up to 6 guests.

bimini summer sailing vacation - july 6-13, 2019

​Join us this summer for a Bimini Sailing vacation! 

Saturday: Guests arrive in Miami and meet the vessel at Miamarina at Bayside. Board vessel, get stowed, pick up any last minute provisions before a relaxing dinner at any of the restaurants surrounding the marina and exploring Miami Beach.

Sunday: Cross to Bimini-clear customs by 2:00 p.m. and go ashore to explore and have a Bahamian dinner. Stay at Bimini Big Fish and Game Club Marina.

Monday: Leave dock mid-morning for the Sapona Wreck to do snorkeling and swimming for most of the day. Enjoy some sailing on the Bahamas Bank before anchoring out for the night near Dollar Harbour off of South Cat Cay.

Tuesday: Swim, explore and play on South Cat Cay. Remain at anchor off South Cat Cay this evening.

Wednesday: Sail north to Gun Cay to feed the stingrays and nursesharks at Honeymoon Harbour. Explore the old lighthouse on Gun Cay and enjoy the harbor beach. Anchor off for the evening.

Thursday: Enjoy a day of sailing in the Bahamas' crystal clear waters. Option to snorkel the famed Bimini Road or head back to Bimini earlier for more exploration. Dock at the Bimini Big Fish and Game Club by 4:00 p.m. to allow time to explore, have dinner and go to the casino if you choose.

Friday: We move the vessel off the dock and anchor off Bimini for guests to continue to enjoy Bimini by dinghy. Captain will weigh anchor and head back to Miami between midnight and 1:00 a.m.

Saturday: Arrive back at Miamarina at Bayside by 9:00 a.m. Guests checkout at their leisure.

Price: $2,250 on a per cabin basis (up to two people per cabin) or $6,000 for a private charter (up to six guests) Includes: All taxes, customs fees, dockage, fuel and captain's fees. Charterer pays for: provisioning of food, any meals ashore and captain's gratuity. See our video on YouTube to get a taste of what you can expect to enjoy: https://www.youtube.com/watch?v=g7E_WRuy1G0&t=15s