Here’s the 2026 Flotilla Cruise Schedule for Sailing Adventurers

Delightful Hosted Bareboat Cruising Vacations You Don’t Want to Miss

The 2026 schedule for Colgate Sailing Adventures® Flotilla Cruises is now set. Four bareboat adventures in diverse cruising vacation destinations are open for reservations. Just choose which flotilla cruise schedule fits your sailing adventures plans. Then contact us to hold your cabin while we get the descriptive web pages ready. All cruising sailors welcome. Rather not fill out a form, call Natalie or Diana in our sales office: +1 888-454-7015 or +1 239-454-1700.

Antigua in the Lesser Antilles of the Caribbean
February 7-14, 2026

• Three 4-cabin catamarans from The Moorings and Sunsail
• Single in private cabin $5,850
• Two sharing a cabin, $5,350 per person
• $500 discount for Offshore Sailing School grads with US Sailing Bareboat Cruising Certification and IPC
• $200 discount for Offshore Sailing School grads with just US Sailing Bareboat Cruising Certification

The Exumas in the Bahamas
April 18-25, 2026

• Four 4-cabin catamarans from The Moorings
• Single in private cabin $6,595
• Two sharing a cabin, $5,995 per person
• $600 discount for Offshore Sailing School grads with US Sailing Bareboat Cruising Certification and IPC

Corfu and The Amazing Greek Islands
July 18-25, 2026

• Four 4-cabin catamarans from Sunsail’s Greek Islands partner
• Single in private cabin $5,795
• Two sharing a cabin, $5,295 per person
• $500 discount for Offshore Sailing School grads with US Sailing Bareboat Cruising Certification and IPC
• $200 discount for Offshore Sailing School grads with just US Sailing Bareboat Cruising Certification

Agana, Split and Croatia’s Island Coastline
September 19-26, 2026

• Four 4-cabin monohulls from Sunsail’s Croatia partner
• Single in private cabin $4,995
• Two sharing a cabin, $4,495 per person
• $500 discount for Offshore Sailing School grads with US Sailing Bareboat Cruising Certification and IPC
• $200 discount for Offshore Sailing School grads with just US Sailing Bareboat Cruising Certification

Your Cruise Leaders – Daniel and Klaudia Jackson

For our 2026 sailing vacations flotilla cruises you will enjoy the leadership and company of the Jacksons. Daniel, originally from England, is manager of Offshore Sailing School’s Ft. Myers Beach, FL location and is a super-popular instructor who teaches Offshore’s cruising courses. He and Klaudia met while working on cruise ships in the Caribbean, Bahamas and through the Panama Canal and back in the early 2000s. They hosted the last St. Lucia flotilla cruise and are about to embark as hosts for the Tahiti cruise starting April 5, 2025. The Jacksons moved to SW Florida from Seattle, Washington where they owned several cruising boats and explored the west coast under sail. They are excited to guide you in exploring these fabulous cruising destinations, and love being with sailors who share the sailing lifestyle.

What’s Included in the Packages Above

• Your cabin on one of the reserved flotilla cruise yachts
• Depending on where you will be cruising, partial provisioning or a starter pack (you eat out a lot in delightful ports)
• Fuel
• Damage waiver
• Tourism and or charter taxes where applicable
• Parks permit if charged in advance
• Wi-Fi (depending on the location you choose)
• Cruise shirt and hat
• Group meet and greet and dinner first night
• Your cruise leaders with you throughout the cruise, sailing on lead boat with participants aboard
• A special and very complete cruise handbook prepared by the Offshore team

Reserve Your Cabin Now

• To make sure you get a cabin on the flotilla cruise of your choice, a $200 per person non-refundable deposit is required now.
• Balance of a 30% deposit on the package price you qualify for is required by April 18, 2025.
• Final payment is due 120 days before the departure date.
• A guide book for the cruise of your choice and descriptive webpage will be available by April 18, 2025.
• Call +1 888-454-7015 or +1 239-454-1700 today to reserve your cabin. Don’t delay!

Learn More About Colgate Sailing Adventures® Flotilla Cruises Here