What is a Learn to Sail Vacation?

A Learn to Sail Vacation is an immersive experience where participants receive professional sailing instruction while enjoying a scenic sailing destination. These vacations blend structured American Sailing courses with hands-on practice, allowing sailors to gain certifications while experiencing the excitement of a real sailing adventure.

What to Expect on a Learn to Sail Vacation?

Professional Instruction

Certified American Sailing instructors teach essential skills based on recognized courses like ASA 101 (Basic Keelboat Sailing) and ASA 103 (Coastal Cruising). More advanced courses, such as ASA 104 (Bareboat Cruising) and beyond, are also available.

Hands-On Experience

Students actively sail, learning navigation, docking, sail trim, and anchoring while exploring picturesque coastlines and islands.

Scenic Destinations

These vacations take place in stunning locations like the Caribbean, Mediterranean, or Pacific Coast, allowing students to learn in ideal sailing conditions.

Combination of Learning & Leisure

Beyond training, participants enjoy swimming, snorkeling, island excursions, and local cultural experiences.

Learn to Sail Vacations

View All Tours

Who Are Learn to Sail Vacations For?

A Learn to Sail Vacation is for anyone who dreams of adventure on the water! Whether you’re a total beginner or looking to refine your skills, this experience is designed for you by the school and your discussions with the instructor.

Beginner Sailors – If you’ve never sailed before, this is the perfect way to start! Learn in a relaxed, hands-on environment while exploring beautiful destinations.

Adventurous Travelers – If you love travel, the ocean, and unique experiences, why just stay on the beach when you can sail to hidden coves, remote islands, and breathtaking coastal towns?

Busy Professionals & Families – Turn your vacation into an unforgettable learning experience! Learn to sail while enjoying a getaway with family or friends—it’s a vacation and a skill-building experience in one.

Aspiring Sailors & Future Boat Owners – If you’ve always dreamed of owning or chartering a boat, a Learn to Sail Vacation gives you real-world experience and the certifications you need to sail confidently.

Couples & Groups – Share the adventure! Whether it’s a romantic escape or a group trip, learning together makes the experience even more memorable.

No matter your experience level, you’ll be learning from professional ASA instructors while sailing in paradise—and with free online prep courses, you can start your journey today! Ask the school about getting a head start on your sailing education.

How to Book a Learn to Sail Vacation

Choose a Program

 Visit American Sailing Vacations to explore available destinations and courses

Enroll in an American Sailing Course

 Some vacations require prior certifications, while others cater to beginners.

Join a Flotilla or Training Charter

Some programs include group sailing experiences where students learn alongside others.

Book Through an ASA-Affiliated School

 Many sailing schools partner with vacation charters to offer structured learning trips.

Here’s a sample of a Weeklong Learn-to-Sail Vacation Itinerary in Corfu, Greece, where participants can earn their ASA 101, 103, or 104 certifications while exploring the stunning Ionian waters. 

(This itinerary is only provided as an example and your course and instruction will differ from this example.)


Day 1: Arrival & Introduction (Mandraki Marina, Corfu)

  • Afternoon: Arrive at Mandraki Marina, located within the historic Old Venetian Fortress of Corfu Town. Check-in, meet your instructor and fellow sailors, and get settled aboard your yacht.

  • Evening: Welcome briefing covering the week’s itinerary, boat orientation, and safety procedures. Explore Corfu Old Town, a UNESCO World Heritage site, followed by a traditional Greek dinner at a local taverna.

  • Topics Covered: Sailing basics, terminology, parts of a sailboat, safety procedures.


Day 2: Corfu to Petriti

  • Morning: Begin ASA 101 coursework with a dockside session at Mandraki Marina. Learn basic sailing theory, sail handling, points of sail, and knots.

  • Midday: Set sail south along the Corfu coastline to Petriti, a charming fishing village (~12 NM).

  • Afternoon: Hands-on training: steering, sail trimming, tacking, and jibing.

  • Evening: Dock at Petriti and enjoy fresh seafood at a waterfront taverna.

  • Topics Covered: Boat handling, sail trim, basic navigation, crew roles.


Day 3: Petriti to Lakka, Paxos 

  • Morning: Review ASA 101 material and complete the practical assessment.

  • Midday: Set sail to Lakka on Paxos Island (~15 NM), practicing coastal navigation and anchoring techniques.

  • Afternoon: ASA 103 introduction—chart reading, tide/wind awareness, and docking procedures.

  • Evening: Explore Lakka, swim in the turquoise waters, and have dinner at a taverna overlooking the bay.

  • Topics Covered: Navigation, tides and currents, docking, anchoring.


Day 4: Lakka to Gaios, Paxos 

  • Morning: Sail from Lakka to Gaios, Paxos’ main port (~7 NM), refining docking skills and sail trim adjustments.

  • Midday: Advanced coastal navigation training, including buoyage, charts, and electronic navigation tools.

  • Afternoon: Anchoring drills in one of the secluded bays near Gaios, followed by a man-overboard drill.

  • Evening: Free time to explore Gaios, known for its Venetian architecture and lively atmosphere.

  • Topics Covered: Weather interpretation, navigation rules, emergency procedures.


Day 5: Gaios to Parga 

  • Morning: ASA 103 practical and written exam.

  • Midday: Set sail to Parga on the Greek mainland (~14 NM), practicing navigation techniques and sail trim.

  • Afternoon: ASA 104 introduction, covering advanced sail controls, sail reefing, and heaving-to techniques.

  • Evening: Explore Parga’s colorful waterfront and historic Venetian Castle before dinner at a seaside taverna.

  • Topics Covered: Advanced sail trim, heaving-to, reefing, docking in varying conditions.


Day 6: Parga to Sivota 

  • Morning: Sail from Parga to Sivota, a picturesque bay (~10 NM). Focus on skipper responsibilities, passage planning, and crew management.

  • Midday: Simulated bareboat charter scenario where students take turns as skipper, plotting the route and making navigational decisions.

  • Afternoon: Mooring and Mediterranean-style docking techniques in Sivota.

  • Evening: Sunset celebration and discussion on bareboat cruising best practices over dinner.

  • Topics Covered: Advanced passage planning, navigation, mooring techniques, provisioning.


Day 7: Sivota to Corfu 

  • Morning: ASA 104 practical and written exam.

  • Midday: Sail back to Mandraki Marina, Corfu (~18 NM), practicing advanced navigation, sail handling, and docking skills.

  • Afternoon: Graduation ceremony and debrief.

  • Evening: Farewell dinner in Corfu Town, celebrating newfound skills and friendships!


Trip Summary & Possible Certifications Earned

  • ASA 101: Basic Keelboat Sailing

  • ASA 103: Basic Coastal Cruising 

  • ASA 104: Bareboat Cruising 

This itinerary balances sailing education, hands-on training, and cultural experiences, making it an unforgettable way to earn your ASA certifications while exploring one of the most breathtaking sailing destinations in the world!

Looking for a Sailing Vacation?

We can help