Urban Oasis

Dragonfly 36 Training & Adventure Sailing

Private, hands-on Dragonfly 36 instruction for owners and prospective owners, from focused demonstration sails to full-day training and multi-day adventure passages.

Download the Full Details

Urban Oasis

Dragonfly 36 Training & Adventure Sailing

Private, hands-on Dragonfly 36 instruction for owners and prospective owners, from focused demonstration sails to full-day training and multi-day adventure passages.

Download the Full Details

Urban Oasis

Dragonfly 36 Training & Adventure Sailing

Private, hands-on Dragonfly 36 instruction for owners and prospective owners, from focused demonstration sails to full-day training and multi-day adventure passages.

Download the Full Details

Who This Training Is For

  • New Dragonfly 36 owners seeking a thorough orientation to their boat

  • Prospective owners evaluating performance, handling, comfort, and the folding system

  • Experienced sailors transitioning to a high-performance trimaran

  • Owners preparing for coastal cruising, offshore passages, or racing

  • Private groups seeking a tailored sailing and adventure program

What You'll Learn

  • Folding, deployment, and Dragonfly-specific operating procedures

  • Close-quarters handling, docking, maneuvering, and anchoring

  • Sail trim, balance, performance sailing, and racing techniques

  • Onboard systems, routine maintenance, and owner best practices

  • Safety procedures, heavy-weather preparation, and seamanship

  • Coastal and offshore navigation, weather, routing, and passage planning

What's Included

  • Private instruction aboard a Dragonfly 36

  • A training plan tailored to your experience and goals

  • Hands-on operation of the boat and its systems

  • Owner orientation, performance coaching, or passage instruction

  • Seasonal programs in Cape Cod with additional regions in development

Program Options

Dragonfly Demonstration Sail: A focused sail for prospective owners who want to experience the Dragonfly 36’s performance, handling, comfort, and folding system. $750.

Full-Day Dragonfly Training: Seven to eight hours of customized, hands-on instruction for up to six participants. Topics can include folding and deployment, docking, sail trim, systems, maintenance, safety, navigation, passage planning, and racing. $2,100 per day.

Multi-Day Adventure & Training Passages: Combine practical instruction with an immersive coastal or offshore itinerary. Programs are tailored to conditions, experience, and destination. From $3,100 per 24-hour day.

Locations & Availability

Cape Cod, Massachusetts: Available July 5–September 30 annually. Programs operate from Hyannis Yacht Club.

Annapolis, Maryland: October annually. Details and dates are coming soon.

Florida, Bahamas & U.S. Virgin Islands: Winter annually. Details and dates are coming soon.

Adventure Itineraries

  • Cape Cod circumnavigation — approximately 5 days

  • Nantucket, Martha’s Vineyard, and the Elizabeth Islands — approximately 3 days

  • Newport and Block Island — approximately 3 days

  • Nantucket or Martha’s Vineyard getaway — approximately 2 days

  • Maine and Acadia — approximately 7 days

  • Custom itineraries based on your goals, schedule, and conditions

Booking Details

Capacity:

Private & Small-Group Programs

Duration:

Demonstration Sail to Multi-Day Passage

Boat Models:

Dragonfly 36

Location:

Cape Cod; Annapolis and Caribbean programs coming soon

Contact us

Book Your Training

Share a few details about your experience and what you’d like to learn, and we’ll reach out with next steps.

Contact us

Book Your Training

Share a few details about your experience and what you’d like to learn, and we’ll reach out with next steps.

Contact us

Book Your Training

Share a few details about your experience and what you’d like to learn, and we’ll reach out with next steps.