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Careers at Gone Sailing Adventures

Join Toronto's Premier Sailing Charter Company

At Gone Sailing Adventures, we’re more than a sailing company — we’re memory-makers, experience creators, and ambassadors of Toronto’s waterfront. Our team delivers unforgettable corporate events, private celebrations, daily scheduled sails, and specialty experiences like Wine & Cheese Sails, Full Moon Sails, and Sunday Brunch cruises.

If you thrive in a dynamic, outdoor environment and love creating exceptional guest experiences, we want to hear from you.

Why Work With Us

Work on the Water

Your office is the Toronto waterfront — one of the city's most beautiful locations. Trade fluorescent lights for sunshine, lake breezes, and stunning skyline views from 9:00 AM to midnight.

Premium Experiences

We don't just offer boat rides. We deliver high-end, customized sailing experiences for corporate teams, private celebrations, public ticketed events, and first-time sailors. Every guest interaction matters.

Professional Growth

Join experienced sailing captains with 10–50 years on the water. Learn seamanship, customer service excellence, and the art of creating transformative experiences — from intimate marriage proposals to corporate team-building events for 40+ people.

Seasonal Flexibility

Our season runs from April to October, offering full-time and part-time opportunities that work around your schedule, perfect for students, seasonal workers, or sailing enthusiasts.

Open Positions

Customer Service Representative (Dock Kiosk + Sales)

Be the first face guests see at Toronto’s waterfront

You’ll welcome walk-up guests at our dockside kiosk, convert inquiries into bookings, and close corporate event sales through phone, email, and social channels. This isn’t order-taking — it’s consultative sales for premium sailing experiences.

What You’ll Do:
  • Greet waterfront visitors and book same-day sailing experiences (daily scheduled sails, specialty events)
  • Handle inbound sales inquiries for private charters, corporate team-building events, and special occasions
  • Convert corporate leads by understanding their team dynamics and recommending the right yacht experience
  • Sell public ticketed events: Wine & Cheese Sails, Full Moon Sails, Sunday Brunch, and seasonal specials
  • Upsell thoughtfully: premium time slots, extended durations, catering add-ons, merch & swag
  • Support guest check-ins and manage last-minute booking changes
  • Maintain organized lead tracking and follow-up systems
  • Handle merchandise sales at the dock kiosk
Who Thrives Here:
  • 1–3+ years in sales, hospitality, tourism, or brand ambassador roles
  • Comfortable starting conversations with strangers and asking for the sale
  • Strong at handling objections (weather concerns, pricing, timing) with empathy and confidence
  • Detail-oriented with booking systems, payments, and CRM tracking
  • Excellent written and verbal communication (bilingual is an asset)
  • Calm under pressure during peak dock times and able to keep guests feeling cared for
Why This Role is Different:

You’re not selling tickets — you’re selling transformation. Corporate teams who’ve never sailed before. Birthday celebrations that become annual traditions. Couples experiencing sunset sails that lead to marriage proposals. Walk-up tourists who will leave with this being their favourite Toronto memory.

Schedule:

Seasonal (April 27–September 7), part-time to full-time. Weekends, holidays, and peak sailing times (evenings, sunset hours) are priority shifts.

Location:

415 Queens Quay W @ Spadina Wave Deck, Toronto

Apply now

Yacht Crew

Deliver world-class hospitality on the water

As a yacht crew, you’re the energy behind every sailing experience. You’ll welcome guests at the dock, assist with boarding, serve food and beverages, support the captain with sailing operations, and ensure every guest leaves with a story worth telling.

What You’ll Do:
  • Greet guests at the dock and create immediate excitement for their sailing experience
  • Welcome guests for daily scheduled sails, specialty events (Wine & Cheese, Full Moon, Brunch), private charters, and corporate events
  • Assist passengers with boarding and provide safety briefings
  • Support the captain with sail handling, docking, and navigation
  • Deliver food and beverage service with hospitality excellence
    Prepare food as required for catered events and specialty sails
  • Maintain yacht cleanliness and daily detailing standards
  • Promote Gone Sailing Adventures to hotel concierges and waterfront businesses
  • Sell charter experiences and public sail tickets to walk-up guests
  • Handle merchandise sales at the dock
Required Skills:
  • Customer service experience in hospitality, tourism, or events
  • Retail service and cash management experience
  • Comfortable with point-of-sale systems and payment processing
  • Excellent English communication (additional languages an asset)
  • Smart Serve and Safe Food Handler certifications (required)
  • Sailing experience is beneficial but not mandatory — we provide training
Physical Requirements:

Outdoor work in sun, wind, and changing weather. Comfortable on boats and able to assist with boarding, docking, and light physical tasks. Shifts can run from early morning through midnight. Ability to swim is essential.

Schedule:

April–October, 25–40 hours/week. Flexible shifts 8:00 AM–12:00 AM, including weekends and holidays.

Compensation:

Hourly wage + gratuities

Apply now

Large Boat Captain (Transport Canada Licensed)

Lead premium sailing experiences on 38–41′ yachts

Your principal responsibilities are the safety, comfort, and enjoyment of our customers. You’ll captain luxury sailing yachts through Toronto Harbour, the Island lagoons, and Lake Ontario — entertaining guests while delivering smooth, professional sailing operations.

What You’ll Do:
  • Captain yachts (38–41′) with passenger groups ranging from corporate teams to private celebrations to public specialty sails
  • Navigate Toronto Harbour, Toronto Islands, and Lake Ontario waters
  • Entertain guests with engaging commentary about sailing, Toronto’s waterfront history, and seamanship
  • Create memorable experiences for daily scheduled sails, Friday Night Wine & Cheese events, Full Moon Sails, Sunday Brunch cruises, and private charters
  • Lead corporate team-building experiences that foster genuine connection and collaboration
  • Maintain vessel safety standards and Transport Canada compliance
  • Mentor crew and foster a positive team environment
Required Qualifications:
  • Minimum 10 years of sailing experience on comparable vessels (keelboats 35’+)
  • Transport Canada SVOP and related requirements
  • Excellent communication skills in English
  • Deep knowledge of Toronto Harbour navigation and marine weather
  • Proven ability to handle challenging weather and sea conditions
  • Customer entertainment and engagement skills
What Sets Our Captains Apart:

Our captains aren’t just skilled sailors — they’re storytellers, educators, and experience creators who understand that guests need more than a boat ride. You’ll facilitate team bonding, teach sailing basics, host intimate celebrations, and create “wow” moments that clients remember long after they return to shore.

Schedule:

May–October with flexible hours, 7 days/week, 9:00 AM–12:00 AM

  • May-June: 10–20 hours/week (FT), 5–10 hours/week (PT)
  • July-August: 30–40 hours/week (FT), 5–15 hours/week (PT)
  • September–October: 10–20 hours/week (FT), 5–10 hours/week (PT)
Compensation:

Hourly wage + gratuities

Apply now

Small Boat Captain (Transport Canada Licensed)

Captain agile sailing yachts for intimate guest experiences
Your principal responsibilities are the safety, comfort, and enjoyment of our customers. Lead sailing experiences on 22–28′ yachts, navigating Toronto’s waterfront with smaller groups. Perfect for captains who love hands-on sailing and creating personal connections with guests.
What You’ll Do:
  • Captain yachts (22–28′) carrying passengers through Toronto Harbour, Island lagoons, and Lake Ontario
  • Provide engaging, educational sailing experiences for groups of 6–10 guests
  • Entertain guests with stories, sailing instruction, and waterfront history
  • Handle all aspects of vessel operation: navigation, sail handling, and docking
  • Lead daily scheduled sails, specialty events, and private charters
  • Create safe, fun, memorable experiences for first-time sailors
  • Maintain vessel cleanliness and Transport Canada safety standards
Required Qualifications:
  • Minimum 3 years sailing experience on comparable vessels
  • Transport Canada SVOP (Small Vessel Operator Proficiency)
  • Excellent communication skills in English
  • Comfortable teaching basic sailing concepts to beginners
  • Knowledge of Toronto Harbour navigation
  • Customer entertainment and engagement ability
Schedule:

May–October with flexible hours, 7 days/week, 9:00 AM–12:00 AM

  • May-June: 10–20 hours/week (FT), 5–10 hours/week (PT)
  • July-August: 30–40 hours/week (FT), 5–15 hours/week (PT)
  • September–October: 10–20 hours/week (FT), 5–10 hours/week (PT)
Compensation:

Hourly wage + gratuities

Apply now

Social Media Specialist

Tell our story across digital channels
You’ll create compelling visual content that captures the magic of sailing on Lake Ontario. From onboard action shots to behind-the-scenes crew stories, you’ll support the social media manager and turn followers into bookings.
What You’ll Do:
  • Work directly with the Manager and President on the social content calendar and create digital assets across all social media platforms
  • Capture photo and video content on the dock and aboard yachts during sailing experiences
  • Manage programs to create unique and memorable experiences for guests by branding and storing photos and videos
  • Design engaging graphics using Adobe Creative Suite (Photoshop, Illustrator, and After Effects)
  • Create weekly newsletters with updates, promotions, and availability for customers and company members
  • Load customer lists and create a data-driven environment for promotions and network growth
  • Track performance metrics and optimize content strategy
Required Skills & Qualifications:
  • Expertise with graphic design and motion graphics (Adobe Photoshop, Illustrator, After Effects)
  • Video editing skills (a plus)
  • Knowledge and proven experience with social media platforms, including Instagram, Facebook, TikTok, Pintrest, Reddit and LinkedIn
  • Experience creating and managing Google Ads and social media advertising campaigns
  • Photo & Video skills — comfortable shooting in outdoor and marine environments
  • Strong computer skills, including Microsoft Office and Gmail
  • Strong copywriting skills — you can tell a compelling brand story
  • Ability to work in a fast-paced environment and go above and beyond to meet deadlines
What Makes This Role Unique:

Your “office” alternates between our waterfront location and luxury yachts. You’ll capture real guest experiences — from corporate team-building challenges to romantic sunset proposals to Wine & Cheese events — and create content that showcases one of Toronto’s most unique activities.

Customer Service Component:

This role includes in-office work AND on-board time on luxury yachts where customer service and photography skills come together to create exceptional guest experiences and branded content.

Schedule:

Flexible hours, primarily April–October (peak season), with off-season content planning and strategy work.

Compensation:

Hourly wage + gratuities

Apply now

How to Apply

We want to hear from you. To apply for any position, click the Apply Now button below or email us atoffice.manager@gosailto.com or call 416-240-0202.

Your Application Must Include:
  1. Email Subject Line:
     “Application: [Position Name] – [Your Name]”

  2. Email Body (200 words maximum – NO MORE):
    • Indicate your qualifications for the position in less than 200 words
    • For sailing positions: Provide boat size/type/position held/years/location
    • For guest-facing roles: Share your proudest customer service or sales story
    • Why this role fits you

  3. Resume (1 PAGE ONLY):
    • Employment history: company/position/date/responsibilities
    • PAGE 2 WILL NOT BE READ! Make page 1 count.

  4. A Photo That Captures Your Personality: We’re looking for people who bring energy, authenticity, and passion to guest experiences. Show us who you are.

Our Standards

Safety First

We operate fully licensed, Transport Canada-certified yachts with comprehensive risk management protocols. Every crew member is trained in safety procedures, emergency response, and guest care. We maintain the highest standards required by Transport Canada and the Alcohol & Gaming Commission of Ontario.

Professionalism

We serve corporate clients from companies like Shell Oil, engineering firms, and professional services organizations, alongside daily public guests, private celebrations, and specialty event attendees. Our crew maintains the highest standards of hospitality and professionalism across all experiences.

Experience Creation

We don't just take people sailing — we create transformative experiences. First-time sailors discover a new passion at our daily scheduled sails. Corporate teams build genuine connections through custom team-building challenges. Couples celebrate engagements during sunset charters. Friends create traditions at our Wine & Cheese Sails and Full Moon experiences.

Our Services

We offer diverse sailing experiences across our Transport Canada-certified fleet:

Public Shared Sails:
  • Daily scheduled sailing experiences
  • Wine & Cheese Sails
  • Full Moon Sails
  • Sunday Brunch cruises
  • Seasonal specialty events
Private Events:
  • Corporate team-building and client meetings
  • Bachelor/Bachelorette celebrations
  • Birthday parties and anniversaries
  • Marriage proposals
  • Weddings and ash scatterings
  • Any reason you can think of
Educational Programs:
  • Sailing lessons and certification courses
  • Private instruction
  • Group sailing education

Frequently Asked Questions

Do I need sailing experience?

Not for all positions. Yacht Crew, Customer Service Representative and Social Media Specialist roles welcome non-sailors with strong hospitality and service skills. Captain positions require significant sailing experience and Transport Canada licensing (or ability to obtain with our support).

Yes. We support crew members who want to develop sailing skills and assist qualified captain applicants with Transport Canada licensing requirements. Training and licensing support is  provided by GSA for eligible candidates.

Our season runs April through October, with peak demand July/August. Schedules vary by position but typically include weekends, holidays, and evening shifts during prime sailing hours (9:00 AM–12:00 AM). Daily scheduled sails, specialty evening events (Wine & Cheese, Full Moon), and private charters mean flexible availability is essential.

Yes. All positions involve working on the waterfront in varying weather conditions — sun, wind, rain. You must be comfortable working outdoors throughout the sailing season.

We focus on both premium corporate team-building experiences AND accessible public sailing events — not mass-market tourism. Whether hosting a Shell Oil corporate retreat with 40 guests, a Wine & Cheese Sail, or an intimate marriage proposal at sunset, we create experiences people remember. You’ll be part of those stories.

Our calendar includes regular public ticketed experiences and special sails like Wine & Cheese Sails, Full Moon Sails, Sunday Brunch cruises, and seasonal specialty events — in addition to daily scheduled sails and private charters.

When we find the right people. Strong applicants who follow instructions (200 words, 1-page resume, personality photo) get priority consideration.

Our Location

415 Queens Quay W @ Spadina Wave Deck
Toronto, Ontario M5V 1A2

Steps from downtown Toronto, Union Station, and the Financial District. Easily accessible by TTC, GO Transit, or waterfront bike paths. Working location is directly on Toronto’s waterfront at the Spadina Wave Deck.

Our Partners & Credentials

Gone Sailing Adventures is proud to be associated with premier organizations representing the best in the business:

  • Transport Canada Safety Certified Yachts — Our entire fleet meets federal safety standards
  • Licensed by Alcohol & Gaming Commission of Ontario — Full licensing for beverage service
  • Toronto Harbour Authority — Authorized waterfront operator
  • Destination Toronto — Official tourism partner

Gone Sailing Adventures is an equal opportunity employer. We celebrate diversity and are committed to creating an inclusive environment for all employees.

Join Our Crew

Ready to create experiences people remember for years — from corporate breakthroughs to romantic proposals to friends sharing wine and cheese under the stars?

Let’s talk.

📧 info@gosailto.com
 📞 416-240-0202
 📍 415 Queens Quay W @ Spadina Wave Deck, Toronto

Apply Now – Send your 200-word introduction, 1-page resume, and a photo that shows your personality.

Operating April through October on Toronto’s waterfront. Licensed, certified, and trusted by Toronto’s leading corporations and thousands of satisfied guests since our founding.

Apply For A Job

YOUR SAFETY IS AT RISK

When considering chartering a yacht in Canada, we know you have many options. Some of these options look super exciting and at ridiculously great prices. Recent trends in the industry have opened the door for many unqualified individuals to purchase boats and offer charter services to the unsuspecting public. It’s easy to create a website and even easier to just list a boat on sites such as Facebook Marketplace, Kijiji, Getmyboat, Boat Setter and many others.

Unfortunately, many of these operators are NOT licensed, insured or qualified to accept your trust on the water.

In order to be licensed and insured a number of items MUST be in place. Listed are just a few.

  • The operator must be licensed by Transport Canada with a commercial license known as either:
    – Limited Master under 60tonne.
    – Small Vessel Operators Permit (SVOP).
  • The name of the vessel must be visible on the stern (back) or the registration number beginning with the letter “C” must be visible on the side of the vessel near the front. Boats with a registration number beginning with “ON” are not licensed for passengers.
  • If the vessel is under 12m (40’) it should participate in the Transport Canada Small Vessel Compliance Program and display a “Blue Decal” and have corresponding certificate.
  • If the vessel is over 12m (40’) or carries more than 12 passengers, it MUST BE INSPECTED by Transport Canada and have an inspection certificate on board.
  • All vessels must have commercial liability insurance and coverage specifically for the number of passengers approved to be carried on board.
  • The vessel must comply with commercial safety requirements beyond recreational standards. Many of these illegal operators do not have the proper training, carry proper safety equipment, nor do their recreational boats meet the design/construction requirements of a commercial, passenger carrying vessel. These illegal operators try to stay under the radar of Police/OPP/RCMP/Transport Canada by:
  • hiding the name of their vessel by hanging items over the stern
  • not letting you know where they will have you board until just before the start of your charter.
  • pick you up at a public park (where docking is not permitted).
  • suggest to you that you are friends of the owner/operator out for a ride and not a paying customer.
  • allow you to drink alcohol while the boat is underway (illegal-same as a car) but tell you to hide your bottles etc.
  • insist on a cash transaction or part of it as a way of defrauding the internet listing company.
  • Make you sign a “Charter Agreement” just before you board without giving you details of the document beforehand.

    Over the last few years there have been a number of deaths and even more accidents resulting from these types of operators. Be safe and know who you are getting on a boat with. All licensed operators should willingly display their credentials, and most are members of the Passenger & Commercial Vessel Association (PCVA).

    Link to Global News Report on Charter Accidents

Check before you book
&
Know before you Go!