Employment | Sailing Jobs

Sailing jobs aboard our boats or shoreside may be one of the coolest jobs you’ll ever have.

With plenty of sailing jobs of all sorts, spectacular sailing, legendary history and a beautiful harbor and bay, Newport is considered by many to be the sailing capital of the world.

You will not find a better place to sail, or a prettier, more historic town, full of mansions, beautiful beaches, spectacular scenery, fantastic festivals and world class entertainment.

Jobs available for 2024 include Captains, Crew and Reservations/Ticketing Staff. Watch our Aquidneck Crew Overview Video below. 

Sightsailing was founded in 1990 and since then, we’ve taken thousands sailing. We are the oldest, locally owned company offering public sails and private sailing charters in Newport.

We are passionate about giving our guests a terrific experience.  We like to say that we are in the sailing business as well as the hospitality business, so we look for people who are friendly and derive satisfaction from providing guests a positive experience. We often hear from many of our guests that their sailing cruise with us was the highlight of their time in Newport.

We seek to employ enthusiastic, hardworking, reliable and organized individuals who will represent Sightsailing and themselves well.  Great attitudes, good work ethics, and a friendly personality are a must when working with the public and teammates.

Staff for all positions have a variety of work experiences, but work in theater, hospitality, restaurant, bartending, outdoor activities, boating, sales, front of house, are all great backgrounds.

For boat crew positions, sailing experience is a definite plus, but we’ll take someone who may lack experience but makes up for it with a positive, sunny disposition and a strong desire to learn.

We invite you to consider the challenge of working in an outdoor environment as part of a team. Our positions require professionalism and commitment, yet offer a terrific learning experience, fun and recreation, friendships that often last a lifetime and a valuable work experience.

Job Descriptions & Applications

Job Descriptions and Online Applications are in the sections below. All applicants for all positions should submit a complete Online Application. If you have a resume, you can substitute that for the work experience section of the application.

We accept applications year-round.  We generally do the majority of our hiring in the late winter and Spring and continue to interview until positions are full.   We encourage you to apply early! An in-person, Skype or Facetime interview is required for all positions.

If you’re applying for crew on Aquidneck, take a look at our Crew Employment Overview video for Aquidneck below! You don’t have to be a rockstar sailor but having some experience helps!




Retail Ticket Sales & Reservations Specialist

Job Description:

These positions are at our open-air pavilion on Bowen's Wharf. Because we're located in a high pedestrian traffic area and easily accessible, a good amount of business comes from people who walk by, stop and are curious about what we offer.

Being able to engage in a friendly, helpful manner and explain and educate potential customers about our boats and sailing options is an everyday and large part of the job. Prospective customers often book a sailing cruise on impulse, based on your helpful conversation with them.

Other responsibilities:

Responding to email inquiries.

Managing & answering phone inquiries.

Checking in guests.

Operating a cash register including balancing a cash drawer and completing End of Day Reports.

Help stock food and drink and inventory supplies.

Run errands to bank or local stores.

Assist with occasional social media and administrative tasks.

Preferred Qualities:

It's great if you're an outgoing, energetic, organized individual who has some knowledge of Newport and who can cheerfully engage with people and offer helpful information about our sailing experiences. Essentially, you're educating people about our sails and boats and are an ambassador to Newport and sailing.

It's important to be alert, have good written and verbal communication skills, and have excellent attention to detail.

Like any job, it's essential that you are punctual and reliable.  Familiarity with cash registers and closing procedures a plus.  Additional marketing skills a plus.

*Prior sales, retail, restaurant, hospitality, customer service, or administrative experience helpful.

Ticket/Reservations Staff Required Availability:

We hire front desk staff that can commit to the entire season (May-October) AND  students returning to school in the fall. If you're a student, you need to be able to commit to working through Labor Day and ideally still work 1-2 shifts per week through the end of October.

Ticket/Reservations staff work a variety of opening, swing, and closing shifts. You should be flexible in your availability, a team player, and able to work weekends and holidays.  We're a seasonal business so we can't always give you two or three weeks off during the height of the season! Our dockside office is open 7 days a week.

Appearance & Dress Code:

Our Appearance, Hygiene and Dress Code standards are similar to many upscale, service-oriented businesses. They have been established to present the image of an approachable, friendly, and professional staff.

We will give you company shirts, outerwear and assorted swag to wear which must be worn while working. Excessive piercing or hairstyles of a fad nature are not permitted.  Additional dress and appearance codes are spelled out in our company handbook.


You get to work with a super friendly, smart and fun staff, can go sailing when you're off, and will have one of the best views in town! Above average wages, plus ticket commissions and bonuses. Food and drink employee gatherings.


Job Description:

Crew have the largest impact on our guests' experience. We like to say that we're in the hospitality business as well as the sailing business, so we like to hire crew who are welcoming, cheerful, make a nice impression, enjoy engaging with guests and derive satisfaction from helping give guests an enjoyable experience. Maintaining a positive can-do attitude even in the face of adversity is huge.

Newport has one of the prettiest harbors in the world and is the sailing capital of the world.  Many of the people we take sailing have never sailed before. Being able to point out sights, talk with guests and help provide a positive experience is vital. We want guests to come back again, write a great review online, or rave to the concierge at the hotel what a great time they had! You don't have to be a superstar sailor but having some sailing knowledge and experience is definitely helpful.

While these jobs are fun, offer a great learning experience, and allow you to make some good money, they are also physically demanding.  We take out scores of people and offer 4-5 trips a day. You'll be hauling up and lowering sails, casting off dock lines, pouring champagne, tacking and gybing and restocking coolers, etc. Add up setup/breakdown time and at the peak of the season it's a long day.  You need the energy and endurance for that.

For the right individuals, these jobs are a lot of fun. It can be hard work however you get paid to meet people from all over the world, show them a good time, hone your sailing skills and sail all day in the sailing capital of the world! If you're interested in becoming a licensed captain and would like to commit to working here, we can help you with that too.


*  Learn about the sights we sail by and be able to speak about them casually. Ability to project voice and address large groups. Interact with guests, engage in casual conversation.

*  Willingness to take direction and initiative, get one's hands dirty, jump willingly into tasks and demonstrate a desire to learn.

* Prepare Aquidneck or Sightsailer for sailing each day including cleaning decks, stocking coolers, sail handling, organizing stowing supplies, etc.

• Ensure guests safely embark and disembark vessel.

• Take active role in sailing vessel including raising, trimming, flaking sails, taking helm etc. Pay attention to sail trim. Demonstrate awareness of what's happening both on boat and vessels nearby.

• Load and unload food and drink for private charters.  Serve drinks on sunset cruises. Stow beverages in coolers.

*Put boat to bed after sailing.

• Assist in performing daily, weekly and monthly safety, & maintenance tasks.

Crew Required Availability by Boat:

We hire crew for Aquidneck, our 80' schooner and Sightsailer our 46' sloop.  These are very different boats so we look at different parts of your experience and background, however one of the most important things that will determine whether you're hired is your availability.  We look to hire crew who are available and can commit to a boat's operating season so we don't find ourselves in the unenviable position of trying to find and train someone come mid to late season.

Aquidneck availability requirements:  Ideally, Aquidneck crew should be available to sail from early May through the end of October so crew train and gets started together.  Since we're a seasonal business and very busy at the height of the summer, the crew should not require any large blocks of time off. For instance, cool as it may be, you shouldn't need two weeks off in July and another two in August!  Occasionally we may hire crew who have to leave before the end of the season, but we prefer to have a crew who can commit to the entire season. 

Sightsailer availability requirements: Sightsailer's season is shorter than Aquidneck however you need to be available weekends from late May through mid to late June, then 5 days a week in July and August,  and weekends only again in September. We usually only hire one crew for Sightsailer who sails 5 days per week on the above schedule.

Required Availability both boats: You should be flexible, a team player and be available to work weekdays, weekends and/or holidays. You should not require any long vacations or large blocks of time off.

Physical Requirements: Make sure to watch our Crew Employment Overview video at the top of the Employment section.  Crew positions on Aquidneck require heavy lifting and physical labor.   Due to the size of her sails crewing on Aquidneck requires a certain amount of strength and stamina. You also need to be agile and surefooted and so you can scramble out on the bowsprit or bow net, have no fear of heights or stability, balance or vertigo issues. Women can do it, but need to be fairly strong and in good condition. Crewing on Sightsailer is much less physically demanding than Aquidneck. You can see videos of Aquidneck and Sightsailer  under sail in the Our Fleet section.

Sailing Experience:  You don't have to be a superstar sailor but having some previous sailing experience and knowledge is definitely helpful. For instance knowing the difference between tacking and gybing, close-hauled and running helps.   If you've got the right availability, sailing experience and personality, you'll be at the top of the list for an interview!


• Pay is very good.  Crew are paid a day rate and also earn tips.  Daily compensation ranges from $225-$350/day.  Many of our crew have spent a season or two as crew and worked their way up to captain.

Appearance/Dress Code & Hygiene Standards:

Our Appearance, Hygiene and Dress Code standards are similar to many upscale, service-oriented businesses. They have been established to present the image of a friendly, professional and hospitality-oriented staff.

We will give you company shirts, outerwear and assorted swag to wear while working. Excessive piercing or hairstyles of a fad nature are not permitted.  You and your clothes must be clean and odor free. No one wants to work or sit next to a stinky crew.  Dress, hygiene and appearance codes are spelled out in our company handbook.

Additional Requirements:

*Crew must pass a Pre-Employment drug test and participate in a mandatory USCG Random Drug Testing Program both of which the company pays for.

*Crew need to adhere to Appearance & Dress Code Standards.

*Since we serve alcohol, you must be over 18.






Job Description & Requirements:

Captains have a large impact on our guests' experience.  We like to hire captains who are friendly, well-spoken, enjoy meeting others, and are good sailors with solid sailing and boat handling skills. It's important to realize that we're in the hospitality business as well the sailing business, so you need to not only like to sail, but also enjoy showing guests our fantastic harbor and bay, talking with them, and being a friendly host.  Many of the people we take sailing have never been sailing before. It's your job to sail the boat well, answer questions and help guests have a nice experience. We want them to write us an excellent review, tell their friends or rave to the concierge at the hotel how great the captain and crew were!

While these jobs are fun, they are physically demanding.  We take out scores of guests and offer four to five sails a day with 20-30 minutes between sails.   You need the energy and stamina for that.

Captains are leaders and mentors for crew and oversee the safety and cleanliness of the vessel.  All captains should take great pride in sail trim, tide, and wind conditions, covering as much ground as possible on trips, and docking in tight quarters.

We currently operate 3 sailing vessels all with different schedules.  Aquidneck is an 80' steel schooner designed by Charles Wittholtz, sailed by one licensed captain and two crew USCG certified for 49.  Sightsailer is a very light, narrow,  46' aluminum sloop with a heap of sail area, designed by Yves Marie Tanton, sailed by one licensed captain and one crew, and certified for 13 guests. Starlight is an O'Day 34 which sails by private charter only with just 2-6 guests.  When applying.  please indicate which boat you think you're interested in.

AQUIDNECK CAPTAINS: Aquidneck, our 80' schooner,  sails with one licensed captain and two crew,  from May until the end of October.   Additional work for handy people who like getting their hands dirty is available in the yard pre and post-season.

We've had Aquidneck captains who sail from May until the end of our season at the end of October and then help down rig the boat and leave for delivery,  and we've had captains who start with us in the yard in March or April and work until Thanksgiving or even later.  Each situation and person are different. The workload is shared between two captains both of whom work around 40 hours per week.

SIGHTSAILER CAPTAINS: Sightsailer sails weekends only from late May until mid-June, then 5 days a week from late June through Labor Day in September. After Labor Day, she sails weekends only until the end of September.  She's sailed by one captain with a Master's license and one crew.  Ideally, the captain and crew should be available from late May through Labor Day and able to sail weekends in September. We usually hire just one captain and crew for Sightsailer.

STARLIGHT CAPTAINS: Starlight, our O'Day 34,  is sailed by one licensed captain. She sails on weekends beginning Memorial Day, seven days a week from late June through Labor Day, and then again on a limited schedule until Columbus Day. We typically hire two captains who work a rotating 4 day/3-day schedule.

All Captains need to have excellent sailing skills as well as outstanding boat-handling skills, docking sailboats under power. Our boats are docked in a congested, high-profile marina surrounded by million-dollar yachts and historic wooden boats.  Aquidneck is 80 feet long with a beam of 17 feet and needs to be consistently backed out of and returned to her slip unscathed as well as without wiping out the ol' wooden Hinckley or Fife at the dock next door. She has a bow thruster but still, you need confidence and experience in tight quarters. Starlight and Sightsailer are easier to handle but your boat handling skills still need to be razor-sharp!

Captains are responsible for performing routine daily, weekly, and monthly maintenance checks.

Captains must learn and adhere to arrival and departure schedules for our boats and others we share the dock with.

Learn the boat, pay attention to sail trim, tides, and current.  Sail the boat well enough that you get it where it needs to go, so you deliver what's described, meet and manage guests' expectations.

Learn the points of interest we sail past so you can help point out sights or answer guests' questions about them. You don't have to talk the entire time, but you shouldn't expect the crew to carry the entire boat to make up for your lack of knowledge.

If sailing on our larger boats with the crew you should enjoy getting to know them, sharing your knowledge, and fostering the camaraderie and mutual respect that will hopefully develop. And if sailing with crew, you are expected to share all work and work side-by-side with them whether it's loading food/drink aboard for a charter or performing maintenance or cleaning tasks.

Appearance/Dress Code & Hygiene Standards:

We will give you company shirts, outerwear and assorted swag to wear which must be worn while working.  You and your clothes must be clean and odor free.  Additional dress, hygiene and appearance codes are spelled out in our company handbook.

Licensing Requirements:

All captains must pass a Pre-Employment drug test (or show proof of having been tested within the past 180 days)  and be enrolled in an industry-required Random Drug Testing Program.

Aquidneck: USCG Master's License, Inland or Near Coastal, minimum 50 tons, with Aux Sail endorsement. FCC MROP.

Sightsailer: USCG Master's License, Inland or Near Coastal, minimum 25 tons with Aux Sail endorsement. FCC MROP.


Captains are paid a flat day rate, plus tips when sailing. On Aquidneck & Sightsailer tips are pooled equally with crew. Tips are frequently very good.

For the right individuals, these jobs are a lot of fun. It can be hard work, however, you get paid to sail all day in one of the prettiest, most interesting, and historic harbors with some of the best sailing conditions to be found anywhere,  and meet people from all over the world.  There is no other place like Newport.  And at the end of the day, you're off the boat.  Think about that!

If you have an up-to-date CV or resume you may email it and skip the Employment Experience section of the online application. Please email to sightsailingjobs@gmail.com.