Trip Leader Guidelines

Thank you for agreeing to serve as a Trip or Assistant Trip Leader. This work is very important to the club and we appreciate you willingness to take on this assignment. Your goal is to design, advertise and run a safe, enjoyable trip for our members. The Club has been encouraging people to become cruising sailors for more than forty years. Over those years, the Club has developed procedures to help you stay organized as you move through the process.

This guide for running a Club trip cannot cover every contingency or difficulty. The Trip and Assistant Trip Leaders' experiences must also be used. For this reason, the Club requires that one of the two leaders is a club-qualified skipper, and one must have previously been a Trip/Assistant Trip Leader.

The Annual Meeting

By now you have planned your trip, the board has accepted it and priced it, and you have submitted your draft trip announcement for the Membership Package provided at the Annual Meeting and on our website. Click here for some guidance on preparing your trip announcement. Your next important step is marketing the trip. The Annual Meeting is the first time you will sell your trip to the general membership, and it’s your chance to get early signups.

You will make a presentation about the trip at the Annual Meeting, and depending on the format of that meeting you might be required to set up a physical display.

Roles

As a trip leader or assistant trip leader you will work with various members of the Board of Trustees and its committees to run and promote your trip.

Charter Liaison: The charter liaison handles all communication with the charter company related to boat reservations, payment, and contracts. By centralizing this activity, we have a single point of contact reporting on boat charter status, and we can negotiate some bulk discounts with companies we use frequently. Trip leadership should only communicate with the charter company if the skippers and crews have specific questions about their boats, which might occur within the weeks just before the trip.

Treasurer: The treasurer issues payments for boat charters and other expenses. The trip leader can request the treasurer to pre-pay budgeted expenses on an approved trip (e.g., pre-pay slip fees that are included in the trip price). The treasurer also receives all deposits and other payments from members for trips.

Training Coordinator: In addition to organizing our on land and on water training activites, the training coordinator keeps track of the qualification of our skippers and first mates. A trip leader should always confirm with the training coordinator whether a member who says on their reservation that they are a qualified skipper or first mate really is (these qualifications can lapse). In addition, the training coordinator might contact the trip leader about arranging a checkout for a skipper or first mate candidate during your trip.

Information Management

Starting in 2020, TSC adopted use of Google Drive (g-drive) for storage of current and historic Club files. There is a g-drive folder for each trip. Trip leaders and assistant trip leaders are granted edit access to their trip’s folder. If you do not receive notification of that access, contact the Commodore to receive it.

All of your trip artifacts should be stored in this folder (and you can create sub-folders for better organization). By the time a trip is complete, its typical set of documents includes:

  • Planning notes (optional)

  • Trip Proposal

  • Trip Announcement

  • Annual Meeting Presentation (typically a slide deck)

  • Trip Accounting and Reconciliation workbook

  • Crew List

  • Pre-Trip Meeting Information, which includes the itinerary.

  • Trip memento information (optional)

  • Trip Report

  • Boat COCIs (Check Out/Check In) forms completed by each skipper

  • Photos

Preliminary Phase

Preliminary trip management starts in the pre-season (Winter of the previous year) and includes specific location selection, planning basic basic itinerary, slip and mooring reservations, restaurant plans, etc. Most of this should have been started during trip planning and included in your trip announcement. Also during this phase, presentations for the Annual Meeting are prepared and delivered.

Trip Pricing

During the pre-season, the Board of Trustees establishes trip prices based on many factors, not just the direct costs for your trip. It is important to remember that unless a specific item was budgeted for (e.g. slip fees), the club cannot provide reimbursement, except in special circumstances, as approved by the Commodore and the Treasurer.

Trip pricing policies are standardized as described in the annual trip package. If the charter company cancellation policy, or the cost of the trip support changes to the standard policies, the trip leader must include these in their trip proposal.

Reservations

If you plan on staying in marinas or taking moorings in busy harbors, it’s not too soon to contact those harbors to make reservations. If you are including this in the price of the trip, then you likely already researched marinas and harbors in order to estimate this cost. In the US, many marinas now use on-line reservation systems like Dockwa. You typically have to know the size of the boats to make reservations. Once the charter liaison has reserved your boats, visit the websites of marinas where you want to stay and find out how they handle reservations. Some require a deposit, some require full pre-payment. In most cases, electrical hookup will not be included and must be paid at the time of your visit.

If your trip has been priced to include this cost, then you can likely have the treasurer prepay directly once you receive an invoice. If each crew will be paying, then you will need to pay any up-front fees out of pocket, and collect them from each boat’s crew when the trip is running. Do not ask the treasurer to pay any costs that have not been included in the trip price.

Enrollment Phase

Enrolling people on your trip officially starts at the Annual Meeting. You might have talked it up before then, but that is when trips open for reservations. The enrollment process is the result of years of refinement and is designed to be as fair as possible to all members.

Sign-up

The Lottery

The sign-up lottery is conducted two weeks after the Annual Meeting. This two week period allows members to review the trip package, decide on trips, and submit their reservations to trip leaders.

All applications received by the designated date are to be drawn in a random order, regardless of possible status of skipper, first mate, or crew (Trip Leader, Assistant Trip Leader, and their companions are assumed to be going and not included in the drawing). To be included in the lottery, a member must submit a Reservation/Release Form and a check covering the deposit for all spaces desired on the boat (Membership is required to participate in a trip, but is not required for inclusion in the lottery — you will confirm membership when you are confirming people). For the lottery, draw couples and family groups as one, but list each individual separately. Each person takes up a spot on the trip.

Shortly following the random draw, the share the preliminary participants list (including waitlist, if any) with the skippers who were selected in the lottery or are on the waitlist. If any potential participant listed anyone they prefer not to sail with, include that information as well. Poll the skippers to determine if there any potential participants the skipper would not sail with. If no skipper will agree to sail with an individual picked in the random draw (as potential participant or waitlisted), then do not confirm nor waitlist that individual. Next steps are covered in The List.

Qualified skippers who want to reserve an entire boat must first contact the Trip Leader to confirm boat availability. Reservations as described above must be submitted for all members of that skipper’s party prior to the lottery.

The List

The purpose of the lottery is to determine the order of priority for everyone who is not the TL, ATL, or their guests. Make a numbered list, with the TL and ATL as numbers one and two, and their guests in order after that. Next list the rest of the reserved sailors in order of the drawing. Note ranks (skipper, first mate, crew) with the names. Be sure to keep couples together. Put any individual determined by the skippers to be unqualified to participate on a separate list.

Determine number of confirmable people

If you are blessed with more reservations than you have available space, start a wait list. If you are blessed with six or more extra people, contact the Charter Liaison about adding a boat.

For each boat-full of people (generally six), you must have a skipper and a first mate. The TL or ATL (whichever is a skipper) is your first skipper. If no Club qualified first mate is in the first six names, but there is one or more further down, promote the first one up to position six. This represents a group of participants you can confirm. Note that these people may not ultimately sail together.

Continue down the list. If there are no skippers or first mates in positions seven through twelve, find the next person of each rank and promote them up to eleven and twelve. Now you have two boats-worth of participants.

When you have fewer than six people on your list, those remaining become the waiting list. It is particularly important to retain the record of their order from the lottery.

It is desirable to have more skippers and first mates than boats, because these people can drop out just like anyone else. It is fine if several skippers and first mates are in your confirmable group. Skippers can and do sail together — with only one as the official skipper. Boats often have multiple first mates. There is a Club procedure for using a Provisional First Mate (contact the training coordinator). The Club does not allow anyone who is not a Club qualified skipper to be a skipper on a Club trip.

Membership

Verify membership status for the current season of everyone on your confirmable list by contacting the membership secretary. If you received membership forms and checks along with reservations, send the forms to the membership secretary and the checks to the treasurer with your trip checks (more on that later).

Send Confirmation Emails

Send an email to each person who submitted a reservation conveying their status from among the four options. If any of the confirmed participants are not current members, remind them that they must join and include a link to the membership form. Use the language provided here to describe their status:

  • Confirmed: You are a confirmed participant. When boat and crew assignments have been made, you will be sent a copy of the crew list.

  • Wait-listed until additional crew and/or skippers sign up: There is still space on the trip, but additional crew and/or skippers are needed before further boat and crew assignments can be made.

  • Wait-listed on a full trip: As of the day your reservation form was received, the trip was full. The Trip Leader will keep you advised of any changes in this status. Reservation checks will not be deposited until you are confirmed on the trip.

  • Not participating on the trip: The Trip Leader and skippers have determined that you are not able to be accommodated on the trip. Your reservation deposit check will be returned. 

Return the reservations and deposit checks, and membership form and check if sent to you, for anyone in the fourth category.

Checkouts

The training coordinator might contact you about including an evaluation for a candidate skipper or first mate on your trip. Sometimes the candidate will also contact you. Candidates may need to sail with specific skippers to get the desired evaluation, and you should note this in your records to be included in the skipper’s meeting discussions. No candidate is guaranteed an evaluation on a specific trip, it serves everyone for you to try to accommodate it.

Wait List

When one confirmed participant cancels, the first person on the wait can be confirmed. If the first person on the wait list is part of a couple. Then you go to the first individual on the wait list and offer them the spot. If you have only a couple on the wait list, you can choose to offer them the single spot—perhaps one of them will want the other to go. Be sure to verify the new participant’s membership status. They must become a member before you can confirm them.

Minors

Minor children are welcome on Club trips as long as they are accompanied by an adult. The minor must be accompanied by their parent/legal guardian(s) on the same boat. The adult(s) and child are treated as any other couple or family group in the lottery and wait list process.

All members of a crew must agree to the presence on their boat of a minor. It’s best to find this out as early as possible. After the lottery, ask all participants (including those on the wait list) if they object to sailing with a minor, identifying the adult who who is bringing the youngster. If any participant says they do not want to sail with a minor, note it along with other preferences for the use of the skippers during the skippers meeting.

When accepting additional reservations, ask each new person their preference, even if they are going on the wait list.

Note that minors pay the full price of the trip unless they will share a berth with their sponsoring adult. Most cabins on the boats we charter contain two berths. An adult and child sharing a cabin means the child is occupying a berth and must pay full price.

Accounting

The Club’s trip Accounting and Reconciliation spreadsheet is a useful tool for ensuring you’ve received all expected payments. This might seem simple, but you must take into account membership payments that you received, skipper, trip leader, and assistant trip leader discounts, late fees, cancellation fees, and gift certificates. The spreadsheet includes formulae for all this. Google sheet. MS Excel sheet.

Enforce late payment fees. Your trip has a payment schedule described in the trip announcement. It is courteous, but not required, to remind your confirmed participants of an upcoming payment due date. When a participant misses a payment deadline, ask them to include the $10 late charge with their payment when they do send it.

Make a Deposit

Only deposit payments from confirmed participants. It is wise to deposit confirmed participant’s deposits fairly soon after confirming them. For later payments, you may want to hold until you have all expected payments in hand. Do not send the treasurer single and even a few checks at a time. Each deposit requires the following:

  • Complete the accounting for these participants on the A&R form.

  • Two sets of copies of all checks in the deposit. One is for you, one goes to the treasurer. This helps confirm that all checks are in the envelope (and not still sitting on the printer glass).

  • Mail the checks, a photocopy of them, and a copy of the up-to-date A&R form with the amount being submitted clearly indicated. Alternatively, create a deposit sheet listing the following:

    • First Name

    • Last Name

    • Payment type

    • Check number

    • Amount

    • Total on the amount column. The A&R worksheet includes a tab with a deposit sheet template.

Cancellation

Most trips follow the Club’s standard cancellation policy: if a confirmed participant notifies you of a need to cancel, that person may be entitled to some refund. For most trips, full refunds are given for cancellations made 30 days or more before the trip departure date. Cancellations less than 30 days before the trip, when no replacement is found, are not refundable, regardless of reason, even medical. There is a $25.00 cancellation penalty when a replacement is found. Refunds (minus any applicable fees) may be paid to participants at any time mutually agreed upon by the trip leader and Treasurer. This is usually after the trip has completed.

Some trips have different cancellation policies, which are described in the trip announcement. Know your trip’s refund policy.

A cancelling participant does not have the right to pick their replacement unless the wait list is empty.

Replacing someone who cancels is done from the wait-list, if any. If the cancellation was a skipper or first mate, the next skipper/first mate on the list is elevated to confirmed status; otherwise the next name on the list is then confirmed on the trip.

If a skipper cancels, and no more skippers are signed up, then the last five people on the confirmed (or a number equivalent to one boat, not including a skipper) are notified that they may be returned to the wait list due to lack of sufficient crew.

Make every effort to recruit another skipper for your trip. Even those who declined earlier might have changed plans and be able to come aboard. If, after a few days, you are unable to recruit another skipper, move the identified crew to the wait list and let them know. Do not immediately return any payments they’ve made—the situation could change again.

If someone cancels less than 30 days before the trip departure date and no replacement is available, he or she will also be required to pay any additional fees and charges that cannot be canceled prior to the trip in addition to forfeiting all trip fees paid to date. For trips that require a more stable crew list, stricter refund policies may be implemented. Trip leaders and participants should read all trip documentation carefully.

Boat Cancellation: The Charter Liaison needs to be notified in advance of the charter company’s deadline for cancellation with minimal penalty. This is often, but not always, 45 days before the trip departure date. At this point you should have a reasonably good idea of your flotilla needs. Be sure to know the cancellation policies of the charter company being used on your trip. The charter liaison has this information.

Performance Phase

It’s time to get ready to sail and you have a few more important tasks to complete to ensure a great trip.

Skippers Meeting

Trip leadership coordinates with the skippers to meet three to four weeks before trip departure date. This is typically a Zoom meeting. Contact the Commodore for access to the Club’s Zoom account to schedule the meeting. Only the skippers who are to command boats participate in this meeting —so the member of the trip leadership team who is not a skipper (if any) does not attend. Nor do any skippers on the trip who are not to actually skipper a boat. This is because the skippers in charge of boats need the freedom to openly discuss personalities and skills.

Share the list of confirmed participants with the skippers prior to the meeting. This list includes ranks, indication of couples, preferences of who to sail with, smoking status, requests for skipper or first mate evaluations, any any other pertinent information.

Share other relevant information such as marina reservations, tide tables, way points, boat layouts, special plans (meals ashore, appetizer party, etc.).

During the meeting, the skippers will allocate crew. Usually they first negotiate for first mates, next they consider evaluation requests. Finally they allocate individuals and couples based on skill. Then the boats are assigned based on crew configurations, skipper request, or sometimes just at random.

The skippers review the itinerary and any specific plans (e.g., marina stays, special events while anchored, particularly tricky navigation…).

Remind the skippers to download, print, and bring along the following:

International and Longer Trips

Often charter companies in foreign ports require crew lists including passport information as much as 30 days in advance. Any charter company can also require skipper, and even first mate, resumes. Sometimes the skippers and first mates need to fill these out on line themselves. The Charter Liaison will inform you of such a request.

In addition to collecting this information, you should create a spreadsheet of travel information for everyone. Include:

  • Name

  • Departure Airport

  • Flight(s) date/time and number

  • Arrival date/time at final destination

  • Lodging if arriving early

  • Return flight(s) date/time and number

  • Arrival airport

Collect this information for longer trips that are further away than the Chesapeake Bay, too. It is very useful to know when to expect everyone. If everyone is driving (say, to Maine), ask for their predicted arrival time and lodging if they are arriving early.

Prepare for the Pre-Trip Meeting

With the final crew list and boat assignments made, it is time to prepare the pre-trip information. Experienced trip leaders will have started on this earlier, and will use at least some of the information from the trip announcement and even the annual meeting presentation.

The purpose of the pre-trip information is to give the crews all the information they need to get to the boat, enjoy themselves on the boat, have fun ashore, and get the boat home safely.

A good pre-trip package includes:

  • The date and time of the pre-trip meeting (more on that shortly)

  • The address, directions, and or a map showing the location of the departure marina

  • A map of the marina showing boat locations, if possible

  • The boats’ layouts and pertinent details (refrigerator? freezer? air conditioning? bow thrusters? dinghies?)

  • The crew list by boat including names, ranks, email addresses, and phone numbers

  • A little history of the sailing area and of specific places the trip will visit

  • Names and contact information of restaurants and other businesses crews might want to visit

  • A day-by-day itinerary including sailing distances and likely departure times

  • Reminder of things not included in the trip

  • Estimate of likely individual expenses

  • Travel information that you’ve collected from everyone. NOTE: do not share everyone’s passport information if you had to collect it for the charter company. Only share flight and lodging information.

  • Any other details that the crew might need. For international trips, information about local currency, emergency phone number, pertinent customs (e.g., nobody tips there), etc.

In addition, your pre-trip package must include the following TSC resources:

If it’s easy for you to incorporate these separate PDFs into one large PDF with your custom information, do so. Otherwise you’ll send an email with a lot of attachments. Do not rely on sharing links — people will not follow them.

Email your participants with a set of dates and times to gather availability for the pre-trip meeting (or use an on-line survey). Pick the date when all your skippers and the most crew can participate.

Unless you plan to do an in-person pre-trip meeting, use Zoom to set up the meeting (allow 2 hours). Set up breakout rooms for each boat. Make the Zoom require RSVP so you will know who is coming and who can’t make it.

Email the pre-trip package to everyone.

Take a deep breath — you’re almost there.

The Pre-Trip Meeting

The purpose of the pre-trip meeting is to orient everyone on the specifics of the trip, to give everyone a chance to meet the people they’ll be spending several days with, and for each crew to plan its meals.

Open the pre-trip meeting with introductions, welcoming any new members. Review the itinerary, highlighting any special events — raft-ups, on-board parties, group dinner ashore, marina stays. Urge participants to contact one another to arrange carpools.

Encourage questions and make notes on items you’ll need to answer later. When the questions have been covered, send everyone to their crew breakout rooms (including yourself).

Skippers know how to handle this portion of the meeting. They will encourage discussion of food preferences and coax individuals into volunteering to prepare certain meals until a plan is made.

Typically crews do not return to the main meeting—when the meal planning is done the meeting ends. As trip leader, you might choose to visit each crew breakout to make sure things are going okay.

At the Marina

You made it. Your role is not over, but during the trip you become more of a servant leader to the skippers who are accountable for the safety of their crews and boats.

Prior to departure:

  • Ensure all skippers have signed copies of their boat contracts. These may have been provided by the Charter Liaison earlier, or the charter company might ask the skippers to sign two copies when they arrive (one for the boat, one for the company).

  • Ensure that skippers document any existing damage or missing items and review with a charter company representative. These must be noted on the Club’s Check Out Check In (COCI) form.

  • Ensure that any no-go issues are addressed by the charter company.

  • You should have release forms from everybody, but if you do not you must have the crew sign one on the spot. (Yes, bring some blanks.) Nobody leaves the dock without having signed a release form.

  • Facilitate a skipper’s meeting before departure.

During the Trip
The “herding cats” phase

Facilitate a skipper’s meeting regularly (typically each morning, but additional meetings might be appropriate when plans change).

Remind skippers and crews of special events and times and places for group events.

Be available to all crew as a leadership figure, answering questions and helping ensure both safety and a pleasant experience.

Back at the Marina

Before leaving the marina, check in with as many skippers as possible to see if there were any additional problems with boats and or crew.

Collect any injury reports.

Collect COCI forms if possible. If any damage occurred, it should be documented on the form, and photos taken. Send or scan and email to the Charter Liaison, and store a copy in your trip folder. Due to the likelihood of boats returning at different times, some skippers will email the form directly to the Charter Liaison.

For international trips, coordinate with the charter company to arrange airport transfers based on the crews’ travel information.

Close-out Phase

Just a few more things for you to do before you can rest on your laurels.

Trip Survey

Feedback on the Club’s trips is essential. Contact the commodore to prepare a trip survey. They will need the boat and skipper names. The commodore is the only person who will see the results, so they have to set it up (typically a Google survey). While the Club has a standard survey, you can add or alter questions. The commodore will share it with you for your approval via a link. When it looks good, you will share the link with your participants in an email, thanking them for participating in the trip. Ask them to complete the survey and assure them that only the commodore sees the results so they can be candid. Also ask them to submit to you any photos they are willing to share.

Trip Report

The trip report is a narrative of the trip including anecdotes from each boat. Within a few weeks after return, the trip leader or assistant trip leader drafts the report and shares it with the skippers to edit and add details from their boats. The trip leader selects photos from among those submitted. Be sure to keep track of who provided photos you use, credit is important. Click here for some guidance on preparing your trip report.

The trip report is published as blog entry on the Club’s website. Submit the draft to the webmaster. The Web team will review it for spelling, grammar, and content to ensure it’s in line with TSC marketing goals (which it most likely is), and post it. Even if you are part of the Web team, it is required that all content posted is reviewed before going live.

Close-out Paperwork

Your last official act is one of the most important, as some of the documents involved either can protect the Club or provide support for claims the Club may have. Documentation goes to four individuals, the Commodore, the Treasurer, the Charter Liaison, and the Membership Secretary, as follows:

Commodore

  • Injury reports, if any

  • Final crew list

Charter Liaison

  • Check-out/Check-in forms

  • Damage reports, if any. Discuss damages with the Charter Liaison immediately after the trip to address with the charter company.

Treasurer

  • Remaining checks for deposit

  • Expense reimbursements/refund requests

  • Final Crew List and Release Forms, sorted by boat with the skipper form on top

  • Final Account and Reconciliation workbook. In g-drive, change the sharing settings for this workbook to make TheSailingClubCloud the only editor. This essentially makes it read-only.

Membership Secretary

  • Final crew list and remaining membership forms

Process Diagrams