If you run a charter out of South Jersey, your best prospects are already in your files: last year's guests. A charter pre-season email to past customers is the cheapest booking tactic you have, because these people know the boat and the captain. This post gives you a dated sequence from January 2027 through Memorial Day weekend, plus the list cleanup and consent basics that come first. It is one piece of a wider fishing charter marketing plan that also covers your website and search. Here is the short version: send five or six plain emails, each with one ask, each tied to a real date.
Who counts as "last year's guests," and what consent means
Start with the people who paid you or booked a trip with you in the 2026 season. Add anyone who asked for a quote, joined a waitlist, or gave you an email at the dock and asked you to keep in touch. Leave out purchased lists, scraped addresses and anyone who has opted out.
Consent is the part owners skip. We are not lawyers, and your own attorney should answer questions about your specific situation. What we can point to is the Federal Trade Commission, whose CAN-SPAM compliance guide for business lists the baseline rules for commercial email.
In plain terms, that guide says your "From," "To" and "Reply-To" details must be accurate. Your subject line must match what is inside. You must make clear the message is an advertisement, and you must include a valid physical postal address. Every message needs a way to stop all marketing email from you, and you have to honor that request. The guide also states how quickly. We have not quoted that window here, so read the current page yourself.
Practical habits that follow from this:
- Put a short consent note on your booking form: "We'll email you about trips and openings. Unsubscribe any time."
- Use a real reply address, not a no-reply box. Guests answer with questions, and those are bookings.
- Store a "unsubscribed" flag and date next to each contact, and never re-import an old export over it.
Clean the list in January, before you send anything
Your guest list probably lives in three places: the booking system, a spreadsheet from the dock, and someone's phone. Pull them into one sheet in the first week of January. Then clean it.
- Remove duplicates. One guest often appears under a work email and a home email. Keep the one they used to book.
- Fix obvious typos. Addresses ending in "gmial.com" or "yaho.com" are common from handwritten sign-ups.
- Suppress opt-outs. Anyone who ever unsubscribed stays off, even if they booked again later through a different channel.
- Tag each guest by trip type. Inshore, offshore, family sightseeing, private party. This lets you send relevant emails instead of one blast.
- Record the last trip date and party size. You will use both in the copy.
Expect some addresses to bounce, meaning the mail server rejects them. That is normal. Remove hard bounces after the first send so your sending reputation does not suffer. We do not have a sourced benchmark for how many charter addresses go stale in a year, so plan to measure yours rather than assume.
If you want this data to live somewhere better than a spreadsheet, that is what a captain's CRM is for. We built the booking site and captain's CRM we built for Sand Bar Joe's, and the same idea applies at any size: one record per guest, with trip history attached.
The dated sequence, January through Memorial Day
Memorial Day weekend is the first big booking test of the year, so work backward from it. The table below is the whole plan. The sections after it explain each send.
| When | One ask | |
|---|---|---|
| Mid-January | Check-in and preferences | Click the trip type you want |
| Early to mid-February | Early-booking window for past guests | Hold a date before public opening |
| March | Season dates and what's new | Book a weekend |
| Mid-April | Gift certificate note | Buy a gift for a spring or summer date |
| Early May | Open dates for the holiday weekends | Pick a remaining slot |
| Week before Memorial Day | Last call and weather policy | Book or ask a question |
Mid-January: the check-in
This is the lowest-pressure email. Say thanks for last season, state that you are planning 2027, and ask one question: what kind of trip would you want? Offer three links, one per trip type. Each click tells you what to send later. It also shows you who is still reading.
February: the early-booking window
Give past guests first pick. Tell them the dates you have set, the deadline for their window, and when you open bookings to the public. Keep the offer honest: it is first access, not a fake scarcity timer. If you offer a deposit option or a rate for repeat guests, state it here in one line.
March: dates and what's new
By now you know your season. Send the opening date, any new boat, trip, departure dock or policy change, and the three or four weekends that fill first. Link straight to the booking page, not your homepage.
April: the gift note
Past guests are often the ones buying a trip for a relative. Put a gift certificate email ahead of Mother's Day and Father's Day. Say how the certificate is delivered, how long it lasts, and who to contact if the recipient needs to move the date. Check the terms with your own advisor if your state has rules about gift expiration.
May: open dates and last call
List the actual open slots for the holiday weekends. A short list of real dates beats a vague "book now." In the final week before Memorial Day, repeat your weather and rebooking policy in two sentences. Guests who know the policy book more calmly. Stop emailing the same people once the weekend arrives.
What goes inside each email
Write like the captain talking to a regular. Keep each email to roughly 100 to 150 words, one ask and one button. Charter guests read these on a phone, often at a desk between other things.
- Subject line: say what is inside. "Memorial Day weekend: 3 open trips" works better than a pun. Remember the FTC guide above requires subject lines that match the content.
- First line: refer to something real, such as their last trip type or the month they sailed. This is where your tagging pays off.
- The ask: one link to one page. Do not stack a gift offer, a fishing report and a survey in a single send.
- Footer: your business name, postal address and an unsubscribe link. Your sending tool will usually add the last one for you.
Do not promise catches. Fish are not guaranteed, and weather calls are the captain's. Describe the trip, the departure time and the policy. Let guests picture the day.
Photos help, but only your own, with permission from anyone recognizable in them. Pick one image per email and keep the file small so it loads on a shore connection.
Match the send to what the guest already did
The most common mistake is emailing someone who already booked. A guest who reserved a June date in February should not receive the March "book a weekend" email. They should get a confirmation, then a short "here's what to bring" note closer to the date.
That requires your email tool to know about bookings. At small volume you can do it by hand: export bookings weekly, tag those guests as booked, and exclude them from the next send. Once the list is larger or the season is busier, connect the booking system to the email tool so the tag updates itself.
For the sending tool itself, email marketing automation tied to your guest records is the version we build. Mailchimp is the common off-the-shelf option, and we are a Mailchimp partner. It handles unsubscribes, postal-address footers and basic tagging. For a list of a few hundred guests, an off-the-shelf tool is usually enough. Custom work only pays off when your booking data and email need to talk to each other.
If you are weighing a bigger system, our guide to CRM software for cruise and charter operators covers what a guest record should hold.
Measure bookings, not opens
Open counts are unreliable, because some mail apps load images automatically and inflate them. Judge the sequence by what you can count yourself.
- Use a separate booking link in each email, or add a tracking tag (a UTM parameter, which is a short label on the URL that analytics tools read) so you can see which send produced a visit.
- Add a "How did you hear about us?" field to the booking form with an "email from the captain" choice.
- Count replies. A reply that asks about a date is a booking in progress.
- Track unsubscribes per send. A spike after one email tells you something about that email.
We do not have a sourced benchmark for charter email performance, so we are not quoting one. Compare 2027 against your own 2026 booking calendar instead. Last year's April and May bookings are your baseline, and nobody can promise a particular lift from any sequence.
After Memorial Day, keep the list warm with one or two useful notes a month, such as a fishing report or open weekdays. Then move into your fall and off-season plan. If the sequence works, you can add a post-trip thank-you and review request to the same system.
What can go wrong
A few things trip up charter operators every spring:
- Sending from a personal Gmail. Large volume from a personal account gets flagged. Use a business domain and your sending tool.
- Forgetting weather. If a trip is cancelled, tell guests how rebooking works before they ask. Our post on weather, crew and rebooking software covers that side.
- Emailing everyone about everything. A sunset-cruise family does not need your offshore tuna report.
- Burying the policy. Deposits, cancellations and age limits belong in the email or one click away.
None of this requires a large budget. It requires a clean list, six dated emails and someone with a calendar reminder.
Frequently Asked Questions
How many emails should a charter send to past guests before the season?
Five or six between January and Memorial Day is a workable range for most operators: a list check-in, an early-booking window, a season-dates note, a spring gift note, and one or two last-call sends. More than that starts to feel like noise. Watch your own unsubscribe and reply counts, and cut back if they climb.
When should I send my first charter pre-season email to past customers?
Mid-January is a good starting point, because you want your list cleaned and your season dates drafted before you announce anything. The first send does not need to sell. It can simply confirm that the guest still wants to hear from you and ask what kind of trip they prefer.
Do I need permission to email people who booked with me last year?
Consent rules depend on how you collected the address and where your guests live, so ask your own attorney. What we can say is that the FTC's CAN-SPAM guide for business lists baseline requirements: accurate sender details, honest subject lines, a postal address, and a working opt-out. Honor every opt-out and keep a record of it.
Should I email last year's guests before announcing dates to the public?
Yes, if you can. Past guests already trust you, so an early-booking window for them costs almost nothing and fills your best weekends first. Give them a clear deadline, such as the date your calendar opens to everyone, and say so plainly in the email so the offer stays honest.
Next step
If you want the list, tags and sends wired to your booking data instead of run from a spreadsheet, talk to us about a custom CRM that keeps guest history in one place. We work with owners in Medford, Burlington County, South Jersey and the Philadelphia metro area, and with clients nationwide. iOLab Digital is a Microsoft Advertising, Semrush, SiteMinder and Mailchimp partner. Where this article mentions a tool we partner with, we say so.
Sources
Every outside claim in this article links to where it came from. These open in a new tab.