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SKYLINE SUITESTOUR GIANTBOOK 10,000TOURSDRIFTLIGHT CHARTERSTOUR TICKETSTour chainMarketplacesHotel packagesCaptain Tess

You run the best trip in town. Guests just can’t find you yet.

Discovery Marketing gets tour operators, charters and hosts found by the travelers planning right now, then makes it easy to book with you directly instead of through a marketplace that keeps a cut.

Book a 30-minute call with Andy

Your website is built and hosted free. We earn a percentage of ad spend only if you choose to advertise.

Captain TessOwner, Driftlight Charters · ChicagoA composite character. Her story shows exactly how we work.

She grew up on a Lake Michigan dock.

Her dad ran a perch charter out of Montrose Harbor, six anglers at a time, out before sunrise. Tess coiled lines, baited hooks and learned to read the lake from the color of the sky.

Then summers crewing on tour boats, a Coast Guard captain’s license and every dollar saved for a 40-foot sailboat. She named her company for the last light on the water: Driftlight Charters.

She knows the lake inside out. Running a business is a different job.

RAY’S PERCH CHARTERS
Montrose Harbor, the mid-1990s. Fishing before sunrise.

The boat’s in the water. The weekday seats are empty.

Her sails are as good as any on the lake. Outside the marketplaces and a few hotel concierges, almost nobody knows her name.

  1. Every week, another app.

    Consumers use an average of six review sites when choosing a business, and every listing wants photos, hours and replies. Running the boat is the easy part.

    BrightLocal Local Consumer Review Survey, 2026

  2. The big names are everywhere.

    Big tour boats fill the river. Marketplaces buy the top of every search. When a visitor asks Google or an AI assistant what to do tonight, those are the names they hear.

  3. Referrals have a ceiling.

    Two hotel concierges send a few groups. Regulars bring friends. It grows, slowly, and stops at the edge of the people who already know her.

  4. CommissionsDirect bookings

    Busy, but not growing.

    Saturdays sell out, but a big slice of every ticket goes to whoever listed it. In 2025, one of the largest experience marketplaces told some operators their commission would rise from 20% to 30%.

    Arival, 2025

She knows the lake. She doesn’t know how visitors choose a boat. So she keeps paying whoever sends them.

Being great isn’t the same as being found.

Visitors plan on their phones, often the night before. They search, watch a video, read the reviews and book whoever makes it easy. A boat that doesn’t show up, doesn’t show the trip, or can’t be booked in a minute loses the guest to a marketplace.

sunset sail chicagoChicago, IL
  1. 1Booking marketplace
  2. 2Tour company chain
  3. 3Big cruise line
  4. 37% of tour and activity bookings went through online travel agencies in 2025.Arival, The State of Experiences, 2026
  5. 4Hotel package
  6. 5Tour kiosk
  7. 9Driftlight Charters5.0 stars · 46 reviews

Illustration. Competitor names are hidden on purpose.

Meanwhile, Chicago welcomed 56.8 million visitors in 2025, and they spent a record $21.5 billion (Choose Chicago, 2026). The guests are here. They just have to find her. Ads can put her boat at the top of the page on day one; the map and AI answers are earned. We’ll never promise a map ranking; nobody can buy one.

Then Captain Tess met Andy.

A guest on her sunset sail sent her one of Andy’s videos about businesses that pay a middleman for every customer. She booked a call on a rainy Tuesday, the only kind of day she had free.

Andy Bedell taking notes while a business owner walks him through the business.
Andy BedellFounder, Discovery Marketing

Andy has run Facebook video ads since 2015, and spent four years in direct marketing for executive education at the University of Chicago Booth School of Business. Direct marketing has one job: get people to act, and buy straight from you.

That’s the whole game for a charter. A marketplace can fill a slow Tuesday. The business gets built on guests who book direct, come back next summer and send their friends. And nothing sells a sunset sail like a video of one.

Career stats
WhereWhat happened
UChicago BoothExecutive Education · 4 yearsManaged budgets above $20 million a year across Google, LinkedIn and direct mail.
KeySmartJoined 2015Took daily sales from about $5,000 to $25,000 within a week, then helped the company reach a peak near $35 million a year.
Facebook videoOne of the earliest specialists in Facebook video ads, running them since 2015.
Career$200 million+ in managed ad spend.

One short call. A working website two hours later.

Andy asked about her boat, her routes and her best nights on the lake. Two hours later she had a link to a complete site: every trip explained, the all-in price per person, a weather policy in plain English, and booking through her own booking system.

Before A marketplace listing and a link in her Instagram bio.

Sail the skyline at sunset.Private sails for up to 6See open sails
Sunset sailsPrivate chartersSkyline toursGift certificates

What if the weather turns?

Is the price all-in?

Can we book the whole boat?

Open sails

Thu 7:30Fri 6:45Sat 10:00
You’re booked. Your confirmation and dock directions are on their way.

Fictional business. Your demo typically arrives about two hours after your call.

Before we write a word, we read what guests already say.

Every claim on her new site came from somewhere real:

  • Public reviews. On every marketplace and map listing, sorted by what guests praise and what worried them before they booked.
  • Her call with Andy. Thirty minutes on her boat, her routes and the trips she’s proudest of.
  • Her market. What visitors search for, what they compare, and how far ahead they book.
  • Her license. What her Coast Guard credential and her boat allow, so the site never sells a seat it can’t fill.
The waves picked up and she never stopped smiling. We felt completely safe.
Steady
She knew every building on the skyline and a story about each one.
Local
Just the six of us and the sunset. Nothing like the crowded cruise boats.
Private
She made the weather call the day before, so we weren’t guessing at the dock.
Steady
Her dad fished off Montrose. She showed us exactly where.
Local
She let my daughter take the wheel for a minute. Best part of our trip.
Private

Composite excerpts written for this illustration, not real reviews.

Three things kept coming up.

Steady
Guests felt safe. She makes weather calls early, briefs everyone before leaving the dock and stays calm when the lake changes its mind.
Local
She grew up on this water. Guests get the Chicago a tour script leaves out, and that’s what they tell their friends about.
Private
Six guests, one captain, no crowd. Every sail feels like it was planned for the people on board.

Now run the plays.

A website that sells every trip on every page. Then campaigns that reach visitors while they plan, and send the booking straight to her own booking system instead of a marketplace.

Every page makes the same three promises.

A bachelorette party and a family visiting from Ohio want different things. Each trip page shows how a steady captain, local stories and a private boat make that trip better, in plain language.

SteadyA weather call by noon, so nobody is guessing at the dock.

LocalThe skyline as the lights come on, and the story behind each tower.

PrivateJust your group, up to six guests, never a crowded deck.

Guests can book without a phone call.

Her site is built so AI assistants like ChatGPT and Meta’s Muse can read her trips, all-in prices and open sails, then finish the booking in her own booking system. No marketplace in the middle.

  1. Five of us are in Chicago this weekend for a bachelorette. Any private sunset sails on Saturday?
  2. Driftlight Charters runs private sunset sails for up to six guests from a downtown harbor. Reviews often mention a calm captain and great skyline stories.
  3. Saturday at 7:15 PM is open for your group, and the price shown is all-in. Want me to book it?Driftlight ChartersPrivate sunset sail · Sat, 7:15 PM5.0 · Chicago
  4. Yes, book it.
  5. Done. Your confirmation, dock directions and weather policy are on their way by email.

Meet guests at the search.

Someone typing “private boat charter chicago” is planning this week. Google Ads put her boat at the top of those searches, with an ad that answers the search and a page built for it. Pick a search:

Sails & tours
Private groups

1 · They search

sunset cruise chicago
Sponsored · driftlightcharters.exampleSunset Sails in Chicago | Six Guests, One Captain

See the skyline light up from a private sailboat. All-in prices. Book in a minute.

2 · They land on the matching page

Driftlight ChartersThe skyline at sunset, from your own boat.See open sails

3 · They book

Charter bookedSent straight to her booking system

Travel search clicks averaged about $2.14 in 2026 industry benchmarks (LocaliQ/WordStream); your market and season will vary. Ad position depends on bids, ad quality and competition.

First on a new field.

ChatGPT started showing ads in 2026, and OpenAI’s own launch example was a lodging ad inside a trip-planning chat. Andy got access early, before most advertisers could. Visitors ask ChatGPT full questions, like “what’s something relaxing to do on the lake with my parents?” Her clearly labeled sponsored answer can be right there.

ChatGPT keeps ads separate from its answers and labels them as sponsored. We never promise a mention in the answer itself.

  1. Visiting Chicago with my parents next weekend. Something relaxing on the lake that isn’t a giant crowded boat?
  2. SponsoredDriftlight Charters · ChicagoPrivate sails for up to six guests. A calm local captain, skyline stories and all-in prices.

Ask everyone. Reply like a captain.

Every guest gets the same review request after the sail, whatever we think they’ll say. Asking works: 83% of consumers who were asked to leave a review went on to write one. When a tough one comes in, the reply is calm, specific and public.

BrightLocal Local Consumer Review Survey, 2026

Captain cancelled our sail two hours before. Ruined our night.

Reply from the owner

We’re sorry your night changed. A thunderstorm was moving across the lake, and we won’t sail into lightning with guests aboard. Your refund went out that afternoon, and we’d love to have you back on a clear evening.

Illustration of a calm, professional reply.

Most guests don’t book on the first visit. Follow up.

Trips get planned over days, in a group chat, with three friends voting. So we stay in front of them: a video of the sail, honest reviews, the all-in price and a site that books in a minute. When they’re ready, hers is the boat they remember.

  1. MondayGoogle

    Searches “sunset cruise chicago” from Indianapolis. Reads the sunset-sail page. Doesn’t book yet.

  2. TuesdayInstagram

    Sees a 20-second video of Tess’s boat gliding past the skyline at golden hour.

  3. WednesdayGoogle reviews

    Reads what guests say about her weather calls, and how she replies.

  4. ThursdayAI assistant

    Asks for a private sail on Saturday. Her clear site makes her easy to recommend.

  5. FridayDriftlight’s site

    Books Saturday’s sunset sail for five, straight into her booking system.

Chicago’s downtown hotels had a record summer in 2025, driven by visitors from within a five-hour drive, while international visits fell 3%. That’s who the follow-up reaches first.Choose Chicago, 2025

Then the calendar started filling.

Direct bookings / month, before14
Direct bookings / month, after52

Illustrative figures from Captain Tess’s composite story, in peak-season months. Not a typical or guaranteed result. Your numbers depend on your boat, season, weather and capacity.

More guests booked on her own site, so more of every ticket stayed with her. Weather reschedules took one tap. And for the first time, she could see which searches and videos brought in charters.

Then we made the videos guests actually watch.

Nobody books a sail from a stock photo. Just Tess and the lake: what to bring, how weather calls work, and the crew who’ll take care of you. The best ad for a trip is the trip.

PACK THIS
How-toWhat to bring on a sunset sail
MYTHFACTOR
Myth vs. factDo you need to know how to sail? Not even a little.
DRIFTLIGHT
WarmthMeet the crew before you board

Concept frames from Captain Tess’s composite story.

From empty weekdays to a waitlist.

DRIFTLIGHT CHARTERSDRIFTLIGHT · SECOND DOCK

  1. Year 1 Full Saturdays, empty Tuesdays.

    Weekends sell out through marketplaces. Weekdays sit open, and nights go to replying on four apps.

  2. Year 2 A first mate and direct bookings.

    Her own site, her booking system, reminders and one-tap weather reschedules. She hires a first mate so she can captain instead of coordinate.

  3. Year 3 A second captain and a private-group calendar.

    Bachelorette parties, proposals and team outings book weeks ahead, so a second licensed captain takes the weekday sails.

  4. Year 5 A second dock office and a waitlist.

    A bigger, Coast Guard–inspected boat for larger groups, and a waitlist for July Saturdays. Her parents still come down to the dock to coil the lines.

The kid who fished off her dad’s perch boat now runs a booked-out charter company, on her terms.

Her one regret: she wishes she’d started booking guests direct sooner.

Got an idea? We test it before we bet on it.

Tess wanted every trip page to show the all-in price per person, fees included, instead of a “from” price with fees added at checkout. Andy liked it, but the page was already booking sails. So they ran a trial: half of visitors saw the current page, half saw hers.

Among U.S. shoppers who abandoned an online checkout for a reason other than browsing, 40% said extra costs like fees were too high.Baymard Institute, 2025

A “From” price, fees at checkout

Visitors
1,000
Bookings
100
Per 100
10.0

B Her idea: the all-in price, up front

Visitors
1,000
Bookings
120
Per 100
12.0

Winner: B. 12 bookings per 100 visitors instead of 10. That’s 20% more guests from the same budget.

Illustrative test from Captain Tess’s story. We call a winner when the difference holds up statistically, not when one page is ahead for a day.

The season is short. Plan all twelve months.

Chicago’s harbors open May 1 and close October 31, and the busiest weeks fall in between. So the campaigns, pages and budget move with the calendar, and the off-season does its own work.

  1. Jan–Apr

    Planning season

    Groups plan summer early. Campaigns lead with private charters, bachelorette weekends and team outings, so the best Saturdays are booked before the ice melts.

  2. May–Jun

    The harbors open

    Harbor season starts May 1. Graduations, birthdays and the first warm weekends fill Saturdays, and weekday sails get their own campaigns.

  3. Jul–Aug

    Peak weeks

    Downtown hotels booked nearly 3.6 million room nights from June through August 2025, a summer record. The budget follows open seats, and every page explains the weather plan.

  4. Sep–Dec

    Fall sails, then gifts

    Quieter fall evenings until the harbors close October 31. Then gift certificates for next summer: 43% of holiday shoppers planned to buy at least one gift card in 2025.

Sources: Chicago Park District harbor season; Choose Chicago summer hotel data, 2025; NRF holiday gift card research, 2025.

It’s standing watch, not a one-time sail.

You don’t check the forecast once in May and call it done. Marketing works the same way. Ads wear out, marketplaces change their terms, competitors copy what works, and new tools arrive every month. We check on it every day, so you can run the boat.

What we watch, every day

  • Budgets and bids, matched to open seats and tomorrow’s forecast.
  • Broken booking links, calendars and tracking. If something breaks, ads pause until it’s fixed.
  • Ad and platform policy changes for travel advertisers.
  • Fresh video before the old clips stop working.
  • What the big tour companies and marketplaces are doing.
ResearchWriteBuildLaunchMeasureTestRepeatevery week

It starts with a 30-minute call.

From “book a call” to campaigns that run while you’re out on the water.

  1. 1 minute

    Book a call

    Pick a 30-minute time on Andy’s calendar and tell us your business name and city.

  2. Behind the scenes

    We gather your footprint

    Your photos, your listings, your public reviews and what guests say about your trips online.

  3. 30 minutes

    Your call with Andy

    Talk about your trips, your guests and your best days on the water. Andy asks the questions; you tell the stories.

  4. About 2 hours

    Your demo website

    Every trip, all-in prices, a weather policy and booking through your booking system, written in your voice.

  5. Follow-up

    Review it together

    We check every claim with you, swap AI images for your real photos, and confirm what your license and boat allow.

  6. Free

    Discovery Platform

    Request edits with our AI, approve drafts, or send our team a ticket.

  7. Kickoff

    A Google Ads test

    The searches visitors use, the weeks you need to fill and pages that answer them. A $500 ten-day test, paid straight to Google, is a common start.

  8. Always

    Measure what books

    Bookings tracked back to the searches and videos that brought them in, so the budget follows what works.

Book a 30-minute call with Andy

Yes, the website’s free. Here’s how we get paid.

We charge 20% of the ad spend we run to start, and the percentage goes down as you grow. No setup fee, no retainer, no contract. The website is built and hosted free. It’s a percentage of ad spend, never a cut of your bookings, and everything below is included.

We start at 20% of the ad spend we run, and the percentage steps down as your monthly spend grows.

Included in the percentage

  • Video production
  • Landing pages for every trip
  • Copywriting
  • Review and reputation guidance
  • Google keyword research
  • Daily budget management
  • Booking and conversion tracking
  • Fresh creative before ads wear out
  • Ongoing A/B testing
  • Seasonal and gift-certificate campaigns
  • Website hosting

Just want the website? That’s fine. We’ll still build it and host it for free.

Happy with the website you have? Keep it. If it’s tied to your booking system, we’ll add the pieces that bring in guests, like trip pages and ad landing pages, and run your campaigns around it. We’ll plan it on your call.

See exactly how our pricing works.

Nothing goes out that you’d have to explain at the dock.

Travel has more rules than most people expect: licenses, prices, reviews and who’s allowed to sell what. We treat them as the brief, not the fine print. Every claim is backed by something real, approved by you, and checked before it runs.

Captain Tess and Driftlight Charters are composites, and this page tells you so. We are not your lawyer; your attorney and your licensing authorities have the final word.

Charters are just the start.

Tour operators, fishing and sailing trips, safaris and outfitters, hotels and B&Bs, vacation rentals and travel advisors. Different trips, different rules, same playbook: find what makes your trip better, show it on video, and put it in front of the people planning right now.

BOUTIQUE HOTELBOAT TOURSVACATIONRENTALSDRIFTLIGHT CHARTERSTRAVEL ADVISORToursRentalsChartersHotelsAdvisors

Book your call with Andy.

Thirty minutes about your business: your trips, your guests and your season. Your demo website typically arrives about two hours later.

  • Free website and hosting
  • No ad spend required
  • Keep your booking system

Calendar not loading? Open it in a new tab.

Keeping your current website? We’ll plan the add-ons with you.

Not in travel? See home services, doctors or everything we do.

Not your industry? See every industry we serve.

Book a call with Andy