
Clearwater & St. Petersburg, Florida
Special Occasion Boat Charters
Bachelorette parties, anniversaries, birthdays, proposals, graduations. The whole boat reserved for your group, your music, your pace — and no occasion surcharge.
A private charter for a celebration costs the same as any other charter. There is no occasion surcharge and no hidden fee. Gulf Escape $395 (2.5 hrs) · Half-Day Island Escape $575 (4 hrs) · Sunset Escape $425 (2.5 hrs, champagne flutes at sundown included). All flat rates for the whole boat, up to 6 guests.
Six is a U.S. Coast Guard limit rather than a preference. Bring decorations, bring your own food and drinks, bring your playlist. Mention the occasion when you book and Captain Keith will make sure the day is shaped around it.
Why the water works for a celebration
A restaurant puts your group at a table for two hours with other people’s conversations either side of you. A boat puts everyone in one place, outdoors, with nothing else competing for attention — and the whole thing belongs to you for the afternoon.
The part guests mention afterward is rarely the thing that was planned. It is somebody floating on their back at a sandbar realising nobody else is around. It is the moment a pod of dolphins turns up during the toast. It is that the phones went in a bag and stayed there because we are taking the photographs anyway.
One practical thing that matters more than it sounds: the price is for the boat, not per person. A group of six pays what a couple pays. For a celebration that means you are not doing arithmetic about who is coming — you are just filling the boat.
What people celebrate out here
Bachelorette parties
Your group, your music, your drinks, and a sandbar stop where everybody gets in the water. The boat becomes the venue — bring decorations, bring a charcuterie board, bring whatever your group brings. Captain Keith handles the rest and stays out of the way of it.
Anniversaries and couples
The Sunset Escape is the one for this. Timed to the evening’s actual sunset, with champagne flutes at sundown, and you choose the backdrop — an island silhouette, the skyline, open Gulf, or the Skyway lighting up from the St. Pete side. No crowd, no background noise, no strangers nearby.
Proposals
The advantage of a private boat is that nobody is watching except the person you want watching. No restaurant audience, no waiter hovering with a dessert plate. Tell us when you book and Captain Keith will work out the timing with you so the moment lands where you want it, without anything feeling staged.
Birthdays
A shared experience rather than a shared meal. Dolphin watching, sandbar swimming, somewhere new — the day becomes the memory rather than just the occasion. Works on any of the three charters depending on how long you want to be out.
Graduations
Something that feels like a reward and an adventure at once. We have had groups drive across the state from Florida’s east coast specifically for the Gulf’s turquoise water, which tells you something about how different this side looks.
Reunions and group celebrations
Friend reunions, men’s groups, milestone gatherings, family get-togethers. Same reason as everything else on this list: being on the water together does something a night out does not, and the boat is entirely yours while you are on it.
Which charter to book
Same rates as any charter. No occasion surcharge.
Gulf Escape — $395
2.5 hours · up to 6 guests
Sightseeing on the way out, dolphins, and a nearby sandbar. Good for a birthday or a group who want a proper afternoon without committing the whole day.
Half-Day Island Escape — $575
4 hours · up to 6 guests
The range to reach the barrier islands and stay a while. The usual pick for bachelorette groups and reunions who want swimming, shelling, and time somewhere quiet.
Sunset Escape — $425
2.5 hours · up to 6 guests · best for celebrations
Timed to the actual sunset, you pick the backdrop, and champagne flutes come at sundown. The charter most guests book for anniversaries and proposals.
If you are the one organising it
Usually the maid of honour, the sibling, or whoever volunteered. Here is what you actually need to know.
- What it costs each person. The rate is for the boat, so split it however you like. The Half-Day Island Escape at $575 works out to $95.83 each across six, or $143.75 across four. The Gulf Escape at $395 is $65.83 across six. The Sunset Escape at $425 is $70.83 across six.
- Everything is included in that number. Licensed captain, fuel, cooler and ice, snorkel gear, floats, restroom, photos. There is no fuel surcharge and no per-guest add-on. What you tell your group is what they pay.
- Gratuity is not included and not expected. If Captain Keith made the day, most guests who tip land around 15 to 20 percent. Cash is easiest. Worth mentioning to your group in advance so nobody is caught out.
- Tell everyone the departure time and the meeting point in advance. The charter starts when it starts. Arrive 15 minutes early — a group of six takes longer to assemble than you think.
- Make the playlist before the day. Bluetooth stereo aboard. Somebody scrolling Spotify in the sun is not the vibe.
- Ask the bride, the birthday person, or whoever it is for. Sandbar and swimming, or cruising and photographs? It changes which charter to book.
One thing worth checking with any operator, not just us: whether there is a restroom on the boat.
A lot of charters do not have one, and the answer you get is that the route includes stops where the group can go ashore. On a celebration where people are drinking, that is a meaningfully different day. Ours has an enclosed restroom onboard, and you are welcome to use it for whatever you need.
What to bring, and one small request
- Your own food and drinks — wine, champagne, beer, a charcuterie board, whatever makes it feel right. Non-glass containers only. We provide the cooler and ice
- Decorations, if you want them — banners, sashes, weighted balloons. The boat can be dressed up
- Your playlist — Bluetooth stereo aboard, your music, your volume
- A waterproof phone case — though we are photographing the day anyway
- Light layers for an evening charter — the Gulf breeze cools off after sunset
- Sunscreen, hats, towels, water shoes — the usual, and a hat that will not blow off
- Flat shoes — flat sandals, boat shoes, or bare feet. Platforms and heels on a moving boat are a genuine safety problem, and this is the one thing bachelorette groups get wrong
- A sash, veil, or hat if it is that kind of celebration — they photograph well. All of them at once, less so
The one request: nothing that can blow overboard. Loose balloons and plastic ribbon end up in the water, and a sea turtle cannot tell the difference between a balloon and a jellyfish.
That is not a rule we invented for a website — it is the reason Tessa exists. Anything tied down is welcome.
What every charter includes
- Completely private — the whole boat, your group only
- Captain Keith at the helm — every charter, not a rotating crew. USCG-licensed, former Navy diver, 11-year submariner, cardiac registered nurse
- Champagne flutes at sundown — included on the Sunset Escape
- Photos of your day — taken throughout and sent afterward, so the person who always ends up photographing everything is actually in the pictures
- Flexible routing — dolphins, sandbars, islands, sunset, or a mix. Your group decides
- Enclosed restroom, freshwater rinse wand, deck sink
- Sunchill float, chair floaties, bean bags — the bean bags come ashore with you
- Cooler and ice · Bluetooth stereo · Departures from Clearwater or St. Petersburg
Minimum guest age is 5, per U.S. Coast Guard Type I life vest requirements. No pets aboard.
Plan the day
Sunset cruises
Choose your backdrop — islands, skyline, open Gulf, or the Skyway lighting up.
See sunset cruises →Sandbar charters
Shallow, calm water everyone can stand in, usually with nobody else on it.
See sandbar charters →Island hopping
Four hours to reach the barrier islands and actually spend time there.
See island hopping →What it costs
Full pricing breakdown, and what a private charter works out to per person.
See pricing →What to expect
How the day actually runs, from arriving at the ramp to the photos landing.
Read what to expect →Common questions
How much does a special occasion charter cost?
Exactly the same as any other charter — there is no occasion surcharge. The Gulf Escape is $395 for 2.5 hours, the Half-Day Island Escape is $575 for 4 hours, and the Sunset Escape is $425 for 2.5 hours with champagne flutes included. All flat rates for the whole boat, up to 6 guests, with no per-guest add-ons.
How many people can we bring?
Six. That is a U.S. Coast Guard limit under Captain Keith's 6-Pack licence rather than a preference, and it cannot be exceeded. If your group is larger, the usual solution is booking two charters on consecutive days or splitting across a morning and an evening slot.
Can we decorate the boat?
Yes — bring banners, sashes, balloons weighted down, whatever suits the occasion. One request: nothing that can blow overboard. Loose balloons and plastic ribbon end up in the water, and sea turtles mistake them for jellyfish. Anything that stays tied down is welcome.
Can we bring alcohol?
Yes, and most celebration groups do. Bring whatever your group enjoys — wine, champagne, beer, cocktails. Non-glass containers only, please. We provide the cooler and ice. Drink responsibly; you are on a boat.
Which charter is best for a proposal?
The Sunset Escape. It is timed to the evening's actual sunset, and you choose the backdrop — an island silhouette, the skyline, open Gulf, or the Skyway lighting up from the St. Pete side. Tell us when you book and Captain Keith will help with the timing so the moment lands where you want it.
Do you help plan proposals?
Yes. Tell us when you book and Captain Keith will work out the timing with you — where to be, when, and how to make the moment happen without it feeling staged. He has done this before and the whole advantage of a private boat is that nobody is watching except the person you want watching.
Is a sunset charter better for celebrations?
Often, yes. The light is better for photographs, dolphins are frequently active at dusk, the water tends to be flatter, and champagne flutes at sundown are included. It is the charter most guests book for anniversaries, proposals, and last nights of a trip.
What about a bachelorette party?
One of the more popular reasons groups book with us. The boat is entirely yours, so it is your music, your drinks, and your pace. A sandbar stop where everyone can get in the water tends to be the centrepiece, and the photos we send afterward mean nobody spends the day behind a phone.
Do you take photos?
Yes, on every charter, and we send them afterward at no charge. It matters more on a celebration than on an ordinary day — somebody in the group is usually the designated photographer and ends up in none of the pictures. This solves that.
Is the captain licensed and included in the price?
Yes. Every charter is captained by Captain Keith, who holds a U.S. Coast Guard licence, and his time is included in the rate. This is not a bareboat rental where you drive it yourself. He is a former Navy diver, an 11-year Navy submariner, and a cardiac registered nurse, and he is at the helm on every single charter rather than a rotating crew.
What does the price actually include?
Licensed captain, fuel, cooler and ice, snorkel gear in kids' through adult sizes, Sunchill float and chair floaties, bean bags, Bluetooth stereo, an enclosed restroom, a freshwater rinse wand, and photos of your day sent afterward. Champagne flutes at sundown are included on the Sunset Escape. There is no fuel surcharge and no per-guest fee.
How do we split the cost between the group?
However you like — the rate is for the boat rather than per seat. Across six guests the Half-Day Island Escape at $575 comes to $95.83 each, the Sunset Escape at $425 is $70.83 each, and the Gulf Escape at $395 is $65.83 each. Across four the Half-Day is $143.75 each. Whoever books pays the charter; the group settles up between themselves.
Should we tip the captain?
It is appreciated but never expected. Guests who tip generally land somewhere around 15 to 20 percent, and cash is easiest. If you are organising for a group, it is worth mentioning in advance so nobody is caught without any. A five-star review and sending friends our way is worth just as much to us.
Is there a restroom on the boat?
Yes — an enclosed restroom, and you are welcome to use it for whatever you need. Worth asking any operator this before booking a celebration, because plenty of charter boats do not have one and the answer is a stop ashore instead. On a day where people are drinking, that is a real difference.
Where do we meet, and when should we arrive?
Clearwater departures meet at Island Way Grill if you are staying on Clearwater Beach island, or the Belleair Causeway Boat Ramp otherwise. St. Petersburg departures meet at the Maximo Park boat ramp, where parking is free. Arrive 15 minutes before departure — a group of six takes longer to gather than you expect. Your exact meeting point is confirmed when you book.
Can we get to a sandbar where everyone can swim?
Yes, and for most celebration groups that turns out to be the centrepiece of the day. The sandbars here are shallow, calm, warm, and usually empty. Captain Keith picks one based on the tide that day — which matters more than the location, because a sandbar that is perfect at one tide can be underwater at another.
Will the captain be in touch before the charter?
Yes. Captain Keith watches conditions in the days before your charter and will reach out directly if anything needs to change, and you can call or text him any time before with questions. On a celebration date, tell him what the occasion is and what matters most to the group and he will plan the day around it.
Can we play our own music?
Yes — Bluetooth stereo aboard, your playlist, your volume. Worth building the playlist before the day rather than handing someone a phone in the sun.
How far ahead should we book a celebration date?
Further ahead than you think. Only one group goes out at a time, so a specific date fills faster than it would with a multi-boat operator. For a weekend in peak season, or any fixed date like an anniversary or a wedding weekend, book as soon as you have the date.
What if the weather is bad on our date?
We will work with you to reschedule, and Captain Keith watches the forecast in the days leading up. On a fixed occasion date that is worth planning around — if your trip has a spare day, mention it when you book and we will treat it as a backup.
Can we do a dock and dine for the celebration?
Yes. Captain Keith can navigate to a waterfront restaurant with boat access, tie up, and your group goes in for lunch, dinner, or drinks. It works well for a birthday or an anniversary where you want the meal to be part of the day. Mention it when you book.
Tell us what you are celebrating
Mention the occasion when you book and Captain Keith will shape the day around it. Celebration dates — especially weekends in season — fill quickly, since only one group goes out at a time.
Sunset Escape
$425
2.5 hours · champagne included
Half-Day Island Escape
$575
4 hours · up to 6
Gulf Escape
$395
2.5 hours · up to 6