2 hours · Private · Up to 6
2-Hour Sandbar Trip
The quick version: out to a sandbar, float, back.
| Whole boat | $350 |
|---|
Editorial spotlight · Hurricane Hole Marina, Stock Island
2026 Conch Shell Awards nomineeBest Eco/Wildlife Tour
Pirate Adventure Charters
One captain, one 26-foot center console with twin 200s, and a day you design: sandbar, snorkel, mangroves, dolphins, a wakeboard, a rod. Private, up to six, all ages, dogs welcome.
- Private trips from
- $350
- Half day
- $699
- Guests
- Up to 6
- 5.0
Editorial spotlight. Pirate Adventure Charters is a nominee in the 2026 Conch Shell Awards. They did not pay for this page and had no say in it. We earn a commission when you book through the links here; your price is the same.
The captain
Sixteen years on this water, first as a commercial fisherman
Capt. Sergey Chashchukhin fished commercially out of Key West from 2008 before switching to charters full time. It is an owner-operator outfit: he runs every trip himself, so the person who answers the phone is the one driving the boat.
The boat is a Sea Born LX 26 center console with twin 200-horsepower Suzukis, fast enough to reach the backcountry or the reef with time to spare. Trips are priced for the whole boat and the itinerary bends to the weather and the group.
“Great for all ages.”
Owner and captain
Capt. Sergey Chashchukhin
Owner-operated; Capt. Sergey runs every charter. Bio on the Pirate Adventure Charters site.
The one to book
Four hours of sandbar, on your terms
The four-hour sandbar trip is the flexible one. Start at a sandbar, add a snorkel stop or a run through the mangroves for dolphins, and come back when the group is done. Snorkel gear and drinks are aboard; bring your own food and drinks, no glass.
Six-hour versions of the sandbar, snorkel and eco trips run $899, and the two-hour sandbar or sunset-and-dolphin trips are the cheapest private boat on this site at $350.
| 2 hours | $350 |
|---|---|
| 4 hours | $699 |
| 6 hours | $899 |
Whole boat, up to six guests. Prices checked against FareHarbor on September 30, 2026.
Check AvailabilityThe boat
Sea Born LX 26
One boat, one captain. Center console with a T-top, GPS, fishfinder, livewell and ice box.
Pirate Adventure
- Make
- Sea Born LX 26 center console
- Power
- Twin 200 hp Suzuki
- Guests
- Up to 6
- Berth
- Hurricane Hole Marina, 5130 Overseas Hwy
- Extras
- Wakeboard, tube, snorkel gear, rods
Book it
Trips
Every trip is private and priced for the whole boat, up to six guests, all ages. Checked against FareHarbor on September 30, 2026.
2 hours · Private · Up to 6
Sunset & Dolphin Watching
Dolphins in the backcountry, then the sunset from the water.
| Whole boat | $350 |
|---|
4 hours · Private · Up to 6
4-Hour Sandbar Trip
The flexible half day; mix in snorkeling or mangroves as you like.
| Whole boat | $699 |
|---|
4 hours · Private · Up to 6
4-Hour Snorkeling
Reef or backcountry snorkel spots picked for the day's conditions. Gear aboard.
| Whole boat | $699 |
|---|
4 hours · Private · Up to 6
4-Hour Eco Tour & Dolphin Watch
Mangrove channels, flats and wild dolphins on a boat small enough to get in close.
| Whole boat | $699 |
|---|
4 hours · Private · Up to 6
4-Hour Wakeboarding or Tubing
Board and tube aboard; twin 200s do the pulling.
| Whole boat | $749 |
|---|
4 hours · Private · Up to 6
4-Hour Fishing Trip
Light tackle with a former commercial fisherman. License, tackle, bait and fish cleaning included.
| Whole boat | $749 |
|---|
6 hours · Private · Up to 6
6-Hour Sandbar Trip
The long sandbar day.
| Whole boat | $899 |
|---|
6 hours · Private · Up to 6
6-Hour Snorkeling
Two or three snorkel stops and time to get farther out.
| Whole boat | $899 |
|---|
6 hours · Private · Up to 6
6-Hour Fishing Trip
Enough time for the reef and the wrecks.
| Whole boat | $949 |
|---|
Also listed: a 6-hour wakeboarding or tubing trip ($949) and a 6-hour eco tour and dolphin watch ($899). Pirate Adventure Charters also rents a houseboat and runs a water taxi; call (305) 509-2882 for those.
Before you go
Know before you go
Where to board
Hurricane Hole Marina, 5130 Overseas Highway #1, Stock Island. Free marina parking. Your confirmation has the dock and time.
Bring
Your own food and drinks, no glass. Snorkel gear, drinks, wakeboard, tube and fishing tackle are aboard depending on the trip.
Fishing
Florida license, rods, reels, tackle, bait and fish cleaning are included on fishing trips.
Kids and dogs
All ages, and the boat is pet-friendly.
Reviews
What guests say
- 5.0GoogleRating as listed September 30, 2026
- 4.8FishingBookerRating as of September 30, 2026
- 5.0TripadvisorRating as of September 30, 2026
Reviewers write about the captain's patience with kids and first-timers, a boat that is new, fast and clean, and itineraries that shift with the weather so a sandbar day picks up a snorkel or a mangrove run without being asked.
Questions
Good to know
How many people can go?
Six, all ages. Every trip is private; the price is for the boat.
Where does it leave from?
Hurricane Hole Marina on Stock Island, 5130 Overseas Highway, about ten minutes from Old Town by car. Free parking.
Can we bring our own drinks?
Yes, including alcohol. No glass aboard.
What does it cost?
Two-hour trips $350, four-hour trips $699 to $749, six-hour trips $899 to $949 for the whole boat. Checked September 30, 2026.
Can we mix activities?
Yes. The four- and six-hour trips are built around whatever the group wants: sandbar, snorkeling, mangroves, dolphins, tubing.
Book the boat
Private, up to six, from Hurricane Hole Marina on Stock Island.
Check Availability