You're in good hands

Book your trip with confidence — We only work with the best local guides that know the area like the back of their hand.

Reserve Your Trip

Total

NEW

Select a date to view pricing. The date you selected is no longer available. Please select another date.

Date

Select a group size to view pricing.

Select an animal to view pricing.

Select a duration to view pricing.

Select a start time to check out.

You won't be charged yet

Total

Browse Similar Trips

You're in good hands

Book your trip with confidence — We only work with the best local guides that know the area like the back of their hand.

About Your Trip

Type

Boat Cruise

Skill Levels

Beginner, Intermediate, Advanced

Weather

You won’t lose your deposit if the trip is canceled due to weather.

About Your Trip

Step aboard with Captain Herman and set sail for an unforgettable day on the water! His 41’ Morgan Out Island sailing yacht is built for comfort, relaxation, and easy adventure—making it the perfect choice for couples, families, or small groups looking to unwind and explore the stunning Gulf Coast in style.

Designed with a spacious center cockpit, wide open deck space, and plenty of shaded areas, there’s no shortage of places to lounge, soak up the sun, or simply enjoy the salty breeze. Below deck, you’ll find all the amenities you need for a relaxing day at sea, including forward and aft bedrooms, two bathrooms, and a roomy galley (kitchen and dining area) for meals or refreshments. Whether you’re planning to kick back or head out for an adventure, this vessel offers the perfect blend of comfort and capability.

Half-Day Sailing Trip (4 Hours)

This 4-hour excursion is ideal for anyone wanting a taste of the sailing lifestyle. Departing from Dunedin Marina, Captain Herman will guide you through the calm waters of the Intracoastal Waterway before heading out into the Gulf of Mexico. Want to stretch out and relax with a drink in hand? Go for it. Prefer to drop anchor and dive in for a swim? You’ve got options. This customizable trip is all about what you want to do—no rush, no stress, just smooth sailing.

Full-Day Charter (8 Hours)

Looking for a full day of fun, exploration, and total relaxation? This 8-hour sailing charter lets you create your own adventure. You can spend the day under sail, visit a nearby island, drop the anchor for lunch and a swim, or mix and match it all. With plenty of time and a boat designed for comfort, you’ll feel like you’ve got the Gulf all to yourself.

Captain Herman brings years of sailing experience and a calm, friendly approach to every trip. Safety is always top priority—your charter includes all the latest navigation and communication tech, including onboard GPS and a satellite phone. And when it’s time to go ashore or get a little closer to the beach, you’ll have access to a 10.4’ Achilles rigid-hull inflatable dinghy powered by a Yamaha 10hp outboard.

Whether you’re looking for a relaxing afternoon, a full-day sailing escape, or something in between, Captain Herman’s charters offer a flexible, comfortable way to experience Florida’s Gulf Coast from the best seat in the house—on the water.

Amenities

Type

Boat Cruise

Skill Levels

Beginner, Intermediate, Advanced

Beer

Feel free to enjoy responsibly, but please no glass.

Boat Restroom

This boat has a restroom.

Weather

You won’t lose your deposit if the trip is canceled due to weather.

Kid Friendly

This trip can cater to small children.

Flexible Cancelation

This trip can be canceled up to 14 days before the trip.

Disability Friendly

This trip is not suited for those with disabilities.

Lunch

Please provide your own food / snacks.

Scroll for more

Pricing Matrix

	4 hours	8 hours
1 Person	$425.00	$825.00
2 People	$425.00	$825.00
3 People	$425.00	$825.00
4 People	$425.00	$825.00
5 People	$425.00	$825.00
6 People	$425.00	$825.00

Pay 15% of the price as a deposit today, with the balance due on the day of the trip.

About Your Guide

Herman

Independent Guide

Captain Herman has over 30 years experience as a charter boat captain with a United States Coast Guard issued 100 Ton Master Captains License with Sailing Endorsement. Captain Herman is very experienced in the waters of Saint Petersburg, Clearwater, and the Tampa area, where he has spent the past 25 years. The Captain is also a PADI Master Scuba Diver Trainer and IANTD Technical Dive Instructor.

About Your Guide

Herman

Independent Guide

Scroll for more

Start Location & Lodging Options

Dunedin, Florida

About Your Boat

Boat photo for Half Day Or Full Day Sailing

Boat Type: Sailboat
Boat Manufacturer: Morgan Out Island
Boat Length: 41'
Boat Restroom: Yes

About Your Boat

Boat Type: Sailboat
Boat Manufacturer: Morgan Out Island
Boat Length: 41'
Boat Restroom: Yes

Scroll for more

Trip Details & Amenities

Type

Boat Cruise

Skill Levels

Beginner, Intermediate, Advanced

Beer

Feel free to enjoy responsibly, but please no glass.

Boat Restroom

This boat has a restroom.

Weather

You won't lose your deposit if the trip is canceled due to weather.

Kid Friendly

This trip can cater to small children.

Flexible Cancelation

This trip can be canceled up to 14 days before the trip.

Disability Friendly

This trip is not suited for those with disabilities.

Lunch

Please provide your own food / snacks.

Everything Else to Know

Everything is included, but we also recommend bringing sunglasses, sunscreen, weather-appropriate clothing, and anything else you might want on the trip.

We use a cashless autopay system. We'll send you a boarding pass, and on the day of the trip, your guide will scan your boarding pass to automatically transfer the remaining balance. The only cash needed is to tip your guide (we recommend 20%).

Cancel for free up to 14 days before the trip and receive credit back to your account. Cancelling within 14 of the trip will forfeit your deposit to the guide. Day-of cancellations and no-shows will be charged the full balance of the trip to their card.

In the event of inclement weather you'll be covered by out 100% Weather Guarantee and will not lose your deposit.

Recent Reviews of Captain Experiences

Lucinda

Verified Review

It was more than I expected and seamless. I would highly recommend Captain Experiences.

Lucinda

Verified Review

It was more than I expected and seamless. I would highly recommend Captain Experiences.

Scroll for more

Trip: Key West On Light Tackle & Flies

Ray

Verified Review

Five stars! Fun trip!

Ray

Verified Review

Five stars! Fun trip!

Scroll for more

Trip: Inshore Family Fun Fishing

Thomas

Verified Review

Great time, great guide. Can’t wait for the next trip.

Thomas

Verified Review

Great time, great guide. Can’t wait for the next trip.

Scroll for more

Trip: Reel Salty Sportfishing

Jamie

Verified Review

Great trip on short notice

Jamie

Verified Review

Great trip on short notice

Scroll for more

Trip: Inshore Emerald Coast

John

Verified Review

Everything went great. The weather was great too.

John

Verified Review

Everything went great. The weather was great too.

Scroll for more

Trip: Inshore Venice

First Time Booking with Us?

Captain Experiences is home to thousands of quality, vetted fishing, hunting, and other outdoor sports guides across the US and beyond. Our mission is to Unlock the Outdoors by making it quick and easy to book the trip of a lifetime every time with our Damn Good Guides.

We vet our guides and only partner with the best of the best. Our guides do their very best to keep you safe, show you a great time, and send you home with a memorable experience shared with family and friends.

Once you've paid your deposit at checkout, we'll send you a QR Code boarding pass. Just show your guide your boarding pass on the day of the trip, they'll scan it, the remaining balance will transfer automatically, and you'll be all set to get out there. Just make sure you bring a cash tip for the guide!

In the event of inclement weather, our guides will check the conditions and make the final call on whether its safe to go on the trip. If they decide the trip needs to be postponed, we'll work closely with you to reschedule or provide a credit for the full deposit, which can be applied to any of our trips in the US and beyond.

Each trip's price is determined by the guide and reflects all associated costs. A significant factor in pricing is often the type of boat and the corresponding fuel expenses. Additional costs may include leases, marina or slip fees, and the expenses involved in providing and maintaining the necessary gear for your trip.

After booking your trip, we'll connect you directly with your guide to discuss additional details. In the meantime, our team is here to answer any questions via email, text, or phone.