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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

Sunset Cruise

Skill Levels

Beginner, Intermediate, Advanced

Weather

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

About Your Trip

End your day in the Florida Keys with a private cruise across the calm waters of Florida Bay as the sun sets behind Islamorada.

This laid-back two-hour experience is all about enjoying the view. Settle into the comfortable seating on a spacious 23' tritoon while your captain handles the ride, timing the trip around golden hour so your group can enjoy the changing colors from the water. Keep an eye out for dolphins along the way, bring a camera for the sunset, or simply sit back with your favorite drink and enjoy the evening.

The boat is stable, comfortable, and offers plenty of cushioned seating along with shade when you want a break from the sun. Best of all, this is a completely private experience for up to six guests, so you'll never be sharing the boat with another group.

Bring along whatever your crew likes to drink and make the evening your own. Ice and bottled water are provided onboard.

Whether you're celebrating an anniversary, planning a proposal, wrapping up a family vacation, or just looking for a peaceful evening on the water, this is one of the best ways to experience an Islamorada sunset.

Amenities

Type

Sunset Cruise

Skill Levels

Beginner, Intermediate, Advanced

Beer

Feel free to enjoy responsibly, but please no glass.

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 30 days before the trip.

Lunch

Lunch / light snacks are available for an additional fee.

Boat Restroom

No, this boat does not have a bathroom on board.

Disability Friendly

This trip is not suited for those with disabilities.

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Pricing Matrix

	2 hours
1 Person	$575.00
2 People	$575.00
3 People	$575.00
4 People	$575.00
5 People	$575.00
6 People	$575.00

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

About Your Guide

Brian E.

Outfitter

About Your Guide

Brian E.

Outfitter

Captain Brian and his crew bring decades of Florida Keys experience to every trip, offering everything from family-friendly reef fishing and sunset cruises to serious offshore adventures for Swordfish, Mahi Mahi, Tuna, Wahoo, Sailfish, and more.

Brian has spent roughly 40 years fishing the waters of the Upper Keys, building experience everywhere from the backcountry to the blue water. A USCG 100-Ton Master Captain and proven tournament fisherman, he leads a team with an incredible amount of experience of its own.

Captain Skip is a longtime Upper Keys charter captain with an impressive reputation earned over decades on the water, while Captain George brings roughly 30 years of experience guiding throughout the islands and has even shared his passion for fishing on television. Captains Shane and Rick round out the captain team, while Gabriela and mates Wyatt, Tyler, and Ricky help keep the operation running smoothly both on and off the water.

The team operates a diverse fleet designed to cover just about any kind of day you could want in Islamorada. Their two large Hatteras sportfishers provide the range and comfort for serious offshore fishing, including overnight Swordfish adventures, while their 25' bay boat gives families and light-tackle anglers access to productive nearshore reefs and calmer waters. For groups that simply want to enjoy the Keys, their 23' tritoon offers a comfortable platform for private sunset cruises.

This is also a family-run and veteran-owned operation with a story that goes well beyond fishing. The fleet was built in tribute to Brian and co-owner David's father, and David, a retired U.S. Air Force veteran, now handles much of the logistics behind the scenes.

Whether you're bringing the kids out for their first fishing trip, chasing pelagics offshore, hunting a Swordfish through the night, or simply watching the sun disappear over Florida Bay, Brian and his crew will work to build the experience around your group.

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Start Location & Lodging Options

Islamorada, Florida

About Your Boat

Boat Type: Pontoon
Boat Manufacturer: Barletta
Boat Length: 23'
Boat Restroom: No

About Your Boat

Boat Type: Pontoon
Boat Manufacturer: Barletta
Boat Length: 23'
Boat Restroom: No

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Trip Details & Amenities

Type

Sunset Cruise

Skill Levels

Beginner, Intermediate, Advanced

Beer

Feel free to enjoy responsibly, but please no glass.

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 30 days before the trip.

Lunch

Lunch / light snacks are available for an additional fee.

Boat Restroom

No, this boat does not have a bathroom on board.

Disability Friendly

This trip is not suited for those with disabilities.

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.

This trip is managed by an outfitter. Brian will be your point of contact and you will go out with one of their guides.

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 30 days before the trip and receive credit back to your account. Cancelling within 30 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.

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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.