Damn Good Boat Cruise Guides In The Florida Keys

Check real-time availability and compare rates on private Florida Keys boat cruise guides. Confidently book your next trip.

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5/5 Average Rating

Recently Booked Boat Cruise Guides In The Florida Keys

Fishing in Destin
Fishing in Destin
Fishing in Destin

Boat Cruise, Snorkeling in Islamorada

Family Fun Mix-It-Up Trip

100% (36)
26 ft 1 - 12 People From $1,275
Fishing in Destin
Fishing in Destin
Fishing in Destin

Eco Tour, Boat Cruise, Snorkeling in Marathon

Coffins Patch Snorkel & Sandbar

100% (4)
28 ft 1 - 6 People From $600
Fishing in Destin
Fishing in Destin
Fishing in Destin

Eco Tour, Boat Cruise, Snorkeling in Marathon

Boating Adventure

NEW
24 ft 1 - 6 People From $550
Fishing in Destin
Fishing in Destin
Fishing in Destin

Eco Tour, Boat Cruise, Booze Cruise in Marathon

Scenic Boat Tours

NEW
34 ft 1 - 4 People From $900
Damn Good
Certified Damn Good Guides offer 10/10 trips. Guides earn this badge through quality reviews, quick and responsive communication, and low cancellation rates.
Fishing in Destin
Fishing in Destin
Fishing in Destin

Eco Tour, Boat Cruise, Snorkeling in Big Pine Key

Big Pine Sandbar

100% (4)
25 ft 1 - 12 People From $600
Damn Good
Certified Damn Good Guides offer 10/10 trips. Guides earn this badge through quality reviews, quick and responsive communication, and low cancellation rates.
Fishing in Destin
Fishing in Destin
Fishing in Destin

Eco Tour, Boat Cruise, Sunset Cruise in Big Pine Key

Sunset Cruise

100% (4)
25 ft 1 - 12 People From $350

What makes Captain Experiences Damn Good?

Damn Good Guides

You will only find quality, vetted guides on Captain Experiences, and we know them all on a first-name basis.

Damn Good Guides

Experts Available 24/7

Our US-based team is available 24/7 to help you with any questions or concerns.

Experts Available 24/7

100% Weather Guarantee

We want to keep everyone safe, so if the weather is bad we'll work with you to reschedule at no cost.

100% Weather Guarantee

4.9 / 5 Average Rating

We hand pick our Damn Good Guides, and our network spans across North America and beyond.

4.9 / 5 Average Rating

“Our Damn Good Guides go above and beyond, and we've handpicked every single one. We're passionate about the outdoors and look forward to getting you out on the trip of a lifetime, every time.”

Jonathan and Attison   |   Co-founders   |   Austin, Texas

More Boat Cruise Guides In The Florida Keys

Fishing in Destin
Fishing in Destin
Fishing in Destin

Inshore, Eco Tour, Boat Cruise in Key West

Private Luxury Boat Charter

NEW
37 ft 1 - 13 People From $799
Damn Good
Certified Damn Good Guides offer 10/10 trips. Guides earn this badge through quality reviews, quick and responsive communication, and low cancellation rates.
Fishing in Destin
Fishing in Destin
Fishing in Destin

Eco Tour, Boat Cruise, Snorkeling in Key West

Island Snorkel & Sandbar Hop

100% (13)
21 ft 1 - 6 People From $649
Fishing in Destin
Fishing in Destin
Fishing in Destin

Eco Tour, Boat Cruise in Key West

4-8 Hour – Sandbar Trip

NEW
27 ft 1 - 6 People From $650
Fishing in Destin
Fishing in Destin
Fishing in Destin

Eco Tour, Boat Cruise, Snorkeling in Key West

Luxury Sandbar & Snorkel Trip

100% (1)
32 ft 1 - 6 People From $1,200
Fishing in Destin
Fishing in Destin
Fishing in Destin

Boat Cruise, Booze Cruise in Key West

Sandbar Trip - 32'

100% (1)
32 ft 1 - 6 People From $1,200
Veteran Operated
This trip is managed by a veteran of the US armed forces.
Fishing in Destin
Fishing in Destin
Fishing in Destin

Eco Tour, Boat Cruise in Stock Island

Sandbar Chillin'

NEW
24 ft 1 - 8 People From $700

Didn't Find What You Were Looking For?

Our guides are Damn Good Guides, which means they’re vetted by our team of outdoor experts who know them on a first-name basis. We hand pick each and every one of them, and our network spans all across the US and beyond.

The proof is in the pudding, and we’re incredibly proud of our 4.9 / 5 average review score. Hit the button below to see more trip options:

Everything to Know About Booking a tours trip in the Florida Keys

What are the best boat cruise trips in the Florida Keys?

The best boat cruise trips in the Florida Keys are:

Why should I book a boat cruise trip in the Florida Keys with Captain Experiences?

Our Damn Good Guides currently offer 24 private boat cruise trips in the Florida Keys, and the most popular trips in the area are Family Fun Mix-It-Up Trip guided by Chris, Coffins Patch Snorkel & Sandbar guided by Kerry, and Boating Adventure guided by Larry.

Our guides in the Florida Keys are rated a 5 out of 5 based on 8347 verified reviews on Captain Experiences.

All guides on Captain Experiences are vetted by our team. You can access their reviews, click through trip photos, read bios to get to know them, and preview trip details like species, techniques, group sizes, boat specs and more.

Looking for private kid friendly boat cruise trips in the Florida Keys? Check out our beginner and family friendly boat cruise trips in the Florida Keys.

What types of boat cruise trips are common in the Florida Keys?

The most commonly sought after species for boat cruise trips are: 1. bottlenose dolphin and 2. green sea turtle.

How much does a private Florida Keys boat cruise trip cost?

Prices for boat cruise trips in the Florida Keys can range anywhere from about $700 to $3,121, but the average price for a half day trip for boat cruise trips in the Florida Keys is $1,551. The average price for a full day trip for boat cruise trips in the Florida Keys is $1,902.

Is booking a guide worth the money?

Hiring a guide provides a number of benefits and many choose to book a guide for a combination of experience, local knowledge, convenience, and cost-effectiveness.

Working with experienced guides who know the best local spots and techniques can dramatically increase your odds of a great day. Having someone who is in the wild every day and knows the area like the back of their hand is going to give you the best chances of having a great trip.

Booking a guide is also more cost effective, especially if you only get out a handful of times per year. When you consider all of the costs you would incur on your own such as the price of a boat, maintenance, insurance, gas, high-quality gear and tackle, repairs, and more, you’ll find that DIY is sometimes not worth the expense.

Even if you’ve got a great setup already in your home waters, booking a guide also provides a great opportunity to experience new techniques, new locations, or even a chance at a new target species to knock off the bucket list.

What month is best for boat cruise trips in the Florida Keys?

The most popular season for boat cruise trips in the Florida Keys is summer, and most people book their trips 19 days in advance.

Recent Reviews

  • ★★★★★
    Zak was an excellent captain and guide! He kept us safe and comfortable for the ride and took us to the perfect sandbar location. We’ll be booking him again next girls trip to Key West!

    Kari B. | July 12, 2026

    Trip: Sandbar Trip - 32'

  • ★★★★★
    This is my 2nd of 3 booked charters with Chris. This one was special. 3 generations on a fishing/swimming/snorkeling fun trip. This man was so patient and enthusiastic with my grandchildren. As I am tucking them in to bed tonight, they want to know when we can do that again! He got special mention in their bedtime prayers... I have no idea how Chris can manage this level of energy day in and day out. Hands down, the best guide I have ever booked.

    Carl L. | March 9, 2023

    Trip: Family Fun Mix-It-Up Trip

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Types of Fishing in the Florida Keys

Other Types of Tours in the Florida Keys

Last updated: July 17, 2026

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See All Boat Cruise Trips in the Florida Keys