Damn Good Boat Cruise Guides In Stock Island

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

Choose a Date

Damn Good Guides

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

Experts Available 24/7

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

100% Weather Guarantee

We want to keep everyone safe, so in the case of inclement weather we'll work with you to reschedule at no cost

Recently Booked Boat Cruise Guides In Stock Island, Fl

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
Fishing in Destin
Fishing in Destin
Fishing in Destin

Boat Cruise, Snorkeling, Sunset Cruise in Stock Island

Sandbar & Snorkel Adventures

NEW
24 ft 1 - 6 People From $700
Fishing in Destin
Fishing in Destin
Fishing in Destin

Eco Tour, Boat Cruise in Stock Island

Sandbar Tour Stock Island

NEW
25 ft 1 - 4 People From $750
Fishing in Destin
Fishing in Destin
Fishing in Destin

Eco Tour, Boat Cruise in Key West

Sandbar Tours

NEW
42 ft 1 - 36 People From $1,299
Hot Trip
people are viewing this trip.
Fishing in Destin
Fishing in Destin
Fishing in Destin

Eco Tour, Boat Cruise, Dolphin Watching in Key West

Remote Island And Sandbar Tour

NEW
27 ft 1 - 6 People From $800
Fishing in Destin
Fishing in Destin
Fishing in Destin

Eco Tour, Boat Cruise, Snorkeling in Big Pine Key

Big Pine Sandbar

100% (2)
25 ft 1 - 6 People From $550

“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 Stock Island, Fl

Fishing in Destin
Fishing in Destin
Fishing in Destin

Eco Tour, Boat Cruise in Key West

Florida Keys Sand Bar Sunset Tour

100% (12)
24 ft 1 - 4 People From $700
Fishing in Destin
Fishing in Destin
Fishing in Destin

Boat Cruise, Booze Cruise in Key West

4 Hour Sand Bar Tour

100% (14)
24 ft 1 - 8 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, Snorkeling in Key West

Island Snorkel & Sandbar Hop

100% (10)
21 ft 1 - 6 People From $649
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

Boat Cruise, Snorkeling, Sunset Cruise in Key West

Snorkeling, Sandbar Or Sunset

100% (125)
27 ft 1 - 12 People From $350
Fishing in Destin
Fishing in Destin
Fishing in Destin

Eco Tour, Boat Cruise, Booze Cruise in Key West

Tiki Boat Tours

NEW
26 ft 1 - 12 People From $949
Fishing in Destin
Fishing in Destin
Fishing in Destin

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

Sunset Cruise

100% (2)
25 ft 1 - 12 People From $325
See All Boat Cruise Trips in Stock Island

Other Captain Experiences Trips in Stock Island

Hot Trip
people are viewing this trip.
Fishing in Destin
Fishing in Destin
Fishing in Destin

Inshore, Flats Fishing in Key West

Key West "Flex" Sportfishing

100% (78)
24 ft 1 - 4 People From $700
Bucket List
The Captain Experiences team chose this trip as one for the bucket list.
Fishing in Destin
Fishing in Destin
Fishing in Destin

Inshore, Nearshore, Flats in Key West

Marquesas Key "Hidden Gem" Trip

100% (78)
24 ft 1 - 4 People From $1,200
Fishing in Destin
Fishing in Destin
Fishing in Destin

Inshore, Flats Fishing in Key West

Key West Tarpon Hunt

100% (78)
24 ft 1 - 4 People From $700
Fishing in Destin
Fishing in Destin
Fishing in Destin

Inshore, Flats Fishing in Key West

Half-Day Tarpon Trip (Seasonal)

100% (78)
24 ft 1 - 4 People From $700
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

Deep Sea, Nearshore Fishing in Key West

Key West Sportfishing Trip

99% (106)
45 ft 1 - 6 People From $1,200
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

Deep Sea, Nearshore Fishing in Key West

Key West Fishing Slam

99% (106)
36 ft 1 - 6 People From $1,050
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

Deep Sea, Nearshore Fishing in Key West

Key West Deep Sea Run - 40' Luhrs

99% (106)
40 ft 1 - 6 People From $1,400
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

Deep Sea, Nearshore Fishing in Key West

Key West Sportfish Trip

99% (106)
37 ft 1 - 6 People From $1,150
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

Inshore, Nearshore Fishing in Key West

Key West Fishing Adventure

100% (51)
24 ft 1 - 8 People From $800
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

Deep Sea, Nearshore Fishing in Key West

Offshore, Reef & Wreck, And Sunset

100% (125)
36 ft 1 - 12 People From $900
Fishing in Destin
Fishing in Destin
Fishing in Destin

Deep Sea, Nearshore Fishing in Stock Island

Key West Nearshore/Offshore Trip

100% (34)
63 ft 1 - 12 People From $1,850
Fishing in Destin
Fishing in Destin
Fishing in Destin

Deep Sea Fishing in Key West

4 Hour Nearshore Fishing Trip

100% (1)
34 ft 1 - 4 People From $1,800

Need a Place to Stay?

Everything to Know About Booking a tours trip in Stock Island

What are the best boat cruise trips in Stock Island?

What do I need to know about Boat Cruises in Stock Island?

Stock Island is where the Keys trade the tourist bustle for something a little rawer, a little more real. Boat cruises here aren’t about showboats or crowded decks—they’re about slipping into the quiet rhythms of mangroves, salt flats, and open water. Whether you’re skimming over glassy bays or threading through hidden channels, each trip offers a chance to disconnect and tap into the wild heart of the Keys. Dolphins race alongside your bow, herons glide overhead, and the occasional manatee surfaces like a gentle ghost in the turquoise shallows.

Local captains bring more than charts and skills—they bring stories. Stories of old fishing haunts, pirate legends, and the natural pulse of this unique coastline. They know where to find the best wildlife, when the light hits the water just right, and how to read the wind before a tropical shower rolls in. A boat cruise in Stock Island isn’t just a ride; it’s a chance to see the Keys like few ever do—unfiltered, untamed, and utterly unforgettable.

For those who want to trade the noise for nature, Stock Island’s boat cruises deliver. No frills, no crowds—just salt on your skin, sun on your face, and the kind of quiet adventure that stays with you long after you’ve stepped back on shore. Pack a hat, bring a sense of wonder, and get ready to explore one of Florida’s best-kept secrets.

What are the most popular months for Boat Cruises in Stock Island?

Stock Island’s seasons shape the water like a well-worn trail shapes a journey. Spring is when the mangroves burst back to life and the wildlife wakes up slow and steady. Early morning cruises catch the water at its calmest, with manatees making their gentle rounds and birds returning from their winter haunts. It’s a season that feels like a fresh start—quiet, hopeful, and full of possibility.

Summer turns up the heat and the hum of life in the Keys. The days stretch long and sticky, with quick afternoon storms sweeping in to cool things down. The magic hours come early and late—the mornings when the Gulf is glassy and the dolphins are playful, and the evenings when the sunset spills gold across the horizon. It’s wild, it’s humid, and it’s when Stock Island feels most alive.

Come fall and winter, the pace slows but the beauty sharpens. Cooler air means clearer skies and calmer waters, perfect for exploring the mangrove tunnels or spotting migratory birds in full flight. These seasons strip the Keys down to essentials—quiet, crisp, and unhurried. Stock Island’s boat cruises then become less about rushing and more about soaking in the wild soul of the place, one quiet moment at a time.

Other Featured Cities

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:

See All Boat Cruise Trips in Stock Island