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adventures in Local Working Waterfront

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Private Sunset Cruise up to 49 people
From $2465whole boat Β· up to 29 passengers
πŸ“ Marathon
Duck Key Watersports

Private Sunset Cruise up to 49 people

All Ages β€’ 1.5 - 2 hours β€’ Flat Rate up to 45 passengers

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Key West Champagne Sunset Sail on Schooner America 2.0
From $108
πŸ“ Key West
Classic Harbor Line - Key West

Key West Champagne Sunset Sail on Schooner America 2.0

πŸ• 2h

The sail usually runs in light rain and other moderate weather situations. The only time we cancel a trip is in the event of severe or unsafe weather conditions.

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ASA 101 - Basic Keelboat Sailing Contact us for availability at info@sunshinesailing.com
From $995
πŸ“ Tavernier
Sunshine Coast Adventures

ASA 101 - Basic Keelboat Sailing Contact us for availability at info@sunshinesailing.com

Hurricane season is from June 1st through November 30th. In the event of extreme weather conditions, the captain will make the final decision regarding whether to continue with the sailing lesson or seek shelter on the mainland.

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Four Passenger Cart Rental
From $125
πŸ“ Key West
Fun Rentals Key West

Four Passenger Cart Rental

Ages 21+ to Rent β€’ Must Have a Valid Drivers License β€’ Hourly, Daily, and Weekly Rentals

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Eco Tour
From $250
πŸ“ Tavernier
Island Time Charters

Eco Tour

πŸ• 1h 30m

All charters are weather permitting and will be up to the Captain’s discretion if the trip needs to be rescheduled. All bookings require a 25% deposit to secure the date.

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2 Tank Combo Dive - Public
From $199per person
πŸ“ Key West
Finz Dive Charters Corporation

2 Tank Combo Dive - Public

## 2 Tank Combo Dive: ___________________________________ ## Finz Dive Center - Combo Dive: - **Important:** All trips include a dive master that is in the water with our divers. - Finz Combo dive is a mix between the adventure of a wreck and the beauty of a reef. - We will start out on one of our 3 major wrecks for our first dive. You will explore the history and mystery of one of the keys artificial reefs with your professional dive guide. - For the second dive we will move to shallower water and explore part of the third largest barrier reef in the world. - You get the best of both dives in a fun relaxed atmosphere. **Finz Dive Center has a 3 person minimum to run a public dive trip. We reserve the right to cancel a dive that does not meet the minimum requirements.**

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8 Hour Private Charter - Andiamo
From $2018
πŸ“ Key West
That's What Sea Said, LLC

8 Hour Private Charter - Andiamo

πŸ• 8h

In the event the Charterer does not want to reschedule, the Charterer has the option to spend time on the boat at the marina until weather allows for departure.

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Perfume Making Class
From $130
πŸ“ Key West
Aqua D’Keys

Perfume Making Class

πŸ• 2h

Visiting Key West and looking for some exciting activities in town? Try our perfume making classes right here in Key West. Discover the world of fragrances in a hands-on way!

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24’ Bently Tritoon
From $450per rental
πŸ“ Lower Keys
Sugarloaf Marina

24’ Bently Tritoon

Enjoy a Perfect Day On the Water! Duration Multi-Day Rental Options About Brand new 24’ Bently Tritoon big enough for the whole family. Tritoon is more stable than the standard pontoon making it more stable and able to go out onto the Oceanside(weather permitting), snorkel Looe Key, and still able to get you out to the sandbars in the Backcountry.

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22' Sea Pro Deck Boat
From $525whole rental unit
πŸ“ Lower Keys
Nothing Better Boat Rentals

22' Sea Pro Deck Boat

$100 Deposit reserves the boat. 22' deck boat with plenty of wrap around seating for 12 people comfortably with a 135 hp motor. Boat is equipped with a GPS that has colored tracks to cool locations. This is a leisure and or fishing boat. We deliver the boat for all rentals to the dock of where you are renting or own. Ask about working full time local deals. Free delivery to locations between Sugarloaf Key and Summerland. Boat rental needs to be back at the dock by 5 PM and is not permitted to go out at night or go past the barrier reef which is 7 miles out in the Atlantic Ocean.

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Cowboy 36' Proven Offshore Fishing Charter
From $850whole boat
πŸ“ Key West
Key West Fishing Deals

Cowboy 36' Proven Offshore Fishing Charter

#Come catch some Mahi, Wahoo, Black Fin tuna, Sailfish, and Marlin! ## Duration & Rates - **4-Hour Private Charter:** $850 **Start Times:** 7am & 1pm - **6-Hour Private Charter:** $1,150 **Start Times:** 7am & 1pm - **8-Hour Private Charter:** $1,350 **Start Time:** 7am - **10-Hour Private Charter:** $1,550 **Start Time:** 7am - **12-Hour Private Charter:** $1,750 **Start Time:** 7am ***All start times can be modified per request*** *All ages welcome! For up to 6 people* ## About Offshore deep sea fishing with our knowledgeable and professional crew for species such as Mahi, Wahoo, Black Fin Tuna, Sailfish, and Marlin. - Special requests welcome, i.e. tarpon, shark, etc.

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Barefoot III
From $750
πŸ“ Key West
Barefoot Charters

Barefoot III

πŸ• 4h

Hang out like the locals! The shallow, clear backcountry waters of the Florida Keys sets us apart from anywhere else in the country. Just a short boat ride will transport you to what feels like a world away!

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Three Hour Public Tour
From $450per group Β· up to 3 people
πŸ“ Islamorada
Reef Quest Eco Boat Tours

Three Hour Public Tour

Up to 6 People Duration 3 Hours About Tour could include either snorkeling, sandbar, site seeing, bird/mammal finds, or historical Island adventure

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Memorial
From $5200
πŸ“ Key West
Restless Native Charters

Memorial

For those wishing to have their ashes scattered at sea, we believe there is no better place than the clear calm waters of the Florida Keys National Marine Sanctuary. We offer sea services for the burial of cremains at sea.

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3/4 Day Sandbar Charter
From $800whole boat Β· up to 6 people
πŸ“ Key West
Nice Guy Charters

3/4 Day Sandbar Charter

$800 per Charter | 6 Hours | All ages | Come see the beauty of the Florida Keys

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24 Yellowfin Bay Boat
From $1200whole boat
πŸ“ Key West
Second Generation Fishing Charters

24 Yellowfin Bay Boat

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Sunset Harbor Tour
From $400whole boat Β· up to 6 people
πŸ“ Key West
Fish Monster Island Jane

Sunset Harbor Tour

1 Hour & 30 Minutes β€’ All Ages β€’ Up to 6 People

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Full Day Fishing Charter
From $1600whole boat Β· up to 6 people
πŸ“ Marathon
Unreel Keys Fishing Co

Full Day Fishing Charter

8 hours of world class fishing in any or all of the three keys marine ecosystems. Reef, wreck & bridge: yellowtail snapper, mangrove snapper, black grouper, red grouper, goliath grouper, amberjack, barracuda, jack crevalle, yellow jacks, a variety of other species and very frequent surprises. Bluewater, deep sea: blackfin tuna, sailfish, wahoo, mahi-mahi, king mackerel, cero mackerel, spanish mackerel, cobia, barracuda, tripletail, sharks. Backcountry: tarpon, snook, permit, bonefish, redfish, snapper, jacks, mackerel, speckled trout.

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Key West Full Day Fishing
From $2300whole boat
πŸ“ Key West
Second Generation Fishing Charters

Key West Full Day Fishing

Experience incredible fishing adventures throughout the Gulf of America and the South Atlantic offshore waters. West of Key West, anglers can experience incredible fishing adventures throughout the Gulf of America and the South Atlantic offshore waters. This area offers diverse opportunities, including fishing around shrimp boats for tuna and bonita, as well as targeting reefs and shipwrecks teeming with species like amberjack, goliath grouper, sharks, and mackerel. Charters can accommodate up to six people, making it perfect for groups or families. The waters west of Key West are renowned…

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Snorkel Tour
From $63.24per person
πŸ“ Marathon
Starfish Snorkeling

Snorkel Tour

#About Starfish Snorkeling Tours... Daily Snorkel Trips To Sombrero Reef. The friendly snorkeling crew of "The Starfish" will take you on a fun filled snorkeling adventure to the Sombrero Reef Marine Sanctuary and Lighthouse where you will see the spectacular living coral reef. Sombrero Reef Marine Sanctuary and Lighthouse is the #1 rated snorkeling spot in the Florida Keys. This 30 acre coral reef is from 2 – 30 feet deep with thousands of tropical fish. PLEASE NOTE: Alternate snorkel sites are utilized based on sea conditions. 24 hour cancellation policy in effect regardless of destination. ___________________________________ ##Rates **Snorkelers** 8:30 a.m. to 12 noon Adults & children 9 years + = $49.00 +tax (fuel surcharge & other tour fees may apply) Children 2-8 years = $39.99 +tax Children 0-2 years = $19.99 +tax 12:30 pm p.m. to 4 p.m. Adults & children 9 years + = $49.00 +tax (fuel surcharge & other tour fees may apply) Children 2-8 years = $39.99 +tax Children 0-2 years = $19.99 +tax Sunset tours (seasonal-off season sunset cruise only) $68.00 +tax (fuel surcharge & other fees may apply) ___________________________________ ##Available Times **7 Days Per Week Year Round** β€’ 8:30 AM, 12:30 PM and Sunset (Seasonal) ___________________________________ ##Duration **3 hours** ___________________________________ ##Check-In Information - **Please arrive 1 hour before your activity's start time to check in.** - *Check in cut-off is 30 minutes prior to departure.* - *Detailed directions will be included in your confirmation email.* - *Wetsuits, prescription masks and more available for rental upon arrival. Underwater cameras, sun lotion, sodas, waters, snacks and more available to purchase.* -Non-swimmers are allowed for the boat ride ONLY, not snorkeling - non adult swimmers may not enter the water* -*NO free dive fins, weight belts, scuba apparatus, coolers or spray sunblock permitted. If you have a full face mask you must sign an additional waiver at check in.* ___________________________________ ##Cancellation Policy Customers will receive a full refund with 24 hours notice of cancellation. Customers will also receive a full refund in case of operator cancellation due to weather or other unforeseen circumstances. Contact us by phone to cancel or inquire about a cancellation. Check in begins 1 hour before departure and Check in cutoff is 30 minutes before departure. If not present by checking cutoff, trip is forfeited and there will be no refund. No-shows will be charged the full price. **Weight restrictions apply. Per United States Coast Guard Title 46 Code of Federal Regulations 178.330. Platform and ladder weight restrictions 275 lb. max.** Alternate locations are utilized based on real time conditions, 24 hour cancellation applies to all destinations.

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Multi-Porpoise Day Excursions
From $699per group
πŸ“ Key West
Luxury Sea Charters

Multi-Porpoise Day Excursions

Join us aboard for a multi-porpoise day on a 29 foot center console WITH a bathroom. Do you crave an extreme fishing adventure? Are you interested in snorkeling or checking out the local sandbars? Or would you prefer a peaceful sunset cruise?

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1/2 Day Fishing
From $1200whole boat
πŸ“ Key West
Second Generation Fishing Charters

1/2 Day Fishing

Some families are looking for a fun day fishing on the water but not to far from home. Lets stay close to Key West. Some families are looking for a fun day fishing on the water but not to far from home. Sometimes you don't need to Run far to find fish.

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8 Hour Offshore Fishing
From $1600whole boat Β· up to 4 people
πŸ“ Islamorada
Snap Em Up Fishing Charters LLC

8 Hour Offshore Fishing

This trip allows you to target mahi, tuna, wahoo, farther offshore and also gives you enough time to fish the Reef if needed to catch snapper, grouper, and sailfish.

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Half Day Fishing Trip
From $800whole boat Β· up to 6 people
πŸ“ Key West
Boa Vida Charters

Half Day Fishing Trip

Life is GOOD when you're on the water- let's go fishing! Duration 4 Hours About The four-hour trip is perfect for when the pelagic are just outside of the reef, target species fishing like shark or tarpon, reef fishing for bottom species and snappers, or if you have time constraints. This one's great for the smaller kids.

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2026 Awards · editorial spotlights

Nominees we wrote up ourselves. They did not pay for these pages and had no say in them.

Best Dive OperatorFinz Dive Center6003 Peninsular Avenue, Stock Island · Two-tank dive $199 Best Boat CharterSix FinsPerry Hotel & Marina, Stock Island · Private boats from $995 Best Eco/Wildlife TourPirate Adventure ChartersHurricane Hole Marina, Stock Island · Private trips from $350 Best Boat TourKey West Boat & Jet Ski Adventures5016 5th Avenue, Stock Island, Cow Key Channel · Jet ski tour $139.95