Key West


KEY WEST · FLORIDA KEYS

15 Best Key West Boat Trips & Tours

Key West’s best days on the water.

The 15 standout trips around Key West. The sails, snorkels and adventures people still talk about long after they fly home.

15 Best Key West Boat Trips & Tours

Key West Sunset Sail with Open Bar, Live Music and Hors D'oeuvres - What You Eat and Drink on This Open Bar Sail
Concerts, Cruises & Boat Tours, Drinking Tours, Evening Experiences, Key West, Sunset Sails & Cruises, Tour Reviews

Key West Sunset Sail with Open Bar, Live Music and Hors D’oeuvres

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1.Key West Sunset Sail with Open Bar, Live Music and Hors D’oeuvres

Sail Key West at sunset on a large catamaran with an open bar, live local music, and filling hors d’oeuvres. Depart from Elizabeth St.

Most Popular★ 4.5

“The captain and crew were extremely attentive to all of the passengers. They even brought drinks and horsdoeuvres to the passengers hanging out on the main deck who were watching the Amazing sunset. They even mingled with the everyone and helped take pictures when asked. This was a highlight of our time at Key West!!”

3,559 reviews2 hours (approx.)From $79.00by Sebago Key West

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Shark and Wildlife Viewing Adventure in Key West - Meeting at Opal Key Resort & Pier B: easy start, quick setup
Key West, Shark & Wildlife Tours, Tour Reviews, Wildlife

Shark and Wildlife Viewing Adventure in Key West

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2.Shark and Wildlife Viewing Adventure in Key West

Key West shark and wildlife tour on the eco-friendly Tiger Cat. Learn, snack, and watch lemon and nurse sharks feed up close.

★ 5.0

“Nature does what it wants. The captain was clear that the temperature affects what we see. Sharks, dolphins, sea turtles all checked off the list.Lots of great stories by Clay and Matt.”

2,962 reviews2 hours (approx.)From $99.00by Key West Extreme Adventures

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Guided Bike Tour of Old Town Key West - The Stops: From Mallory Square to Mile Marker Zero and Beyond
Bike Tours, Cycling Tours, Guided, Key West, Tour Reviews, Tours

Guided Bike Tour of Old Town Key West

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3.Guided Bike Tour of Old Town Key West

Guided bike tour through Old Town Key West with stops at Mallory Square, Mile Marker Zero, and the Southernmost Point, plus key lime pie.

★ 5.0

“Informative and relaxed biking tour. Salty was funny also! The bikes were easy to use. Why a 100 character review? LOL”

2,611 reviews2 hours (approx.)From $59.00by Key Lime Bike Tours

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Key West Mangrove Kayak Eco Tour - Wildlife spotting: what you can look for on the water
Canoes & Kayaks, Kayak Tours, Key West, Tour Reviews, Tours

Key West Mangrove Kayak Eco Tour

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4.Key West Mangrove Kayak Eco Tour

Paddle Key West mangrove creeks on a calm, guided 2-hour eco tour with wildlife spotting, cool geology stories, and small groups.

★ 5.0

“Our guide was very knowledgeable about the marine environment. Made it fun and enjoyable. Thank you so much Brett!”

2,205 reviews2 hours (approx.)From $80.00by Lazy Dog Adventures

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Southernmost Food & Cultural Walking Tour by Key West Food Tours - Small-Group Format and the 3-Hour Pace on 1.2 Miles
Food, Food & Drink, Food & Walking Tours, Key West, Tour Reviews, Tours, Walking Tours

Southernmost Food & Cultural Walking Tour by Key West Food Tours

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5.Southernmost Food & Cultural Walking Tour by Key West Food Tours

Southernmost Key West Food & Cultural Walking Tour packs 5 tastings, Cuban stops, and Old Town stories into a small-group 3-hour walk.

★ 5.0

“We enjoyed everything about this tour. Marissa our tour guide provided a nice balance of history, food and local lore. The walking was pretty easy and now there are so many new places to try. Well worth it!”

1,730 reviews3 hours (approx.)From $90.19by Key West Food Tours

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Key West Sunset Cruise: Dinner, Live Music & Drinks Included - Dinner Is a Tropical Buffet (And How to Make It Yours)
Concerts, Cruises & Boat Tours, Dining Experiences, Dinner Experiences, Evening Experiences, Key West, Sunset Sails & Cruises, Tour Reviews

Key West Sunset Cruise: Dinner, Live Music & Drinks Included

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Half-Day Trip from Key West with Kayaking, Snorkeling & Sunset - Getting to the boat: what to bring and what to expect at 255 Front St
1-Day Tours, Canoes & Kayaks, Evening Experiences, Half-Day, Kayak Tours, Key West, Reef Snorkeling Tours, Snorkeling, Tour Reviews

Half-Day Trip from Key West with Kayaking, Snorkeling & Sunset

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7.Half-Day Trip from Key West with Kayaking, Snorkeling & Sunset

Half-day Key West sailing with mangrove kayaking and snorkeling in protected waters, with wetsuits, drinks, snacks, and a sunset option.

★ 5.0

“This was out second time with Danger, and we really enjoyed both outings. Smaller crowds, lovely boat, informative guides, and great time on the water. I appreciated the use of wet suits, it was a thoughtful addition to the experience.”

1,683 reviews4 hours 30 minutes (approx.)From $115.00by Danger Charters

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Key West Afternoon Snorkel Sail with Unlimited Cocktails! - Head to the Florida Reef: What You’re Actually Snorkeling
Cruises & Boat Tours, Key West, Reef Snorkeling Tours, Tour Reviews

Key West Afternoon Snorkel Sail with Unlimited Cocktails!

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8.Key West Afternoon Snorkel Sail with Unlimited Cocktails!

Sail the 69-foot Marquesa to the Florida Reef for easy snorkeling, unlimited drinks after swimming, and the chance to spot dolphins.

★ 4.5

“It was exactly as we anticipated. There were a lot of people on the boat, but the staff was great and well prepared. The equipment they provided was in good condition, but I felt the water wasn't that clear and I had a hard time seeing a lot on the reef.”

1,572 reviews3 hours (approx.)From $59.00by Sebago Key West

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Key West Hop-On Hop-Off Trolley Tour - Timing Tips: Start Times, Last Departure, and When Crowds Slow You Down
Key West, Tour Reviews, Tours, Trolley & Train Tours

Key West Hop-On Hop-Off Trolley Tour

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9.Key West Hop-On Hop-Off Trolley Tour

Hop-on hop-off trolley tour of Key West with 13 stops, live narration, and free Sails to Rails Museum included, great for port days.

★ 4.5

“You can’t beat these tours for the ability to see so much of an area. Our driver was knowledgeable and funny! Highly recommend!”

1,530 reviews1 hour 30 minutes (approx.)From $55.60by Historic Tours Of America

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Key West Small-Group Sunset Sail with Wine and Hors d'oeuvres - The on-water timing: check-in, how long you’ll be out, and what to watch for
Cruises & Boat Tours, Evening Experiences, Key West, Sunset Sails & Cruises, Tour Reviews, Wedding Cruises, Wine Tours

Key West Small-Group Sunset Sail with Wine and Hors d’oeuvres

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10.Key West Small-Group Sunset Sail with Wine and Hors d’oeuvres

Key West small-group sunset sail with up to eight wines, beer, and hors d'oeuvres on a schooner. Intimate, romantic start to night.

★ 5.0

“Great experience on the Key West Sunset Sail and Wine Tasting. Beautiful sunset and smooth sailing. The crew was professional and attentive. The wine selection was good and paired well with simple hors d”oeuvres. We’d book again with Danger Charters!”

1,366 reviews2 hours (approx.)From $125.00by Danger Charters

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Key West Island Adventure Jet Ski Tour: Bring a Partner for Free - Price math: bring a partner for free (and what that means for value)
Bachelor Party Cruises, Jet Ski Tours, Jet Skis, Key West, Skiing, Tour Reviews, Tours

Key West Island Adventure Jet Ski Tour: Bring a Partner for Free

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11.Key West Island Adventure Jet Ski Tour: Bring a Partner for Free

Ride 28 miles around Key West on a guided 90-minute jet ski loop. Tandem riding is free, gas is included, and you get a real sightseeing plan.

★ 5.0

“Great ride around the island! Very comfy seats for 2 people bouncing around for 90 min. Gets cool out there so dress warm or rent a wet suit.”

1,362 reviews1 hour 30 minutes (approx.)From $155.95by Sunset Watersports

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Key West Ghosts and Gravestones Trolley Tour - Where You Start: Front and Duval Is the Hub
Ghost & Haunted Tours, Key West, Tour Reviews, Tours, Trolley & Train Tours

Key West Ghosts and Gravestones Trolley Tour

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12.Key West Ghosts and Gravestones Trolley Tour

Cruise Key West after dark on the Trolley of the Doomed, hear graveyard lore, then add a quick Shipwreck Museum stop.

★ 4.5

“In hindsight, the trolley concept for a haunted tour probably wasn't a good choice for us. Not the same feel as a walking tour where can absorb a little more.”

1,217 reviews1 hour (approx.)From $39.85by Historic Tours Of America

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Key West Dolphin Watch and Snorkel Tour - Eco Adventure - Getting Oriented at Greene Street (And Why Timing Matters)
Dolphin Watching, Dolphin Watching Tours, Key West, Reef Snorkeling Tours, Tour Reviews, Tours

Key West Dolphin Watch and Snorkel Tour – Eco Adventure

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Key West Ghost and Mysteries Guided Tour - Meet at 429 Caroline St and End at Hard Rock Cafe
Ghost & Haunted Tours, Guided, Key West, Tour Reviews, Tours

Key West Ghost and Mysteries Guided Tour

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14.Key West Ghost and Mysteries Guided Tour

Nighttime ghost tour of Key West’s haunted addresses and Hemingway’s home, with dowsing rods and a walk to Hard Rock Cafe.

★ 4.5

“Nice and well organized tour guide. She spoke clearly and kept us engaged. The path we took was beautiful and well done.”

1,079 reviews1 hour 30 minutes (approx.)From $33.00by Key West Ghost and Mysteries Tour

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Small Group Key West Adult Sunset & Moët Sail & Amazing Cheeses - Stop 1 Catamaran Echo: calm sailing, smart positioning, and room to breathe
Bachelorette Party Cruises, Cruises & Boat Tours, Evening Experiences, Key West, Tour Reviews, Wedding Cruises

Small Group Key West Adult Sunset & Moët Sail & Amazing Cheeses

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15.Small Group Key West Adult Sunset & Moët Sail & Amazing Cheeses

Adults-only Key West sunset cruise on a small Echo catamaran with champagne-inspired drinks, gourmet cheeses, and Moët upgrades available.

★ 5.0

“It was romantic and peaceful. The girls who were taking care of us were so friendly and the wine was perfect and the cheese was awesome.”

954 reviews2 hours (approx.)From $108.91by Dolphin Echo Inc. (Catamaran Echo)

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More Key West Boat Trips & Tours

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Every way to get out on the water, and every reason to stay for the sunset.

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