USA · KEY WEST TOURS

15 Key West Tours That Earn the Road Trip

66 tours  ·  from $33

Think of this as the shortlist you would text a friend the week before they fly: 15 key west tours, what each costs, and the one thing to know before you commit.

Key West Sunset Sail with Open Bar, Live Music and Hors D'oeuvres - The Route Past Key West Landmarks
Boat Tours in Key West, Concerts, Cruises & Boat Tours, Florida Tours, Jazz & Live Music, Key West Tours, Sunset Cruises, Sunset Cruises in Key West, Tour Reviews

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

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

★★★★★★★★★★4.5 · 3,559 reviews · 2 hours (approx.) · from $79Our pick

Sail from Key West for about two hours aboard a spacious catamaran, with sunset views toward Mallory Square, Fort Zachary Taylor, and Sunset Key. Your ticket includes an open liquor bar, champagne, wine, sangria, premium beer, soft drinks, hors d’oeuvres, and live music from local performers. Bring a photo ID if you plan to drink.

“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!!”

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Shark and Wildlife Viewing Adventure in Key West - Reaching the shark site four miles offshore
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Shark and Wildlife Viewing Adventure in Key West

2.Shark and Wildlife Viewing Adventure in Key West

★★★★★★★★★★5.0 · 2,962 reviews · 2 hours (approx.) · from $99Top rated

Board the 34-foot Tiger Cat at Pier B behind the Westin and cruise through mangroves toward a shark-viewing site four miles offshore. Guides including Clay, Matt, and Tanner explain the Keys ecosystem while bait brings lemon, nurse, and other sharks beside the boat. Dolphins, turtles, stingrays, birds, drinks, snacks, shade, and a restroom round out the two-hour trip.

“We all had a great time!!! Definitely saw sharks and learned a lot about them too! Highly recommend!”

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From Miami: Key West Day Trip with Pickup at Selected Hotels - What the coach ride is really like
1-Day Tours, Florida Tours, Key West Tours, Tour Reviews

From Miami: Key West Day Trip with Pickup at Selected Hotels

3.From Miami: Key West Day Trip with Pickup at Selected Hotels

★★★★★★★★★★4.3 · 2,918 reviews · 14 hours · from $39

You’ll ride an air-conditioned coach from selected Miami Beach and Downtown Miami hotels to Key West, with about 3.5 hours each way and six hours to explore. Guides such as Tamara, Pepe, Marbela, and Lily help with plans and optional activities, while you can walk Duval Street, visit Hemingway’s home, shop, eat, or book water sports.

“It was an amazing trip, the guide told us a lot of interesting information about Key West during the trip. Everything was smooth and nice, highly recommend!!”

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Guided Bike Tour of Old Town Key West - Starting at 122 Ann Street
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Guided Bike Tour of Old Town Key West

4.Guided Bike Tour of Old Town Key West

★★★★★★★★★★5.0 · 2,611 reviews · 2 hours (approx.) · from $59

Ride through Old Town Key West with guides such as James, Lenny, Salty, or Ryan, stopping at Mallory Square, Mile Marker Zero, the Southernmost Point Buoy, and other historic sites. The relaxed two-hour route includes bottled water and a slice of key lime pie, with morning and afternoon departures.

“James was a terrific guide! Very informative and entertaining! We had a great time in spite of the rain! Very easy ride and I’m an out of shape old lady!”

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From Miami: Key West Day Tour by Motor Coach Bus - Arriving in Key West with a loose plan
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From Miami: Key West Day Tour by Motor Coach Bus

5.From Miami: Key West Day Tour by Motor Coach Bus

★★★★★★★★★★4.2 · 2,483 reviews · from $62

Spend a long but rewarding day traveling from Miami to Key West by motor coach. Your English or Spanish-speaking guide shares local history along the four-hour route, then gives you free time for Hemingway’s House, Mallory Square, beaches, museums, or optional snorkeling and trolley rides. Hotel pickup costs extra.

“Our guide was wonderful, charismatic and extremely helpful. Would recommend to anyone wanting to go visit key west from Miami!”

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Key West Mangrove Kayak Eco Tour - A relaxed two hours on the water
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Key West Mangrove Kayak Eco Tour

6.Key West Mangrove Kayak Eco Tour

★★★★★★★★★★5.0 · 2,205 reviews · 2 hours (approx.) · from $80

At Lazy Dog Adventures, you’ll paddle quiet mangrove creeks near Hurricane Hole Marina with guides such as Brett, Rachel, Heather, and Bethany. Expect shallow water, tropical fish, crabs, sea stars, jellyfish, birds, and stories about Florida Keys geology. Single and double kayaks suit beginners, families, and dogs.

“Our time with the Lazy Dog team was relaxing and informative. Highly recommended. This is an adventure you will remember for sure.”

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Southernmost Food & Cultural Walking Tour by Key West Food Tours - Starting at El Siboney on Catherine Street
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Southernmost Food & Cultural Walking Tour by Key West Food Tours

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

★★★★★★★★★★5.0 · 1,730 reviews · 3 hours (approx.) · from $90

Walk 1.2 miles through quieter Old Town streets, stopping at family-run restaurants for five tastings, Cuban coffee, key lime pie, and a rum drink. Guides such as Marissa, Kieran, Mike, and Kayla add local history and food tips. The three-hour tour feeds you a hearty lunch and ends near Duval Street.

“Great food and good variety! Portions were good, more than just getting a couple of bites! Mike (our guide) was fun and informative!”

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Key West Sunset Cruise: Dinner, Live Music & Drinks Included - The first drink sets the tone
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Key West Sunset Cruise: Dinner, Live Music & Drinks Included

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

★★★★★★★★★★4.5 · 1,707 reviews · 2 hours (approx.) · from $92

Board a 65-foot yacht at Key West’s historic seaport for a two-hour sunset cruise. Enjoy a crew-served tropical buffet, unlimited well drinks, beer, wine, and soft drinks, then head upstairs for sunset views, live music, and a pass by Mallory Square.

“Was cold, but captain made it fun and the drinks were flowing! The SUN came out just in time! Great time.”

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Half Day Snorkel Trip on Reefs in the Florida Keys - What happens at the reef sites
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Half Day Snorkel Trip on Reefs in the Florida Keys

9.Half Day Snorkel Trip on Reefs in the Florida Keys

★★★★★★★★★★5.0 · 1,699 reviews · 3 hours 30 minutes (approx.) · from $75

Set out from Key Largo aboard a spacious catamaran for a half-day snorkel at the Florida Keys National Marine Sanctuary and John Pennekamp Coral Reef State Park. You’ll use provided gear, a vest, water, and reef-safe sunscreen while guides such as Captain Brad and Nate share tips and point out fish, barracuda, turtles, dolphins, and the Christ of the Abyss statue.

“Captain Brad and Scuba Joe were awesome! Great trip!! The reefs are filled with amazing fish and aquatic life . The crew did a great job of keeping it entertaining!”

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

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

★★★★★★★★★★5.0 · 1,683 reviews · 4 hours 30 minutes (approx.) · from $115

Spend about four and a half hours with Danger Charters sailing from 255 Front Street, snorkeling in the Florida Keys National Marine Sanctuary, and kayaking around mangrove islands. The crew, including guides such as Mary, Micah, Katie, and Laura, supplies gear, wetsuits in winter, snacks, and drinks. Choose morning or afternoon, with sunset on the PM trip.

“It was good. The guides were nice and accommodating. Had a good time and it was a good beginners ride.”

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Key West Afternoon Snorkel Sail with Unlimited Cocktails! - Getting ready for the water
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Key West Afternoon Snorkel Sail with Unlimited Cocktails!

11.Key West Afternoon Snorkel Sail with Unlimited Cocktails!

★★★★★★★★★★4.5 · 1,572 reviews · 3 hours (approx.) · from $59

Sail from Key West’s historic seaport aboard the 69-foot catamaran Marquesa to the Florida Reef. You’ll receive gear and a safety briefing, snorkel in shallow reef water, then enjoy beer, wine, cocktails, and soft drinks on the ride back. Captain Brett and the crew may spot dolphins, fish, turtles, or nurse sharks, but marine life and water clarity vary.

“Too many people and not enough snorkeling. It took an hour to get to the spot,15 minutes to park. Only 45 minutes of snorkeling and they don’t serve drinks until the ride back.”

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Key West Hop-On Hop-Off Trolley Tour - Stop 1: Mallory Square and the waterfront
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Key West Hop-On Hop-Off Trolley Tour

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

★★★★★★★★★★4.5 · 1,530 reviews · 1 hour 30 minutes (approx.) · from $55

Ride Key West’s narrated trolley loop, then hop off at Mallory Square, Hemingway House, Bahama Village, the Southernmost Point, and more. Guides such as Patrick, Bailey, and Adam bring local history and humor to the 90-minute circuit. Your all-day ticket also includes the Sails to Rails Museum and two walking tours.

“The tour was very informative. The instructions do not tell you that you need to go to their office to redeem the tickets and get a sticker.”

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Key Largo Two Reef Snorkel Tour - All Snorkel Equipment Included! - Check-in at Garden Cove
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Key Largo Two Reef Snorkel Tour – All Snorkel Equipment Included!

13.Key Largo Two Reef Snorkel Tour – All Snorkel Equipment Included!

★★★★★★★★★★5.0 · 1,520 reviews · 3 hours (approx.) · from $78

Spend about three hours snorkeling two Key Largo reef sites, with 45 minutes in the water at each stop. Silent World Dive Center provides masks, fins, water, soda, chips, and reef-safe sunscreen. You may see rays, turtles, eels, barracuda, and the Christ of the Abyss statue. Good swimming ability is required.

“Awesome experience. Amazing views and very professional and fun crew that made sure everyone had a great time.”

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Key West Small-Group Sunset Sail with Wine and Hors d'oeuvres - Checking in at 255 Front Street
Boat Tours in Key West, Cruises & Boat Tours, Florida Tours, Key West Tours, Sunset Cruises, Sunset Cruises in Key West, Tour Reviews, Wine Tours

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

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

★★★★★★★★★★5.0 · 1,366 reviews · 2 hours (approx.) · from $125

Set sail from 255 Front Street for about two hours with a maximum of 26 passengers. The Danger Charters crew serves up to eight wines, five beers, soft drinks, and small hors d’oeuvres while you watch the Key West sunset. Mary, James, Connor, Tony, and other crew members have been praised for warm service and helpful local stories.

“The crew were helpful and friendly. It was a small group. I highly recommend. It is a mini wine tasting with an amazing view. We met new friends on the boat. Will definitely book again.”

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Key West Island Adventure Jet Ski Tour: Bring a Partner for Free - What Happens at the 2801 North Roosevelt Boulevard Meeting Point
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Key West Island Adventure Jet Ski Tour: Bring a Partner for Free

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

★★★★★★★★★★5.0 · 1,362 reviews · 1 hour 30 minutes (approx.)

Ride a new WaveRunner around Key West for 90 minutes with a guide leading the way. You’ll see the Southernmost Point, historic harbor, submarine pens, Boca Chica Sandbar, and more. Tandem riding costs no extra. Guides such as Eric, Tyler, Gavin, Jake, and Barrett have earned praise for patient instruction and a lively approach.

“Great time full of action and great scenery. It's the 4D experience to fully enjoy and appreciate the Keys.”

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New in Key West Tours

★ 4.5All-Inclusive Watersports Adventure with Lunch & BeerFrom $179351 reviews
★ 5.0The Original Key West Island Jet Ski Tour from Barefoot Billy’s350 reviews
★ 5.0Sunset Sail in Key West with Beverages IncludedFrom $79907 reviews
★ 4.5Key West Ultimate Watersports Adventure with Snorkeling UpgradeFrom $142436 reviews
★ 4.5The Dark Side of Key West Ghost TourFrom $34334 reviews
★ 4.5Key West Rum and Reggae: Reef Snorkel Adventure and Sunset SailFrom $59370 reviews
★ 4.5Shallow Water Snorkeling and Dolphin Watching in Key WestFrom $108465 reviews
★ 5.0Key West SNUBA ExperienceFrom $160490 reviews
★ 5.0Key West Historic Seaport Food & Walking TourFrom $93642 reviews
★ 5.0Private Looe Key Snorkel from Big Pine Key431 reviews
★ 5.0Key West Parasailing Adventure above Emerald Blue WatersFrom $53387 reviews
★ 5.0Key West Schooner Sunset Sail with Bar & Hors d’oeuvresFrom $122804 reviews
★ 4.5Key West Sunset Sail with Live Music, Drinks and AppetizersFrom $79952 reviews
★ 4.5Key West Champagne Sunset Catamaran CruiseFrom $59586 reviews
★ 4.5Key West Reef Morning Snorkeling with Breakfast and MimosasFrom $35579 reviews

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