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The 15 Best Key West Tours & Sunset Sails

37 tours  ·  from $26 a head

The island is two miles by four and the day is built around when the sun goes down. These 15 compare the sunset sails, the reef snorkels, the trolley loops and the day trips from Miami on price and how much of it is the drive.

Key West Sunset Sail with Open Bar, Live Music and Hors D'oeuvres - Boarding at 205 Elizabeth Street
Concerts, Cruises & Boat Tours, Dinner & Sunset Cruises, Dinner and Sunset Cruises in Key West, Drinking Tours, Evening Experiences, Jazz, Gospel & Live Music Tours, Tour Reviews, Tours in Key West

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

Spend about two hours aboard Sebago’s spacious Key West catamaran, passing Mallory Square, Fort Zachary Taylor, and Sunset Key as daylight fades. Enjoy champagne, wine, sangria, premium beer, cocktails, soft drinks, shrimp, small bites, and live music from local performers. Arrive 30 minutes early at 205 Elizabeth Street.

“Sunset was beautiful. Music and food were good. Dancing was fun. Would recommend to a friend. The time of the excursion was perfect.”

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Shark and Wildlife Viewing Adventure in Key West - From Key West harbor to mangrove islands
Tour Reviews, Tours in Key West, Wildlife

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 in Key West for a two-hour wildlife trip through mangrove shallows and out to shark country. Guides such as Matt, Clay, and Tanner share local ecology as bait brings lemon, nurse, bull, blacktip, and possible hammerhead sharks close to the boat. Polarized sunglasses, drinks, snacks, shade, and a restroom are included.

“Great experience. Also learned some shark facts. As we were heading back to shore, we also saw a bunch of dolphins swimming. The captain circled around so we could watch them for a bit”

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Guided Bike Tour of Old Town Key West - Pedaling through Old Town Key West
Cycling Tours, Guided, Tour Reviews, Tours, Tours in Key West

Guided Bike Tour of Old Town Key West

3.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 a local guide such as James, Lenny, Salty, or Ryan. Over about two relaxed hours, you’ll see landmarks including Mallory Square, Mile Marker Zero, the Southernmost Point Buoy, and the former US Navy dock, with history stops, bottled water, and key lime pie included.

“Great way to get to see the sights of Key West. Our guide was very knowledgeable and gave us a real insight into how the Keys were developed. We arrived late but they were really helpful and got us caught up with the party really excellent customer service.”

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Key West Mangrove Kayak Eco Tour - Getting Comfortable in a Single or Double Kayak
Canoes & Kayaks, Tour Reviews, Tours, Tours in Key West

Key West Mangrove Kayak Eco Tour

4.Key West Mangrove Kayak Eco Tour

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

Kayak through the shallow mangrove creeks of Key West with guides such as Brett, Rachel, Heather, and Bethany. Expect a relaxed two-hour outing, easy instruction, wildlife sightings, and stories about Keys geology. Single and double kayaks are available, dogs are welcome, and groups are limited to 10.

“Excellent and informative tour with a fantastic guide who was incredibly knowledgable and energetic about the tour, made it a fantastic experience.”

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

Southernmost Food & Cultural Walking Tour by Key West Food Tours

5.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 while tasting five local dishes, Cuban coffee, key lime pie, and one alcoholic drink. Guides such as Kieran, Marissa, Mike, Kayla, and Kyle add local stories about food, architecture, and Conch culture. The tour lasts about three hours and ends near Duval Street.

“Great tour guide, many places we haven’t explored and such great food to experience Great value and time well spent”

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Key West Sunset Cruise: Dinner, Live Music & Drinks Included - A buffet built for a casual Key West evening
Concerts, Cruises & Boat Tours, Dining Experiences, Dinner & Sunset Cruises, Dinner and Sunset Cruises in Key West, Dinner Experiences, Evening Experiences, Jazz, Gospel & Live Music Tours, Tour Reviews, Tours in Key West

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

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

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

Set out from Key West’s historic seaport aboard a 65-foot yacht for a tropical buffet, unlimited well drinks, beer, wine, and soft drinks. You’ll pass Mallory Square and the Florida Keys National Marine Sanctuary, then head upstairs for sunset and live music. Arrive 60 minutes early, and bring a light jacket for the open deck.

“Love it and it's candid experience!!! We didn't have experience the sunset but the majestic sights are awesome. The dancing bonding was fun. I love the music that was played by the dj. The crews are awesome especially the captain and the dj.”

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Half-Day Trip from Key West with Kayaking, Snorkeling & Sunset - Sailing out through Key West Harbor
1-Day Tours, Canoes & Kayaks, Evening Experiences, Half-Day, Snorkeling Tours in Key West, Snorkeling, Shark & Manta Ray Tours, Tour Reviews, Tours in Key West

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

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

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

Sail from 255 Front Street with a small crew such as Micah, Katie, or Bible, then snorkel above a coral reef and kayak through mangrove channels. You get gear, wetsuits in cooler months, fruit, snacks, beer, wine, and soft drinks. Choose the afternoon trip for a Key West sunset.

“Only disappointment was not seeing a lot of fish while snorkeling. But the rest was excellent. Crew was fun, helpful and scenery was gorgeous.”

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Key West Small-Group Sunset Sail with Wine and Hors d'oeuvres - Hors d’Oeuvres That Work on a Moving Boat
Cruises & Boat Tours, Dinner & Sunset Cruises, Dinner and Sunset Cruises in Key West, Evening Experiences, Tour Reviews, Tours in Key West, Wine Tours

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

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

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

Meet the Danger Charters crew at 255 Front St, then spend about two hours sailing Key West waters with up to 26 passengers. You’ll taste as many as eight wines, sample beer and soft drinks, and enjoy small bites such as cheese, fruit, and skewers while crew members including Mary, Connor, Lexi, Tony, and Molly may share stories and handle the pours.

“This was such a wonderful experience! We are eloping in Key West and opted to do this sunset sail with family in lieu of a traditional rehearsal dinner. It was so so enjoyable. The staff was so friendly, attentive and warm. One of them serving wine even memorized everyone’s name aboard. The nibbles were so perfect for a boat experience and easy to eat as well as a great wine selection + beer options, sodas and waters. We would absolutely book this again. I highly recommend Danger Charters and will use them the next trip down here!”

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Key West Ghosts and Gravestones Trolley Tour - Boarding at Front and Duval Streets
Ghost, Cemetery & Haunted History Tours, Tour Reviews, Tours, Tours in Key West, Trolley & Hop-On Hop-Off Tours

Key West Ghosts and Gravestones Trolley Tour

9.Key West Ghosts and Gravestones Trolley Tour

★★★★★★★★★★4.5 · 1,217 reviews · 1 hour (approx.) · from $39

Board the Trolley of the Doomed at 501 Front Street for a costumed evening tour of Key West’s darker side. A professional ghost host, such as Violet or Kate, tells local tales tied to the Marrero House, Porter Mansion, Hanging Tree, and Robert the Doll. The ride also includes the Key West Shipwreck Museum.

“Thoroughly enjoyed this. Our guide was wonderful. It was a very entertaining way to learn about the history of the area.”

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Key West Dolphin Watch and Snorkel Tour - Eco Adventure - A good first snorkel, with one firm requirement
Dolphin & Manatee Tours, Dolphin and Manatee Tours in Key West, Snorkeling Tours in Key West, Snorkeling, Shark & Manta Ray Tours, Tour Reviews, Tours, Tours in Key West

Key West Dolphin Watch and Snorkel Tour – Eco Adventure

10.Key West Dolphin Watch and Snorkel Tour – Eco Adventure

★★★★★★★★★★4.5 · 1,163 reviews · 3 hours (approx.) · from $79

Cruise from 631 Greene Street with Fury Water Adventures to search for wild bottlenose dolphins, then snorkel 6 to 12 feet deep among patch coral, sponges, and small fish in the Gulf backcountry. The crew provides instruction and gear, with beer and wine served after swimming. You must know how to swim.

“What an amazing day! It started off a lil rough, but before we knew it there were dolphins all over playing in the water. The captain made sure we were in the right position to view them. The crew were very accommodating, had water, sodas and alcohol of we wanted it. I highly recommend doing this.”

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Key West Ghost and Mysteries Guided Tour - Robert the Doll Brings the Eerie Reputation
Ghost, Cemetery & Haunted History Tours, Guided, Tour Reviews, Tours, Tours in Key West

Key West Ghost and Mysteries Guided Tour

11.Key West Ghost and Mysteries Guided Tour

★★★★★★★★★★4.5 · 1,079 reviews · 1 hour 30 minutes (approx.) · from $33Best value

Walk through Old Town Key West with guides such as Dawn, Ted, Lafayette, or Fast Eddie, hearing stories tied to Hemingway, Robert the Doll, Count von Cosel, and local legends. The 90-minute route visits nine sites, ends at the Hard Rock Cafe, and may include dowsing rods for a hands-on paranormal activity.

“It was a really good time. Fast Eddie was fun and funny and we learned a lot and even some history of Key West along with some Key “Weird” stories. Would book again!”

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Small Group Key West Adult Sunset & Moët Sail & Amazing Cheeses - Starting at Key West Bight Marina
Cruises & Boat Tours, Evening Experiences, Tour Reviews, Tours in Key West

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

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

★★★★★★★★★★5.0 · 954 reviews · 2 hours (approx.) · from $108

Sail aboard Catamaran Echo from Key West Bight Marina for two relaxed hours of sunset views, unlimited Domaine Chandon Brut Classic, wine, beer, and a gourmet cheese buffet. The adults-only boat carries no more than 14 passengers. Crew members including JP, Sara, Bailey, and Captain Sandy have earned praise for attentive service and smart sunset positioning.

“A great intimate evening with amazing sunset. Excellent range of cheeses and wines. The crew were amazing.”

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Key West Sunset Sail with Live Music, Drinks and Appetizers - Three decks and several ways to watch the sun go down
Concerts, Cruises & Boat Tours, Dinner & Sunset Cruises, Dinner and Sunset Cruises in Key West, Evening Experiences, Jazz, Gospel & Live Music Tours, Tour Reviews, Tours in Key West

Key West Sunset Sail with Live Music, Drinks and Appetizers

13.Key West Sunset Sail with Live Music, Drinks and Appetizers

★★★★★★★★★★4.5 · 952 reviews · 2 hours (approx.) · from $79

Board Fury’s 65-foot catamaran at 631 Greene Street for a two-hour sunset sail with live local musicians, unlimited margaritas, beer, wine, champagne, soda, and seasonal appetizers. Choose the sundeck or shaded lounge, watch the sun set near Mallory Square and Fort Zachary Taylor, and return to the dock in time for dinner.

“You will have a great time on this sunset cruise. The band was great and played all our favorite songs. People were happy and dancing. Seeing the Christmas lights from the water was a wonderful experience!”

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Key West Conch Tour Train - Front Street is the starting point
Tour Reviews, Tours, Tours in Key West, Train Experiences

Key West Conch Tour Train

14.Key West Conch Tour Train

★★★★★★★★★★4.5 · 792 reviews · 1 hour 30 minutes (approx.) · from $45

Take a narrated Conch Tour Train ride through Key West’s historic districts, passing landmarks tied to Audubon, Hemingway, Truman, railroads, cigars, and the Southernmost Point. Guides such as Ian, Kenny, Curtis, and James bring local color to the trip. Expect a covered, sometimes bumpy ride, a short break, and free admission to the Sails to Rails Museum.

“A quick trip to see all the sights! Driver was very knowledgeable and pointed out all of the landmarks!”

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Key West Full-Day Ocean Adventure: Kayak, Snorkel, Sail - Sailing the Key West National Wildlife Refuge
Canoes & Kayaks, Cruises & Boat Tours, Full-Day, Snorkeling Tours in Key West, Snorkeling, Shark & Manta Ray Tours, Tour Reviews, Tours in Key West

Key West Full-Day Ocean Adventure: Kayak, Snorkel, Sail

15.Key West Full-Day Ocean Adventure: Kayak, Snorkel, Sail

★★★★★★★★★★5.0 · 767 reviews · 6 hours 30 minutes (approx.) · from $152

Spend 6.5 hours aboard a 65-foot schooner exploring the Key West National Wildlife Refuge and Florida Keys National Marine Sanctuary. You will sail, snorkel, kayak through mangroves, and enjoy a buffet lunch with unlimited beer, wine, and soft drinks. Crew members such as Daniel, Joe, and Captain Janet are praised for clear guidance and friendly service, though assignments vary.

“Captain kid rock, James and Kylie did AMAZING!! It was so fun. Super knowledgible and friendly!! Cannot say enough great things. BOOK THIS TRIP!!”

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New in Tours in Key West

★ 4.5Key West Half-Day Fishing CharterFrom $95408 reviews
★ 4.5Key West Haunted Pub Crawl and Ghost Tour with Free T-ShirtFrom $32549 reviews
★ 4.5Key West Afternoon Reef Snorkeling with Open BarFrom $59419 reviews
★ 4.5Key West Dolphin and Snorkel ExperienceFrom $69334 reviews
★ 5.0Key West Craft Cocktail CrawlFrom $93543 reviews
★ 4.5Harry S Truman Little White House AdmissionFrom $25451 reviews
★ 4.5All-Inclusive Sandbar Safari with Dolphin Playground EncounterFrom $149451 reviews
★ 4.5Dry Tortugas National Park Day Trip by Catamaran from Key WestFrom $220433 reviews
★ 4.5Key West Reef Snorkel & Sail AdventureFrom $79540 reviews
★ 4.5Key West Signature Sunset Cruise with Open Bar, Food & MusicFrom $79418 reviews
★ 4.7Jet Ski Island Tour with Sandbar Stop384 reviews
★ 4.4Reef Snorkeling with Drinks and Sunset OptionFrom $34419 reviews
★ 4.5Old Town Trolley 13-Stop Hop-On Hop-Off TourFrom $55395 reviews
★ 4.4Dolphin Watching and Snorkeling Sunset CruiseFrom $79493 reviews
★ 4.33-Hour Afternoon Reef Snorkel with DrinksFrom $59351 reviews

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