Tours in Key West

258 results

Private Key West Sunset Sail

47
2 Hr. Private charter sailing from downtown Key West onboard Key West's First sailing charter boat, the pretty green sloop "High Tide" USCG Certified for up to 12 passengers, the Sloop High Tide and Sunset Sail Key West make for the perfect Key West sunset sail Peaceful, private and exclusive! Your captain and mate will take you out to watch the sunset from your own private classic sailing vessel, with soft drinks, bottled water and coolers stocked with ice provided for any adult beverages you choose to bring. Reserve ahead, there is after all, only one High Tide sunset sail per day! Price is for up to 6 guests, 12 guests max!.
2 hours
From
$695.00

Key West: Sunset Sail Full Bar, Live Music & Dinner & Early Morning Snorkeling

1
Key West Water Fun with Snorkeling, Sunset Cruise, Dinner, Live Music and open Bar. Enjoy a bright and early morning snorkel Catamaran cruise departing 9 am for a full morning of Snorkeling fun. Return at 12:00pm and have 4 hours of free time before you come join us for an incredible Key West 2 hour Catamaran Sunset happy hour tropical dinner cruise with margaritas, rum runners, wine, beer and live music.
5 hours
Free Cancellation
From
$159.99

Key West Boat Rental with Seat Sound and Fishing Upgrades

Discover the unparalleled joy of exploring Key West waters aboard this center console! Our fleet boasts the newest, most luxurious vessels, fully equipped with top-tier upgrades for your comfort and convenience. Nestled within our full-service marina, we've proudly served our community for 39 years, earning our reputation as the go-to destination for boat rentals in Key West. Join us and embark on an adventure of a lifetime – where every wave carries the promise of unforgettable memories!
4 hours
Free Cancellation
From
$475.00

Key West Waterfront Cocktail Walk to Mallory Square’s Sunset Celebration!

16
We invite you to take an exclusive cocktail & food taste tour on the Waterfront in Downtown Key West! Our seasoned local guide will dive into the history of Old Fisherman’s Wharf & how it has transformed into Yacht Harbor! Learn about the historic wrecking and rum running days of old Key West! Sit at the bar Mel Fisher did while his treasure sat out front, on display, in the trunk of his car! Transition into the sunset where you’ll visit the area where locals have their annual celebration for the succession of our Conch Republic from the United States! Open your ears to live music and island vibes as you cocktail into World Famous Mallory Square’s Sunset Celebration!
2 hours to 3 hours
Free Cancellation
From
$139.00

Private Secret Food Tour of Key West

11
On our Secret Food Tour: Key West Old Town, we'll walk far from the tourist traps of Duval to show you the real city and its best food. You'll gain insight into how the diverse cultural influences of Key West have shaped the island into a unique destination that's globally renowned for its exceptional gastronomic experiences. Our local guides will take you on a journey to explore the history and culture of "The Key to the Caribbean," sharing their passion and passing down stories that have been told from generation to generation. You'll discover the oral history of Key West's prosperity and how treasures transformed this small island into a worldwide attraction. As a private tour, everything works around you! Our start times are much more easy going, dates can open up. It's a much more intimate and cozy experience. No need to shout over other tourists, you will have every question answered, and leave feeling like a native yourself!
2 hours 30 minutes
Free Cancellation
From
$370.00
Hire Photographer, Professional Photo Shoot - Key West
Special Offer

Hire Photographer, Professional Photo Shoot - Key West

Professional photo shoot in unique Key West locations. The Photo Experience will create amazing photo memories from your visit. You will be able to see undiscovered locations and get the best photo story from your Key West visit. We can tailor each photo shoot to meet your requirements; we can travel to your location or we can suggest a location for the photo shoot. Our Photoshoots are ideal for any Tourists - Solo Traveller - Couples - Groups - Hen/Bachelorette & Stag/Bachelor Parties - Families - Secret proposal/Engagement - Honeymoon - Experienced Influencers and Models - New Influencers and Models What's Included: A Private online viewing gallery - 1 hour = 20 Final photos* - 2 hours =30 Final photos* - 3 hours =40 Final photos* - 4 hours =50 Final photos* * same set of images - A unique location professional shoot experience - DELIVERY - Up to 14 days after photoshoot. What's Excluded: - Transportation - Entry fees
4 hours
Free Cancellation
From
$195.97
$206.28
$10.31 savings

4 Hours Pontoon Rental in Key West

Create your own adventure: fish, snorkel, paddleboard, or just cruise in style! The newest fleet in town! Our spacious pontoons provide plenty of space and shade while you make your way through our beautiful local waterways! What’s Included: 12 Passenger Pontoon Boat Rental (Children and babies count as passengers) Safe, reliable, and well-maintained equipment Includes a 70qt cooler (purchase ice at check-in) Life vests for all passengers Guests are welcome to bring their own snack and drinks, or purchase upon arrival at our fully stocked Marina Store! Alcohol permitted for guests 21+ Optional Add Ons: Paddleboards- A fun and suitable activity for people of all ages and abilities. Lily Pad- This floating foam island allows you to rest, kick-back, tan, run, and play on.
4 hours
Free Cancellation
From
$400.00

Six Fins Key West Sandbar Charter – Swim, Snorkel & Island Escape

1
Discover the “backyard” of Key West locals with our Secret Sandbars Charter—hidden gems few visitors ever see. Unlike crowded party boats, this is your private slice of paradise. Imagine stepping off your boat into ankle-deep water, surrounded by endless blue sky and shimmering ocean, with no other boats in sight. Explore uninhabited islands, search for starfish and conch in the tide pools, or relax on a floating mat as the captain takes care of everything. This isn’t just a boat ride—it’s the ultimate Key West daydream, brought to life.
4 hours
From
$1,195.00

Marathon Reef Fishing Charters

Experience the beauty of the Florida Keys, gorgeous turquoise water and abundant fish. Marathon the hub for fishing in the Florida Keys, great beaches, shopping, and fantastic food. View the beautiful scenery, while experiencing the thrill of a chance to catch species such as Wahoo, Mahi Mahi, Tuna, Snapper, Grouper, King Mackerel and Shark that all swim around the reefs. Your tour is guided by a licensed Captain in a modern 30' open fishing style boat with t-top for shade. All the fishing rods and reels, right and left-handed and all the tackle you need, as well as all other necessities including safety equipment. Booking with confidence on TripAdvisor, it makes this charter an easy, reliable and enjoyable decision. Reserve Today to get hooked up! Travelers that have enjoyed our fishing charters also have enjoyed The Turtle Hospital, a tour down Seven Mile Bridge or a beautiful sunset at Sombrero Beach.
4 hours
Free Cancellation
From
$1,100.00

Six Fins Key West Patch Reef Fishing – Private Family Charter

This is a private Key West fishing charter focused on accessibility, fun, and variety. Unlike specialized sportfishing trips, Six Fins Patch Reef Fishing offers a welcoming experience for beginners and seasoned anglers alike. With comfortable reef depths, diverse species, and a flexible approach, this trip is perfect for anyone who wants the excitement of Florida Keys fishing without the intensity of offshore trophy hunts. ✅ Highlights Private patch reef fishing charter in Key West Target snapper, grouper, porgies, hogfish & more Light trolling for mackerel, bonito, or mahi-mahi Flexible for families, beginners & seasoned anglers Fun, relaxed trip with stories — and maybe dinner
4 hours
From
$1,395.00

Sweet Treats of Key West: A Tasty Walking Tour of Old Town

13
Discover the sweeter side of paradise on the Key West Sweets Tour! This fun and flavorful walking tour takes you through the heart of Old Town, along the harborfront and seaport, with stops at some of the best local spots for delicious donuts and sweet treats. Along the way, you’ll learn all about Key West’s rich and colorful history, from pirates and pioneers to artists and eccentrics. With plenty of photo-worthy moments, historic sites, and tasty bites, it’s the perfect outing for families, friends, and anyone looking to explore Key West in a unique and memorable way. Come hungry, bring your camera, and get ready to enjoy a one-of-a-kind tour through this tropical island treasure!
1 hour 30 minutes to 2 hours
Free Cancellation
From
$70.00

Marathon: COMBO- Snorkel & Sandbar (Coffins Patch Reef)

41
Solé Watersports is Marathon's premier watersports operator. Winner of Best in Marathon 2023, 2024. Florida Mom owned. This best selling excursion features two gems: Coffin's Patch and the Grassy Key Sandbar. * 1st Stop: Reef Snorkeling at Coffin's Patch. A Protected Sanctuary Area of the Reef boasting some wreckage remains from a Spanish Galleon that sank around 1733. Also the home of abundant tropical SEALIFE! 8-15' deep. * 2nd Stop: Grassy Key Sandbar. First try some shallow water snorkeling above the Turtle Grass flats. Discover Conch, Bahamian Starfish, horseshoe crabs and more. Then soak up some Florida Sunshine, chill and relax on the white sandy bottom or the giant floating mat! 0-4' deep. Conditions vary each day and waves and currents fluctuate. MUST BE A PROFICIENT SWIMMER. Included: - All snorkel gear - Noodles, balls, giant floating mat at the sandbar - Water, iced coolers - Restroom on boat Beverages, snacks and essentials can be purchased at the Marina Store.
3 hours 30 minutes
Free Cancellation
From
$139.00

Six Fins Private Key West Eco Tour – Wildlife Refuge Adventure

This is the only private eco boat trip that focuses exclusively on the Key West National Wildlife Refuge in such depth. Rather than hitting common tourist spots, you’ll venture into parts of the Refuge that most tours skip — winding mangrove fingers, quiet flats, and hidden inlets. With a private charter, you set the pace and direction; there’s no fixed route. Whether you want to snorkel, birdwatch, photograph or quietly drift among wildlife, this experience gives you deep access and unmatched natural beauty — all guided by permitted, knowledgeable local captains who respect the refuge’s delicate ecology. Private boat charter through Key West National Wildlife Refuge Guided mangrove, sea grass & island exploration Wildlife sightings: birds, turtles, dolphins & more Snorkel stops in calm backwaters (optional) Photography & nature immersion away from crowds
3 hours
From
$995.00

Six Fins Key West Freestyle Jet Ski Adventure – 1 Hour of Freedom

2
Top Key West Jet Ski Rental — Your Hour, Your Way. Skip the crowds and strict routes — this 1-hour freestyle jet ski adventure is all about freedom. After a short escort ride with a Six Fins guide, you’ll reach a calm, open-water zone where the ride is yours to create. ✅ Ride fast and kick up spray for an adrenaline rush ✅ Cruise slowly and take in Key West’s stunning coastline ✅ Anchor at a sandbar to swim, float, or simply relax ✅ Enjoy a private, flexible alternative to large group tours ✅ Perfect for repeat riders, thrill-seekers, or anyone short on time Whether you’re looking for speed, sightseeing, or simply space to play, this freestyle session delivers pure Key West jet ski freedom — no fixed itinerary, just maximum fun.
1 hour
Free Cancellation
From
$160.00

Six Fins Key West Private Sunset Cruise – Luxury Charter Boat

Unlike crowded party boats, this is a private Key West sunset cruise reserved exclusively for your group. You’ll enjoy personalized service, spacious seating, and the flexibility to customize your evening — whether you want music, quiet conversation, or just the peaceful rhythm of the waves. It’s the most intimate way to experience Key West’s legendary sunsets, blending comfort, privacy, and natural beauty. ✅ Highlights Private sunset cruise aboard a luxury charter boat Stunning, unobstructed views of Key West’s horizon Personalized service and flexible itinerary Perfect for couples, families, and special occasions Toast the day with drinks as the sun sets in paradise
3 hours
From
$895.00

Key West Stargazing Cruise aboard Schooner America 2.0

1
Join us aboard Schooner America 2.0 in Key West for a fun night time experience. During this stargazing cruise, guests can enjoy unobstructed views of the sweeping night sky and a fun adventure in Key West at night. Please note that select departures will have live narration from a seasoned local astronomer!
1 hour 45 minutes
Free Cancellation
From
$83.85

Key West Christmas Cruise with Live Band and Drinks

3
Join us for a family-friendly holiday sail aboard Schooner America 2.0 decorated with festive Christmas lights! Sing along to your favorite Christmas music with our live band and celebrate the holidays and Christmas in Key West. Enjoy a festive hot cocoa and holiday treats as we glide along with water for a fun night in Key West. Our beautiful 105-foot Schooner America 2.0 in full holiday decor that's sure to get you into the Christmas spirit in Key West harbor.
1 hour 30 minutes
Free Cancellation
From
$97.61

VIP Key West Paranormal Investigation: Old Firehouse # 3

8
This is your chance to go beyond the ghost stories and become the investigator in a place where the past refuses to rest. Exclusive inside access after hours. More than a ghost tour - its an experience. Tickets benefit local non-profits. Locally owned and operated by the Sloan Family.
2 hours
Free Cancellation
From
$99.00

Key West Airport (EYW) to Key West - Round-Trip Private Transfer

Book your Private Round-Trip Transfer from Key West Int Airport (EYW) to Key West hotels and return. Don't go through all the hassle of waiting in a long taxi or shared shuttles queues and use our private ,door to door airport transfer. Your driver will be waiting for you at a scheduled time and you will travel comfortably to your destination. Meeting with a Nameplate We track your Flight Door-to-door Service No Hidden Charges Clean cars & Professional drivers
30 minutes
Free Cancellation
From
$320.62

Bimini charters - Private 2 hour Catamaran sail and snorkel

1
Only the best! Owner operated, you have a luxurious yacht all to yourself with a captain and first mate! Snorkel, dolphin watch, and sunset with Bimini Charters! We cater the day to your desires, and our guests always say that their trip with us is the highlight of their vacation!
2 hours
Free Cancellation
From
$525.00

Key West Combo: Hop On Hop Off Afternoon Snorkeling

Hop On Hop Off in Key West for one full day of an adventure. Enjoy a early morning or afternoon 3 hour Snorkel trip on a catamaran. Explore the world’s 3rd largest living coral reef. This trip is perfect for professionals and beginners. Our professional staff provide expert snorkeling instruction and equipment. Afternoon Snorkeling includes unlimited draft beer, mixed well drinks, margaritas, rum runners, wine or champagne, once completed with snorkeling.
6 hours
Free Cancellation
From
$115.99

Key West Nighttime Full Moon Sail

7
Sail around Key West on a romantic, nighttime sailing experience aboard Schooner America 2.0! This 1.5-hour sail by moonlight is perfect for date night or an evening out with family and friends. Departing in the evening as the moon comes up over Key West, enjoy star gazing opportunities and a moonlit sky as the boat glides through the majestic waters at night.
1 hour 30 minutes
Free Cancellation
From
$83.85

Sharkeys Glass Bottom Fish Feeding LED Night Tour Key West

The glass bottom kayaks is an amazing experience with your tour guides paddling in calm shallow waterways under the stars! Your tour guides will point out sea birds and various sea-life such as different fish species, shrimp, crabs, conch shells which will be well illuminated with your high powered underwater custom LED lights. We paddle along mangrove shorelines and canals so we sometimes even see wild animals such as Racoons along the shoreline. We've also experienced manatees and dolphins on many of the tours. Definitely one of the most exciting things about your kayak tour is that we will feed fish at a certain point of our tour as well which is a blast for everyone! With very little to do at night this is an amazing rare experience under the stars that you'll never forget!
1 hour 15 minutes
Free Cancellation
From
$62.00
Kooky Key West Scavenger Hunt
Special Offer

Kooky Key West Scavenger Hunt

2
Our very unique, immersive adventures are the only ones of their kind. We, unlike other companies, provide your very own remote, interactive, live host to assist and encourage you along through your phone. We are an Austin, TX-based global custom event design company offering scavenger hunts and other events in 300+ cities in North America and beyond. Our specially hand-crafted adventures are equal parts tour, creative challenge, detective hunt, and social experiment! Guests get to discover in an alternate reality our favorite hidden gems off the beaten trail and creatively interpret fun art, history, and culture clues - for points! They get to enjoy fame and glory while appearing on our website’s international leaderboard, no matter what their score. They get to essentially race other teams in other cities, even if they don’t have competitors who have signed up in their city that day. Get ready to discover unusual oddities, laugh out loud, and make the experience your own!
2 hours
Free Cancellation
From
$23.20
$29.00
$5.80 savings