Key West Boat Tours

Hit the water on an extraordinary adventure with our diverse range of Key West boat tours. Explore the Keys' turquoise waters and choose your own fun from a variety of tours including snorkeling adventures, sunset champagne cruises, dinner cruises, reef tours, eco tours, and more. Discover hidden coves and vibrant coral reefs, encounter diverse marine life, and enjoy spectacular sunset (or sunrise!) views as you tour our pristine surroundings. Our knowledgeable captains will share fascinating insights about Key West's rich history and ecosystem, ensuring an educational and enjoyable experience for all ages.

Read more

Featured Boat Tours in Key West

Sorting:
Best Match
Jan 24 - Jan 30
Narrow your search
Swim Friendly
Cruise Only
Restroom
Captain Included
13-20 passenger
21-40 passenger
75+ passenger
Half Day Trip (if duration 3-6 hour)
Kid Friendly
Water Toys Available
Handicap Accessible
Morning Departure (5am-11:59am)
Afternoon Departure (12pm-4:49pm)
Evening Departure (4:49-11:59pm)
image-2445-903
image-2445
image-2445-915
image-2445-903
image-2445

Southernmost Sunset Sail with Bar and Hors d’Oeuvres

211 ratings
2 Hrs.
Entice yourself with the starburst blaze of colors that is the Key West sunset on a luxurious sunset sail. See local landmarks and sail past Sunset Key and historic Fort Zachary Taylor as you dine on a tasty selection of varied hors d'oeuvres. Watch the sunset with your favorite drink in your hand and your loved ones by your side. Enjoy live music from local musicians! These are moments you’ll savor long after you leave town! Don't miss the boat. Book your spot today!
Read more
image-3041-648
image-3041
image-3041-899
image-3041-648
image-3041

Glass Bottom Boat Reef & Eco Tour

40 ratings
1.5 - 2.5 Hrs.
Hop aboard for an adventure through the most diverse underwater ecosystem in the United States with the Glass Bottom Boat Reef & Eco Tour. Enjoy traveling the tropical and sun-kissed waters of the Florida Keys on a sleek and comfortable catamaran as you scope stunning seascapes through a glass bottom. Take an underwater adventure in North America’s only living coral reef without even getting wet. See the home to elkhorn, brain coral, and hundreds of diverse fish species. Come along on a fun and informative tour of the Florida Keys on Key West's only window to the sea! Book now!
Read more
image-15958
image-2560
image-16401
image-15958
image-2560

Reef Dive or Snorkel Excursion

33 ratings
4 Hrs.
Experience tropical diving or snorkeling and swim with abundant marine life on a thrilling excursion to two different reef locations. Whether you are a certified diver or beginner snorkeler, this is the best way to enjoy the beauty of the only barrier reef in North America. Glide through the shimmering waters in search of coral, tropical fish, sea turtles, and more! Just a short boat ride away from shore, this tour delivers unmatched natural beauty in a small group atmosphere.
Read more
image-2424-473
image-2424
image-2424-945
image-2424-473
image-2424

Rise & Reef Snorkeling Trip With Breakfast & Unlimited Mimosas

39 ratings
3 Hrs.
Embark on an unforgettable snorkeling adventure to explore Florida's best reef aboard the Sandie Cat, Key West’s newest and fastest catamaran. Spend less time traveling and more time in the crystal-clear waters. Enjoy a complimentary breakfast, unlimited mimosas (mango, strawberry, and orange), and draft beer during this all-inclusive experience. Join the crew for a true Key West experience with family and friends. Reserve your spot today!
Read more
Booked 5 times in last 48 hrs
image-2435-888
image-2435
image-2435-904
image-2435-888
image-2435

Do It All Water Sports Adventure Package

45 ratings
6 Hrs.
Don't miss your chance to “Do it All” with a day-long Watersport Adventure Package in Key West. This all-inclusive experience gives you full access to a variety of awesome activities like kayaks, paddleboards, snorkeling, jet skis, floatables, water trampolines, and banana boat rides. Choose your activities and have your day your way with this Do It All Water Sports Adventure Package. Book today!
Read more
image-2431-339
image-2431
image-2431-788
image-2431-339
image-2431

Key West Safari Eco Tour

12 ratings
2.5 Hrs.
Are you looking for the best kept secret in Key West?! If so, then hop in your own personal, mini speedboat and follow your knowledgeable guide into Key West's backcountry. You'll race through lush mangrove islands and see amazing marine wildlife along the way while boating in Key West's magical tropical waters. Book today and set out on an amazing adventure on the water with this Key West Safari Eco Tour!
Read more
image-2694-458
image-2694
image-2694-792
image-2694-458
image-2694

Seabreeze Sunset Harbor Cruise with Wine and Beer

19 ratings
2 Hrs.
Escape the hustle and bustle and experience a breathtaking Key West sunset with a Seabreeze Sunset Harbor Cruise. Your journey takes you away from commonly charted boat paths to unobstructed views and miles of turquoise waters, while snacking on delicious sushi and snacks. Travel to where the Gulf meets the Atlantic and on to the Southernmost Point of the United States. For an intimate and romantic evening that is sure to help you unwind, book a Sunset Harbor Cruise and toast to life!
Read more
image-17399
image-2692
image-17400
image-17399
image-2692

Seabreeze Dolphin & Snorkel Tour

18 ratings
3.5 Hrs.
Be on the lookout for Key West’s magnificent dolphins while cruising the crystal-clear backcountry waters of the Gulf of Mexico. On this family-friendly outing filled with amenities, observe dolphins and other Key West wildlife mingling in their natural habitat among deserted tropical islands. Don't forget to dive in and snorkel Key West's warm, gentle water to see all the ocean has to offer with a Seabreeze Dolphin & Snorkel Tour. Book today!
Read more
image-15308
image-2505
image-15310
image-15308
image-2505

Sunset Sail Aboard the Historic When and If

20 ratings
2 Hrs.
Set sail on Key West’s most elegant historic schooner, the When and If. Built in 1939 for General George Patton’s dream of sailing around the world “When and If” he was able, is available to the public for the first time in the yacht's lifetime. Sit back and experience the beautiful Key West sunset in style as the wooden schooner glides through the water driven by wind power alone. Meet the crew as they serve up a beautiful array of gourmet cheeses and share their stories of old Key West and the sea. Book your Sunset Sail today!
Read more
image-23077
image-3210
image-23078
image-23077
image-3210

Schooner Champagne Sunset Sail

11 ratings
2 Hrs.
Come along on this Champagne Sunset Sail and step into luxury in Key West, Florida. Sip, relax, and unwind aboard a gorgeous wooden schooner. Enjoy your authentic sailing experience as you cruise the crystalline water to landmark sites while sampling a wide variety of complimentary drinks. Come toast to an idyllic Key West sunset on the schooner cruise that is sure to become your favorite new Key West tradition. Book yours today!
Read more
image-2452-704
image-2452
image-2452-813
image-2452-704
image-2452

Day Sail Aboard Schooner America 2.0

17 ratings
1.5 Hrs.
Explore the high seas in style on the Schooner America 2.0, the namesake of the first sailboat to win America's Cup in 1851. This stunning 105-foot sailboat features teak decks, mahogany trimmings, and ample seating for the whole family. The sights you’ll see along the way include a waterside view of Fort Zachary Taylor, the famed Sand Key Lighthouse, Mallory Square, and Sunset Pier. So sit back and feel the warm breeze dance across your skin as you watch the sights of the beautiful water around Key West. Book your spot today!
Read more
image-4553-805
image-4553
image-4553-850
image-4553-805
image-4553

Rum Runner Downtown & Island Tour

Be the first to review!
4 Hrs.
Enjoy this Rum Runner Downtown & Island Tour and get out on the water for some fun in the sun. Cruise the gorgeous water on the best value bar boat in Key West and give a cheer for every gorgeous sight you see. Perfect for you and up to 15 of your crew to kick back and chill or snorkel and swim at the stop at Wisteria Beach. See Sunset Key, Wisteria Island, a 100-year-old shipwreck, and more. You can BYOB and/or sample rum on board. So, don't miss the boat! Book this experience today!
Read more
image-4863-729
image-4863
image-4863-956
image-4863-729
image-4863

Ultimate Sandbar & Dolphin Watch Adventure

Be the first to review!
5 Hrs.
Join this Ultimate Sandbar & Dolphin Watch Adventure and journey through the crystal-clear water of Key West, Florida searching for dolphins! Cruise to a secluded sandbar where you can relax and have fun. Decide to swim, snorkel, or simply bask in the glow of the warm sun. When you are ready to recharge, indulge in a delectable feast featuring a range of fresh, local delights from Cuban sandwiches to crispy fried chicken tenders, there's something for everyone. Vegetarian options like veggie wraps, fruit and veggie trays, cheese and cracker platters, and pita and hummus platters are also available. Book today!
Read more
image-4853-715
image-4853
image-4853-892
image-4853-715
image-4853

Stock Island Wind & Wine Sunset Sail

Be the first to review!
2 Hrs.
Climb aboard a 65-foot historic Schooner for a luxurious experience that has been rated one of the top two sunset tours in all of North America by Coastal Living Magazine. Join this unforgettable Wind & Wine Sunset Sail in Stock Island, Florida! Embark on this journey and indulge your senses with a selection of wines and light appetizers that beautifully pair. Whether you're a wine enthusiast, a sunset lover, or simply seeking an exceptional experience, this journey promises to exceed your expectations. Book your experience today!
Read more

Frequently Asked Questions

1. What are some of the best ways to see Key West from a boat?

Some of the best ways to see Key West from a boat include a glass bottom boat (the water is so clear). Also a sunset cruise on a boat is an amazing way to experience Key West.

2. What are some unique ways to learn about Key West on a boat?

There are many boat tours that include the history and many facts about Key West. Boat tours always give you a unique perspective of this fascinating city!

3. What are some activities you can do on a boat in Key West?

Some of the best activities on a boat in Key West are fishing, snorkeling, and suba diving. What makes these activities so stellar is the reefs and clear water around Key West.

4. For scuba diving what are some areas to explore?

There are many boat wrecks and reefs offshore and off the beaches in Key West. Make sure to include a scuba or snorkeling boat adventure on your trip!

Plan Ahead & Save Up to 20% with Exclusive Savings From TripShock

  • 5% OFF (7 days in advance)
  • 10% OFF (14 days in advance)
  • 15% OFF ( 30 days in advance)
  • 20% OFF ( 45 days in advance)

Fill out the form below to receive promo codes to apply to your order!

Destinations

FacebookYoutubeTiktokInstagram
© 2025 Tripshock
This website uses cookies. Please visit our Privacy Policy to learn how we use cookies and how to control your cookie settings. By clicking or navigating this site you consent to our use of cookies.