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Popular Sunset & Dinner Cruises Charters in Key West  , United States. Good availability and great rates. Read unbiased reviews and choose the best deal for your trip.

Sunset & Dinner Cruises in Key West, FL- BoatBooker

Key West

Key West, United States

key-west

Experience the vibrant charm of Key West, Florida, with a variety of Key West boat tours that showcase the island's stunning marine life and breathtaking landscapes. Located at the southernmost tip of the United States, Key West offers a unique blend of tropical beauty and rich history, making it an ideal destination for boating enthusiasts.

From sunset sailing trips with open bars and live music to dolphin watching and snorkeling eco-cruises, there's something for everyone in Key West. Explore the crystal-clear waters of the Gulf of Mexico and witness bottlenose dolphins in their natural habitat. Discover the vibrant coral reefs, home to an incredible array of marine life, including sea turtles, stingrays, and colorful fish.

For those who prefer a more leisurely experience, glass bottom boat tours offer a unique opportunity to view the underwater world without getting wet. Enjoy educational commentary while staying cool and comfortable in air-conditioned comfort.

Whether you're looking for adventure, relaxation, or simply a chance to soak up the sun and scenery, Key West boat tours provide an unforgettable experience. With its laid-back atmosphere and stunning natural beauty, Key West is the perfect place to create lasting memories on the water.

Price per Day

Welcome to Kilo Whiskey Charters, the premier destination for unforgettable aquatic adventures in the pristine waters of Key West, Florida. With over 10 years of experience, Kilo Whiskey Charters is dedicated to providing top-tier, personalized charter ex

Kilo Whiskey Charters

Experience the ultimate Key West adventure aboard Rising Tide Fishing Charters, a fully restored 2008 Pathfinder 2200 Bay boat (2025 upgrade). Perfect for up to five guests, this sleek vessel is powered by a 200 HP Yamaha outboard, reaching speeds up to 5

Rising Tide Fishing Charters

Ditch the ordinary and immerse yourself in a tropical escape with Tiki Boat Adventures in Key West! These custom-built tiki boats offer the ultimate setting for a fun and relaxing day on the water. With their signature thatched roofs providing shade, a bu

Tiki Boat Adventures - Key West

Always Somethin&#039; Shallow Water Tours offers an intimate and unforgettable experience on the pristine waters surrounding Key West. Designed for small groups of up to four guests, this nimble vessel is powered by a reliable 115 HP Mercury outboard engi

Always Somethin' Shallow Water Tours

Making Memories Charters Key West invites you to discover paradise aboard their sleek 2019 SeaRay 270 SDX-OB Deck Boat, departing from Stock Island. This spacious vessel accommodates up to six guests and is powered by a robust 300 HP Mercury outboard engi

Making Memories Charters Key West

Step aboard a beautifully restored 1985 SeaVee Ocean Center Console, meticulously updated in 2010, and get ready for an unforgettable adventure. With space for up to six guests, this versatile vessel is powered by a reliable 250 HP Suzuki outboard engine,

Sandbar/Snorkel/ Dolphins/Sunset Trips

Climb aboard Mayhem Sportfishing, a sleek 2007 Proline Supersport Center Console&mdash;fully restored in 2022 and ready to deliver unforgettable adventures out of Stock Island. With twin 250HP Mercury outboards and cruising speeds up to 55 knots, this ves

Mayhem Sportfishing

Step aboard FloAlong Charters, a 2018 Pathfinder 2500 Bay boat perfect for up to six guests, and experience the best of Key West&rsquo;s waters. Powered by a 300 HP Yamaha engine, this versatile vessel reaches speeds of up to 30 knots, making it ideal for

FloAlong Charters

Step aboard our sleek 24&rsquo; center console for an unforgettable private boat tour through Key West&rsquo;s most breathtaking waters! Designed for up to six guests, this captain-guided experience takes you to pristine sandbars, secret beaches, and vibr

Danger Charters

Experience the ultimate escape aboard the 2021 Robalo R 247 Dual Console, expertly captained by Dolphin Safari Charters out of Stock Island. Perfect for up to six guests, this sleek vessel is powered by twin 300 HP Yamaha engines, delivering smooth, thril

Dolphin Safari Charters – Vitamin Sea

The waters are shallow and inviting! A short boat ride can get you to a secluded sandbar, or a busy one, or you can choose to explore the waters of the backcountry and wildlife, stop for a swim or snorkel or just dangle your feet off the boat, this charte

Downtime: Vitamin Sea Tours

Nice Guy Charters is a 2004 Everglades 243cc Center console (restored in 2024), based out of Stock Island. It can take up to six guests. The boat is powered by one 300 HP gasoline outboard Suzuki engine, offering a maximum cruising speed of 50 knots. The 

Nice Guy Charters

Start your morning with a calm and refreshing escape to one of Key West’s beautiful shallow-water sandbars. Captain John Hoover will guide you through the clear backcountry to a quiet, scenic spot perfect for relaxing, swimming, and soaking up the peaceful morning sun. 

Purple Heron Charters

Step aboard Purple Heron Charters for a personalized adventure on the water in Key West. This Dolphin 18 Backcountry Pro Skiff, perfect for up to three guests, is designed for an intimate and exciting experience. Powered by a reliable 115 HP Mercury outbo

You can feel free to choose how you would like to spend your trip. The boat comes with a captain and we can go swimming, snorkeling, or just cruising around.

Strawhat Charters

Embark on an unforgettable journey aboard Strawhat Charters, a beautifully restored 2006 Intrepid 323 Center Console (refurbished in 2024), departing from the vibrant shores of Key West. This sleek vessel comfortably accommodates up to six guests and is p

Join me for an authentic experience of how the locals enjoy their time on the water! With my extensive local knowledge and a variety of incredible spots to explore, I’ll make sure you have an unforgettable adventure. As a locally owned and operated business, I take pride in delivering top-quality trips, ensuring every detail exceeds your expectations.

This is our most popular trip. Enjoy a 4-hour private charter in Key West, featuring snorkeling at a beautiful reef, relaxing at the sandbar and an exciting dolphin watching experience. The boat is equipped with shade, comfortable seating, and a restroom for your convenience, ensuring a relaxing and memorable adventure on the water. All trips are private and catered to your groups interests and comfort levels. We match unparalleled service with the most beautiful waters in the country.

Good Times Key West 24’ Center Console.

Good Times Key West LLC is a 2011 Sailfish 2360 Center console based out of Key West. It can take up to six guests. The boat is powered by one 300 HP gasoline outboard Suzuki engine, offering a maximum cruising speed of 30 knots. The vessel comes equipped

Hop aboard one of the nicest boats in town for a sunset cruise in Key West Harbor. On this 2-hour trip, you'll see famous sights like Mallory Square, Sunset Key, and even the Southernmost Point. We have plenty of cooler space, so grab some friends or family, bring a few beverages, and let's set sail for an unforgettable cruise. Departure times vary depending on sunset, typically 2 hours prior.

Good Times Key West 35’ Offshore Express

Good Times Key West LLC is a 2001 Carolina Classic Express Motor yacht based out of Key West. It can take up to six guests. The boat is powered by two 450 HP diesel inboard Cummins engines, offering a maximum cruising speed of 30 knots. The vessel comes e

Sail into the famous Key West sunset aboard The Sandie Cat! This lively 2-hour cruise features unlimited tropical drinks, delicious appetizers, and live music from top local entertainers. Enjoy a night of dancing, sipping, and soaking in paradise on Key West’s newest luxury catamaran. From rum runners and margaritas to Hawaiian chicken sliders and more, this all-inclusive experience is the perfect way to celebrate your evening in paradise. Book now and see why it’s one of Key West’s top-rated cruises.

Sunset Watersports Key West – Sunset Sail

Are you ready to experience the Key West sunset like never before? Join us on the ultimate Sunset Sip &amp; Sail adventure aboard The Sandie Cat, our luxurious sailing catamaran! This is more than just a sunset cruise&mdash;it&rsquo;s an experience that&r

A local favorite! This 4-hour private Sandbar Snorkel Trip for up to 6 guests explores Key West’s clear, shallow waters aboard Cowfish, our smooth, fast Glacier Bay catamaran. Choose two activities: snorkel, relax on a sandbar, or search for dolphins.


We'll provide fresh organic fruit and water. Feel free to bring extra beverages or snacks if you'd like. We have coolers on board. 

Honest Eco – COWFiSH

22&prime; Glacier Bay dual console Catamaran Cowfish offers a smooth and comfortable ride, with versatility and ample space for up to 6 people in a compact package. Cowfish provides a great platform for your sandbar tour and other activities, whether you 

Absence Adventures

Absence Adventures is a sleek 1999 Hydrasports Vector 2000 Center Console, based in beautiful Big Coppitt Key. Perfect for up to six guests, this agile vessel is powered by a robust 225 HP Suzuki outboard engine, reaching exhilarating speeds up to 34 knot

Explore the best of Key West with a fully customizable boat adventure! From island hopping, snorkeling, and dolphin watching to shopping excursions, historical tours, sandbar stops, and breathtaking sunsets, you can tailor your itinerary to fit your perfect day on the water. Whether you want a mix of relaxation, exploration, or adventure, this trip lets you create your ultimate Key West experience.

Screaming Lines Adventures

Experience the ultimate Key West adventure aboard Screaming Lines Adventures, a beautifully restored 1980 Egg Harbor Sportfishing vessel (restored in 2010). Comfortably accommodating up to six guests, this powerful boat is driven by twin 400 HP diesel inb

Mallory Square is a popular spot for watching the sunset, and experiencing it by boat offers a unique view from the water. We can cruise by the area during sunset and enjoy the atmosphere. Lady of the Sea Charters offers a safe, private charter focused on peace and privacy, rather than large, crowded boats. The Glastron is well suited for enjoying the sunset near Mallory Square and visiting nearby sandbars.

Lady of the Sea LLC

Enjoy a memorable day on the water exploring the beautiful Florida Keys aboard an 18-foot Glastron, perfectly suited for small groups seeking a safe, quiet, and personal boating experience. Whether your ideal outing includes cruising the coastline, visiti

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