Sunset Cruises Key West

Pristine Sandbar Excursion #1 Trip in Key West!

A sandbar trip to the backcountry of the lower Florida Keys will be the highlight of your Key West Vacation. The picturesque scenery, clear water, beautiful sandy beaches and remote islands will be ingrained in your memories forever. Go where few visitors ever venture and for the lucky ones that do, they always return. Enjoy light snacks, soft drinks and water and explore the clear waters of the Florida Keys in style! Floats and snorkel gear also included!

Daily Trips @:
9 AM
1 PM
5 PM includes sunset

Duration: 3 to 3.5 Hours

Location:
The Perry Hotel
7001 Shrimp Road
Key West, FL 33040
Free parking!

Locals favorite!

Experience a beautiful sunset sail on a spacious catamaran with live music from local Key West musicians. Enjoy stunning views of Sunset Key and historic Fort Zachary Taylor, as you cruise past the seaport and Mallory Square. With a full premium bar, including champagne, wine, and beer, plus complimentary appetizers like shrimp, caprese skewers, and key lime tarts, this relaxing evening offers everything you need to unwind. The limited passenger count ensures plenty of space, and you can upgrade to top-shelf liquor at checkout or on board.

Daily: 4.30 PM to 6.30 PM
Duration: 2 Hours
Location: Historic Seaport Key West
Tour Price:
Adults – Starting at *$69.95 (Regular price $79.95)
Child – $49.95 (Ages 11 & under)

*blackout dates apply

Live Music Sunset Sail

Daily: 4.30 PM to 6.30 PM
Duration: 2 Hours
Tour Price:
Adults $79.95
Children (Ages 4-10) $55.95
Children under 4 Free

*blackout dates apply

Champagne Sunset Sail! #4 on Map

Experience Key West’s world-famous sunset aboard a 69’ sail catamaran. With over 2,300 feet of deck space, you’ll have plenty of room to relax and enjoy the breathtaking views. Sip on complimentary champagne, sangria, chilled beers, wine, and soft drinks while sailing past iconic landmarks like Mallory Square and Fort Zachary Taylor. As the sun sets, your experienced captain positions the vessel for the perfect view, offering an unforgettable conclusion to your day in paradise.

Daily: 6.30 PM to 8 PM
Duration: 1.5 Hours
Tour Price:
Adults – *$49.95
Regular Price $59.95
Child – $39.95 (Ages 4-11)
Young Child – Free (0-3)

*blackout dates apply

Schooner America 2.0 #5 on map

Experience a historical and elegant sunset sail aboard a replica of the 1851 America's Cup champion schooner. This smooth two-hour cruise offers stunning views of Key West's vibrant sunset while you sip champagne, wine, or beer and enjoy appetizers like shrimp cocktails, a cheese plate, and fresh veggies. Glide through the crystal-clear waters of the lower keys, taking in the serene beauty of one of the most famous sunsets in the world. With complimentary drinks and hors d’oeuvres, this is a must-do experience for those looking for a unique and refined way to enjoy Key West.

Daily: 4 PM to 6 PM
Duration: 2 Hours
Tour Price:

Adults $108
Children (2-12) $62
Children under 2 Free

Please select Adult ticket first

Sunset Sail – Wines from around the world! #6 on Map

Danger’s Wind and Wine Sunset Sail offers a refined experience with up to 8 varieties of fine wines, craft and domestic beers, and carefully selected hors d’oeuvres. Enjoy two hours aboard a historic Key West schooner, taking in breathtaking sunset views while savoring a selection of cheeses, summer sausage, caprese skewers, crudités, and dark chocolate. Ranked by Coastal Living Magazine as one of the top sunset sails in North America, this intimate and upscale cruise is perfect for those seeking a unique and luxurious way to enjoy Key West's natural beauty.

Daily: 4 PM to 6 PM
Duration: 2 Hours
Location: Old Town Key West
Tour Price: Adults $109

Appledore Schooner Champagne Sunset Sail

Experience the perfect Key West sunset aboard a romantic 2-masted schooner. Feel the wind in your hair as the ship sails toward the southernmost point of the U.S. Enjoy champagne, boutique wine, tropical sangria, premium beer, and soft drinks while savoring chef-selected hors d’oeuvres and cocktail shrimp.

Leaving the Historic Seaport behind, you’ll have the opportunity to help hoist the sails or take the wheel. As you sail past landmarks like Mallory Square and Fort Zachary Taylor, your captain will position the boat for the ideal sunset view. Enjoy drinks, appetizers, and stunning sights as the sun sets on your unforgettable Key West sailing adventure.

Daily: 4 PM to 6 PM
Duration: 2 Hours
Location: Historic Seaport
Tour Price: All Ages – $89.95

Sunset Sail and Dolphin Watch

• Experience an intimate dolphin watch and sunset cruise aboard a spacious sail catamaran, limited to just 34 guests. Enjoy a more private, relaxed atmosphere, perfect for couples or families looking to avoid the crowds. As you sail, enjoy chef-selected tapas, including shrimp cocktail and tuna poke, prepared daily in their own catering kitchen.

  Sip on boutique wines, champagne, or beer, all included in your tour. With ample space to relax, you can choose to sit in the shade or enjoy the sundeck while taking in the beautiful ocean breeze. This unique sunset sail and dolphin watch offers one of the best Key West experiences, combining scenic views, delicious food, and plenty of space to unwind.

Daily: 4 PM to 6.30 PM
Duration: 2.5 Hours
Location: Historic Seaport
Tour Price:
Adults – $79.95 (Regular $89.95)
Child 0-11 – $49.95

Cruise on a 45' Catamaran!

Set sail on a 2-hour cruise aboard a 45-foot stable power catamaran. Enjoy a historic tour of the island and seaport plus the spectacular Key West sunset. This tour includes a complimentary selection of fine wine, premium beer, prosecco, and soft drinks. Indulge in a large sushi boat, meat and cheese platters, and delicious desserts while you relax on a spacious sundeck or shaded seating area.

Your journey takes you past Key West's landmarks, including the Southernmost Point buoy and Fort Zachary Taylor. The tour offers ample space for you to stretch out and unwind, with a focus on comfort and relaxation. Free parking or a complimentary shuttle is also provided for your convenience. This sunset sail is the perfect way to celebrate your time in Key West with friends and family.

Days Operated: Daily from 4 PM to 6 PM
Duration: 2 hours
Location: Key West Bight
Free parking!

Snorkel & Sunset Combo

#7 on Map
• Snorkeling & Sunset Sail Combo
• Large Sail Catamaran
• Snorkel Gear & Instruction
• Sunset Sail with Music
• Complimentary Rum Punch, Beer, Wine, Soda & Water

Snorkel into Key West’s most popular attraction: the reef and crystal blue waters surrounding our island paradise. Your sailing adventure begins as you board a state-of-the-art catamaran, part of the largest and most luxurious catamaran fleet in the Florida Keys. Feel the excitement as you sail to North America’s only living coral reef, where the wonders of Mother Nature await you. During your trip, unlimited sodas and water will be served. Complimentary beer, wine and rum punch are served after snorkeling. Then, sail off into Key West’s famous sunset, through the surrounding islands and into the historic seaport.

Days Operated: Daily from 4 PM
Duration: 3 hours
Location: Old Town Key West
Tour Price:
Adults $59.95
Children (4-10) $42.95
Children (3 & under) Free

Glassbottom Boat Tour

• Unique & Informative Eco-Tour
• Air-Conditioned Viewing Areas
• State-of-the-art Catamaran
• “Window to the Reef”
• Large Seated Sundeck

Explore dramatic underwater vistas generally reserved for scuba divers. A wide variety of fish and other sea creatures await you as you gaze into the underwater world of Key West. Along the way, the experienced captain and crew will provide a unique and informative eco-tour and point out some of the most interesting marine life that inhabits the waters that surround this incredible island. Key West’s Glass Bottom Boat offers passengers a smooth ride on our modern catamaran with a seated sun deck and an air-conditioned enclosed viewing area. Restrooms and snack bar are also available onboard.

Days Operated: 3 tours Daily

12 PM
2 PM
6 PM – Sunset

Duration: 2 hours
Location: Old Town Key West
Tour Price:
Adult – $69.95
Children $45.95 (4-10)
Children Free (0-3)

Argo Navis Brunch Sail

About

Duration: 2 hours
Tour Price:
*Adult – $135
Children- $99 (4-10)

Argo Navis Sunset Sail

Duration: 2 hours
Location: 0 Duval Street – Ocean Key Resort Marina 
Tour Price:
$111