We noticed that you're using an unsupported browser. The Tripadvisor website may not display properly.We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.
Support this operator:Times are tough for the travel community right now. To show your support, consider leaving a review or posting photos of tours and experiences you have taken. Your support will go a long way in helping tour operators worldwide get back on their feet down the road

Sunset Sail Key West

Features Animals
Key West, FL, USA
More
About Sunset Sail Key West
There's no better way to experience the Florida Keys than right on the water, and there's no better charter to trust with your tour than Sunset Sail Key West. With years of experience and a lifetime of passion, our fleet of locally owned sailboats and personable sailors will show you all the beauty that Key West has to offer. As you join us for a sunset, starlight, or snorkel sail, you'll find that the sparkling waters of the Florida Keys have a way of bringing people together. Our dedicated team is flexible, accommodating, and dedicated to making your sailing experience as smooth and personalized as possible.
Open Now
Hours Today: 8:00 AM - 10:00 PM
Certificate of Excellence
Travelers talk about
Tours and Tickets by Sunset Sail Key West

Sunset Sail on Historic Schooner in Key West

Leave the tourist crowds of Key West behind for the evening and head out on the water on the historic and elegant When And If!, built for General Patton in the late 1930s. Cruise around the Florida coast with the boat’s crew looking after you the whole time, providing a complimentary cheeseboard and even letting you take the wheel if you want to try your hand at boating. Watch the sunset from the ocean before heading back.
Read more
2 hours
from $89.48

Private 90 Minute Customized Sailing Charter

Enjoy a morning or afternoon of sailing on this private, 90-minute cruise off the coast of Key West. Spend a relaxing time on board a boat headed to Sunset Key and the Key West National Wildlife Refuge. Led by a captain and mate, pass some of Key West’s top attractions and look for more than 600 species of colorful fish, coral and other sea life.
Read more
1 hour 30 minutes
from $314.66

Private Afternoon Snorkel with Sunset Sail

Watch the sun set off the coast of Key West on this private, 4-hour snorkeling cruise. Enjoy the scenery and peaceful calm of a late afternoon sail. Pass some of Key West’s top attractions, then dive into the water to see more than 600 species of colorful fish, coral and other sea life. Then watch a legendary Key West sunset as the sun glistens off and gently settles into the water. This cruise includes a gourmet cheese platter with a variety of light refreshments to sample along the way.
Read more
4 hours
from $723.96
846Reviews7Q&A
Traveler rating
  • 780
  • 33
  • 4
  • 6
  • 8
Traveler type
Time of year
Language
Selected filters
  • Filter
  • English
Popular mentions
Thanks to Captain Joanne and crew Elijah our small group of friends had a spectacular time on the water. The weather was perfect which made for a tranquil and relaxing sail. Even spotted a dolphin! The sloop High Tide is the perfect size to get close to the beautiful waters off
Read more
My husband, sister, brother-in-law and I wanted a personal sunset sail when visiting Key West at the end of February. We got exactly what we were hoping to find with Sunset Sail. We chartered the High Tide that holds up to six guests. We were in extremely capable hands with
Read more
Review collected in partnership with this attraction
wonderful family and friend experience. Beautiful boat. Crew was very very knowledgeable and friendly
Read more
Review collected in partnership with this attraction
There is nothing like sailing on history. The When and If was Patton's boat and he told his wife "When and if I come home from the war they would sail around the world". The crew now taking people out were excellent. It was a sporty ride which we enjoyed. Not just a booze
Read more
Review collected in partnership with this attraction
Crew Was AMAZING in their work and INTERACTING with guests .I would suggest this to anyone visting KEY WEST .Just close your eyes and ENJOY .If I get back I will be on board AGAIN
Read more
Review collected in partnership with this attraction
Previous