Key West Sunset Charters, Cruises & Sails | Key West Attractions Association

Classic Harbor Line

  • 202 William Street
  • 305-293-7245

Dedicated to providing the most perfect hospitality and sailing experience one could find in Key West, Classic Harbor Line hopes for the privilege of escorting you on a breathtaking excursion aboard the most elegant vessel in the local schooner fleet: America 2.0. While visiting Key West, Florida you will find a number of land and…

Appledore Tall Ships

Come aboard an Appledore tall-ship schooner and re-live maritime history. Sebago Watersports offers several Key West excursions on the historic 2-masted wooden Appledore II and the Appledore Star. Sailing a tall ship on our turquoise calm waters, you will enjoy a true sailing experience like nothing else. Choose from romantic Key West sunset sails, an…

Sebago Watersports

  • 205 Elizabeth Street
  • 800-507-9955

For over 25 years, Sebago Watersports has delighted guests on Key West’s pristine waters. We take great pride in being Key West’s favorite on-the-water tour company sailing the island’s only fleet of both modern sail catamarans and historic tall-ship schooners. Share a romantic sunset sail, snorkel the reef, or spend a full day of family…

sunsetsail_daysail

Sunset Sail Key West

Authentic private boat sailing in the Keys Offering exclusive small-boat sailing charters at an affordable price, Sunset Sail Key West is a locally-owned fleet of sailboats run by experienced, fun sailors in beautiful Key West, Florida. Our boats are carefully selected to be intimate, historic and characterful – each one has her own story. Our captains…

sadie cat

Sunset Watersports

Sunset Watersports, the Oldest Parasailing Company in the United States has been leading the way in Watersports excursions for over 30 years. Don’t trust just anybody with your hard earned Key West vacation, take a trip with Sunset Watersports and see why we have been a leader in providing fun, safe, watersports activities for over…

Danger Charters

  • 245 Front St. Westin Marina
  • 305-304-7999

When you sail with Danger Charters, you sail to another world and time; to a place where the wildlife is still “wild”, and your interaction with nature is intimate and authentic. You feel as if you’ve stepped back in time, back to the days when the Florida Keys backcountry was home to traditional, shallow-draft sailing…

Fury Water Adventures

  • 241 Front Street
  • 866-283-5439

 Fury Water Adventures Phone: (866) 283-5439 Website: Visit Website One of Key West’s most popular attractions is the crystal blue water surrounding our island paradise. For almost three decades, visitors and locals alike have been choosing Fury Water Adventures as their #1 excursion in and on the waters of Key West. Fury’s got it all….

Classic Harbor Line

  • 202 William Street
  • 305-293-7245

Dedicated to providing the most perfect hospitality and sailing experience one could find in Key West, Classic Harbor Line hopes for the privilege of escorting you on a breathtaking excursion aboard the most elegant vessel in the local schooner fleet: America 2.0. While visiting Key West, Florida you will find a number of land and…

sadie cat

Sunset Watersports

Sunset Watersports, the Oldest Parasailing Company in the United States has been leading the way in Watersports excursions for over 30 years. Don’t trust just anybody with your hard earned Key West vacation, take a trip with Sunset Watersports and see why we have been a leader in providing fun, safe, watersports activities for over…

Fury Water Adventures

  • 241 Front Street
  • 866-283-5439

 Fury Water Adventures Phone: (866) 283-5439 Website: Visit Website One of Key West’s most popular attractions is the crystal blue water surrounding our island paradise. For almost three decades, visitors and locals alike have been choosing Fury Water Adventures as their #1 excursion in and on the waters of Key West. Fury’s got it all….

Appledore Tall Ships

Come aboard an Appledore tall-ship schooner and re-live maritime history. Sebago Watersports offers several Key West excursions on the historic 2-masted wooden Appledore II and the Appledore Star. Sailing a tall ship on our turquoise calm waters, you will enjoy a true sailing experience like nothing else. Choose from romantic Key West sunset sails, an…

Sebago Watersports

  • 205 Elizabeth Street
  • 800-507-9955

For over 25 years, Sebago Watersports has delighted guests on Key West’s pristine waters. We take great pride in being Key West’s favorite on-the-water tour company sailing the island’s only fleet of both modern sail catamarans and historic tall-ship schooners. Share a romantic sunset sail, snorkel the reef, or spend a full day of family…

sunsetsail_daysail

Sunset Sail Key West

Authentic private boat sailing in the Keys Offering exclusive small-boat sailing charters at an affordable price, Sunset Sail Key West is a locally-owned fleet of sailboats run by experienced, fun sailors in beautiful Key West, Florida. Our boats are carefully selected to be intimate, historic and characterful – each one has her own story. Our captains…

Sebago Watersports

  • 205 Elizabeth Street
  • 800-507-9955

For over 25 years, Sebago Watersports has delighted guests on Key West’s pristine waters. We take great pride in being Key West’s favorite on-the-water tour company sailing the island’s only fleet of both modern sail catamarans and historic tall-ship schooners. Share a romantic sunset sail, snorkel the reef, or spend a full day of family…

Appledore Tall Ships

Come aboard an Appledore tall-ship schooner and re-live maritime history. Sebago Watersports offers several Key West excursions on the historic 2-masted wooden Appledore II and the Appledore Star. Sailing a tall ship on our turquoise calm waters, you will enjoy a true sailing experience like nothing else. Choose from romantic Key West sunset sails, an…

Classic Harbor Line

  • 202 William Street
  • 305-293-7245

Dedicated to providing the most perfect hospitality and sailing experience one could find in Key West, Classic Harbor Line hopes for the privilege of escorting you on a breathtaking excursion aboard the most elegant vessel in the local schooner fleet: America 2.0. While visiting Key West, Florida you will find a number of land and…

sadie cat

Sunset Watersports

Sunset Watersports, the Oldest Parasailing Company in the United States has been leading the way in Watersports excursions for over 30 years. Don’t trust just anybody with your hard earned Key West vacation, take a trip with Sunset Watersports and see why we have been a leader in providing fun, safe, watersports activities for over…

Danger Charters

  • 245 Front St. Westin Marina
  • 305-304-7999

When you sail with Danger Charters, you sail to another world and time; to a place where the wildlife is still “wild”, and your interaction with nature is intimate and authentic. You feel as if you’ve stepped back in time, back to the days when the Florida Keys backcountry was home to traditional, shallow-draft sailing…

sunsetsail_daysail

Sunset Sail Key West

Authentic private boat sailing in the Keys Offering exclusive small-boat sailing charters at an affordable price, Sunset Sail Key West is a locally-owned fleet of sailboats run by experienced, fun sailors in beautiful Key West, Florida. Our boats are carefully selected to be intimate, historic and characterful – each one has her own story. Our captains…

Fury Water Adventures

  • 241 Front Street
  • 866-283-5439

 Fury Water Adventures Phone: (866) 283-5439 Website: Visit Website One of Key West’s most popular attractions is the crystal blue water surrounding our island paradise. For almost three decades, visitors and locals alike have been choosing Fury Water Adventures as their #1 excursion in and on the waters of Key West. Fury’s got it all….

Barefoot Billy's

Barefoot Billy’s

  • 714 Seminole Street
  • 305-735-2241

Barefoot Billy’s “Home of the Island Jet Ski Tour” is the premium jet ski company in Key West. Whether you’re looking for the original guided island jet ski tour (wave runner tour), or looking to snorkel, kayak, paddle board or do your own thing with a jet ski rental we are here to serve you….