Home
305-293-7245
Key West, FL
Buy Tickets Now

Sailing

Book Now Call to order 305-293-7245

Sailing with Classic Harbor Line A must do while on vacation is some Key West Sailing!  Join us with our professional crew and take to the waters of Key West. Let our crew dazzle you with their skills of sailing our yacht and taking care of you with the up most hospitality. Sailing is fun, but sailing and sightseeing is the most magical way to experience this Island of wonder.

Enjoy a Key West Sunset Sail or sail past Mallory Square, and cruise by Fort Zachary Taylor. Allow the dolphins to take your breath away as they surf the bow of our boat on our Key West Day Sail.  You will truly enjoy the excitement and art of Key West sailing.

While sailing aboard the 105 foot Schooner America 2.0 you will experience the most premium sailing. This stunning classic boat was designed for comfort and speed.  So snap some photos and sip on Champagne as you cut through the emerald green waters of Key West. 


A large schooner sailing in Key West with the sun peaking through the sails for a Key West Sunset Sail

Key West Sunset Sail on Schooner America 2.0

Enjoy the best sunset sail in Key West on the Schooner America 2.0!  Take in the vibrant colors of Key West’s famous sunset as you sip complimentary champagne.  On this Key West Sunset Cruise, you will magically glide through the crystal clear surrounding waters whilst being taken care of by our professional and friendly crew.

This two-hour Key West sunset cruise features complimentary champagne, wine, beer, soft drinks, and water and passed hors d’oeurves- veggie crudite, cheese and crackers, and shrimp cocktail. There is a cocktail bar on board for purchase. Sit back and relax while Schooner America 2.0 plies effortlessly through the turquoise green Key West sailing waters and off towards the horizon for the quintessential Key West Sunset experience! (Call us directly to save 6% online processing fee)

  Duration: 2 hrs   Boat: America 2.0   Cost: Adult $104 | Child $36

Family sitting in the cockpit of the Schooner America 2.0 enjoying a Mother's Day Sail in Key West FL

Momas & Mimosas: Mother’s Day Mimosa Sail aboard Schooner America 2.0

Join us on the best Key West Mother’s Day Mimosa Sail!  Take to the water on the Schooner America 2.0, namesake off the first sailboat to win the America’s Cup in 1851. This stunning 105-foot sailboat features teak decks, mahogany trimmings and ample seating. Her 3,600 square feet of sail will propel you smoothly through the crystal green waters of Key West. Guests are encouraged to make the most of the event by bringing aboard their own picnic lunch! Mom’s sail FREE! And Adults get one complimentary Mimosa or Bloody Mary.

  Duration: 1.5 hrs   Boat: Schooner America 2.0   Cost: Adults $56 | Child $24

Schooner America 2.0 sailing in the morning sunlight for a Key West Mimosa Sail

Private Morning Sail on Schooner America 2.0

Step aboard the stunning America 2.0 for a Key West Morning Charter. This 1.5 hour sail is available to book privately with your close friends and family. Start your day off right and take the helm and experience the power of this sailing machine or sit back and relax as you sail smoothly through the crystal clear waters of Key West. Either way and above all, it doesn’t get much better for a morning sail in Key West. Options to extend your trip are available. Charter includes soda, juice, and water. Bar and food packages are available upon request. (Call us directly to save 6% online processing fee)

  Duration: 1.5 hrs   Boat: America 2.0   Cost: Starting at $750

Key West Day Sailing

Classic Day Sail aboard Schooner America 2.0

It is true! When in Key West you must soak in the sun while you do some classic Key West day sailing. We think the best way to spend an afternoon is to take to the water on the Schooner America 2.0 for a Key West Day Sail! Named after the first boat to win the America’s Cup in 1851. Our stunning 105-foot sailboat features teak decks, mahogany trimmings, and ample seating. There is over 3,600 square feet of sail that will propel you smoothly through the crystal green waters of Key West. We boast a full bar on board which is available for credit card purchase. Soda and water are complimentary. Guests are encouraged to bring aboard their own picnic lunch! (Call us directly to save 6% online processing fee)

  Duration: 1.5 hrs   Boat: America 2.0   Cost: Adult $56 | Child $26

Stern of the schooner America 2.0 with the sails raised and the Captain Turned around waving while sailing for a Key West Wreckers Race

Wreckers Race aboard Schooner America 2.0

All hands on deck!  If you enjoy a good sailboat race, it is an absolute must for you to sail on board the Schooner America 2.0 for the Key West Schooner Wharf Bar Wrecker’s Cup Race! 

A little history…back in the days of old Key West, ships from afar often ran aground on Sand Key Reef. When all the scallywags in Key West heard there was booty to be had, they jumped in their boats and raced to the reef. The first one there could claim the ship’s cargo! Arrggh!

Today, we celebrate this Key West tradition annually with a set of monthly races from January to April. It all starts with the firing of the cannon at 1:00 PM.  Enjoy the excitement aboard Schooner America 2.0 as we race to defend our title of fastest schooner in Key West!

One round of beer, wine, champagne, and a boxed lunch are complimentary with your ticket purchase. Purchase a Beverage Package during the booking process, or additional drinks for credit card purchase while on board. (Call us directly to save 6% online processing fee)

  Duration: 3 hrs   Boat: America 2.0   Cost: Adult $104

Schooner America 2.0 sailing in the night for a Full Moon Sail!

Full Moon Sail Aboard Schooner America 2.0

Sail through the Key West waters by full moonlight on this romantic Full Moon sailing adventure aboard one of Key West’s most stunning modern sailboats, the 105 ft Schooner America 2.0. This special sail is only offered for a limited time every month! Ticket price includes 1.5 hours of sailing, complimentary soft drink, and water. Drinks and snacks available for purchase. Pro Tip: Call us directly at 305-293-7245 to avoid the 6% online processing fee.

  Duration: 1.5 hrs   Boat: America 2.0   Cost: Adult $68 | Child $36

Schooner America 2.0 decorated for the Key West Lighted Boat Parade

Lighted Boat Parade aboard Schooner America 2.0

Join us for the Schooner Wharf Bar Annual Key West Lighted Boat Parade, a favorite maritime holiday event. Sit aboard the most elegant schooner decked out in holiday decor.  The America 2.0 will parade through the Bight and Harbor of Key West. We will be showing off our crew’s creative design of twinkling lights that will dazzle all! (Call us directly to save 6% online processing fee) 

  Duration: 3 hrs   Boat: America 2.0   Cost: Adult $104

The Schooner America 2.0 decorated for the New Year's Eve Lowering of the Pirate Wench

New Year’s Eve Dockside Bash aboard Schooner America 2.0

Do you want the best seat in the house for New Year’s Eve in Key West? Join us aboard America 2.0 for an epic Dockside New Year’s Eve Bash! Your ticket grants you VIP dockside access to the famous Schooner Wharf Bar “Lowering of the Pirate Wench” as we lower her from the rig of our very own Schooner America 2.0! Enjoy this timeless celebration on the most exclusive boat in the Historic Bight. Our special ’21 and older’ event features complimentary beer, wine, champagne, well drinks, soda, water, and delicious hors d’ oeuvres all night! (Call us directly to save 6% online processing fee) 

  Duration: 3 hrs   Boat: America 2.0   Cost: Adult $246

Key West Brunch Sail aboard the Schooner America 2.0 with guests in the cockpit enjoying food

Christmas Day Brunch Sail aboard Schooner America 2.0

Are you dreaming of a crystal clear, blue Christmas? Then, spend your Christmas morning aboard the Schooner America 2.0 for a brunch sail that you and your loved ones will never forget! Start your day with complimentary mimosas, bloody mary’s, or champagne as you sail into the Christmas spirit. This two-hour sail includes a fully-catered brunch that will be sure to help you start Christmas day the right way! On this peaceful holiday sail, you can relax to the natural sounds of the wind and waves, and appreciate the beauty of Key West during the holiday season. (Call us directly to save 6% online processing fee)

  Duration: 2.5 hrs   Boat: Schooner America 2.0   Cost: Adult $136 | Child $63

a couple being served Champagne on a Key West Valentine's Day Sunset Sail

Champagne Sunset Valentine’s Day Sail

Join us for our Key West Valentine’s Day Sunset Sail aboard the Schooner America 2.0!  This is a day to celebrate your loved one.  So spend Valentine’s Day in Key West aboard our elegant Schooner. It truly is the perfect way to show your love and appreciation. Sail through Key West with a glass flute of French champagne in hand and cruise aboard our classic boat for an evening of elegance.  Watch the sun dip beyond the horizon.  Snuggle up with your loved one to celebrate your love for each other.  Reflect on your relationship aboard this Valentine’s Day cruise.Our professional crew will cater to your every need. We will wine and dine you and make you feel like royalty. Key West sailing is a magical way to capture a moment in time.  So what better cruise to do this on then the Key West Valentine’s Day Sunset Sail.  This magical Key West sunset sail will take your breath away and your loved one will be swept off their feet all over again. (Call us directly to save 6% online processing fee)

  Duration: 2 hrs   Boat: America 2.0   Cost: $136

Schooner America 2.0 night sailing for a stargazing evening

Starry Night: Guided Stargazing Sail Aboard Schooner America 2.0

Join us aboard the Schooner America 2.0 after the sun goes down, setting the stage for an enchanting stargazing journey unlike any other. As the boat gently glides across the tranquil waters, your guide, a seasoned astronomer, narrates the celestial spectacle unfolding above. Pointing out constellations and tracing the mythology behind their names, they weave together tales of ancient cultures and their interpretations of the stars.

Wrapped in the darkness of the night sky, you marvel at the intricate details of distant planets, shimmering nebulae, and elusive galaxies. Each sighting is accompanied by insightful commentary from your guide, illuminating the mysteries of the universe. It’s an experience that transcends time, leaving you with memories that will twinkle brightly in your heart for years to come.

  Duration: 1.5 hras   Boat: America 2.0   Cost: General Admission $76

Buy Tickets Now