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What to do in December in Key West

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Guests on Schooner America 2.0

Are you looking for something to do in the month of December when you visit Key West?  We all know that December in Key West offers a variety of activities and events to enjoy, thanks to its mild weather and festive atmosphere! Here are some ideas for your visit to Key West in December!

Key West Lighted Boat Parade

Key West is famous for its Lighted Boat Parade and we offer tickets to join us in this extravaganza!  The Lighted Boat Parade in Key West is a dazzling and magical annual event that takes place during the holiday season, typically in early December. This beloved tradition illuminates the waters around Key West Harbor as boats of all sizes and types are decorated with an array of colorful lights and holiday-themed displays.

Being on the schooner America 2.0 in the Lighted Boat Parade in Key West is a magical and unforgettable experience that combines the charm of sailing with the festive spirit of the holiday season.

As the day begins, the excitement on our schooner builds. Our crew works diligently to create a masterpiece!  The boat is carefully adorned with an array of twinkling lights, holiday decorations, and festive displays, transforming it into a floating work of art.

Come Along!

Embark on a journey with us!  Our passengers make the schooner shine brighter than all the lights we put on this magical sailboat.

Imagine being on the 105 foot schooner America 2.0 in Key West as the sun begins to set.  The Schooner America 2.0 and all the other participating boats start gathering at Key West Harbor, near Mallory Square and the Historic Seaport.  The atmosphere is one of anticipation and camaraderie as boat owners and captains exchange smiles and greetings.

Spectators line the shores, docks, and vantage points along the harbor to get the best views of the America 2.0. The atmosphere around the harbor becomes electric with anticipation. Families, tourists, and locals all come together to celebrate the holiday season in this unique and tropical style.

Much to Behold

As darkness falls, the parade kicks off, with the boats slowly making their way through the harbor and along the waterfront. The parade route usually covers the waters from Key West Bight to the Historic Seaport, offering plenty of viewing spots along the way. Wave “Hello” to those on shore as you cruise by aboard our magical 105 foot schooner decked out in holiday decor!

All of the boats are a sight to behold. Especially the Schooner America 2.0! The creativity and effort put into these displays are truly impressive! The Key West Lighted Boat Parade is a cherished tradition that encapsulates the spirit of the holiday season in this tropical paradise.

It’s a joyful and enchanting event that brings the community together and captivates visitors with its unique blend of maritime creativity and holiday cheer. Whether you’re a local or a tourist, experiencing this dazzling spectacle aboard the schooner America 2.0 is a must during your December visit to Key West.

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
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Schooner America 2.0 decked out in Holiday Lights for the Lighted Boat Parade in Key West Florida

Choosing the Best Sunset Sail in Key West in the month of December

Our ratings are over the top! Our crew works extremely hard to give you the best experience for your Sunset Sail in Key West in the month of December!  The Schooner America 2.0 is known for offering a luxurious and memorable sunset sail experience. Its rich history, beautifully crafted yacht, stunning views, and amazing crew make it a popular choice! Take the Key West sunset to a whole new level and grab tickets for one of our Sunset Sails aboard the Schooner America 2.0!  This is one of the best sunset sails in Key West.

The sunset in Key West is a world-renowned spectacle. Often it’s described as one of the most breathtaking sunsets in the United States. Key West offers a stunning view of the sun as it dips below the horizon and gives you a chance to see the ‘Green Flash’!

A Key West sunset sail aboard the Schooner America 2.0 is a sensory feast! It evokes a deep sense of wonder and appreciation for the beauty of the natural world. Whether you’re a romantic couple seeking a serene moment or a traveler looking for a lively celebration, the sunset sail aboard the Schooner America 2.0 in Key West is a daily event that captures the hearts of all who witness it.

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. Additionally, we’ll have 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. Sailing 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
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Best Sunset Sail in Key West

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A couple sitting on the decks of Schooner America 2.0 for a Valentine's Day Sunset Sail in Key West

Are you looking for the best sunset sail in Key West? Well, a sunset sail aboard the Schooner America 2.0 in Key West is an exquisite and unforgettable experience. The Schooner America 2.0 is a modern interpretation of the historic yacht that famously won the first America’s Cup race in 1851. Indeed, it offers a combination of luxury and tradition.

As you step aboard this elegant schooner, you’re greeted by a professional and friendly crew who make it their mission to ensure your voyage is exceptional. The polished wooden deck gleams in the late afternoon sun. The vessel’s sleek lines and tall masts create an emphatically striking silhouette against the backdrop of the Key West harbor.

The sails of the Schooner America 2.0 are a brilliant white, catching the gentle trade winds as the boat glides into the famous Key West sunset.

Schooner America 2.0 sailing in the Ocean in Key West Florida

Setting the Scene

You find your way to a comfortable spot on deck, perhaps a cushioned seat or the boat’s bow, where you have an unobstructed view of the horizon. The anticipation builds to catch the ‘Green Flash’. You watch the sun lower in the sky, casting warm hues of orange and pink across the water.

Accordingly, the crew serves you a glass of champagne or a refreshing drink. Then you clink glasses with fellow passengers as you toast to the beauty of the evening. After that the ambiance is serene. The only sounds are the soft whispers of the wind and the occasional creaking of the ship’s rigging.

As the sun nears the horizon, the sky transforms into a breathtaking canvas of colors. The warm, golden light of the setting sun is reflected in the water, creating a shimmering pathway toward the disappearing sun. Finally, it’s a moment of pure tranquility and natural wonder. The sight is made even more magical by the historical significance of the yacht you’re on.

As you look out to the horizon, you’re by and large filled with a deep sense of appreciation for the beauty of the natural world. A unique experience of sailing on this historic yacht. This sunset sail aboard the Schooner America 2.0 in Key West is a blend of tradition, luxury, and the breathtaking beauty of a Florida Keys sunset. It’s a memory that will forever be etched in your heart. This is truly the best sunset sail in Key West!

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. Additionally, there will be 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
 Read Our Reviews

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Schooner America 2.0 sailing at sunset in Key West

Sunset Sail Key West

What best way to experience Key West than on a Key West Sunset Sail aboard a classic schooner!? Cruise with us into the horizon.  Sip on Champagne as we take you to a place you have never been before.  Our expertly trained Captain and Crew will give you a new kind of experience that is sure to last a lifetime.  We will take you on a magical sailing ride with the wind in your hair a your soul filled with joy.

We also know that experiences become legendary stories for future generations to come.  Let us host you on an adventure that will leave you breathless and become the next story told to friends and family.

Why would you pick us over the many Sunset Cruises in Key West?  Because our yacht is a contemporary design for a classic experience.  You will have old world charm with the speed and grace of the new.  So get your tickets now for your Key West Sunset Cruise and let us dazzle you as you kick back and relax.

Key West Sunset Sail on Schooner America 2.0

Enjoy the best Key West sunset sail on Schooner America 2.0!  Take in the vibrant colors of Key West’s famous sunset as you sip champagne, and dine on passed hors d’oeurves. On this Key West Sunset Cruise you will magically glide through the crystal clear surrounding waters.

This two-hour Key West sunset cruise features complimentary champagne, wine, beer, soft drinks, and water. Passed hors d’oeurves are provided, including shrimp cocktail, a cheese plate, and delicious veggies! Sit back and relax while she plies effortlessly through the turquoise green Key West sailing waters and off towards the horizon for the quintessential Key West Sunset experience!

  Duration: 2 hrs  Boat: America 2.0  Cost: Adult up to $96
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Come sail with us for the SAIL PHILADELPHIA event!

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Sail with us aboard the Schooner America 2.0 for this epic event!

Spend your Memorial Day Weekend with us at Sail Philadelphia for four days of waterfront festivities, ship tours, and sailing excursions on the Delaware River. Tall ships from U.S. and international ports will dock at Independence Seaport Museum and Penn’s Landing from May 24– 28. Details and information will be available at sailphiladelphia.org in the coming weeks, but you can begin planning your Memorial Day Weekend in Philadelphia, now by booking Ship Tour tickets here: and 90-minute Day Sails and 120-minute Twilight Sails here.

Schooner America 2.0 is our stunning, black-hulled, 105 foot sailing yacht and a tribute to the first Schooner America – winner of the first America’s Cup in 1851.  Sit on the open decks that feature comfortable seating and bar service for up to 76 and take in the view of these magical ships.

The Schooner America 2.0 will glide effortlessly through the waters and get upfront and personal views of the stunning yachts that will visit the Delaware River this coming May.  

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Schooner America 2.0 Aerial View from Classic Harbor Line on Vimeo.

Best Key West Sunset Sail

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group of people enjoying a sunset view board the schooner america 2.0

Soak up the unique history as you walk through the old Key West Historic Seaport also known as the Key West Bight.  Home of many fabulous restaurants, bars and the famous Schooner America 2.0.  Breathe in the refreshing salty air. Listen to the sounds of the lines clanking on the masts of the tall ships docked in the marina.  Stop in at the legendary Schooner Wharf bar for a drink. Listen to some live music by the local talented Key West musicians before embarking on your sunset sail aboard Schooner America 2.0.  Get your tickets from our friendly sales representative located at our ticket booth just outside of the bar.  Step aboard and experience the best Key West sunset sail that the Keys has to offer aboard Schooner America 2.0. 

Reaching at 105 feet, this Schooner is a tribute to the original “Low black schooner: Yacht America” that won the very first Americas Cup Race in 1851.  The open teak deck features comfortable seating and bar service for up to 76.  Let our most professional crew cater to your needs as you watch the sun dip beyond the horizon.  Kick back and relax as the boat cuts through the emerald green waters and sip on a beverage of your choice to catch a glimpse of the green flash.  

Key West is known for its famous sunset, so why not do that aboard this tribute to the famous “Low black schooner”!  Whether you join us for a day sail, special event or go sailing for sunset you are sure to grab some amazing photos! It will definitely be a memory that will last a lifetime. 

Click here for your Key West Sunset Tickets.

 

Romantic Valentine’s Day Cruise

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Key West Valentine's Day Sunset Sail | Classic Harbor Line

Looking to get out on the water for a romantic cruise in Key West for Valentine’s Day?  Grab your loved one or your best friend and join us aboard the Schooner America 2.0 for a memorable evening sail in the emerald green waters of Key West.  Step aboard this stunning sailboat for a 2 hour Valentine’s Day Key West Sunset Sail and tickle your taste buds for a Champagne and Aphrodisiacs Pairing.  Sip on Champagne as you glide through the water and watch the sun dip behind the horizon.  You may even get a chance to see the famous Key West green flash!

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The Art of Giving: Holiday Gift Certificates

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Family sitting on the decks of schooner America 2.0 in Key West FL

What better gift to give than a Classic Harbor Line Key West gift certificate for a sunset sail aboard the stunning Schooner America 2.0 in Key West FL. You cannot go wrong and will not disappoint with a Key West Holiday Gift Certificate!

Sometimes there is a lot of pressure to give the perfect gift. Why? Because you want to make sure that you are giving the most perfect present to the person you love. You want to feel good about what you are giving them and know that they will enjoy every piece of it with all of their heart. That’s enough pressure to make you go crazy. Well stop pulling out your hair and jump aboard! Classic Harbor Line will be sure to take care of your friend or loved one by surrounding them with the warm and friendly service that our crew has to offer! They will be in good hands with the Captain and Crew and will have an experience that will be a lasting memory of a lifetime aboard an elegant schooner!  Whether you give a Key West Sunset Sail or a Key West Afternoon Day Sail you are sure to put a smile on your loved ones face!

Gift certificates are available for almost all of our unique cruises, and are easy to get!

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Key West Lighted Boat Parade

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Key West Lighted Boat Parade

Join us for the Key West Lighted Boat Parade!  Step aboard the Schooner America 2.0 for this famous Key West annual celebration.  This festive holiday event pulls the local community of seafaring sailors together to compete with their artistic styles!  Enjoy the view of their many creative and imaginative holiday decorations! 

Motor yachts and sailboats.  Kayaks and Schooners.  All decked out in Holiday Lights parading around the beautiful Key West Bight showing off their twinkle.  Have the best seats in the house and watch up to 30 boats compete for first place in this Schooner Wharf Bar tradition.   

Relax aboard the Schooner America 2.0 for a memorial experience. Parade through the vast darkness of the ocean and see a sea of holiday lights floating magically through the night.   Cozy up and sip on Champagne and join us for this wonderful tradition.

Key West Lighted Boat Parade

Lighted Boat Parade aboard Schooner America 2.0

Join us for Key West Lighted Boat Parade, a favorite maritime holiday event. Sit aboard the fastest, most elegant schooner, the brand new eco-friendly, America 2.0 as we parade through the Bight and Harbor of Key West!  She’ll be fully decorated in Holiday decor with up to 30 other Key West vessels in the annual Key West Lighted Boat Parade. Cruise aboard America 2.0 while taking in this magical display of holiday spirit. All of these vessels will have the opportunity to show off their creative and imaginative holiday decorations as they glide by the viewers and judges at the Schooner Wharf Bar.

  Duration: 3 hrs  Boat: America 2.0  Cost: Adult $85 | Child $45
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New Year’s Eve in Key West

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Couple celebrating New Year's Even on Schooner America 2.0 in Key West with decoration in the background

Join us for the best seats in the house on this annual tradition of the “Lowering of the Pirate Wench”!  Each year we hoist the famous Schooner Wharf Bar Pirate Wench to the top of our 100 foot mast aboard the Schooner America 2.0.  Count down lights are hung from the top of the mast all the way down to the schooner deck. She is hoisted up for all to see and then dramatically drops down the mast with the count down lights to bring in the New Year!  Sit aboard with us and have the best seats in the house to celebrate New Year’s Eve in Key West.  Crowd free and comfortable sit with us and let our professional crew serve you your drinks and hors d oeuvres.  

 

Click here to purchase tickets.