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Celebrate The Holidays

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“The Florida Keys Is an Unexpectedly Festive Destination During the Holidays—Here’s How to Plan a Visit”

Guests onboard the Schooner America 2.0 in Key West

Celebrate the Holidays with Classic Harbor Line Key West

Classic Harbor Line Key West is thrilled to share recent coverage in Travel + Leisure. The publication highlighted our festive holiday sailing experience aboard Schooner America 2.0. We are honored to appear in such a respected travel magazine. Their feature celebrates joyful seasonal traditions across the Florida Keys.

Fly South for the Holidays

The Florida Keys offer warm weather and bright holiday spirit each December. Visitors enjoy sunny skies instead of snow and ocean breezes instead of chilled air. Key West becomes lively with lights, music, and waterfront celebrations. Travelers visit for warmth, beauty, and a refreshing holiday escape.

Travel + Leisure described the Harbor Walk of Lights at the Historic Seaport. Thousands of sparkling bulbs drape boats, docks, and palm trees. The waterfront shines with color and feels wonderfully festive. The walk stretches from Elizabeth Street to Grinnell Street. Guests can enjoy the lights throughout December.

The feature also highlighted the beloved Lighted Boat Parade. Local captains decorate vessels with glowing holiday designs. The boats cruise through the Historic Seaport in a bright procession. Crowds cheer along the docks as each boat passes. It remains one of Key West’s favorite holiday events.

We are especially proud of our part in this celebration. Travel + Leisure named Schooner America 2.0 as a prime viewing option. Guests can watch the boat parade from the water aboard our elegant schooner. We offer music, refreshments, and unbeatable views of the celebration. This sail is a cherished seasonal tradition for our team. We love sharing this magical night with our guests.

The article also mentioned other Keys adventures. Travelers can dive the Christmas Tree Cave in Key Largo. Visitors can experience real snow during Islamorada’s Holiday Fest. Though we are not involved in these activities, we enjoy seeing the region shine.

Thank you Travel + Leisure!

We appreciate the recognition from Travel + Leisure. We feel grateful for our supportive guests and passionate crew. Their enthusiasm helps highlight our special sailing experiences. We look forward to welcoming visitors aboard Schooner America 2.0 this holiday season. Join us for a warm and festive celebration on the Key West waterfront.

Shout out from Key West Food Tours

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Guests sitting the in the cockpit of schooner America 2.0 for a Easter Brunch Sail in Key West FL

A big “thank you” to Key West Food Tours for giving us a shout out at being in the top 10 Fabulous Key West February Events!  Ranked at number 5 we offer a romantic sunset sail on Valentine’s Day as well as running a classic key west sunset sail daily.  

Take a look to see what they suggest for the month of February!  Click here to read more.  

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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.

 

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.  

 

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