Check Availability Buy Tickets Now

Celebrate The Holidays

“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.

Christmas/New Year’s

Christmas / New Year’s Events and Cruises

New Year’s Day Champagne Sunset Sail Aboard Schooner America 2.0

Start your year off right with an unforgettable New Year’s Day Champagne sunset sail on the Schooner America 2.0 in Key West
Duration: 2 hrs
Boat: Schooner America 2.0
Cost: $124 Adult, $62 Children
/public-cruise-reviews/#1731526884191-9758fa8e-3a57
Embark on an unforgettable New Year’s Day sunset sail aboard the Schooner America 2.0. Drift through the enchanting waters of Key West with the wind in your hair and the sea breeze on your face. Revel in an elegant and relaxing atmosphere as our crew serves delectable refreshments, including beer, wine, champagne, and hors d’oeuvres. Marvel at the breathtaking Key West sunset, celebrated for its vibrant hues and the elusive “Green Flash,” and watch for playful dolphins. Conclude your evening with a special champagne toast and take home a souvenir champagne flute to remember your perfect vacation. This picturesque New Year’s Day celebration is the ultimate way to begin your year in Key West!

The Schooner America 2.0, constructed in 2011, boasts elegant teak decks, comfortable seating, and a vast 3,600 square feet of canvas. Unwind and enjoy the final sunset sail of the year as she gracefully navigates the turquoise waters of Key West.

New Year’s Eve Champagne Sunset Sail Aboard Schooner America 2.0

Celebrate with a memorable New Year's Eve sunset sail Key West style aboard the Schooner America 2.0
Duration: 2 hrs
Boat: Schooner America 2.0
Cost: $124 Adult, $62 Children
/public-cruise-reviews/#1731526864310-72979699-b6da
Start your Key West New Year’s eve celebration off with a sunset sail. Experience an unforgettable Key West New Year’s Eve sunset cruise aboard the Schooner America 2.0! Get into the holiday spirit with your friends or family as you sail through the beautiful waters of Key West with the wind in your hair and the sea breeze on your face. Enjoy an elegant and relaxing atmosphere while our crew serves you delicious refreshments, including beer, wine, champagne, and hors d’oeuvres on this Key West New Year’s Eve sunset cruise. Witness the breathtaking Key West sunset, renowned for its vibrant colors and the elusive “Green Flash,” and keep an eye out for playful dolphins. Finally, finish your sunset sail with a special champagne toast and a souvenir champagne flute to take home and remember your perfect vacation. This picturesque New Year’s Eve celebration is the perfect way to end your year in Key West!

Cocoa and Carols Christmas Holiday Lights Cruise Aboard Schooner America 2.0

Join us for a festive 1.5-hour Christmas cruise on the decorated 105-foot Schooner America 2.0 in Key West harbor
Duration: 1.5 hrs
Boat: Schooner America 2.0
Cost: $72 to $84 Adult, FREE for Ages 0-12 on select dates
/public-cruise-reviews/#1731526834732-9ea8c33d-47ea
Please join us for this special Key West warm and cozy holiday cruise tailored for friends, family, and all your loved ones during the Christmas season. Step aboard our beautiful 105-foot Schooner America 2.0 decorated in CHristmas lights and other fun holiday decor for a 1.5-hour cruise in Key West harbor while we listen to some of our favorite Christmas hits! Delicious Hot cocoa, cookies, and other treats for all our guests are included! Sit back and enjoy your Christmas in Key West on this family holiday cruise! America 2.0 features the best in comfort- teak decks, mahogany-trimmings, and a soaring rig! Sit back and take a ride on this decorated schooner while you enjoy the festivities of the evening with your family and friends. Join our courteous and professional crew for this evening celebration cruise that will highlight your Key West Christmas experience!

Dockside New Year’s Eve Party Aboard Schooner America 2.0

Experience the ultimate New Year's Eve celebration, with this exclusive event in Key West aboard the Schooner America 2.0
Duration: 3 hrs
Boat: Schooner America 2.0
Cost: $256 Adults
/public-cruise-reviews/#1731526869978-dcf47847-e4c7
Prepare to be dazzled as you join fellow guests for the ultimate Key West New Year's Eve party. Enjoy VIP dockside access to the famous Schooner Wharf Bar "Lowering of the Pirate Wench" from the rig of Schooner America 2.0! From the moment you step onto the boat for this fun Key West dockside event, the Schooner America 2.0 provides the perfect backdrop for revelry, with spacious decks offering panoramic views of the harbor as your party into the night.This special '21 and older' New Year’s Eve event features complimentary delicious hors d' oeuvres and a full bar. Gather with friends and join our courteous and professional crew for this late night Key West New Year’s Eve boat party that will be the highlight of your Key West experience! This is a special New Year’s Eve celebration to ring in the New Year as the pirate wench is lowered as we countdown to midnight!

Christmas Eve Sunset Sail Aboard Schooner America 2.0

Enjoy a Christmas Eve sunset sail aboard Key West's most elegant sailboat, the 105-foot Schooner America 2.0
Duration: 2 hrs
Boat: Schooner America 2.0
Cost: $124 Adult, $62 Children
/public-cruise-reviews/#1731526841259-b948d563-cede
Experience an enchanting Christmas Eve sunset sail aboard the Schooner America 2.0, a state-of-the-art 105-foot vessel. Glide through the emerald green waters of Key West with the wind in your hair and the sea breeze on your face. Enjoy an elegant and relaxing atmosphere, complete with comfortable bench seating and refreshments, including beer, wine, champagne, and holiday themed hors d’oeuvres. Witness the breathtaking Key West sunset, renowned for its vibrant colors and the elusive “Green Flash,” and keep an eye out for playful dolphins. This picturesque sail is the perfect way to end your day in Key West, creating unforgettable holiday memories.

Built in 2011, the Schooner America 2.0 is equipped with teak decks, bench seating, and a vast 3600 square feet of canvas. Relax as she sails smoothly through the turquoise waters of Key West, offering a quintessential holiday sunset sail experience.

Christmas Day Sunset Sail Aboard Schooner America 2.0

Enjoy a family-friendly Christmas Day sail aboard Key West's most elegant sailboat, the 105-foot Schooner America 2.0
Duration: 2 hrs
Boat: Schooner America 2.0
Cost: $124 Adult, $62 Children
/public-cruise-reviews/#1731526856619-5ee39656-6694
Experience a magical Christmas Day sunset sail aboard the Schooner America 2.0, a cutting-edge 105-foot vessel. Drift through the emerald waters of Key West, feeling the wind in your hair and the sea breeze on your face. Relax in an elegant atmosphere with comfortable bench seating and enjoy refreshments, including beer, wine, champagne, and holiday-themed hors d'oeuvres. Marvel at the breathtaking Key West sunset, famous for its vibrant colors and the elusive "Green Flash," and keep an eye out for playful dolphins. This picturesque sail is the perfect way to conclude your day in Key West, creating unforgettable holiday memories. Schooner America 2.0, constructed in 2011, boasts teak decks, cozy bench seating, and an impressive 3600 square feet of canvas. Enjoy a serene voyage through the turquoise green waters of Key West, gliding towards the horizon for an ideal Key West sunset sail experience.

Christmas Day Brunch Sail aboard Schooner America 2.0

Celebrate Christmas morning in Key West with us on a Christmas sail aboard the elegant 105-foot Schooner America 2.0
Duration: 2.5 hrs
Boat: Schooner America 2.0
Cost: $168 General Admission
/public-cruise-reviews/#1731526850215-22e49481-dbbc
Enjoy the vibrant colors of Key West as you sip champagne, dine on a delicious brunch, and glide through crystal clear surrounding waters on one of Key West’s premiere holiday cruises. This Christmas brunch Key West-style features complimentary mimosas, bloody marys, champagne, wine, beer, soft drinks, and water. Brunch includes spiral ham, bagels and pastries, meats and cheeses, smoked salmon, crudite, quiche, and other delicious treats! This is one of the few Christmas Day events in Key West not to be missed! Built in 2011, Schooner America 2.0 features teak decks, mahogany-trimmings, and 3600 square feet of canvas! 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 holiday brunch experience!

Key West Lighted Boat Parade aboard America 2.0

Experience the magic of the Annual Key West Lighted Boat Parade aboard the festively adorned Schooner America 2.0
Duration: 3 hrs
Boat: Schooner America 2.0
Cost: $104 Adult, $48 Children
/public-cruise-reviews/#1731526827593-0ede2fa7-dddd
Join us for the Key West Annual Lighted Boat Parade aboard Schooner America 2.0! Adorned in festive lights, the America 2.0 is a dazzling spectacle on the water. Watch from our beautiful teak decks and comfortable bench seating as boats of all sizes glide through Key West harbor, illuminated in a vibrant display of colors and decorations. Onboard, enjoy the holiday atmosphere with music, refreshments, and the company of fellow revelers. As the Christmas parade progresses, marvel from a prime viewing spot onboard at the creativity and ingenuity of each boat's decorations. This enchanting event aboard Schooner America 2.0 offers a unique perspective on the holiday season and creates lasting memories for all!

Please Note: We will not be raising sails during the parade due to maneuverability.

Celebrate with One of Our Special

Key West Holiday Cruises!

Planning a trip to Key West during the holidays? With its lighted palm trees and historical houses decorated to the max, Key West is embracing the spirit of Christmas in all its glory during this festive season.  Celebrating the holidays in Key West aboard the Schooner America 2.0 offers a unique and enchanting experience aboard a Key West holiday boat ride that’s not to be missed. This stunning, eco-friendly yacht hosts a variety of special events, from the festive Key West Lighted Boat Parade cruise to our famous VIP New Year’s Eve Party and the lowering of the Schooner Wharf pirate wench! We also offer fun Key West Christmas events including a festive Christmas Eve Sunset Sail, Cocoa & Carols Christmas Holiday Lights Cruise during the month of December, or a Key West Christmas Day Brunch cruise, the Schooner America 2.0 combines the spirit of the season with the beauty of the sea, providing a truly magical setting for any holiday celebration. Whichever Key West holiday cruise you choose, guests can enjoy panoramic views of the island’s illuminated shoreline, savor gourmet hors d’oeuvres, and sip on delicious cocktails all while sailing through turquoise waters. Sailing aboard Schooner America 2.0 is truly an unforgettable way to experience Key West’s holiday charm.

You May Also Like