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Here Are Our Favorites:
Schooner Appledore Star AVAILABLE YEAR ROUND
68 all-wooden schooner built in Maryland in 1982. This impressive double-masted sailing vessel has a length-on-deck of 49 feet, draws 4-feet of water with the centerboard up, and has 14.5 feet of beam . The chair-height cabin top provides comfortable roomy seating. On-board is a marine bathroom . She is an elegant vessel on the water with a capacity of 22 passengers.
What to expect:
Check-in 30 minutes prior to your trip start time at the Historic Seaport. Youll sail from downtown, leisurely entering the harbor and out to sea. Many ships will be sailing nearby, and you will have plenty of scenery to enjoy, including an expansive view of Key West and the spectacular sunset. Includes hors doeuvres, premium beer, and wine, champagne, soft drinks.
6:30pm 8:30pm daily during summer, 5pm 7pm during winter.
Schooner America AVAILABLE DURING WINTER MONTHS ONLY
The Schooner America is quite an impressive vessel. This majestic ship is a reproduction of the famous and fast sailboat that won the Americas Cup race in the mid-nineteenth century. Measuring 105 overall, this ship is an engineering marvel, combining modern construction techniques with her classic lines.
What to expect:
4:30 pm 6:30 daily. Available November to April.
Schooner Appledore II NORMALLY AVAILABLE DURING WINTER MONTHS ONLY, BUT NOT WINTER OF 2020-2021
Traditional, 86-foot, double-masted schooner.
What to expect:
Additional Ui Design And Readability Adjustments
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You Will Be Sailing On Sebago’s Appledore Star A Two
This is a non-smoking tour. Boarding Starts 1/2 Hour Before. Spring and Fall times vary by the sunset please check with us for exact departure times. Please bring a valid, government issued photo ID. Some activities and enjoying alcoholic beverages require that we verify your age. All prices do not include Florida sales tax.
- Sail Past Local Landmarks as you Enjoy a Famous Key West Sunset
- Chefs Selection of Hors doeuvres & Cocktail Shrimp
- Champagne, Sangria, Boutique Wine, Premium Beer, Full Cocktail Bar, Soft Drinks and Filtered Water
Wide decks with room to walk around
Maximum of 22 passengers for an intimate evening
Key West Sunset Sail On Schooner America 20
Enjoy the best sunset sail in Key West on the Schooner America 2.0! Take in the vibrant colors of Key Wests 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 doeurves- 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!
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Schooner Spirit Of Independence Sunset Sail Key West
A Sunset Sail to Remember
One of the best things to do in Key West is a Sunset sail cruise aboard Schooner Spirit of Independence. Its the passengers that make a fun trip !!! We try to make our sunset sail an almost magic Key west adventure, not just a boring boat ride. Many passengers say our sunset sail was the best experience of theyr vacation.
We are family-owned & operated, paying great attention to detail,
Sailing Key West
Our course and sail trim will match the wind and weather of the day.. Some days we might sail the beaches off Key West or on windy days the calm waters of the northwest passage Our goal is a safe thrilling Key west schooner adventure . We are not a party boat, We are sharing a lifetime of sailing schooner history and adventure. KEEP THE DREAM ALIVE !!!
Key West Schooner
The Spirit of Independence is a shipbuilders masterpiece. Its an 80 foot Schooner built to an 1800s design with exotic hardwood interior. Spirit was built with no regard for expense, all her systems are big ship quality. She took 16 years to build in Independence, Missouri.
Boy Scouts Of America High Adventure Operation Sea Base
Pictured here is 20 boy scouts enjoying dinner aboard our schooner anchored off the Marquesa islands with a Florida Keys sunset in the background.
Key West Weddings
Where Is The Meeting Point For This Activity
Detailed check-in instructions including meeting point address, Google map, and parking information for Schooner Appledore Key West Premium Sunset Sail with Hors D’oeuvres and Full Bar will be included in your confirmation email from Key West Water Sports. Please be sure to double and triple check your email address is correct at checkout so this important email makes its way to you!
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Wreckers Race Aboard Schooner America 20
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 Wreckers Cup Race!
A little historyback 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 ships 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!
Beer, wine, champagne, and a boxed lunch are complimentary with your ticket purchase.
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Q: What Kind Of Wine Is Served On The Key West Wind & Wine Sunset Sail
A: Looking for a sunset cruise with a focus on fine wine to go with the fine view? The Key West Wind & Wine Sunset Sail is a legend with locals and visitors alike. This elegant and awesome sunset cruise has pulled down top ratings on Trip Advisor for several consecutive years in addition to earning a Top Sunset Cruise designation from Coastal Living Magazine. The Wind & Wine is a cruise that stands above the rest because it is one of very few sailing excursions in the United States that offers a selection of real fine wines from America and around the world.
A small group will gather on deck beneath the billowing sails to enjoy an intimate atmosphere, tropical music, and the incredible Key West sunset along with 8 different wines from around the world and 5 types of domestic and imported beer. There are usually 4 red and 3 white wines plus a champagnoise open for the tasting. The charcuterie and cheese board goes far beyond simple sailors rations to deliver the perfect wine pairings with Dill Havarti, Smoked Gouda, fresh Mozzarella, and Brie cheeses. Caprese skewers, summer sausage, honey-drizzled green apple slices, fruit, water crackers and more make for the ultimate water-borne wine tasting session.
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Q: What Type Of Boats Are Used For Key West Sunset Cruises
A: The diversity of available sunset cruise vessels is one of the things that make Key West Sunset Cruises so special. Guests who enjoy sailing can choose a 65-foot skipjack schooner with authentic lines that replicate the sailboats used by 19th century Florida Keys fishermen and wreckers. Or a modern sailing catamaran with the stability, speed, and generous deck space these craft are known for. Power catamarans are fast and smooth, perfect watersports or dolphin-watching platforms. And of course, enjoying a buffet dinner and cocktails aboard a 65-foot custom party catamaran should be on everyones bucket list. For a wedding, anniversary, or other special occasion, try a private charter to have a sail or power yacht all to yourself.
All the boats used for these popular Key West Sunset Cruises are top-of-the-line designs built for safety, comfort, and fun on the waters around Key West. The United States Coast Guard regularly inspects every Key West Sunset Cruise boat, and all required safety equipment is aboard and properly updated at all times. This is luxury sunset cruising at its best, with expert local captains and crew members, high-tech navigation gear, and the latest in quiet, efficient, low-emission engines. Plus, there are those added touches to enjoy like room for cocktail and wine service, deck space for top local musicians to perform, and even a bit of space to dance on some cruises.
Best Sunset Cruise Key West
Looking for the best sunset cruise in Key West? Each comes with unlimited drinks and appetizers, as well the best sunset spots in town!
The perfect way to experience the Key West sunset is to sail off into the ocean on a sunset cruise.
Far away from the hustle and bustle of the crowds, you can truly appreciate the beauty of the setting sun as it disappears into the Atlantic.
There is an array of different Key West sunset cruises to choose from, which can make picking the best cruise near impossible.
So to help make your decision easier, weve rounded up the best three.
Each one is unique, so whether youre after a party on the waves, or a more romantic, intimate evening, theres a sunset cruise for everyone.
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Classic Harbor Line: Key West
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 Key West fleet: Schooner America 2.0. While visiting Key West, Florida you will find a number of land and water based activities. However, a classic schooner sail, whether it be a day sail, or sunset sail, is well known to be the quintessential Key West activity that will highlight your stay and be the lasting memory forever.
South Florida sightseeing is all about getting on the water, seeing the wildlife, watching the Key West sunset with a loved one, and experiencing the adventure sailing in the great Key West Florida breeze. A 2 hour sailboat ride is a great way to take advantage of your time in Key West to enjoy all of these things.
Whether buying tickets for one of our Champagne Sunset Sails, Afternoon Key West day sail, Full Moon, Star-Gazer Sails or Privately Chartering the schooners for a special family event or corporate event, you will be amazed by America 2.0s beauty and comfort. It is maintained by the same creators of Key Wests former pride, Schooner America.
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Make Your Plans Now For The Biggest Party Of The Summer With The 25th Annual Key West Lobsterfest From August 11th To August 14th
Seafood lovers can chow down on Floridas clawless lobster during a tasty feast-ival that features a savory schedule of events ranging from a traditional lobster boil to a lively street fair starring the sensational crustacean prepared in a variety of ways. The flavorful festivities celebrate the bounty of the Florida Keys lobster season that opens Aug. 6. Famous for its sweet and tender meat, the Keys spiny lobster often is served steamed with drawn butter, paired with a seasoned stuffing or cold in savory salads.
Purchase tickets and get the full schedule of events here:
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Y Catamaran Sunset Cruise
*Spring Breaker Favorite* Grab a tropical mixed drink and dance to a live performance from the newest and biggest sailing catamaran in Key West! Live music, open bar, and hors doeuvres included.
Option 1: Sunset Sail Option 2: Sunset Sail & Snorkel and a trip to the reef with option to snorkel at no additional cost!)
Q: Which Key West Sunset Cruise Is Best For Me
A: The only easy choice among the many popular Key West Sunset Cruises is deciding to go on one. After that, the variety of attractive options may easily lead a visitor to decide that the only solution is to enjoy more than one sunset on the water! But if a choice of just one must be made, the best strategy is to consider what you like best and who is joining you for what could easily be the highlight of any Key West visit.
Naturally, the idea of gliding smoothly over turquoise water under sail while toasting a perfect day with a cold beer, glass of wine, or cocktail is very tempting. A Sunset Sip & Sail or Premium Sunset Sail with Hors Doeuvres and Full Bar will provide a perfect happy hour start for a couple planning an evening on the town.
For an active family, or anyone who enjoys the water, taking an afternoon snorkeling trip that winds down with a beautiful sunset offers the best of both worlds. A Key West Sunset Snorkel Sail is just the ticket. Nature lovers should try a Glass-Bottom Boat Tour Sunset Combo or take the Dolphin Watch Sunset Snorkel Cruise.
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Choose Your Style Of Sunset Cruise
Live Music Happy Hour Sunset Cruise: Enjoy cocktails while listening to a local Key West musician play throughout the sunset cruise.
Private Sailing Adventure: Aboard your own private sailboat the captain will sail around Key West Harbor enjoying the sites of Mallory Square and Sunset Key.
Historic Schooner Sail: Help raise sail, take a turn at the helm or simply relax and enjoy the ride as our captain and crew sail you out to catch the breeze!
Luxury Catamaran Sail: Step aboard and relax in comfort and luxury while you sail into a Key West sunset.
Local-Style Boat Charter: Live like a local and explore the many beautiful spots surrounding Key West.
Our Promise Is An Enjoyable Experience
Spirit of Independence is conveniently located in Old Town Key West in the Historic Seaport
Our Key West sunset cruise begins out of the historic Schooner Wharf bar.
We are NOT a loud booze cruise, Its the passengers that make our cruise fun, and we are usually lucky in that!
The Spirit of Independence is licensed to carry 49 passengers. However, we limit our cruises to approximately 26 passengers, so its never crowded. Our average trip size is 15 passengers. That way, our roomy decks allow you to walk around while sailing and, if you wish, mingle with the other passengers. The steel hull makes her very stable providing for a smooth sailing experience, not a rocky boat ride.
We love both public and private cruises, as we enjoy getting to know our guests. Public walk-ons allow us to meet and make new friends. A private sail aboard Schooner Spirit of Independence creates the perfect venue for private events, weddings, corporate events, parties, and all types of social functions. Our professional crew make excellent hosts and will provide you and your guests with five-star service.
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New Years Eve Bash Aboard Schooner America 20
Do you want the best seat in the house for New Years Eve in Key West? Join us aboard America 2.0 for an epic New Years Eve Bash! Our Key West New Years Eve Event aboard the Schooner America 2.0 is one that must not be missed. You will experience VIP dockside access to the famous Schooner Wharf Bar Lowering of the Pirate Wench. We are the very venue that hosts the Lowering of the Pirate Wench from the rig of our Schooner America 2.0! So 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! Our Key West New Years Eve Bash will separate you from the crowds and give you the best seat in the house for a front row viewing of this epic event.
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SEE OUR CALENDAR OF EVENTS
PRIVATE YACHT CHARTERS
Sail out into the emerald green waters of Key West and impress your guests. Step aboard the legendary Schooner America 2.0 for a private charter. This yacht is perfect for Corporate outings, Birthdays, Anniversaries, Weddings, Team Building and more. Read more »
Sail out into NY Harbor and impress your guests. Step aboard one of our classic vessels for a private charter. These yachts are perfect for Corporate outings, Birthdays, Anniversaries, Weddings, Team Building and more. Read more »