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  1. Key West Sailing Adventure and Sunset Sails

    A Key West sailing adventure aboard the Schooner Jolly II Rover takes you back in time on a classic 80' tall ship to an era of pirates, rum runners and privateers seeking freedom and solitude. Their spirit of independence lives on daily on the Jolly II Rover. Roling Thunder Happy Hour from James Papagno on Vimeo.

  2. Key West Sunset Sailing Pirate Cruise 2024

    While most boat tours travel on small private vessels or luxury yachts, this sunset cruise takes travelers around Key West on Jolly II Rover, the only square-rigged, topsail schooner in the area. Board your ship at the historic Seaport at the corner of Elizabeth and Greene streets and sail out to see some of Key West's best sights, including the Man O War Harbor, Christmas Tree Island, Fort ...

  3. TOP 10 BEST Pirate Ship near Key West, FL

    Top 10 Best Pirate Ship in Key West, FL - August 2024 - Yelp - Schooner Jolly II Rover, Schooner Wolf - 74' Flagship of Conch Republic, Schooner Appledore, BluQ, Jolly Roger 2, Emerald Coast Sailing, Danger Charters, Pirate Adventure Charters, Kaleidoscope Wellness Retreats , Sunset Watersports Key West ... "A great sunset cruise on a pirate ...

  4. Key West Sailing Adventure and Sunset Sails

    This is a very popular and very exciting event. Seating will be limited to 16 passengers and ear protection will be provided to all passengers. A Key West sailing adventure aboard the Schooner Jolly Rover takes you back in time on a classic 80' Caribbean coastal sailing ship to Key West's colorful history. Key West Sunset Sails, day Sails ...

  5. All You Need to Know BEFORE You Go (2024)

    The Tall Ship Schooner Jolly II Rover is the most photographed ship in Key West! A top Key West attraction is the Rover's famous "Red Sails in the Sunset" two hour sail. ... A sunset 2 hour cruise on This tall ship in Key west is one of the best decisions we made on this trip. I can't stop talking about how wonderful the crew was and what an ...

  6. Water Tours in Key West

    Pirate Adventure Charters. Key West Pirate Adventure Charters offers private Key West boat cruises to tourists and locals looking to have an ocean adventure without the crowd. Snorkeling tours, sandbar, sunset cruises, dolphin watching, fishing. From boat proposals and photoshoots to birthdays and weddings or business meetings.

  7. Schooner Jolly II Rover

    There are various cruises one can try in Key West. After reading the reviews and observing, we picked this one on the last day of our trip, and glad we did! This sailing schooner is clean and professionally run by captain and crew. It was fun and lighthearted during the cruise, and you learn a little bit about the boat, sailing and key west.

  8. 2024 (Key West) Sunset Sail Cruise in Key West

    Itinerary. You'll start at. 631 Greene St. 631 Greene St, Key West, FL 33040, USA. 15 minutes before sailing time - In the Historic Seaport at the corner of Elizabeth and Greene streets. At the ticket booth on the dock along side the Conch Republic Seafood Company Restaurant. See address & details. 1.

  9. A friendly pirate ship

    We did a day cruise for two hours on this ship and it really showed off the wonders of nature in Key West, with the sparkling water and views of the shore, marine life, and all the watercraft. The captain was called Rio, very personable and full of information. everyone aboard loved it, several were returning passengers.

  10. Key West Express Ferry Official Page

    Experience the ultimate getaway as our jet powered catamarans whisk you away to Key West ~ the Vacation Spot of Pirates, Poets, Presidents & Partygoers! Famous for artists, explorers, musicians, fun filled events and the best in recreational water activities. Indulge in a refreshing tropical beverage from our bar or savor a delicious snack from ...

  11. Schooner America 2.0: A premium sailing experience in Key West

    Call to order 305-293-7245. Schooner America 2.0 sailing offers our most premium sailing experience in Key West Florida. America 2.0 is the newest, largest, most elegant yacht designed for Classic Harbor Line. Added to the fleet in 2011, America 2.0 offers the most exceptional Key West day sailing and sunset sailing one can find.

  12. 9 Highest Rated Sunset Cruises In Key West

    Book the Sunset Tiki Boat Tour. 2. Sunset Cruise With Sushi And Drinks. Photo credit - Barefoot Billy's. Tour Rating: 4.5 Stars ⭐️⭐️⭐️⭐️ Length: 2 Hours Check Rates Here. This beautiful sunset and dinner cruise allows you to escape the crowds that are often found on land for a cruise around the waters of Key West.

  13. Key West Award Winning Schooner Sailing Cruises

    Step aboard the Appledore II for a true sailing adventure. This two-masted hand-built wooden schooner calls both Camden, Maine and Key West, Florida home. During warm weather months enjoy a scenic sail along Maine's magnificent rocky coast. When the weather turns cold, the Appledore II heads south and sails Key West's tropical waters.

  14. THE TOP 10 Key West Sunset Cruises (Prices from $65)

    Key West Small-Group Sunset Sail with Wine. 1,078. Escape to the still waters off the coast of Key West on this small-group, sunset wine-tasting cruise. Enjoy the scenery and peaceful calm of a late afternoon sail on board a 65-foot schooner. Sample up to eight different wines and/or five different beers.

  15. Key West Catamaran Cruises & Tours

    Escape the Downtown Crowd - Cruise with Billy. Key West's nautical history is all based on its proximity to the world's 3rd largest living coral reef. From pirates and privateers to ship wreckers and fisherman the draw has always been the sanctuary provided by the Florida Great Barrier Reef. Key West's coral rock islands trace a ...

  16. Pirate's Choice Sunset Cruise and Snorkeling Tours Florida Keys

    Enjoy a private sunset cruise or a snorkeling tour in the Florida Keys aboard Key Largo's only pirate ship! Make great memories. Book your cruise now! Skip to content. Call Us Today! +1 305-451-7057 OR Text Us +1 305-451-7057. Menu. Menu. Home; Rates; Gallery; Things To Do; Contact us;

  17. Pirate Style Sunset Cruise

    Pirate Style Sunset Cruise - Review of Schooner Jolly II Rover, Key West, FL - Tripadvisor. Schooner Jolly II Rover. 1,271 Reviews. #4 of 352 Boat Tours & Water Sports in Key West. Boat Tours & Water Sports, Tours, Outdoor Activities. 631 Greene St, Historic Seaport, Key West, FL 33041.

  18. Sunset Sail Key West

    Welcome to Sunset Sail Key West, Key West's most versatile custom charter experience. With three beautiful vintage boats, great local captains and crew, and the pristine waters of the Florida Keys at our disposal, we're confident that we'll have everything you need to make your dream sail come true. ... Private Trips Shared Trips Fleet About ...

  19. Key West Cruise Port

    6. Key West Butterfly and Nature Conservatory. The Key West Butterfly and Nature Conservatory is a tranquil refuge about a 25-minute walk/8 minutes drive from Key West cruise port. This charming conservatory allows you to enter the fascinating world of butterflies, exotic birds and tropical flora.

  20. Key West New Year's Eve Party: The Lowering of the Pirate Wench

    Book Now Call to order 305-293-7245. Yes, it is true. The Schooner America 2.0 is the venue for the Lowering of the Pirate Wench! This is the best Key West New Year's Eve Party in town. Join us for this famous local tradition! So enjoy a Key West New Year's Eve Party aboard our boat. Certainly you want to celebrate New Year's Eve aboard ...

  21. Pirate Rentals Key West

    Pirate Rentals Key West, Key West: See 210 reviews, articles, and 55 photos of Pirate Rentals Key West, ranked No.175 on Tripadvisor among 175 attractions in Key West. ... However the morning of the reservation the Cruise Ship I was on wasn't able to dock due to high winds. I sent an email explaining this and it was past the 24 hour ...

  22. Pirate's Choice Sunset Cruise and Snorkeling Tours

    About. Key Largo Snorkeling Pirate Ship includes - rental mask, fins and vest. Sailing adventures aboard the 52' World Famous Pirate ship, "the Pirates Choice", Snorkeling the Coral reef on a Glass bottom port hole Pirate Ship. Sailing daily out of Key Largo on 2 and 4 hours sailing and snorkel adventures. Our 2-hour Sunset trip is a ...

  23. Pirates, Wreckers and Treasure Hunters Helped Shape Florida Keys

    The Florida Keys' seafaring history, shaped by pirates and wreckers and treasure hunters, still lives in magnificent vessels like the Schooner Wolf. In 1822, when Key West was a brand-new seafaring settlement, the U.S. government sent Commodore David Porter to banish pirates from area waters. With his "anti-piracy squadron" of small ...