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Sunset Sail Cruise in Key West

4.8 (179)
Key West, US
4.8 (179)
Key West, US
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Experience the thrill of sailing on the Schooner Jolly II Rover, Key West's famous "Red Sails in the Sunset" Tall Ship! This traditional sailing adventure offers a Hint of Piracy with cannons on board for an authentic experience. Get up close and personal with the stunning sights of Key West, including the Historic Seaport, Man O War Harbor, Christmas Tree Island, and the mansions of Sunset Key. Sail by Mallory Square, Fort Zachary Taylor, and the State Park, before venturing out into the open Atlantic to witness the breathtaking sunset. Whether you want to help raise the sails, steer the ship, or simply relax and enjoy the scenery, there is plenty of room to mingle with fellow guests. Don't miss out on this unique and memorable sunset sail cruise in Key West!

About this experience

  • Free Cancellation For a full refund cancel at least before the start of your booking
  • Suitable for 1-15 Participants
  • Private Tour, Small Group Tour
  • Self Guided Experience
  • Sailing on the Rover, a traditional sailing experience
  • Most photographed ship in Key West
  • Opportunity to raise the sails and steer the ship
  • Shoot the cannons for a hint of piracy
  • Relax and enjoy the sunset cruise
  • Snacks
  • Coolers of ice with cups and bottled water
  • Sunset Sail
  • Alcoholic beverages
  • Soda-pop

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More about this experience

Introduction

Sailing on the Rover is an exciting and unforgettable experience that combines tradition with a hint of piracy. Step aboard Key West's most iconic ship, the Schooner Jolly II Rover, and embark on a journey unlike any other. This beautifully crafted squared-rigged topsail schooner stands tall in the Historic Seaport and is the epitome of Key West's famous "Red Sails in the Sunset" Tall Ship. Leave the hustle and bustle behind as you set sail on this unique adventure.

What to expect?

During your 120-minute sailing excursion, you can anticipate breathtaking views and an itinerary filled with Key West's most famous sights. From the Historic Seaport to cruising into Man O War Harbor and passing by Christmas Tree Island, each moment on this cruise is destined to be memorable. Feast your eyes on the mansions of Sunset Key, catch a glimpse of Mallory Square from the water, and discover the Navy Mole and Civil War Fort Zachary Taylor. As you sail out into the open Atlantic, prepare to witness the captivating colors of the sunset, a sight that changes every day.

Who is this for?

This remarkable experience is perfect for individuals of all ages seeking a unique and adventurous escape. Whether you are a couple looking for a romantic sunset cruise, a group of friends wanting to explore Key West's maritime history, or a family seeking a fun-filled outing, the Sunset Sail Cruise on the Rover offers something for everyone.

Why book this?

Immerse yourself in the magic of sailing as you participate in raising the sails, steer the ship, or even fire the cannons—yes, there are cannons on board! Unlike typical tourist cruises, there is no loud music or band playing. Instead, guests have plenty of room to mingle with other like-minded adventurers and enjoy the serene ambiance and the beauty of the open water. Aboard the Rover, you will experience the thrill of sailing firsthand, making memories that will last a lifetime.

Good to know

When booking the Sunset Sail Cruise on the Rover, be sure to arrive 15 minutes before the sailing time at the Historic Seaport, located at the corner of Elizabeth and Greene streets. The meeting point is the ticket booth on the dock beside the Conch Republic Seafood Company Restaurant. The total duration of the cruise is 120 minutes, allowing ample time to soak in the sights and enjoy the sunset. Please note that the package includes various inclusions, with specific exclusions mentioned in the itinerary.

Reviews

Customers who have sailed on the Sunset Sail Cruise aboard the Rover rave about the authenticity of the experience. They highlight the friendly crew, the opportunity to actively participate in sailing the ship, and the breathtaking views throughout the journey. Guests also express their delight in the absence of loud music and appreciate the chance to relax and enjoy the natural beauty surrounding them. Overall, the feedback emphasizes the Sunset Sail Cruise on the Rover as a must-do activity when visiting Key West.

How long before the event do I need to book?

  • You can book at any time before the event

Vouchers accepted in the following formats

  • Mobile

Is an adult required for the booking?

  • At least one adult or senior required per booking

Reviews

(179)

4.8 (179)

Sightseer64733437743

5 stars! We picked this cruise from the TripAdvisor reviews. It was awesome. The crew was amazing and so friendly. They were great with the kids onboard. There were about 25 people on this tour. We stopped to watch dolphins and the sunset. The best part is the crew shooting off the cannons playfully at other boats. (don't worry, no cannon balls!) A fun and relaxing trip!

Adventure11979660720

If you're looking for a non-party type relaxing sunset cruise in Key West - look no further - this is the sunset cruise for you! My partner and I celebrated our 20th anniversary on the Jolly II and we had the best time! The crew engaged us by allowing guests to hoist the sails and steer the schooner into the sunset. Also, the cannon blasts along the route were so fun! This is a BYOB and snacks cruise which was great, too. We put together a small charcuterie box and enjoyed ice cold Pear cider. The Schooner Jolly II Rover crew are amazing!! Highly recommend!!

jruiz305

Returning guests-Always have a great time on board! The crew is amazingly friendly and really attentive. You can bring your own snacks and libations and they are great at always keeping your glass full. They also offer to take pictures at sunset and we have beautiful memories each time. The cannon is super fun for the young little pirates too! Highly recommended!

LINDA_N

Wonderful crew, sailing ship and exciting experience! They made us feel comfortable and at home at sea and made my granddaughter's birthday celebration a precious memory. We wanted to stay longer than two hours! What a beautiful experience! We will certainly come back every year.This will be part of our family tradition!

deborahfM4471CM

Absolutely wonderful! The crew was courteous and informative. They had someone in training, so it was fun listening to their instructions. We brought a bottle of wine to celebrate our anniversary, and enjoyed a peaceful evening with warm winds, a stunning sunset, and great conversation. We sat next to the ship’s owner who shared the history of the ship, and another couple also celebrating their anniversary. This was our second time sailing on the Jolly II Rover, and we’ll back again next time we’re in Key West!

Kathyjb1011

The Jolly River is always a MUST DO during our stays in Key West! We have tried others over our 40+ years of visiting and settled on this incredible experience. The captain and crew make the Sunset Cruise relaxing, fun, and interactive. You will get the opportunity to hoist a sail and do a photo op at the helm with pirate hat and sword to boot! They encourage ranting to other sunset cruises with cannon shots back and forth. Yet when the sunset is the star, and the engines are quiet it is a surreal experience. Crew is always available to take those memorable photos of you and your group and serving you water and your drinks you brought on board. There is not a bad seat on this cruise (saw some cattle boats where most passengers had to stand). This is an incredible way to highlight a day in the beautiful waters of Key West!

deborahb77

BEST SUNSET CRUISE in KEY WEST!! It was easy to find the marina and fast check in !! Capt Rachel was warm and welcoming and had a very nice commentary!! The crew had us out of the slip and sailing under wind quickly and comfortably and the VIEWS WERE SPECTACULAR!! We packed a bottle of champagne and charcuterie and soaked in the views and are still enjoying the memories! We will be sailing on Jolly II Rover again!!

carlosnpatti

Great views, tons of pics. The crew was awesome and fellow passengers were fun too. The sunset was beautiful, and, at the end, the cannon actually did thunder, lol. Don’t miss this one.

Andrew_F

I’ve always wanted to sail, it was an amazing experience to be out there to watch the sun go down. The crew were super friendly and attentive, the captain was great! Really chill and really knowledgeable, pointing out facts about various boats and islands and answering any other questions anyone had. The boat wasn’t super full so it made for an even better experience as you could move around easily. It was fun to watch them shoot off the canon at other passing ships. Choose this over a loud party catamaran you won’t regret it.

bradleydmb

Perfect for a romantic evening trip to watch the sunset. My wife and I thoroughly enjoyed it. This was a much more relaxing experience than the party tours that go out. And the crew (and owner) are all extremely professional and kind. I would definitely do this again.
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2024-06-02 09:08