Schooner Jolly II Rover, Sunset Sail, Key West, FL

Sunset Sail in Key West: Schooner Jolly II Rover

Sunsets in Key West are a big deal–every evening Mallory Square hosts a sunset celebration where thousands of people gather to watch the sun dip below the horizon. With gorgeous colors and the elusive green flair, more often than not, you will catch a great sunset in the midst of street performers, vendors and visitors clamoring to watch and celebrate the beginning of the evenings likely debauchery.

Schooner Jolly II Rover, Sunset Sail, Key West, FL

We have seen many a sunset from the west-facing Mallory Square, but this time we opted for a sunset sail since we were celebrating our anniversary and all. I have always wanted to take a sunset cruise in the keys, but the typical sunset cruise is jam-packed with people looking to party like crazy with blaring music or the other option of an expensive, upscale wine and cheese sail–neither are my ideal conditions for sitting on a boat. There is enough craziness to participate in on Duval street, so when I’m on the water, I want to relax, and not for a price tag of over $100 per person. After some online browsing, I came across the perfect option for us and I couldn’t have been more excited! I booked our tickets on the Schooner Jolly II Rover Sailboat for a price of $40 per person with a coupon ($45 original price, and although not exactly cheap, much more affordable than the other sailboat options).

Schooner Jolly II Rover, Sunset Sail, Key West, FL

Schooner Jolly II Rover, Sunset Sail, Key West, FL

The cruise departs from the Historic Seaport area of Key West and lasts for about 2 hours. Unlike all of the other sunset cruises, the Jolly II Rover does not serve any food or drinks, but they do supply water bottles. You can bring your own snack, picnic and beverages, which honestly, I prefer as it keeps the ticket cost down and you are able to bring what you actually prefer to drink or snack on.

Schooner Jolly II Rover, Sunset Sail, Key West, FL

Schooner Jolly II Rover, Sunset Sail, Key West, FL

Schooner Jolly II Rover, Sunset Sail, Key West, FL

Schooner Jolly II Rover, Sunset Sail, Key West, FL

Schooner Jolly II Rover, Sunset Sail, Key West, FL

The captain and crew could not have been nicer–this boat actually gets out and sails around the waters and passengers can help with the ropes and steering if they want. Of course, we had to try our hand at being the captain and both took a turn at the wheel.

Schooner Jolly II Rover, Sunset Sail, Key West, FL

Schooner Jolly II Rover, Sunset Sail, Key West, FL

We also set out in search of dolphins and actually found some! They weren’t feeling like playing much, but we did get to stop and watch the dolphins swim around for a bit. Another fun feature on the Jolly II Rover is the cannon–we got to fire at the noisy party cruises when sailing by which was fun, but beware, it is loud! I didn’t heed the warnings too well and my ears were ringing for quite some time afterwards! We also listened to stories about the pirates and rum runners who roamed the Florida straights and waters around Key West.

Schooner Jolly II Rover, Sunset Sail, Key West, FL

Schooner Jolly II Rover, Sunset Sail, Key West, FL

After playing with the cannons, dolphins and hearing pirate stories of the 1800’s, it was time for the famous sunset. We sailed over toward Mallory Square and watched the sun disappear before our eyes, but not before putting on a beautiful, golden show.

Schooner Jolly II Rover, Sunset Sail, Key West, FL

Schooner Jolly II Rover, Sunset Sail, Key West, FL

Schooner Jolly II Rover, Sunset Sail, Key West, FL

Schooner Jolly II Rover, Sunset Sail, Key West, FL

Schooner Jolly II Rover, Sunset Sail, Key West, FL

Schooner Jolly II Rover, Sunset Sail, Key West, FL

Sailings are only available on the weekends, as during the week the boat sets out on weeklong Boy Scout trips where the boys can live like pirates by walking the plank, jumping into the water and shooting off cannons. I can only imagine it would be quite the exciting week!

Schooner Jolly II Rover, Sunset Sail, Key West, FL

Schooner Jolly II Rover, Sunset Sail, Key West, FL

We loved our sunset cruise and would definitely consider trying one of the day cruises as well–if you are looking for something a little different from the traditional sunset cruise, the Jolly II Rover has you covered!

 

16 Comments
  • Les Petits Pas de Juls
    Posted at 18:37h, 07 October Reply

    Love the idea of this sunset cruise in the Keys… you’re giving me too many options for my short stay in Florida! Stop now! 😉 kidding, go on, please!
    Les Petits Pas de Juls recently posted…Weekly Photo Challenge : Good Morning!My Profile

    • Jenna Kvidt
      Posted at 20:37h, 09 October Reply

      Lol! I have lots more about Florida coming up…sorry! 🙂 Glad you are finding some things you are interested in! We really loved the sunset sail–it’s a fun way to get out on the water if you have time.

  • Anna
    Twitter:
    Posted at 18:31h, 08 October Reply

    Did you like the keys? I felt a little disappointed that there were no beaches. I guess I expected it to be more tropical. In retrospect I think the best way to enjoy the keys is on or in the water! Or at a bar…hehe…

    What else did you do?
    Anna recently posted…CO Restaurant-Charleston, South CarolinaMy Profile

    • Jenna Kvidt
      Posted at 20:41h, 09 October Reply

      We love the keys!! They definitely don’t have the tropical beach atmosphere like I expected as well, but there are some beaches here and there. We like being in the water more than on the beach though, so the lack of beaches doesn’t bother us too much. Lol, water and bars pretty much sums it up! 🙂

      I love the history of the area, so we have visited quite a few museums, but most everything else we have done is out on the water and walking around and exploring too.

  • Jennifer
    Twitter:
    Posted at 04:34h, 09 October Reply

    Such gorgeous sunset photos! I love sunset cruises and I really like the idea of being able to bring your own picnic.
    Jennifer recently posted…We Want to Go With Oh to Dublin! #GwOGuestTesterMy Profile

    • Jenna Kvidt
      Posted at 20:42h, 09 October Reply

      Thanks! We loved that you could bring your own picnic as well–it made it more affordable and then you could bring what you actually wanted to eat and drink. It wasn’t crowded either which was nice–we would definitely recommend it–it was a great time!

  • Kimmy
    Twitter:
    Posted at 01:09h, 10 October Reply

    Looks like you had a great time and beautiful view! I’ve never seen the green flash. Did you get to see it? Or have you at any other time?
    Kimmy recently posted…Travel Tips: Staying Healthy While FlyingMy Profile

    • Jenna Kvidt
      Posted at 01:20h, 14 October Reply

      It was a beautiful evening! No, we didn’t and haven’t seen the green flash! I keep hearing so much about it though–I hope we can see it one of these days!

  • Mike
    Twitter:
    Posted at 01:25h, 10 October Reply

    Jenna, it’s so different to you and Micah back here in the states as I’ve been following your posts as a Subscriber with you overseas! That sailing trip looks fantastic and my dream trip is on Windstar Cruises in Tahiti! That would be the best ever! Great to hear from you guys 🙂
    Mike recently posted…Easy Ground Turkey, Pasta, Veggie and Cheese CasseroleMy Profile

    • Jenna Kvidt
      Posted at 01:24h, 14 October Reply

      The trip was really great! We always love the beautiful skies in Key West. Tahiti would be amazing–hope you get to do that one day!

      And yeah, I suppose we haven’t written much about the states for awhile! After we finish up with some more Florida stories, we will have more overseas places to write about again 🙂 Thanks for following along!

  • Jennifer
    Twitter:
    Posted at 00:00h, 11 October Reply

    I just found your blog and love it! Your pictures are beautiful! I have no plans to visit Key West, but I should make some soon! Thanks!!
    Jennifer recently posted…What Travel TeachesMy Profile

    • Jenna Kvidt
      Posted at 01:26h, 14 October Reply

      Thanks so much–really appreciate it! We really love Key West and would definitely recommend it. Hope you enjoy it if you make it there! 🙂

  • Bret
    Twitter:
    Posted at 12:16h, 14 October Reply

    This looks lovely in general, but especially so right now, after several frustrating and exhausting work weeks. I’ve been to the Keys once, over 20 years ago, but never made it to Key West. Hoping to go back soon and Scuba John Pennekamp Park.
    Bret recently posted…TAHITI: Pearl Diving in Bora BoraMy Profile

    • Jenna Kvidt
      Posted at 00:42h, 15 October Reply

      Hope you can get some relaxation soon! We’ve been wanting to go down to John Pennekamp as well, have heard its nice by always seem to bypass it! Would love to see your diving photos when you do get there!

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