Sailing Into the Sunset – An Evening on the Mantanzas

The mysteriousness of the ocean has attracted adventure-seekers for thousands of years, and the thrill of setting sail upon it brings one in direct contact with that mysteriousness.

Cover Photo

The Schooner Freedom

By JP Chartier

The heat and humidity of the day now only a memory as a refreshing breeze blows in from the Mantanzas Bay and ruffles my hair. Soon the sun will be sinking behind 18th and 19th century architecture turning the world a wonderful golden hue, a final farewell to the day that was from the setting sun.

We’re dressed in shorts and light attire for the evening, I have my camera case wrapped around a shoulder and hanging at a hip, there is a happy buzz in the air, it’s going to be a good evening ride on the Schooner Freedom.

We arrive at what seems to be a full sail boat, but when the captain sees us he points with a smile to a hidden seat for two. The crew of three begin their procedures for take-off and before I know it we’re away from the dock and off for a sunset cruise around the Mantanzas Bay.

The wooden sailboat begins to creak and moan under the pressure of the shifting waves, a soothing sound that lulls me into a dreamy state of mind, when suddenly the breeze picks up, filling the large sail overhead and turning our sailboat toward the Bridge of Lions ahead.

With sails open to the wind, the bridge rises for us, stopping traffic momentarily so we can pass underneath.

Bridge of Lions

The Bridge of Lions

Opening the Bridge

The bridge rises so we can pass on our way back

We (me and my girlfriend Michelle) are aboard the 72’ Topsail Schooner Freedom for their Sunset Tour on the Mantanzas Bay in St. Augustine, Florida. We have a full sailboat this evening, maybe 25-30 people, we are spread out and comfortably seated on various parts of the sailboat.

Aboard sailboat 1

Sails up & off we go!

Aboard sailboat 4

Enjoying ourselves on the Schooner Freedom

Sailing Into the Sunset

The tour lasts two  hours and serves beverages (including alcohol) once out on the water. The cost for the Sunset Tour is $45.00 a person. The highlight of the tour of course is the brilliant sunset!

Sunset 1

The Great Cross stands proud near the sinking sun

Sunset 2

The setting sun kisses the day goodbye


Gutter Puppies living the life

The tour doesn’t cover a large distance, it sails lazily around the Mantanzas Bay stopping at nearby popular tourist attractions, giving spectators excellent water-side views of St. Augustine, the Castillo de San Marcos Fort, the Great Cross and Anastasia Island.

The Sunset Tour is a great way to unwind, see a romantic sunset and enjoy quality sailing time. It’s a wonderful way to start your evening festivities while in St. Augustine!

Now we’re off to dinner and a night out on the town.

The route of the Sunset Sailing Tour

St. Augustine Map



JP Twitter Pic2

JP Chartier

Hi my name is JP Chartier and I write for Gutter Pup where you can expect to read well-written and entertaining articles about the people and places that often get overlooked at many popular vacation destinations around the world. You will also find articles on camping, hiking, kayaking and several other popular vacation activities here too.

My goal is to seek out the hidden ‘gems’ for you and bring them alive through my writing and photographs, so your next trip or vacation will be a much more rewarding and fulfilling experience.

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12 Comments on Sailing Into the Sunset – An Evening on the Mantanzas

  1. Rena McDaniel // October 10, 2014 at 9:26 am // Reply

    Looks like an amazing time and some really fantastic photography!
    Rena McDaniel recently posted…CHEROKEE, NC THE HISTORY OF THE SMOKY MOUNTAINSMy Profile

  2. Dennis Kopp // October 8, 2014 at 6:47 pm // Reply

    That sunset sail looks like a rally nice thing to do JP! I have only been once to St. Augustine and remember being really surprised about the nice historical architecture of the town. Getting on a sailboat and cruising into the sunset did not occur to us, but it will be a great thing to keep in mind for the next visit…:)
    Dennis Kopp recently posted…5 Must-See D-Day Locations of NormandyMy Profile

    • It’s a great start to an evening out on the town Dennis. It’s cool because you get a different perspective of a few of the tourist attractions and of course the sunsets are phenomenal!!

  3. Suzette - // October 7, 2014 at 3:17 pm // Reply

    Looks like a nice trip JP, thanks for sharing.
    Suzette – recently posted…Visiting the Elephants in ChicagoMy Profile

  4. what a great way to pass some time!

  5. Ryan Biddulph // October 6, 2014 at 11:38 pm // Reply

    Hi JP,

    I absolutely love that sunset shot! Great post and I must say I’m appreciating the sea more each day living beside a bay.

    We watch sail boats cruise in and out of Savusavu each day. Really popular spot for cruising, docking and battening down the hatches when heavy storms blow into and around Vanua Levu, Fiji. We stop by the harbor every week or so to eat at The Captain’s Cafe.

    So much fun, and it’s so darn inspiring to live by the water… least for 4 months 😉

    Thanks for sharing. Tweeting soon.

    Signing off from Fiji.

    Have a great week JP!

    Ryan Biddulph recently posted…15 Tips for Living the Digital Nomad LifestyleMy Profile

    • Thank you Ryan. I’m lucky enough to live by the water here in St. Pete too, and I love watching the sailboats come in & leave the marina! I’ve got to make it to Fiji one day, looks amazing!

      Have a great week too Ryan!

  6. Lovely post. It definitely makes me wanna go on a sailing tour.

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