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Sunset Sail on Historic Schooner in Key West

4.8 (86)
Stock Island, US
4.8 (86)
Stock Island, US
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Experience the breathtaking beauty of a Key West sunset aboard the historic schooner When And If! Commissioned by Colonel George Patton, this stunning vessel invites you to set sail and fulfill his dream of circumnavigating the globe. Feel the warmth of the teak decks under your feet as you help raise the sails or take a turn at the wheel. Or simply sit back, relax, and let Sunset Sail Key West whisk you away into the sunset. With a total duration of 120 minutes, this sunset sail promises to be an unforgettable experience. Boarding at slip H16 at the Stock Island Marina, right in front of the new Sloppy Joe's Dockside bar and restaurant, ample free parking is available for your convenience. Make sure to arrive 15-30 minutes early to ensure plenty of time to find the boat. Don't miss out on this incredible opportunity to witness the magical Key West sunset from the deck of a historic schooner.

About this experience

  • Free Cancellation For a full refund cancel at least before the start of your booking
  • 2 hours
  • Suitable for 1-15 Participants
  • Private Tour, Small Group Tour
  • Self Guided Experience
  • Beautiful Key West sunset
  • Sail on historic schooner
  • Help raise sail
  • Take a turn at the wheel
  • Relax as we sail into the sunset
  • Bottled water
  • Restroom on board
  • Alcoholic beverages
  • Wine tasting
  • Gratuities

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More about this experience

Introduction

Experience the breathtaking beauty of a Key West sunset aboard the When And If, a historic schooner steeped in rich naval history. Commissioned by Colonel George Patton himself, this magnificent vessel promises an unforgettable adventure on the open seas. Step aboard and be transported to a bygone era as you set sail on the teak decks of this stunning schooner. Whether you choose to lend a hand raising the sails, take the helm, or simply relax and enjoy the tranquil ambiance, Sunset Sail Key West guarantees an enchanting journey into the glowing horizon.

What to expect?

During this magical two-hour excursion, prepare to be awestruck as you witness the mesmerizing transformation of the sky at dusk. As the sun descends, casting a warm golden glow across the water, you'll experience a sense of peace and serenity that only nature can provide. Allow the sea breeze to gently caress your face and the soothing sound of the waves to lull you into a state of complete relaxation. This sunset sail is an opportunity to disconnect from the stresses of everyday life and reconnect with the beauty of the natural world.

Who is this for?

This sunset sail is perfect for anyone with a love for adventure, nature enthusiasts, or those seeking a romantic and unique way to celebrate a special occasion. Whether you're traveling solo, with a loved one, or a group of friends, Sunset Sail Key West welcomes everyone aboard. Embrace the chance to be surrounded by like-minded individuals who share a passion for exploration and a desire to create unforgettable memories.

Why book this?

Escape the ordinary and embark on a journey you'll cherish forever. Sunset Sail Key West offers a one-of-a-kind experience aboard a historic schooner, allowing you to relive the golden age of sailing. The When And If schooner, with its rich history and elegant craftsmanship, provides the perfect setting for an evening of tranquility and beauty. Let the gentle sway of the waves and the kaleidoscope of colors in the sky captivate your senses, transporting you to a world where time seemingly stands still. This sunset sail promises to be a truly magical and unforgettable adventure.

Good to know

Make sure to arrive 15-30 minutes before the start of the sail to have ample time to find the boat. The When And If schooner is docked at slip H16 at the Stock Island Marina, directly in front of the new Sloppy Joe's Dockside bar and restaurant. There is plenty of free parking available, ensuring a hassle-free start to your journey. Dress comfortably and bring a light jacket or sweater, as evenings on the water can be slightly chilly. Don't forget your camera to capture the breathtaking views of the sunset and the picturesque schooner against the backdrop of the Key West skyline.

Reviews

Customers who have experienced the Sunset Sail Key West aboard the When And If schooner have been raving about their unforgettable journey. They commend the knowledgeable and friendly crew, who create a warm and welcoming atmosphere for all guests. The beauty of the sunset and the peacefulness of the sail have left lasting impressions on travelers, who highly recommend this experience to anyone visiting Key West. Prepare to be enchanted by the stunning views, the rich history of the schooner, and the sense of tranquility that can only be found while sailing into the sunset on this extraordinary adventure.

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

Your Itinerary

Stock Island Marina Village

Boarding location

Reviews

(86)

4.8 (86)

K5891YZwilliaml

Captain Andy and the crew were wonderful - helped answering questions about “When and If”, the cruise and how they sailed the boat. “when and If” was custom built for General George Patton and has quite a history. Don’t forget to explore below deck to see the true beauty of this twin masted schooner. The cruise itself was awesome and the relaxation of moving through the water under sail cannot be understated … not to mention the spectacular sunset! This is a “must do” item for your visit to Key West!

JessieroseRN

My husband and I thought this would be a fun change from a standard dinner/party boat and booked this on our recent trip to Key West. It was overall a good time and the staff were awesome, but there are a few things I didn't expect that I want other people to know before booking this cruise. There are tons of sail boats cruising around in front of Mallory Square in the calm harbor waters during sunset and that's what I thought this cruise would be, however, this boat leaves from Stock Island. To have an unobstructed view of the sunset we had to sail about 45 minutes out into the gulf in open water. It was a fairly breezy day and the waves were 3-4ft. For most of our sail the boat was cruising at a steep angle and rocking enough to splash some waves on to the front seats. It was really difficult to get up and move around (I didn't except to use the bathroom which felt scary, and I had worn a dress which made it worse, lol). By the time the sun was setting, I had to think hard about not feeling sea sick. I'm a Florida native and have spent plenty of time on the water. I know this is a sail boat which means some waves and wind, but I was hoping for a smooth sail in the harbor. There was nothing on the website or in the reviews that mentioned all of this, so I just want anyone else who books to be able to account for this (and not wear a dress, lol). The boat was neat though and the sunset was gorgeous of course. Thanks to the crew who were fun, helpful, and engaging.

Jo_Freddie

We did our research and wanted a beautiful scooner, made out of wood, neither crowded nor a party boat. This one experience surpassed our expectations! Great history behind this gorgeous and well cared vessel. The captain and crew were very welcoming, caring, and knowledgeable. Highly recommend it!!!

Stephanie_S

So much fun! Great time on a historic ship! Would recommend this to anyone who wants to get out to see the sunset or looking for an enjoyable evening.

Harold_R

A must when visiting Key West! The captain and crew were outstanding! It was cloudy so we didn’t see much of a sunset but the sailing was wonderful. We will be in Salem Mass. this summer and will sail with them again up there!

516SueA516

Captain Andy and his crew gave us a perfect sunset cruise experience. It was a smaller group which gave a more intimate experience. I would definitely do it again

ckbarnes

We had a very nice sunset cruise. The crew was very friendly and helpful. Good conversation with crew and guests. Would go again!

Linda_W

Cancelled trip when we saw the schooner. Looked like the haul needed some work. Was disappointed in appearance and cancelled. Was told no refunds which was fine with us.

Julie_Z

The crew were delightful and skilled with the historic vessel and a range of passengers from 5-75 years in age. I’m prone to motion sickness but had little worry by taking a ginger supplement before boarding. We sailed with the wind about 5 miles out from shore then back so everyone had a view of the beautiful sunset.

Bradley_L

The boat was beautiful, the sunset cruise was awesome and crew was very friendly. The only hiccup was the time shown on this site (Trip Advisor), whom we booked it through was completely off…by about 1hr 45mins. Trip advisor needs to update the time so that individuals won't have to wander around wondering where the crew is at, etc. Fortunately for us, the Bad Boy Tacos restaurant was only a few steps away, where we waited until we could board. They start boarding just before 6:00pm for the sunset cruise. The sun sets at 7:35-ish. Other than that, my family really enjoyed the history of the boat and the beautiful sunset. I would highly recommend this cruise - and make sure you bring some cash to tip the crew, they worked hard to give us the best experience and deserve it!
Collected by Evendo, Tripadvisor & Viator
2024-05-21 03:30