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2-Hour Sunset Sail On Schooner When And If

4.2 (40)
Stock Island, US
4.2 (40)
Stock Island, US
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Experience the magic of a sunset sail on the historic Schooner When And If in Key West. Step aboard this stunning wooden yacht, built for General George Patton before the war, and feel the elegance and grace of a bygone era. As you relax on the teak decks, our experienced Key West Captain and Crew will pour wine and share their passion for sailing, the sea, and, most importantly, sunsets. Sip on complimentary wine and beer as you take in the wind and the sea on Key West's best sailing tour. This 2-hour sail is a truly unforgettable experience, allowing you to unwind like no other Key West sunset cruise. Don't miss the opportunity to create memories of a lifetime on this historic schooner.

About this experience

  • Free Cancellation For a full refund cancel at least before the start of your booking
  • Suitable for 1-12 Participants
  • Private Tour, Small Group Tour
  • Self Guided Experience
  • Sail on a Truly Historic Schooner Yacht
  • Sip on Complimentary Wine & Beer
  • Take in the Wind and the Sea
  • Key West's Best Sailing Tour
  • Unwind Like No Other Key West Sunset Cruise
  • Alcoholic beverages
  • Gratuities

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More about this experience

Introduction

Experience the magic of a breathtaking sunset sail on the historic Schooner When And If. Step aboard this exquisite 1939 wooden yacht, built for General George Patton before the war, and embark on a journey that promises to create memories that will last a lifetime. Named by Patton himself, the Schooner When And If was meant to sail the world after the war, and now you have the opportunity to be a part of its remarkable story. With its teak decks and classic design, this yacht offers a unique blend of comfort, style, and grace that will transport you to a bygone era of sailing.

What to expect?

During this 2-hour sunset sail, you can expect to be mesmerized by the beauty of the Key West coastline as the sun paints the sky with vibrant hues of orange and pink. Sit back, relax, and let the experienced Key West Captain and Crew take care of everything as they navigate the open waters. Sip on complimentary wine and beer as you feel the wind in your hair and the gentle sway of the yacht beneath your feet. This sailing tour is the perfect opportunity to unwind and enjoy the tranquility of the sea, while basking in the warm glow of the setting sun.

Who is this for?

This sunset sail is for anyone looking to experience the sheer joy and romance of sailing on a historic yacht. Whether you're a seasoned sailor or a first-time adventurer, this tour is designed to cater to all. Couples seeking a romantic getaway will find the intimate setting of the Schooner When And If perfect for creating unforgettable moments. Friends and families can come together to enjoy quality time surrounded by the beauty of nature. This tour is inclusive and welcomes individuals from all walks of life who appreciate the elegance and serenity of sailing.

Why book this?

What sets this sunset sail apart is the unique opportunity to voyage on a historic yacht with a rich history. The Schooner When And If was once a private yacht, loved and enjoyed by many, and now you have the chance to experience its timeless beauty. The knowledgeable crew will share their passion for sailing, Key West, and the sea, adding an extra layer of authenticity to your journey. The complimentary wine and beer will enhance your experience, allowing you to truly unwind and savor the moment. This sunset sail promises to be a one-of-a-kind adventure that combines history, elegance, and natural beauty in a way that will leave you in awe.

Good to know

It's important to arrive at least 15 minutes prior to your scheduled departure to ensure a smooth boarding process. The Schooner When And If is conveniently located on H Dock, opposite the Sloppy Joes Dockside Pool at the Perry Hotel. Ample parking is available on the Marina premises, making it easy for you to access the boat. Please note that gratuity is not included in the package, so if you appreciate the exceptional service provided by the crew, feel free to show your gratitude.

Reviews

Customers who have experienced the Schooner When And If sunset sail have been captivated by its beauty and charm. They rave about the stunning views, the attentive crew, and the overall sense of tranquility that envelops them throughout the journey. Many describe it as a magical experience that exceeded their expectations. Whether it's a special occasion or simply a desire to immerse oneself in the beauty of nature, this sunset sail has left a lasting impression on those who have embarked on this voyage. Don't miss out on the opportunity to create your own unforgettable memories aboard the Schooner When And If.

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

(40)

4.2 (40)

223philippt

What a great sail!! Capt. Andy and crew were the best! I've been sailing over 30 years and they guys know what they're doing!! Philipp

Rebecca_C

This was so much fun! The crew was absolutely phenomenal and went out of their way to make sure we were comfortable. Drinks were provided and nice and cold. The ship was gorgeous. Definitely a highlight of our trip. Thank you for everything!

wittmeyerj

This was a fun trip. The schooner "When and If" is a bit smaller than the typical touristy boats in Key West and feels more comfortable. The captain and crew are good at their jobs and very personable. Also, since the boat is docked on Stock Island versus downtown, it is much easier to access, free parking, and zero traffic to deal with.

wdwright0408

It was my 70th Birthday and I made the reservation nearly 2 months in advance. The weather was perfect. Captain Andy and crew are the best and made for a most enjoyable two hours. Captain Andy let me pilot a bit and I helped a small amount on a tack. What a most wonderful experience.

95billr

Just do it. The historical background, the amazing views, and, of course, the AMAZING CAPTAIN AND CREW!!! My wife and I went with two other couples and we now have fantastic memories. Just an absolutely wonderful experience all the way around. Very highly recommended.

chestersparks

This is probably my 20th sailing trip with Sunset Sail Key West, and as usual it was a glorious day on the water thanks to the amazing crew and the wonderful historic yacht (When and If). I've also sailed many times on their smaller sailboat (High Tide) when I want a more private experience. Whether it is a day sail, sunset sail or Wrecker's Race, you will always be treated like royalty.

Ann K

Absolutely beautiful! Guys were all great and the boat is very cool. There might have been more comfortable seating but actually idk how that would be accomplished.

kebriggs

We absolutely loved this sunset sail. The crew, the ship and the sunset… all exceptional. One disappointing thing - Expedia really messed up and had the tour departure listed at 4:30 instead of 5:30 so we sat around for an extra hour. They did not account for the time change with daylight savings. 😒 Otherwise, a fantastic experience. Highly recommend.

Barbara_H

From start to finish, the experience was amazing. The crew was friendly and attentive to all passengers on board. The captain and crew had great communication as well. Can’t say enough about the captain and her expert handling of the schooner, particularly the docking. It was a fabulous experience and will easily be a highlight of our stay in Key West.

Odyssey778039

We were looking for a relaxing, somewhat romantic way to make an unforgettable memory while in Key West. Neither of us had ever been sailing before, and this oneneven has a bit of history, which we both love. You can rent this boat for private tours, but we opted for the "shared" experience (meaning with other people we didn't know previously) because it was significantly less expensive. The entire experience was fantastic. Captain Matt and his crew were friendly and knowledgeable. 10/10bwould do again!
Collected by Evendo, Tripadvisor & Viator
2024-05-19 08:41