Key West Historic Schooner When And If Sunset Cruise

Recommended by 97% of travelers

Badge of Excellence

Key West, USA

Popular pick

Booked 5+ times last week!

2 hours (approx.)
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Why travelers loved this

4.9

· Mark_T ·

Mar 2026

This was a very nice and beautiful sail. The crew was awesome and the yacht is beautifully restored. It is nice to actually SAIL on a sailboat vs. using the motor all the time like so many companies do. The sunset was amazing!

· Olga_P ·

Mar 2026

Gorgeous sunset sail on a beautiful sailboat that is meticulously maintained. Fantastic crew! Very relaxing and romantic. No loud music - just you, the wind, and the waves. Highly recommend!

Overview

Leave the tourist crowds of Key West behind for the evening and head out on the water on the historic and elegant schooner built for General Patton in the late 1930s. Cruise around the coast with the boat’s crew looking after you the whole time, and even letting you take the wheel if you want to try your hand at boating. Watch the sunset from the ocean before heading back.

Enjoy a sunset sailing cruise in Key West on a historic schooner
Keep an eye out for dolphins and other exciting Floridian wildlife
Sip on select beers and wines as you soak up the sunset view
A great family cruise: children can hop on board for a discount

What's Included

Alcoholic Beverages

Select Beer and Wine Included. Sunset Champagne Toast and Bottle Service Upgrade Available
Restroom on board
Opportunity to Take the Wheel and Help Raise Sail
Experienced Captain and Crew
Soda/Pop
Bottled water

Gratuities
Private transportation

Transportation to and From Vessel
Ships Souvenirs Available for Purchase Onboard

Meeting and Pickup

Meeting point

The Perry Marina
7001 Shrimp Rd, Key West, FL 33040, USA
We are docked at slip H16 at the Perry Marina. Directly in front of the Bad Boys Taqueria bar and restaurant. There is ample free parking. Please arrive 15-30 minutes before the start of the sail to ensure plenty of time to find the boat.

End point

This activity ends back at the meeting point.

Itinerary

Sunset Sail Key West

2 hours • Admission Ticket Included

Florida Keys National Marine Sanctuary (Pass By)

Additional Info

Confirmation will be received at time of booking
Not wheelchair accessible
Children must be accompanied by an adult
Service animals allowed

Near public transportation
Infants must sit on laps
Most travelers can participate
This tour/activity will have a maximum of 28 travelers

Supplied by

Cancellation Policy

You can cancel up to 24 hours in advance of the experience for a full refund.

Traveler Photos

Gallery picture 1 (from a traveler's review)

Gallery picture 2 (from a traveler's review)

Gallery picture 3 (from a traveler's review)

Gallery picture 4 (from a traveler's review)

Gallery picture 5 (from a traveler's review)

Featured review

Mark_T

Reviews

4.9

based on 129 reviews

Total reviews and rating from Viator & Tripadvisor

We perform checks on reviews

Sporty seas, but a great crew!

Michelle_k, Apr 2026

We had a great time, however there were a number of folks who would have benefited knowing that the sail will be sporty😆. Captain and crew were amazing, took good care of us as guests, and our family had a great time!

Amazing sail and sunset!

Mark_T, Mar 2026

Perfect sunset sail

Olga_P, Mar 2026

Gorgeous sunset sail on a beautiful sailboat that is meticulously maintained. Fantastic crew! Very relaxing and romantic. No loud music - just you, the wind, and the waves. Highly recommend!

The Best Sunset Cruise !!

Drew_J, Feb 2026

Outstanding, highly personal, great crew, old boat experience, creating great pictures and memories …would recommend!!

Best excursion in Key West

Kimberly_M, Feb 2026

Great crew! Loved hearing all the history. Very relaxing!! The most beautiful sunset I have ever seen!

Please bring a sweater or...

Susan_C, Feb 2026

Please bring a sweater or jacket. It gets cooler than you think. We were on the sunset cruise. They offered beer and wine.

Historic wooden schooner...

Chet_S, Feb 2026

Historic wooden schooner built by Alden yachts for Gen Patton in 1932. Captain and 2 woman crew were awesome and the sunset was beautiful! 2 hour adventure was perfect with a chance for everyone to participate in the tasks at hand...

Sunset sail

Bruce_T, Jan 2026

Dress warm as it can be a little cooler on the water. Captain Zach was great as well as first mates Veronica and Jahn. The boat also summers in historic Salem MA. Highly recommend.

Don't hesitate to book! A+

Mila_B, Jan 2026

Amazing experience! We did a sunset sail. The crew is very friendly and knowledgeable about the history of the sailboat.

Enjoyed the sailing, crew...

Nancy_S, Jan 2026

Enjoyed the sailing, crew was friendly and knowledgeable. Engaged the passengers to help raise the sails

The crew was amazing! ...

Tina_P, Jan 2026

The crew was amazing! The white wine is superb!! It’s made from a friend of theirs. Highly recommend it.

Do it

William_H, Jan 2026

Relaxing cruise. Weather was perfect, light wind and mild temperatures. Friendly crew. Historic vessel.

Beautiful sunset

Alicia_H, Jan 2026

Beautiful boat, beautiful, sunset, and great crew. Nice way to end the year, even though it was cool and breezy we still had a great time sipping wine and watching the sunset.

We loved this cruise. ...

Don_G, Dec 2025

We loved this cruise. Nothing to do but enjoy, drinks provided and lots of stories to share. The cruise does not leave from Key West Schooner Wharf but from Stock Island marina. We got back just in time to see the Christmas Boat parade.

Great crew. They made the...

Lori_M, Apr 2025

Great crew. They made the trip personal and informative! Beautiful boat and amazing sunset! Highly recommend!

Key West sunset sail.

David_C, Jan 2025

A unique and memorable experience. Beautiful vessel with an interesting history. The crew was great!

Response from Host, Jan 2025

Thank you David! We love what we do and we continue to do it because of all of you! Thank You!

Historic Sunset Sail

Parke_M, Jan 2025

Great experience onboard General Patton’s schooner When and If. Crew was welcoming, knowledgeable, and capable. Highly recommended!!

perfect birthday celebration

Stephanie_S, Apr 2024

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.

Highlight of our week!

Harold_R, Apr 2024

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!

Schooner looked like it needed some work.

Linda_W, Mar 2024

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.

Trusty Crew

Julie_Z, Mar 2024

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.

Awesome Boat - Trip Advisor not so much

Bradley_L, Mar 2024

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!

Matt and his crew were...

Chad_L, Feb 2024

Matt and his crew were fantastic. Very knowledgeable and you can tell they enjoy what they do. Highly recommend.

"When and If" says it all

Bud_W, Feb 2024

What a wonderful experience and the knowledge you were walking the same deck as General Patton was special. I would have to say the interaction we had with Captain Matt and his crew will be the most memorable part of the sailing for us.

Question Not - "When and If" but Do It Now...

Terry_L, Feb 2024

Fabulous sunset cruise on General Patton's former yacht- staffed by a very capable all femaie crew. Weather and views were fantastic - most enjoyable. Do not procrastinate like the original owner on life's adventures, it may not happen. Take full advantage of enjoying the future adventures with your loved ones - Today.

Beautiful Experience

DavidC, Feb 2024

We had a great time from the moment we stepped onto the ship. The ship is beautiful and has a great history. Cold alcoholic and nonalcoholic beverages were offered. Watching the sunset at sea was beautiful.