Key West Historic Schooner When And If Sunset Cruise

Key West , United States

Key West Historic Schooner When And If Sunset Cruise

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(100 reviews)

For a full refund, cancel at least 24 hours before the scheduled departure time.

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Mobile or paper ticket accepted

About this experience

Historic Schooner. Champagne Sunset Toast. Elegant and Exclusive.

Step aboard the historic schooner When And If, commissioned by General George Patton in the late 1930s, and sail into a breathtaking Key West sunset. Raise a champagne glass as the sun dips below the horizon, while your experienced crew handles the sails — or try your hand at steering this classic wooden schooner yourself. Glide along turquoise waters, spot playful dolphins and local wildlife, and enjoy an unforgettable evening that blends history, luxury, and adventure.

Highlights:

Historic schooner experience aboard the When And If, commissioned by General George Patton in 1939.

Champagne sunset toast included

Elegant and exclusive cruise - Avoid the crowds

Hands-on sailing opportunity: take the wheel under guidance from your experienced crew.

Spot dolphins, sea birds, and local marine wildlife.

Perfect for romantic evenings, family adventures, or history enthusiasts — children sail at a discounted fare.

Available options

Key West Historic Schooner When And If Sunset Cruise

What's included

Soda/Pop

Bottled water

Select Beer and Wine Included. Sunset Champagne Toast and Bottle Service Upgrade Available

Experienced Captain and Crew

Restroom on board

Opportunity to Take the Wheel and Help Raise Sail

Detailed itinerary

Vessel is docked at the Perry Marina at slip # H16. Look for Bad Boys Taqueria and you will see the Schooner with varnished wooden masts. Check in and boarding happens directly at the boat and begins 15 minutes prior to departure.

Stop 2 Pass by

Sailing through the National Marine Sanctuary offers the unique opportunity to view marine wildlife. Sea turtles, bottle nose dolphin and marine birds.

What's not included

Gratuities

Transportation to and From Vessel

Ships Souvenirs Available for Purchase Onboard

Reviews breakdown

Viator 4.6

12 reviews

5★

4★

3★

2★

1★

Tripadvisor 4.9

88 reviews

5★

4★

3★

2★

1★

Important information

Service animals allowed

Public transportation options are available nearby

Infants are required to sit on an adult’s lap

Suitable for all physical fitness levels

Children must be accompanied by an adult

Meeting point

We are docked at slip H16 at the Stock Island Marina. Directly in front of the new Sloppy Joe's Dockside 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.

About Key West

Key West is a vibrant island city known for its tropical climate, rich history, and laid-back atmosphere. As the southernmost city in the continental U.S., it offers a unique blend of Caribbean and American cultures, stunning beaches, and a thriving arts scene.

Top Attractions

Duval Street

The heart of Key West's nightlife and shopping, Duval Street stretches from the Gulf of Mexico to the Atlantic Ocean, offering a mix of bars, restaurants, shops, and galleries.

Entertainment Half day to full day Free to explore, costs vary for attractions and dining

Dry Tortugas National Park

A remote and pristine national park accessible only by boat or seaplane, featuring Fort Jefferson and stunning coral reefs for snorkeling and diving.

Nature Full day trip Ferry: $185-$220, Seaplane: $300-$350, Park entry: $15 per person

Key West Butterfly and Nature Conservatory

A lush tropical garden filled with free-flying butterflies, birds, and other wildlife, offering a serene and educational experience.

Nature 1-2 hours $22 for adults, $12 for children (6-17)

Must-Try Local Dishes

Key Lime Pie

A tangy and sweet pie made with key lime juice, egg yolks, and sweetened condensed milk, topped with whipped cream or meringue.

Dessert Contains dairy and eggs, can be made gluten-free

Conch Fritters

Deep-fried fritters made with conch meat, vegetables, and spices, served with a dipping sauce.

Appetizer Contains seafood, can be made gluten-free

Grouper Sandwich

A sandwich featuring fresh local grouper, often blackened or fried, served on a toasted bun with lettuce, tomato, and tangy sauce.

Lunch Contains seafood, can be made gluten-free

Popular Activities

Snorkeling Diving Kayaking Paddleboarding Fishing Beach lounging Spa treatments Sunset cruises

Best Time to Visit

November to April

This is the most popular time to visit Key West, with pleasant weather and lower humidity. It's ideal for outdoor activities and festivals.

21-28°C 70-82°F

Practical Information

Language

Official: English
Widely spoken: Spanish
English: Widely spoken

Currency

U.S. Dollar (USD)

Time Zone

Eastern Time Zone (ET) (UTC-5:00, UTC-4:00 during daylight saving time)

Electricity

120VV, 60HzHz

Safety Information

Overall Safety Rating: Generally safe

Key West is generally a safe destination for travelers, with low violent crime rates. However, petty crime, such as pickpocketing and theft, can occur in tourist areas. Exercise caution and common sense to ensure a safe and enjoyable trip.

Important Precautions:

• Keep valuables secure and out of sight
• Use ATMs located inside banks or reputable establishments
• Be cautious when using public transportation or taxis, and always use licensed services

Getting there

By air

Key West International Airport • 4 miles from downtown

Getting around

Public transport

Affordable and convenient, with multiple routes serving popular destinations.

Taxis

Available • Apps: Uber, Lyft

Rentals

Car, Bike, Scooter

Neighborhoods

Old Town New Town

Day trips

Dry Tortugas National Park

70 miles by ferry or 30 minutes by seaplane • Full day

A remote and pristine national park featuring Fort Jefferson and stunning coral reefs for snorkeling and diving.

Big Pine Key

30 miles north of Key West • Half day to full day

A scenic island known for its pine rocklands, wildlife, and the famous Key deer.

Looe Key Reef

5 miles west of Big Pine Key • Half day to full day

A popular snorkeling and diving spot featuring a vibrant coral reef and diverse marine life.

Festivals

Fantasy Fest • Late October Key West Food and Wine Festival • Early November Key West Highlight Film Festival • Early November

Pro tips

Visit Mallory Square for the famous sunset celebrations, which feature street performers, local vendors, and stunning views of the sunset.
Explore the island by bike or scooter, as it's a great way to get around and see the sights.
Try key lime pie, a local specialty made with fresh key limes and sweetened condensed milk.
Visit the Key West Butterfly and Nature Conservatory, a lush tropical garden filled with free-flying butterflies, birds, and other wildlife.
Take a day trip to Dry Tortugas National Park, a remote and pristine island featuring Fort Jefferson and stunning coral reefs for snorkeling and diving.