Adventure Collective
Sunset Sail on When and If in Key West, Florida - Miami

Sunset Sail on When and If in Key West, Florida

Key Westeasy

Difficulty

easy

Duration

2–3 hours

Fitness Level

Suitable for all fitness levels; minimal physical effort required.

Overview

Sail into the sunset aboard the charming schooner When and If in Key West. Discover vibrant skies, calm waters, and serene moments on this private boat tour.

Boat Tour
Sailing
Key West, Florida

Sunset Sail on When and If

2hrs • Up to 32 Guests • Shared Experience • $109pp

Select participants and date

Adventure Photos

Sunset Sail on When and If photo 1

About This Adventure

Sunset On A Gorgeous Classic Yacht

"When the war is over, and if I live through it, Bea and I are going to sail around the world" declared General George S Patton of his beloved custom-built yacht.

Sunset Sail Key West is proud to be home to the schooner yacht When and If: the peacetime dream of an American war hero. This octogenarian beauty is open to the public as part of a fund-raising programme to preserve her flag, keep her in her current excellent condition and fulfil her destiny to sail around the world.

Come sail with Sunset Sail Key West and be part of her story as we sail into the sunset, enjoying the unspoiled view and blue water sailing to be had off the Keys' Atlantic coast.

Help raise sail, take a turn at the helm, or simply relax and enjoy planning your next trip with Sunset Sail Key West as our captain and crew sail you out to catch the breeze!

!Description of image

Duration

2 Hours

Trip Includes:

  • Seats on a shared experience on the schooner When and If with her captain and crew
  • Two boutique wines made in honor of the boat, and select beers
  • Bottled water and La Croix

Please Bring:

  • Any necessary sun protection
  • Appropriate weatherwear for the day - it can be cool on the water after sunset

Please Note:

  • All Ages welcome
  • Children under 12 must be accompanied by an adult
  • Gratuity for the crew customary and very much appreciated! It is not included in the fee for your trip, so if you think they did a good job, please do remember them at the end of your sail.

!Description of image

Adventure Tips

Arrive Early for Best Seating

Ensure you get the best spots on deck by arriving at least 15 minutes early.

Bring a Light Jacket

Evenings on the water can be cooler; a light jacket keeps you warm during the sail.

Apply Reef-Safe Sunscreen

Protect your skin and the fragile marine environment with reef-safe sunscreen.

Limit Alcohol Consumption

Enjoy light refreshments but drink responsibly to stay safe while aboard.

Local Insights

Wildlife

  • Bottlenose dolphins often seen swimming alongside the boat
  • Brown pelicans diving near the shoreline

History

The When and If schooner was originally built as a U.S. Coast Guard vessel and now serves as a cherished part of Key West’s maritime heritage.

Conservation

The company emphasizes eco-friendly practices, including use of reef-safe products and efforts to minimize plastic waste during tours.

Select participants and date

Adventure Hotspots in Miami

Frequently Asked Questions

Recommended Gear

Light Jacket

Essential

Keeps you warm during cooler evening breezes on the water.

fall specific

Reef-Safe Sunscreen

Essential

Protects your skin and the marine ecosystem during sunny days.

summer specific

Wide-Brim Hat

Provides extra sun protection during late afternoon before sunset.

summer specific

Camera or Smartphone

Essential

Capture the stunning colors and moments during the sunset sail.