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What to expect on a Key West Sunset Cruise

May 16, 2021 | Florida | 0 comments

Are you running out of ideas for a romantic date with your partner? This sailboat cruise is perfect for couples who want to sip on champagne and watch the sunset, while surrounded by picture perfect blue seas. It’s even great for friends who are looking for something different to do while staying in Key West. This sail out to sea will not disappoint even the most hardened critics.

Woman posing on a boat with the sunset behind her. | What to expect on a Key West Sunset Cruise, on a Schooner America Sailboat

I have partnered with The Florida Keys & Key West Tourism and Classic Harbor for this post. The best part for me, is they had zero restrictions when it came to my blog post. This is my honest opinion, with no constraints. For the record, I pick locations that I want to personally go to.

COVID-19 Warning: In the Florida Keys, wearing masks is no longer mandatory following an order from Florida Gov. Ron DeSantis. However, individual businesses in the Keys may require that masks be worn inside their establishment, so it is suggested that people carry a facial covering available for immediate use. Based on my personal experience, all establishments are currently requiring face masks, so be prepared. A face mask is required when boarding the sailboat, but once seated in your assigned seating, then you are allowed to take the mask off.

Due to limited seating make sure you purchase your tickets in advance.

There are many reasons to take a cruise before dusk. Key West is home to some of the most picturesque sunsets in the world. Like Justin Bieber says, “Picture perfect, you don’t need no filter.”

Sunset over the ocean in Key West. | What to expect on a Key West Sunset Cruise, on a Schooner America Sailboat

What to expect

If you are looking to see a spectacular sunset and have a relaxing evening on the water then this cruise is for you. You will feel beyond blessed to sail abroad the American 2.0, which is a replica of the ship that won the First American World Cup. While on-board you will be able to enjoy views of the sunset, Fort Zachary Taylor, Mallory Square, Sunset Pier, and Sand Key Light Tower. With a drink in hand, lie back as you travel over the smooth, turquoise-green Key West waters. Below is a video of our breathtaking views of the sunset from the gorgeous American 2.0 sailboat.

Fun Fact: Key West is 90 miles from Cuba. Sometimes at night you can even see Cuba’s city lights from the sailboat.

Cruise ship in the ocean water in Key West. | What to expect on a Key West Sunset Cruise, on a Schooner America Sailboat

What is included

This two-hour cruise features complementary wine, beer, and champagne. Also, included to eat are: hors d’oeurves, veggie crudite, cheese and crackers, shrimp cocktails, soda, and water. These are perfect snacks to have after dinner or even after a large lunch. There is even a cash bar on board for those who prefer to have a mixed drink. This two hour cruise will give you plenty of time to get away for the evening and to enjoy some much needed time with your partner or family/friends.

Woman holding cup of wine on cruise ship with sunset and ocean blurred in background. | What to expect on a Key West Sunset Cruise, on a Schooner America Sailboat

You can even try their local beer while on board.

Woman holding can of India Pale Ale Channel Marker PA | What to expect on a Key West Sunset Cruise, on a Schooner America Sailboat
Woman holding a plate of crackers and cheese on a boat. | What to expect on a Key West Sunset Cruise, on a Schooner America Sailboat

Romantic evening with your loved one

When in Key West there are countless activities, you can plan for your loved ones. However, this should be on your list. It is the perfect romantic adventure for any couple looking to have a relaxing evening on the water. This is your chance to indulge in food, wine, and beer while the sun sets all around you. How romantic.

Couple smiling at the camera on a boat in Key West. | What to expect on a Key West Sunset Cruise, on a Schooner America Sailboat

What to bring

A tip for the hard working crew

Warm sweater or jacket




Credit Card (for mixed drinks)

Medicine (if prone to sea sickness)

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Hi, I’m Misty! Welcome to Glam Journey, where you’ll find travel-related content, itineraries and booking services for the adventurous mom who is living her version of a glamorous life.

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