December is, by far, the most festive month in Key West. With holiday lights adorned from every street light, and the houses decked out in holiday decor, it’s hard not to get into the holiday spirit in Key West this time of year! Sailing in December aboard the Schooner America 2.0 is no exception, with our December cruises being some of our most special sailing events in addition to our romantic sunset cruises and sightseeing boat rides! Our holiday Christmas cruises and New Year’s Eve cruises are some of Key West’s most popular sailboat rides in town, and for good reason! We simply cannot think of a better way to celebrate December in Key West than with a holiday cruise aboard the Schooner America 2.0 surrounded by your loved ones and our awesome crew!

Ahhhhh, November. Our favorite month. Why, you ask? Because it’s the start of the Schooner America 2.0’s Key West sailing season, of course! Sailing in November in Key West is special for several reasons: the weather is pretty perfect, the sunsets are stunning, and there are a lot of things to do in town, including Key West activities around Thanksgiving. And as if that wasn’t enough, Schooner America 2.0 has special events like the Full Moon Sail or our nighttime narrated Stargazing Sails. Of course, you can always join us for one of our November cruises, including our romantic Sunset Sail or a family-friendly Afternoon Sightseeing Cruise to round out your Key West vacation experience. But no matter which of our November cruises you choose, we guarantee you’ll have an unforgettable time aboard Schooner America 2.0 in Key West.

As summer begins to heat up, Key West comes alive with a myriad of exciting activities and events. Check out all the best things to do in Key West aboard Schooner America 2.0! May presents a unique opportunity for sailing enthusiasts and visitors alike, as it’s your final chance to experience the beauty of Key West aboard the Schooner America 2.0 before the boat returns to New York for the summer season. This is your moment to immerse yourself in the quintessential Key West sailing experience for day sails and sightseeing boat rides along the waterfront to romantic sunset sails that are perfect for date night – our Key West events may be the best decision you make all month!  

Don’t miss out on our popular Key West Sunset Sails, where you can take in the breathtaking colors of the sun setting over the horizon, or indulge and join us on one of our relaxing afternoon Day Sails to soak up the sun. For a truly memorable experience, join us for our special May event—the Mamas and Mimosas Mother’s Day Sail. This unique Mother’s Day cruise is a perfect way to celebrate the special women in your life with a delightful combination of mimosas and stunning views.

With so many fantastic Key West boat tours available, sailing aboard the Schooner America 2.0  will provide an unforgettable experience, combining professional service with unparalleled scenery. Don’t let this Key West sailing opportunity slip away—make the most of your time while in town and create lasting memories with us!

Experience the charm of Key West this April with a sail aboard the Schooner America 2.0! Join us for some Key West April sailing if you are looking for fun things to do in Key West this month. Create lasting memories and join us with friends, family or a loved one during the month of April in Key West

This month, we have an exciting lineup, including our stargazing sail and a magical full moon cruise. Celebrate Easter in style aboard one of our Easter cruises including a festive Easter Brunch Cruise. For thrill-seekers, don’t miss the Wreckers Race sail—race to the finish line at Sand Key Lighthouse—or join us for one of our nighttime Key West events for an enchanting nighttime sail that promises to be a highlight of your Key West visit.

If you prefer soaking up the Florida April sunshine, our afternoon day sails provide the perfect opportunity to relax. And, of course, joining us on one of our classic Key West sunset sails is always a must-do. While there are a lot of Spring Break cruises in Key West, a sail aboard Schooner America 2.0 is a one of a kind experience on the water. Our professional crew will ensure you feel like royalty throughout your journey on one of our Key West boat tours!

If you are looking for Key West things to do then don’t miss out on these April cruises while in town! We can’t wait to welcome you aboard our classic sailboat. Secure your tickets now and make the most of your time in paradise!

It’s March and things are heating up in Key West! Join us for some Key West events on the water aboard the schooner America 2.0! Our March cruises are a must do while visiting Key West this month. We offer a variety of Key West sailing experiences that are sure to create lasting memories aboard our stunning sailboat.

There are a lot of spring break cruises available in Key West. A sail aboard Schooner America 2.0 offers a relaxing and more intimate sightseeing experience that’s great for friends or family.   

If you are looking for things to do in Key West to soak up the Florida sunshine then the perfect way to do that is aboard our classic afternoon sightseeing boat ride.  Or join us for a good old Wreckers Race, where we sail against other local sailing yachts and race to cross the finish line at Sand Key Lighthouse. The schooner America 2.0 offers the most premium sailing experience in Key West. 

In town for St. Patrick’s Day? While we don’t offer specific St. Patrick’s Day Cruises, we do offer memorable sailboat rides that will surely make you feel like you have the luck of the Irish. One of the best things to do in Key West is the famous sunset sail!  Enjoy cocktails with friends or family and catch a glimpse of the green flash.  We also host two different Key West evening boat tour cruises that are sure to give you the peace and serenity we all need in life. 

Don’t miss out on these Key West activities in the month of March!  We look forward to hosting you when you are in town.

Looking for some fun things to do in Key West this month? Our February cruises in Key West are a vibrant blend of sunshine, sea breeze and warm sightseeing boat tours.  This month marks the beginning of the high season for tourism in Key West! Join us for some fun Key West sailboat rides in the month of February. 

We know that love is in the air during the month of February with Valentine’s Day being the highlight.  Join us aboard the Schooner America 2.0 for a romantic Key West Valentine’s Day Champagne Sunset Sail. This Valentine’s Day Cruise is by far one of the best Key West events. 

Sailing aboard Schooner America 2.0 is one of the best activities in Key West to do in the month of February. If you are looking for things to do in Key West we have something for everyone! February offers a month full of fun events including sail racing aboard Schooner America 2.0 for the famous Wrecker’s Race, enjoying a peaceful nighttime sail while stargazing or enjoying a full moon sail, and more!

Our Key West February events are perfect if you want to soak up the sun for an afternoon day sail to catch a glimpse of some wildlife or have a Key West romantic evening on the water for a magical sunset sail.

Happy New Year! It’s January in Key West and there’s a lot of fun boat tour activities happening around town. We’re offering a few New Year’s Day cruises to help you kick off the new year! It’s true, the water might be a bit too cold for a snorkeling trip, but some of the best Key West January events take place aboard the stunning Schooner America 2.0. There are many reasons to join us for a fun afternoon or sunset activity in Key West. We recommend our Key West Day Sail boat tour aboard classic Schooner America 2.0, or Key West Sunset Sail for those looking for a romantic date night activity. Looking for a fun race event in Key West? Try out our famous Key West Wreckers Race, which kicks off in January, and experience the thrill of sailboat racing! And of course, during all of our January boat ride cruises, enjoy the best hospitality and incredible service from our friendly crew! Key West locals and visitors alike can’t go wrong with sailing in January aboard the Schooner America 2.0!