Gale Wins - Yacht To Sea Key West, like a local

11/14/2015

Come on down and enjoy a Key West sunset celebration onboard Gale Wins - Yacht To Sea Key West, like a local!

Crowds gather for the morning show, then adjourn for eggs at Midway Cafe.

11/11/2015

Thank you to all who served!

10/29/2015

If you'e in Key West enjoying the festivities, it's a great time to book a trip with Gale Wins - Yacht To Sea Key West, like a local! Enjoy a day on the water with Captain Kelly and let Gale prepare a gourmet lunch or dinner made to order just for you! Call us at 850-225-3069 to design YOUR Fantasy Day at Sea! http://yachttoseakeywest.com/

09/19/2015

Happy International Talk Like a Pirate Day!

Cap'n Slappy and Ol' Chumbucket discuss the importance of finding yer inner pirate.

09/18/2015

The Overseas Highway wins another accolade! Head on down to Key West via this famous scenic route and let Captain Kelly and Gale show you how to live like a local with a private yacht charter!

There are dozens, if not hundreds of magnificently beautiful places in the world to visit, that are all indescribably breathtaking in their own right.And when you're going on vacation to one of these places, you're not painfully concerned with how exactly you get there, so long as it gets you there…

09/15/2015

Poker Run Bikers to Travel Florida Keys' Overseas Highway Sept. 17-20. There's always something going on in Key West! Come see us soon and enjoy a day on the water with Captain Kelly. Emjoy an intimate dinner cruise, a fun day of snorkeling with the family, or a spectacular sunset at sea! Read more about the Poker run here:

Key West is the Southernmost city in the Continental USA. It is host to many festivals and tournaments including Fantasy Fest and the Hemingway Days as well as the Drambuie Marlin Tournament. There are many opportunities to get out on the water in Key West, Florida. Explore the coral reef, see the s…

09/02/2015

September is a GREAT time to visit the Keys! Call Captain Kelly to book your intimate dinner cruise on Gale Wins - Yacht To Sea Key West, like a local and make a special memory at sea! Click the link to find out what's going on!

The Official Florida Keys and Key West Web Site is your Premier Travel Guide to the Florida Keys: Key Largo, Islamorada, Marathon, Lower Keys, Key West. Accommodations, Real Estate, Diving & Snorkeling, Fishing & Boating, Museums & Tours, Restaurants & Bars, Theaters & Art Galleries, Events and more…

08/27/2015

What's your favorite place to stay when you visit Key West. There are so many great Bed and Breakfasts, Hotels, and Resorts. Take a look at this list of the TOP TEN and let us know if you agree!

Find Key West's Best Hotels and lodging by reading Key West, FL hotel reviews. Trust 10Best to provide the best Key West hotel ratings.

08/26/2015

Key West, Marathon, and Key Largo all made this list of top snorkelling spots in the U.S.

Yahoo Travel went in search of easily accessible and interesting places to snorkel. You might be surprised by just how close to home a few of these are.

08/25/2015

Are you on Instagram? Follow us at -wins :-)

See Instagram photos and videos from Yacht to Sea Key West ()

08/15/2015

The Florida Keys join national parks and other natural landmarks on Esquire Magazine's list of 20 American places every man should see before he dies. While you're here, enjoy a day at sea on Gale Wins - Yacht To Sea Key West, like a local! Visit us at yachttoseakeywest.com!

Look no further than the U.S.A. to scratch your wanderlust itch, whether you crave culture and history, spectacular natural landscapes, or serious adventure.

08/05/2015

Here's what one of our customers had to say: "This is our 6th trip to Key West and 6th dinner cruise with Capt Kelly and his wife Gayle. They never disappoint! We love ever minute of it. They are very accommodating when it comes to drink/dinner requests. Capt Kelly is a wealth of knowledge and interesting facts about the island. Of course the sunset view is always amazing as well! The Gaylewinds dinner cruise is always on our itinerary when we vacation in Key West. Thanks again to you both!" We'd love to hear from YOU! Find us on TripAdvisor - click the link: http://www.tripadvisor.com/Attraction_Review-g34345-d6467667-Reviews-Yacht_to_Sea_Key_West_Private_Charter-Key_West_Florida_Keys_Florida.html

Ranked #474 of 547 attractions in Key West. Been here too? Add it to your map!

07/30/2015

Look who!

07/29/2015

Tyler and Rory enjoying their honeymoon on the "Gale Wins" with the Dolphins! Awesome day.

07/24/2015

We love to see our little island make this top 10 list!

These unique, water-bound metropolises redefine urban living. No. 1 Trogir, Croatia Take an afternoon

07/24/2015

Beautiful sunset tonight!

06/06/2015

It's a beautiful day in the Keys today!

06/24/2014

Dolphin mating at Boca Grande. Awesome. Gestation period 11 - 12 months.