Sailing Trips, Boat Charters, Dinner Cruise in Key West, FL.Plan to visit Emerald Coast Sailing and other customer-reviewed, writer-recommended Key West attractions using our Key West travel route planner.
Take a break from the beach for the day and explore the ocean onboard the Red Wing. Each trip is private and tailored specifically to your family or group. Perfect for proposals, anniversaries, family reunions or for a quick getaway. Choose one of four sailing options aboard the most beautiful schooner in the harbor.
The Red Wing is an all wooden forty foot sharpie schooner that was built in Sugar Loaf Key, Florida. She is one of ten replica schooners built by Alan Miller. The people of Key West used this type of vessel to deliver mail or terrapins to the islands before engines were created. She has been restored over the past five years by Captain Shane Sekul. When you sail her on the emerald green water it is like going back in time before engines and bridges.
Emerald Coast Sailing Reviews
Thank you so much for a wonderful private excursion! My family had the best time ever. It was definitely the highlight of our vacation. Capt. Shane was knowledgeable and took us to the perfect spot to... more »
We took the sunset cruise with the family and it was fantastic. Shane ( Capt. ) and Sherie ( 1st mate? ) were awesome. They were professional and laid back all at the same time, and the boat! OMG what... more »
Not only do I wish I could give this 0 stars, my family drove 1 hour across town each way to not even find this place. Once we got there we got a call from them saying it was canceled😒. Not only was it canceled we got a confirmation call this morning. How does this place have 5 stars? Maybe a few people enjoy it if they actually get on the boat?
We took the sunset cruise on the most beautiful boat in the harbor. We were blown away by the boat. It is a 40 foot all wood sharpie schooner fully restored by the boats Captain. Shane Sekul. Shane and Sherie were an amazing crew and very knowledgeable about the area and extremely entertaining. Often times you take sailing trips and the crew feels somewhat disconnected or puts on an act. Shane and Sherie were either authentic or Oscar worthy actors. My wife and I brought our young children and they had a blast, they even let my daughter drive! I highly recommend this trip for couples or families! Next year we will be taking the fireworks cruise!
Places to stay near Emerald Coast Sailing
Plan your trip to Key West
Get a personalized planA complete day-by-day itinerary
based on your preferences
Customize itRefine your plan. We'll find the
best routes and schedules
Book itChoose from the best hotels
and activities. Up to 50% off
Manage itEverything in one place.
Everyone on the same page.
View all >
View all >
Hidden gems in Key West
Side trips from Key West
View all >
Nearby attractions in Key West
Plans in Key West by other users
15 days in Florida BY A USER FROM UNITED KINGDOM November, popular sights PREFERENCES: November ATTRACTION STYLE: Popular sights PACE: Medium 4 days in Florida BY A USER FROM UNITED STATES November, popular sights PREFERENCES: November ATTRACTION STYLE: Popular sights PACE: Medium 4 days in Key West BY A USER FROM UNITED STATES March, popular sights PREFERENCES: March ATTRACTION STYLE: Popular sights PACE: Medium 17 days in Florida BY A USER FROM ISRAEL September, popular sights PREFERENCES: September ATTRACTION STYLE: Popular sights PACE: Medium 15 days in Florida BY A USER FROM UNITED KINGDOM March, popular sights PREFERENCES: March ATTRACTION STYLE: Popular sights PACE: Medium 14 days in Miami, Key West & Orlando BY A USER FROM UNITED STATES April, popular sights PREFERENCES: April ATTRACTION STYLE: Popular sights PACE: Medium