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Florida Keys Sailing Vacations

Second Wind anchored in Biscayne Bay - Miami skyline in backgroundMulti-day, overnight vacation charters are a great way to enjoy The Keys from an ocean view. These cruises are typically 4 to 6 days and we are flexible on start / end dates. Our charters are private and all-inclusive - meals, drinks and boat expenses are included for both guests.  There are no additional costs unless you would like to visit specific places that have an entry fee or you would like to stay in a marina.  All meals and drinks are prepared on-board and planned according to your tastes.  You fill out a "likes and dislikes" questionnaire ahead of time and we'll stock the boat with all your favorites. Call to custom design your charter and a great experience.

"I must say we are still talking about how much fun we had and when I talk to people I tell them what a joy it was spending time on a sailboat with you and Laura.  .... You made us feel very welcome."  J.S., Des Moines, IA

Multi-day custom charters are limited to a single couple.  Second Wind is a two cabin boat with one at each end of the vessel (forward and aft-cabin layout).  The crew will be sleeping in the aft-cabin while our guests enjoy their own private forward-cabin with full-sized bed and private head. (See our Pictures and Videos page for a full-size picture of the floor plan)

"Kim & I spent 3 nights with on the Second Wind last week. It was an amazing experience. Bill and Laura were incredible hosts and made us feel right at home throughout the entire trip. Thanks again for everything!!!!"  Jim, Mt. Pleasant, MI

"But.... what's the boat really like inside?"   We've created a great video tour of the boat to help our potential guests see what a beautiful boat they will be sailing on.  Click HERE to view the video now in a new window.

Here is a sample itinerary.  We'd love to customize a special trip for you!

Keys Sunset from Marathon MarinaDay 1 - Fly into Miami airport (MIA) in the afternoon.  Rent a car at the airport and enjoy a 2 hour drive through lower Florida and The Keys.  Arrive at the boat in time for a sunset cocktail, then a great dinner on the boat.  We'll spend the night at the marina while you settle in to your private cabin.

Day 2 - An early morning departure puts us in the Hawk Channel for a beautiful sail to one of our local snorkel / swimming spots.  We'll spend some time enjoying the clear waters before a scrumptious lunch on the boat.  An afternoon sail along The Keys might end with anchoring in calm waters to enjoy a beautiful sunset while served a gourmet dinner. 

Second Wind Anchored off Boca GrandeDay 3 - Another day on the water starts with a sail to one of our favorite anchorages - Newfound Harbor. Lunch underway and maybe more snorkeling (if the weather permits) will get us into the anchorage just in time for evening cocktails.  A quiet night on the anchor under a blanket of stars makes a perfect end to our day.

Day 4 - We'll start our trip back east to Marathon and stop at Bahia Honda State Park for great pictures and a walk along the beach.  An enjoyable dinghy ride along the beaches and reefs is a great way to work up an appetite for another scrumptious dinner.  Maybe an after-dinner cocktail while you watch the moon rise then a quiet evening on the boat.

Beach at Bahia Honda State ParkDay 5 - Sleep in this morning while we prepare you a great breakfast.  We can take you into Boot Key Harbor for sightseeing then to Sombrero Beach for a picnic lunch.  Tearful good-byes then a drive back up through the keys to the Miami airport for your flight back home.  Or, stay in South Beach for a day or two and enjoy the atmosphere of the famous sea-side community.

** Shuttle service available from Miami or Key West Airports **

We would love to customize a multi-day charter for you and can provide some great options based on our extensive experience in these beautiful cruising areas.  Please call us for a free trip plan.  These are all-inclusive charters - gourmet meals, snacks, boat drinks and all boat expenses are included.

Multi-Day Vacation Rates

      1     $1,100 
      2     $2,100
      3     $3,000
      4     $3,900
      5     $4,800
      6     $5,700

*  Additional nights are $900 each

Discounts Available!

     $100 per day discount for single guest

Marinas Extra - Our sailing vacations are a great way to experience cruising at its best.  We anchor each evening in beautiful places and will take you exploring or into town with our new tender (12 foot hard-bottom dinghy).  But, if you would like to experience an evening dockside, we would be happy to arrange for a marina on any night of your cruise.  Marina costs are not included in the charter fees and would be the responsibility of our guests.  We can tell you exactly what these costs would be ahead of time so there would be no surprises.

Protection for your charter investment - We provide an industry standard Yacht Charter Agreement for all charters longer than one day.  A sailing vacation on a crewed yacht is a large investment of your money and valuable time.  This agreement provides you guarantees on our crew, boat and facilities along with details of any clothing or gear you might want to bring.  Click HERE to download a blank Yacht Charter Agreement.  Please call if you have any questions.

Ready to take the next step?  Visit our Reserve Your Cruise page and fill out our easy Guest Information form.  Or, please call us at (518) 210-3309 if you have any questions.