Multi-day, overnight vacation charters are a great way to enjoy The Keys from an ocean view. Enjoy an awesome sailing vacation to Key West, Key Largo or even Biscayne Bay. 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 bow while our guests enjoy their own private aft-cabin with queen-sized bed, private head and private stand-up shower. (See our Pictures and Videos page for a full-size picture of the floor plan)
"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!
Day 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, downwind sail to Key West. We'll anchor outside Key West harbor or pick up a mooring at the City Marina. A short dinghy ride into town and you can browse the Key West waterfront or take a short walk to great shopping on Duval Street. Back to the boat in time for the famous Key West Sunset and your gourmet dinner. After a quiet evening on the boat you'll sleep to the sound of tiny waves against the hull.
Day 3 - Sailing out of Key West we continue downwind to our favorite anchorage - Boca Grande. After anchoring in the beautiful blue-green waters we'll dinghy to shore for snorkeling or swimming off the white-sand beach and bring along a picnic lunch. You can walk along the beach to search for shells or just relax in the sun. Dinner on the boat is a perfect ending to the day.
Day 4 - We'll start our trip back east to Marathon past Key West and Boco Chica. Enjoy the warm tropical sun as we sail to another great anchorage at Big Pine Key or off the beach at Bahia Honda State Park. 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.
Day 5 - Sleep in this morning while we prepare you a great breakfast. We can take you into the park for walking the beach or shopping at their nautical gift shop. A short sail back to Marathon completes the trip as we tie up at the marina. Tearful good-byes then a drive back up through the keys to the Miami airport for your flight back home. Or, say in South Beach for a day or two and enjoy the atmosphere of the famous sea-side community.
** Shuttle service available from Miami Airport (MIA) or fly into Marathon (MTH) for a 10 minute taxi ride to the boat
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
Total Nights
Charter Fee
1
$900
2
$1,700
3
$2,400
4
$3,100
5
$3,800
6
$4,500
* Additional nights are $700 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.
Multi-day, overnight vacation charters are a great way to enjoy The Keys from an ocean view. Enjoy an awesome sailing vacation to Key West, Key Largo or even Biscayne Bay. 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.
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 bow while our guests enjoy their own private aft-cabin with queen-sized bed, private head and private stand-up shower. (See our 
Day 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 3 - Sailing out of Key West we continue downwind to our favorite anchorage - Boca Grande. After anchoring in the beautiful blue-green waters we'll dinghy to shore for snorkeling or swimming off the white-sand beach and bring along a picnic lunch. You can walk along the beach to search for shells or just relax in the sun. Dinner on the boat is a perfect ending to the day.
Day 5 - Sleep in this morning while we prepare you a great breakfast. We can take you into the park for walking the beach or shopping at their nautical gift shop. A short sail back to Marathon completes the trip as we tie up at the marina. Tearful good-byes then a drive back up through the keys to the Miami airport for your flight back home. Or, say in South Beach for a day or two and enjoy the atmosphere of the famous sea-side community.