Charlotte Harbor Sailing School 
Charlotte Harbor Sailing
Sailing Lessons in Southwest Florida Sailboat Charters in Southwest Florida
 

Calypsa Cruises

Sailing Charlotte Harbor,
Exploring the Gulf Islands,
Navigating S.W. Florida,
Sail the Gulf of Mexico and Beyond...

Why charter the entire boat unless you need the whole boat? Our sail cruises are limited to six passengers. Buy as many or as few of the six spaces as you wish.

Our Planned Cruises

The Calypsa is available for private charters where you set the agenda and course.

Sunset Cruises
90 Minutes
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$35
Half Day with Sunset Cruise
4 Hours
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$55
Full Day with Lunch Cruise
8 Hours
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$75
Naples Cruise
2 Days
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$150-$200
Dry Tortugas Cruise
3 Days
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$250-$300
Key West & Dry Tortugas Cruise
Week
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$600-$750
Cozumel, Honduras, Caymans, Jamaica, Cruise
Month
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$120-$150 per day
$600-$750 per week
$1,800-$2,250 Month
All prices are per person and do not include sales tax, food, or gratuity. Prices include drinking water, eye patch, and cannon smoke

An Adventure Awaits You!

Fire the Cannon
Hoist a Sail
Take the Helm
Ride the Sea
Play with a Dolphin
Steal some Sun
Kiss a Wave
Pull in the Anchor
Explore an Island
Rekindle a Relationship

Awaken your Soul and Live

Photo Gallery of Calypsa

Click any of the images above for a larger view.
Click any of the images above for a larger view.