Private sailing charters, shared retreats and sailing lessons from Madeira Beach, Florida, on Boca Ciega Bay near John’s Pass. About 30 minutes from Clearwater Beach, downtown St. Petersburg and St. Pete Beach. Every trip sails with a USCG-licensed captain, and most of our captains are women and American Sailing Association (ASA) instructors.
Private charters
Your group only, aboard a 45-foot sailboat with up to 6 guests. Prices are per boat and include the captain. Bring your own food and drinks; we provide water, ice and a cooler.
| Charter | Length | Guests | Price |
|---|---|---|---|
| Sunset Sail | 3 hours | Up to 6 | $650 |
| Half Day Sail | 4 hours | Up to 6 | $750 |
| Full Day Sail | 8 hours | Up to 6 | $1,200 |
| Overnight Charter | 2 to 30 days | Up to 6 | From $2,400 |
| Dry Tortugas Passagemaking | 10 days | Private | $10,000 |
| Teambuilding | 3 hours | Up to 6 per boat | $160 pp |
| Events St. Pete | 3 days | Up to 6 | $3,000 |
| Special Occasions | Full day | Up to 6 | A la carte |
Sunset Sail
Sail out through John’s Pass into the Gulf of Mexico and watch the sun go down from the deck. We leave about two hours before sunset, year round. Our most popular charter for birthdays, anniversaries and visiting friends.
Half Day and Full Day Sails
A half day takes you to Shell Key or the sandbars to anchor, swim, snorkel and watch for dolphins. A full day reaches Egmont Key and its lighthouse, Fort De Soto, or open water in the Gulf with lunch at anchor.
Overnight Charters
Sleep aboard Opal or Serenity, our air-conditioned 45-foot cruising sailboats with private cabins, a galley and a generator. Head north to Clearwater, Dunedin and Tarpon Springs, or south to St. Pete Beach, Longboat Key, Sarasota and Venice. Longer trips reach the Florida Keys.
Dry Tortugas Offshore Passagemaking
A 10-day private offshore passage from St. Petersburg to the Dry Tortugas and back, with night watches and real sea miles.
Teambuilding, Events and Special Occasions
Corporate teams sail with everyone taking a turn at the helm. Events St. Pete puts you on the waterfront in your own yacht; the next date is March 11 to 14, 2027. For proposals, weddings, milestone birthdays, memorials and photo shoots, tell us the occasion and we plan the sail.
Shared charters and retreats
Join other women on a scheduled trip. Priced per person.
| Trip | Length | Dates | Price |
|---|---|---|---|
| Yoga Charter | 2 days | See calendar | From $495 pp |
| Book Club: First Light | 3 days | Mar 20 to 22, 2027 | $1,200 pp |
| Book Club: Gift from the Sea | 6 days | June 2027, TBA | $2,000 pp |
| Girls Getaways | Weekend | On Instagram | See calendar |
The Book Club trips bring a book to life on the water, all inclusive: First Light by Cole Brauer and Gift from the Sea by Anne Morrow Lindbergh. Girls Getaways are women-only weekends with a female captain; learn as much or as little as you like.
Learn to sail
Taught by USCG captains who are ASA-certified instructors, aboard our Catalina 25 and our 45-footers. Couples and women-only sessions welcome.
| Course | Length | Class size | Price |
|---|---|---|---|
| Private Instruction | 4 to 8 hours | Up to 6 | From $450 |
| Anchoring Clinic | 5 hours | Up to 6 | $225 pp |
| Docking Clinic | 5 hours | Up to 5 | $275 pp |
| Night Sailing Intro | Overnight | Up to 5 | $600 pp |
Good to know
- Booking: online on our Charters page, or call or text 727-238-7715.
- Weather: the captain makes the call on the day. Weather cancellations are rebooked or refunded in full.
- Guests: adults 18 and over; ages 5 to 17 with a parent or guardian. No pets.
- Gift cards: any amount, redeemable on any charter or class. See Gift Cards.
- Where we meet: 410 150th Ave, Madeira Beach, FL 33708.
- More questions: see our FAQ.
Ready to get on the water?