Private sailing charters in Key West

Thirsty Lady is a 45-foot Beneteau sailing yacht run by a family of USCG licensed captains. Every charter is private, so the whole boat is yours.

Private Overnight Charter

Thirsty Lady under full sail on turquoise water at sunset off Key West

Your own 45-ft sailboat with three private cabins and a captain. Sail by day and spend your nights at Key West resort marinas with pools, restaurants and live music.

Stay aboard for 2, 3 or 4 nights. A sunset sail and daily sailing and snorkeling are included, for up to six guests.

From $1,100 per night, plus tax

Private Sail and Snorkel

Snorkeler swimming beside a sea turtle on the reef during a Thirsty Lady sail and snorkel trip

A private half-day sail to the reef for up to 6 guests. Snorkel gear included, about 4 hours on the water.

About four hours on the water for up to six guests. Snorkel the reef or spend the day sailing.

$800 for the whole boat, plus tax

What our guests say

★★★★★

“Hands down the best part of our Key West trip.”

Todd · Avon, Connecticut

★★★★★

“This was the best place we've ever stayed at and we travel quite a bit.”

Rebekah

★★★★★

“They truly made you feel like you were part of their family.”

Kristina · Laramie, Wyoming

Read all guest reviews or check dates and book