Events Calendar

October 2026
Sun	Mon	Tue	Wed	Thu	Fri	Sat

27	28	29	30	1 Bachelorette/Bachelor Party Cruise Beer Tasting Cruise Full-Day Private Sail Half-Day Private Sails Marriage Proposal Engagement Cruise Two Hour Chesapeake Day Sail on Lady Patty Two Hour Relaxing Chesapeake Day Sail on Epiphany Wine Tasting Cruise Happiest of Hours at The Corner Bar at Corahs’s Chesapeake Bay Sunset Champagne Cruise on Epiphany Chesapeake Bay Sunset Champagne Cruise on Lady Patty St Michaels Running Company Fit Friends	2 Bachelorette/Bachelor Party Cruise Beer Tasting Cruise Full-Day Private Sail Half-Day Private Sails Marriage Proposal Engagement Cruise Two Hour Chesapeake Day Sail on Lady Patty Two Hour Relaxing Chesapeake Day Sail on Epiphany Wine Tasting Cruise Happiest of Hours at The Corner Bar at Corahs’s Friday Sandwich Special at The Fool's Lantern Chesapeake Bay Sunset Champagne Cruise on Epiphany Chesapeake Bay Sunset Champagne Cruise on Lady Patty	3 St. Michaels Farmers' Market Bachelorette/Bachelor Party Cruise Beer Tasting Cruise Full-Day Private Sail Half-Day Private Sails Marriage Proposal Engagement Cruise Two Hour Chesapeake Day Sail on Lady Patty Two Hour Relaxing Chesapeake Day Sail on Epiphany Wine Tasting Cruise Chesapeake Bay Sunset Champagne Cruise on Epiphany Chesapeake Bay Sunset Champagne Cruise on Lady Patty
4 Bachelorette/Bachelor Party Cruise Beer Tasting Cruise Full-Day Private Sail Half-Day Private Sails Marriage Proposal Engagement Cruise Two Hour Chesapeake Day Sail on Lady Patty Two Hour Relaxing Chesapeake Day Sail on Epiphany Wine Tasting Cruise All Day Happy Hour, Sundays at The Fool's Lantern Chesapeake Bay Sunset Champagne Cruise on Epiphany Chesapeake Bay Sunset Champagne Cruise on Lady Patty	5 Bachelorette/Bachelor Party Cruise Beer Tasting Cruise Full-Day Private Sail Half-Day Private Sails Marriage Proposal Engagement Cruise Two Hour Chesapeake Day Sail on Lady Patty Two Hour Relaxing Chesapeake Day Sail on Epiphany Wine Tasting Cruise MARGARITA MONDAYS at San Miguels Happiest of Hours at The Corner Bar Chesapeake Bay Sunset Champagne Cruise on Epiphany Chesapeake Bay Sunset Champagne Cruise on Lady Patty Monday Night Trivia with DJ Chuckie	6 Bachelorette/Bachelor Party Cruise Beer Tasting Cruise Full-Day Private Sail Half-Day Private Sails Marriage Proposal Engagement Cruise Two Hour Chesapeake Day Sail on Lady Patty Two Hour Relaxing Chesapeake Day Sail on Epiphany Wine Tasting Cruise Happiest of Hours at The Corner Bar at Corahs’s TACO TUESDAY at San Miguels Chesapeake Bay Sunset Champagne Cruise on Epiphany Chesapeake Bay Sunset Champagne Cruise on Lady Patty	7 Bachelorette/Bachelor Party Cruise Beer Tasting Cruise Full-Day Private Sail Half-Day Private Sails Marriage Proposal Engagement Cruise Two Hour Chesapeake Day Sail on Lady Patty Two Hour Relaxing Chesapeake Day Sail on Epiphany Wine Tasting Cruise Chesapeake Bay Sunset Champagne Cruise on Epiphany Chesapeake Bay Sunset Champagne Cruise on Lady Patty	8 Bachelorette/Bachelor Party Cruise Beer Tasting Cruise Full-Day Private Sail Half-Day Private Sails Marriage Proposal Engagement Cruise Two Hour Chesapeake Day Sail on Lady Patty Two Hour Relaxing Chesapeake Day Sail on Epiphany Wine Tasting Cruise Happiest of Hours at The Corner Bar at Corahs’s Chesapeake Bay Sunset Champagne Cruise on Epiphany Chesapeake Bay Sunset Champagne Cruise on Lady Patty St Michaels Running Company Fit Friends	9 Bachelorette/Bachelor Party Cruise Beer Tasting Cruise Full-Day Private Sail Half-Day Private Sails Marriage Proposal Engagement Cruise Two Hour Chesapeake Day Sail on Lady Patty Two Hour Relaxing Chesapeake Day Sail on Epiphany Wine Tasting Cruise Happiest of Hours at The Corner Bar at Corahs’s Friday Sandwich Special at The Fool's Lantern Chesapeake Bay Sunset Champagne Cruise on Epiphany Chesapeake Bay Sunset Champagne Cruise on Lady Patty	10 St. Michaels Farmers' Market Bachelorette/Bachelor Party Cruise Beer Tasting Cruise Full-Day Private Sail Half-Day Private Sails Marriage Proposal Engagement Cruise Two Hour Chesapeake Day Sail on Lady Patty Two Hour Relaxing Chesapeake Day Sail on Epiphany Wine Tasting Cruise Chesapeake Bay Sunset Champagne Cruise on Epiphany Chesapeake Bay Sunset Champagne Cruise on Lady Patty
11 Bachelorette/Bachelor Party Cruise Beer Tasting Cruise Full-Day Private Sail Half-Day Private Sails Marriage Proposal Engagement Cruise Two Hour Chesapeake Day Sail on Lady Patty Two Hour Relaxing Chesapeake Day Sail on Epiphany Wine Tasting Cruise All Day Happy Hour, Sundays at The Fool's Lantern Chesapeake Bay Sunset Champagne Cruise on Epiphany Chesapeake Bay Sunset Champagne Cruise on Lady Patty	12 Bachelorette/Bachelor Party Cruise Beer Tasting Cruise Full-Day Private Sail Half-Day Private Sails Marriage Proposal Engagement Cruise Two Hour Chesapeake Day Sail on Lady Patty Two Hour Relaxing Chesapeake Day Sail on Epiphany Wine Tasting Cruise MARGARITA MONDAYS at San Miguels Happiest of Hours at The Corner Bar Chesapeake Bay Sunset Champagne Cruise on Epiphany Chesapeake Bay Sunset Champagne Cruise on Lady Patty Monday Night Trivia with DJ Chuckie	13 Bachelorette/Bachelor Party Cruise Beer Tasting Cruise Full-Day Private Sail Half-Day Private Sails Marriage Proposal Engagement Cruise Two Hour Chesapeake Day Sail on Lady Patty Two Hour Relaxing Chesapeake Day Sail on Epiphany Wine Tasting Cruise Happiest of Hours at The Corner Bar at Corahs’s TACO TUESDAY at San Miguels Chesapeake Bay Sunset Champagne Cruise on Epiphany Chesapeake Bay Sunset Champagne Cruise on Lady Patty	14 Bachelorette/Bachelor Party Cruise Beer Tasting Cruise Full-Day Private Sail Half-Day Private Sails Marriage Proposal Engagement Cruise Two Hour Chesapeake Day Sail on Lady Patty Two Hour Relaxing Chesapeake Day Sail on Epiphany Wine Tasting Cruise Chesapeake Bay Sunset Champagne Cruise on Epiphany Chesapeake Bay Sunset Champagne Cruise on Lady Patty	15 Bachelorette/Bachelor Party Cruise Beer Tasting Cruise Full-Day Private Sail Half-Day Private Sails Marriage Proposal Engagement Cruise Two Hour Chesapeake Day Sail on Lady Patty Two Hour Relaxing Chesapeake Day Sail on Epiphany Wine Tasting Cruise Happiest of Hours at The Corner Bar at Corahs’s Chesapeake Bay Sunset Champagne Cruise on Epiphany Chesapeake Bay Sunset Champagne Cruise on Lady Patty St Michaels Running Company Fit Friends	16 Bachelorette/Bachelor Party Cruise Beer Tasting Cruise Full-Day Private Sail Half-Day Private Sails Marriage Proposal Engagement Cruise Two Hour Chesapeake Day Sail on Lady Patty Two Hour Relaxing Chesapeake Day Sail on Epiphany Wine Tasting Cruise Happiest of Hours at The Corner Bar at Corahs’s Friday Sandwich Special at The Fool's Lantern Chesapeake Bay Sunset Champagne Cruise on Epiphany Chesapeake Bay Sunset Champagne Cruise on Lady Patty	17 St. Michaels Farmers' Market Bachelorette/Bachelor Party Cruise Beer Tasting Cruise Full-Day Private Sail Half-Day Private Sails Marriage Proposal Engagement Cruise Two Hour Chesapeake Day Sail on Lady Patty Two Hour Relaxing Chesapeake Day Sail on Epiphany Wine Tasting Cruise Chesapeake Bay Sunset Champagne Cruise on Epiphany Chesapeake Bay Sunset Champagne Cruise on Lady Patty
18 Bachelorette/Bachelor Party Cruise Beer Tasting Cruise Full-Day Private Sail Half-Day Private Sails Marriage Proposal Engagement Cruise Two Hour Chesapeake Day Sail on Lady Patty Two Hour Relaxing Chesapeake Day Sail on Epiphany Wine Tasting Cruise All Day Happy Hour, Sundays at The Fool's Lantern Chesapeake Bay Sunset Champagne Cruise on Epiphany Chesapeake Bay Sunset Champagne Cruise on Lady Patty	19 Bachelorette/Bachelor Party Cruise Beer Tasting Cruise Full-Day Private Sail Half-Day Private Sails Marriage Proposal Engagement Cruise Two Hour Chesapeake Day Sail on Lady Patty Two Hour Relaxing Chesapeake Day Sail on Epiphany Wine Tasting Cruise MARGARITA MONDAYS at San Miguels Happiest of Hours at The Corner Bar Chesapeake Bay Sunset Champagne Cruise on Epiphany Chesapeake Bay Sunset Champagne Cruise on Lady Patty Monday Night Trivia with DJ Chuckie	20 Bachelorette/Bachelor Party Cruise Beer Tasting Cruise Full-Day Private Sail Half-Day Private Sails Marriage Proposal Engagement Cruise Two Hour Chesapeake Day Sail on Lady Patty Two Hour Relaxing Chesapeake Day Sail on Epiphany Wine Tasting Cruise Happiest of Hours at The Corner Bar at Corahs’s TACO TUESDAY at San Miguels Chesapeake Bay Sunset Champagne Cruise on Epiphany Chesapeake Bay Sunset Champagne Cruise on Lady Patty	21 Bachelorette/Bachelor Party Cruise Beer Tasting Cruise Full-Day Private Sail Half-Day Private Sails Marriage Proposal Engagement Cruise Two Hour Chesapeake Day Sail on Lady Patty Two Hour Relaxing Chesapeake Day Sail on Epiphany Wine Tasting Cruise Chesapeake Bay Sunset Champagne Cruise on Epiphany Chesapeake Bay Sunset Champagne Cruise on Lady Patty	22 Bachelorette/Bachelor Party Cruise Beer Tasting Cruise Full-Day Private Sail Half-Day Private Sails Marriage Proposal Engagement Cruise Two Hour Chesapeake Day Sail on Lady Patty Two Hour Relaxing Chesapeake Day Sail on Epiphany Wine Tasting Cruise Happiest of Hours at The Corner Bar at Corahs’s Chesapeake Bay Sunset Champagne Cruise on Epiphany Chesapeake Bay Sunset Champagne Cruise on Lady Patty St Michaels Running Company Fit Friends	23 Bachelorette/Bachelor Party Cruise Beer Tasting Cruise Full-Day Private Sail Half-Day Private Sails Marriage Proposal Engagement Cruise Two Hour Chesapeake Day Sail on Lady Patty Two Hour Relaxing Chesapeake Day Sail on Epiphany Wine Tasting Cruise Happiest of Hours at The Corner Bar at Corahs’s Friday Sandwich Special at The Fool's Lantern Chesapeake Bay Sunset Champagne Cruise on Epiphany Chesapeake Bay Sunset Champagne Cruise on Lady Patty	24 St. Michaels Farmers' Market Bachelorette/Bachelor Party Cruise Beer Tasting Cruise Full-Day Private Sail Half-Day Private Sails Marriage Proposal Engagement Cruise Two Hour Chesapeake Day Sail on Lady Patty Two Hour Relaxing Chesapeake Day Sail on Epiphany Wine Tasting Cruise Chesapeake Bay Sunset Champagne Cruise on Epiphany Chesapeake Bay Sunset Champagne Cruise on Lady Patty
25 Bachelorette/Bachelor Party Cruise Beer Tasting Cruise Full-Day Private Sail Half-Day Private Sails Marriage Proposal Engagement Cruise Two Hour Chesapeake Day Sail on Lady Patty Two Hour Relaxing Chesapeake Day Sail on Epiphany Wine Tasting Cruise All Day Happy Hour, Sundays at The Fool's Lantern Chesapeake Bay Sunset Champagne Cruise on Epiphany Chesapeake Bay Sunset Champagne Cruise on Lady Patty	26 Bachelorette/Bachelor Party Cruise Beer Tasting Cruise Full-Day Private Sail Half-Day Private Sails Marriage Proposal Engagement Cruise Two Hour Chesapeake Day Sail on Lady Patty Two Hour Relaxing Chesapeake Day Sail on Epiphany Wine Tasting Cruise MARGARITA MONDAYS at San Miguels Happiest of Hours at The Corner Bar Chesapeake Bay Sunset Champagne Cruise on Epiphany Chesapeake Bay Sunset Champagne Cruise on Lady Patty Monday Night Trivia with DJ Chuckie	27 Bachelorette/Bachelor Party Cruise Beer Tasting Cruise Full-Day Private Sail Half-Day Private Sails Marriage Proposal Engagement Cruise Two Hour Chesapeake Day Sail on Lady Patty Two Hour Relaxing Chesapeake Day Sail on Epiphany Wine Tasting Cruise Happiest of Hours at The Corner Bar at Corahs’s TACO TUESDAY at San Miguels Chesapeake Bay Sunset Champagne Cruise on Epiphany Chesapeake Bay Sunset Champagne Cruise on Lady Patty	28 Bachelorette/Bachelor Party Cruise Beer Tasting Cruise Full-Day Private Sail Half-Day Private Sails Marriage Proposal Engagement Cruise Two Hour Chesapeake Day Sail on Lady Patty Two Hour Relaxing Chesapeake Day Sail on Epiphany Wine Tasting Cruise Chesapeake Bay Sunset Champagne Cruise on Epiphany Chesapeake Bay Sunset Champagne Cruise on Lady Patty	29 Bachelorette/Bachelor Party Cruise Beer Tasting Cruise Full-Day Private Sail Half-Day Private Sails Marriage Proposal Engagement Cruise Two Hour Chesapeake Day Sail on Lady Patty Two Hour Relaxing Chesapeake Day Sail on Epiphany Wine Tasting Cruise Happiest of Hours at The Corner Bar at Corahs’s Chesapeake Bay Sunset Champagne Cruise on Epiphany Chesapeake Bay Sunset Champagne Cruise on Lady Patty St Michaels Running Company Fit Friends	30 Bachelorette/Bachelor Party Cruise Beer Tasting Cruise Full-Day Private Sail Half-Day Private Sails Marriage Proposal Engagement Cruise Two Hour Chesapeake Day Sail on Lady Patty Two Hour Relaxing Chesapeake Day Sail on Epiphany Wine Tasting Cruise Happiest of Hours at The Corner Bar at Corahs’s Friday Sandwich Special at The Fool's Lantern Chesapeake Bay Sunset Champagne Cruise on Epiphany Chesapeake Bay Sunset Champagne Cruise on Lady Patty	31 St. Michaels Farmers' Market Bachelorette/Bachelor Party Cruise Beer Tasting Cruise Full-Day Private Sail Half-Day Private Sails Marriage Proposal Engagement Cruise Two Hour Chesapeake Day Sail on Lady Patty Two Hour Relaxing Chesapeake Day Sail on Epiphany Wine Tasting Cruise Chesapeake Bay Sunset Champagne Cruise on Epiphany Chesapeake Bay Sunset Champagne Cruise on Lady Patty

Events Calendar

October 2026