Open Search Modal

Wine Tasting Cruise

Wine Tasting Cruise

101 N Harbor Rd, St Michaels, MD 21663, USA
WebsiteDirections

Sip, savor, and sail! Experience a unique blend of wine tasting and scenic sailing with St. Michaels Sailing Charters.

Visit Host Website

Other Upcoming Events

Fajita Fridays at San Miguels
JUL 31 – JUL 30

Fajita Fridays at San Miguels

🔥 **Fajita Fridays at San Miguels** 🔥 There's nothing quite like the sound of sizzling fajitas arriving a…

Ladies Night - Fridays at The Galley
JUL 31 – JUL 23

Ladies Night – Fridays at The Galley

Ladies Night at The Galley Friday evenings deserve something special. Join us every Friday from 4:00–7:00 P…

Live Music at Foxy’s! Jackson Cole! 🎶🎶
JUL 31 – AUG 1

Live Music at Foxy’s! Jackson Cole! 🎶🎶

Jackson Cole making his live music debut at Foxy’s! Come show him some love the Foxy’s way!

Easton Farmers Market
AUG 1 – DEC 26

Easton Farmers Market

Produce, vegetables, baked goods (including "The Bread Guy"), artisans, and coffee. Pedestrian market, plen…

SMCC Sunrise Yoga
AUG 1

SMCC Sunrise Yoga

SMCC Sunrise Yoga

St. Michaels Farmers Market
AUG 1 – NOV 21

St. Michaels Farmers Market

A free weekly producer-only farmers market and community gathering space featuring the Eastern Shore's best…

Cars & Coffee at the Oxford Community Center
AUG 1

Cars & Coffee at the Oxford Community Center

August 1, 2026, 8:30-10:30am – Cars and Coffee at the OCC Sponsored by Prestige Auto Vault, Eat Sprout & Do…

Floral Atelier
AUG 1 – FEB 27

Floral Atelier

Whether it's Mother's Day or any day, treat yourself to a three-hour intensive floral arranging class with…

Sample Saturdays: Free Wine Tasting at Simpatico, Italy's Finest
AUG 1 – DEC 26

Sample Saturdays: Free Wine Tasting at Simpatico, Italy's Finest

Are you a lover of Italian wines? In addition to our complimentary daily wine tastings, join us every Satur…

Classic Sicilian Bites Cooking Class 12 Noon
AUG 1

Classic Sicilian Bites Cooking Class 12 Noon

Join us for a class where we explore classic Sicilian flavors with 3 courses and 3 wines! Taught by Chef Da…

Classic Sicilian Bites Cooking Class 2 PM
AUG 1

Classic Sicilian Bites Cooking Class 2 PM

Join us for a class where we explore classic Sicilian flavors with 3 courses and 3 wines! Taught by Chef Da…

Patriot Cruises: Live Music Cruises with Michael Waskey
AUG 1 – AUG 2

Patriot Cruises: Live Music Cruises with Michael Waskey

On Saturday, Aug. 1, Michael Waskey will be performing during our Evening River Cruise at 5pm and Sunset Ri…

Patriot vs. Loyalist Debate
AUG 1

Patriot vs. Loyalist Debate

The debate features Patriot Edward Lloyd IV portrayed by Mickey Terrone and Tory James Tighlman portrayed b…

Live music at Foxy’s! Dubtone Vibration! 🎶🎶
AUG 1 – AUG 2

Live music at Foxy’s! Dubtone Vibration! 🎶🎶

DubTone Vibration live at Foxy’s! Come hang

Jump: America’s Van Halen Experience | VH1 Tour
AUG 1 – AUG 2

Jump: America’s Van Halen Experience | VH1 Tour

JUMP is one of the top David Lee Roth-era Van Halen tributes on the planet! Their sound reflects the same s…

FREE Avalon Outdoor Concert Series: US Naval Academy Band Electric Brigade
AUG 1 – AUG 2

FREE Avalon Outdoor Concert Series: US Naval Academy Band Electric Brigade

Celebrate America’s 250th anniversary all summer long with the Avalon Foundation’s Outdoor Concert Series!…

Talbot250 at the Avalon Summer Concert Series: U.S. Naval Academy Band
AUG 1

Talbot250 at the Avalon Summer Concert Series: U.S. Naval Academy Band

Join Talbot250 for an evening of music, community, and celebration at the Avalon Summer Concert Series feat…

Electric Brigade in Easton, Maryland: Avalon Foundation Summer Concert
AUG 1 – AUG 2

Electric Brigade in Easton, Maryland: Avalon Foundation Summer Concert

Be there live to see Jump – Van Halen Experience perform at Avalon Theatre – MD in Easton on Saturday, Augu…

Come Alive!
AUG 1

Come Alive!

Come Alive!: Music from Stage and Screen featuring selections from Bernstein, Copland, Sondheim, Pasek and…

Concert: Steve Lowe and the Lowe Downs
AUG 1 – AUG 2

Concert: Steve Lowe and the Lowe Downs

August 1, 2026, 7:30pm – Concert: Steve Lowe and the Lowe Downs Steve Lowe is one of the Eastern Shore’s mo…

An Evening with Isabel Dumaa
AUG 2

An Evening with Isabel Dumaa

Rising artist Isabel Dumaa brings her acclaimed indie-pop sound to the stage LIVE! at The Ebenezer

Bottomless Mimosas - Sunday Brunch
AUG 2 – MAY 30

Bottomless Mimosas – Sunday Brunch

Sunday mornings were made for this. Join us in the heart of St. Michaels for award-winning brunch, bottomle…

Sangria Sundays at San Miguels Mexican Food
AUG 2 – JUL 25

Sangria Sundays at San Miguels Mexican Food

Sundays at San Miguels are made for slowing down, sipping longer, and savoring every moment. Join us for Sa…

Live music at Foxy’s! Uncle Ward! 🎶🏝️
AUG 2

Live music at Foxy’s! Uncle Ward! 🎶🏝️

Sunday Funday with Uncle Ward? What a treat! See you from 4-7 on the patio!

C420 Beginner - Week 8
AUG 3 – AUG 7

C420 Beginner – Week 8

This class is for students over 100 pounds and beginners in sailing personal sailboats. We expect students…

Opti Beginner - Week 8
AUG 3 – AUG 7

Opti Beginner – Week 8

This class is for students under 100 pounds and eight or older who are beginners in sailing personal sailbo…

Baltimore Symphony Orchestra
AUG 4 – AUG 5

Baltimore Symphony Orchestra

August 4, 2026, 7:00pm – Baltimore Symphony Orchestra The BSO's Music for Maryland Summer Tour heads to the…

Live music at Foxy’s! Kenny Haddaway! 🎶🎶
AUG 5 – AUG 6

Live music at Foxy’s! Kenny Haddaway! 🎶🎶

Who says you have to save the fun for the weekends?? Come hang Wednesday at foxys!

Rum Running on the Skipjack
AUG 5 – AUG 26

Rum Running on the Skipjack

Join us every Wednesday, June – August, from 5:30–7:00 PM for an evening of sailing, storytelling, and hand…

Spy Nights with William Ehrhart, PhD
AUG 5 – AUG 6

Spy Nights with William Ehrhart, PhD

“Bill Ehrhart is the finest combat veteran poet to come out of the Vietnam War. But his poetry transcends h…

Shaping Her Path: The Importance of Mentoring Young Women
AUG 6

Shaping Her Path: The Importance of Mentoring Young Women

Women to Watch is excited to present the 4th Annual Women to Watch Summer Speaker Series.

Oxford Regatta, including Log Canoes
AUG 7 – AUG 9

Oxford Regatta, including Log Canoes

Watch the races along the Tred Avon River from one of our numerous waterfront areas in Oxford, Maryland! Ox…

Intro to Sailing Small Craft II
AUG 7

Intro to Sailing Small Craft II

Join us for the second part of our introductory course in sailing small craft on the Miles River.\n

Coffee & Wood Chips
AUG 7 – SEP 4

Coffee & Wood Chips

Join CBMM’s Vessel Conservation Manager Sam Hilgartner in the Shipyard for Coffee & Wood Chips. Sam will gi…

A MIDSUMMER EVENING
AUG 7

A MIDSUMMER EVENING

A Midsummer Evening Join us for a special evening celebrating the seasonal bounty of Maryland’s Eastern Sho…

First Friday Gallery Walk
AUG 7 – DEC 4

First Friday Gallery Walk

Join us every First Friday April to December in downtown Easton for the First Friday Gallery Walk! Our gall…

Live music at Foxy’s! Dave Hawkins! 🎶🎶
AUG 7 – AUG 8

Live music at Foxy’s! Dave Hawkins! 🎶🎶

Come hang with Dave Hawkins from 6-9!

The Rocketeer - Outdoor Movie Night @ The Easton Airport
AUG 8

The Rocketeer – Outdoor Movie Night @ The Easton Airport

The Rocke-who? The Rocketeer! Bring a chair and a blanket for cinema under the stars! Our movie nights are…

Cars and Coffee
AUG 8 – OCT 10

Cars and Coffee

Join the Classic Motor Museum the second Saturday of the month from 9 a.m. to 11 a.m. for cars and coffee….

Log Canoe Racing
AUG 8 – AUG 23

Log Canoe Racing

For more than a century, log canoe racing has been the heartbeat of Chesapeake Bay summers — a breathtaking…

Nearby Places to Explore

5 miles range
No nearby places found for this filter.