Acoustic Brunch Sail with Ink + Ash (feat. Gareth Asher + Nicki Thrailkill)

Schooner Woodwind at Annapolis Waterfront Hotel Dock 80 Compromise Street, Annapolis, MD

An Intimate, Acoustic Show with Ink + Ash (feat. Gareth Asher + Nicki Thrailkill) aboard the Schooner Woodwind for a concert on a beautiful sailing boat, including a light delicious brunch on Memorial Day. Band's BIO: In this life, we spend our days in blissful ignorance as to what lies ahead. We work, we play, we ... Read more

Sunset Sail with Eastport Oyster Boys

Schooner Woodwind at Annapolis Waterfront Hotel Dock 80 Compromise Street, Annapolis, MD

 Appointed as the Musical Goodwill Ambassadors by the City of Annapolis and the Maritime Republic of Eastport, the Eastport Oyster Boys love to share their musical celebration and stories of life in Annapolis and on the salty waters the Chesapeake Bay. For over two decades they have educated, amused and delighted thousands with their wit, ... Read more

Sunset Sail with Crab Alley Lite

Schooner Woodwind at Annapolis Waterfront Hotel Dock 80 Compromise Street, Annapolis, MD

Crab Alley founders Jeff Holland and Janie Meneely will join up for a Woodwind cruise and regale the crew with their original songs of the Bay and beyond. Serious or saucy, their songs shed light on recreational boating as well as Chesapeake traditions here on the Bay. www.janiemeneely.com  

June Wine in the Wind – Tommasi Family Estates

Schooner Woodwind at Annapolis Waterfront Hotel Dock 80 Compromise Street, Annapolis, MD

Join us for a two hour sail around the Chesapeake Bay while sampling wonderful wines from Italy.  The representative from the winery will introduce you to four special wines while we are under sail as we explore Italy through the Tommasi Family Estates. The cruise will be a relaxing sail including 3-oz samples of each of the four wines featured. Along ... Read more

$81.00

Sunset Sail with Mike & Kelly Lange

Schooner Woodwind at Annapolis Waterfront Hotel Dock 80 Compromise Street, Annapolis, MD

Mike and Kelly Lange are a husband and wife ukulele duo.  Lifelong boaters, Mike & Kelly sing original and classic material, some with a maritime theme and some with a broader reach. Mike has played thousands of gigs in the mid-Atlantic and a handful overseas during the past several decades. Over the years he has ... Read more

Father’s Day Brunch

Schooner Woodwind at Annapolis Waterfront Hotel Dock 80 Compromise Street, Annapolis, MD

Our Father’s Day Brunch Sail departs Annapolis for a three-hour Brunch cruise at 10:00 am and returns at 1:00 pm. Sailing cruise includes one free Bloody Mary or Mimosa and delicious food: homemade scones, bacon & swiss quiche squares, blackened salmon with cusabi sauce served with hearty bread, grilled flank steak, fresh fruit salad, orange ... Read more

$92.00

Father’s Day Brews in the Breeze Lunch Cruise

Schooner Woodwind at Annapolis Waterfront Hotel Dock 80 Compromise Street, Annapolis, MD

Sail on a lunchtime cruise on the Chesapeake Bay.  Lunch will consist of all your Chesapeake favorites, including crab cakes, served buffet style while sailing on the beautiful Bay! Tickets are $86 per adult and include lunch, two beers, and unlimited soda and water. Additional beer will be available for purchase.  Children under 12 are $49 ... Read more

$86.00

Sunset Sail with Kyle Offidani

Schooner Woodwind at Annapolis Waterfront Hotel Dock 80 Compromise Street, Annapolis, MD

Born and raised in the bay area of Delaware- Kyle Offidani is a Musician and Songcatcher . Musically- Kyle draws inspiration from World music, Instrumental guitar, Roots, Blues, Soul, and Americana music. When listening to the sounds of Kyle, you will hear echoes of these genres Woven into the tapestry of his songs. Kyle writes ... Read more

Sunset Sail with Deanna Dove

Schooner Woodwind at Annapolis Waterfront Hotel Dock 80 Compromise Street, Annapolis, MD

Deanna Dove is best known as the “Island Girl” in her hometown for her compositional writing style about her lifelong experiences on the Chesapeake Bay. She has earned a loyal audience for her ability to craft songs that include elements of rock, pop, blues, alt-country and gospel into a distinctly individual style with a universal ... Read more

Fireworks Cruise

Schooner Woodwind at Annapolis Waterfront Hotel Dock 80 Compromise Street, Annapolis, MD

Join us for a festive cruise celebrating the 4th of July. We will depart from the Annapolis Waterfront Hotel dock at 6:30 pm for a sunset sail with live entertainment by "Ship's Company". We will then anchor close to the fireworks barge for the 9:15 pm fireworks display and return to the dock after the ... Read more

$91.00