SKIPJACK TOURS

Annapolis Sailing Cruise

Wilma Lee’s Sailing Season for 2026 is from April 12th through October 31st! We can’t wait to welcome you aboard!

Heritage Tours	Sunset Cruises	Wednesday Night Race Watch Party	Specialty Cruises
April 12th April 18th April 19th April 25th	April 25th	April 22nd April 29th	Wilma Lee True Crime Cruise – Murder on the Waterfront
Book a Heritage Tour ticket here	Book a Sunset Cruise ticket here	Book a WNR Cruise ticket here	Book a ticket here

Heritage Cruise

Explore Annapolis’s maritime history and Chesapeake Bay ecology aboard the historic Skipjack Wilma Lee. Learn about the city’s boat building industry, Chesapeake Bay Waterman history, and oyster harvesting. Discover local landmarks like Carr’s and Elktonia Beach, Eastport, and the Naval Academy. Guides will highlight native Chesapeake Bay wildlife. Ideal for Bay enthusiasts and professionals. Complimentary water provided onboard.

We had a really great time! We asked a lot of questions- to the point where I was a tiny bit worried that we were annoying the crew, but instead when we disembarked, they thanked us- which made my day. An excellent experience.

Excellent experience low-cost relative to time/experience. The crew is amazing, friendly, informative, and great with kids. I highly recommend it.

We signed up to go while visiting our grandson and his girlfriend. All of us enjoyed the tour and were grateful the weather remained pleasant on the 11th even though storms were threatening. We also enjoyed seeing the museum displays and meeting Mac!

Sunset Cruise

Cruise with us for a memorable two-hour voyage, soaking in the golden hour on the Chesapeake Bay. Enjoy complimentary snacks and beverages! 21+

I had the best time on the Wilma Lee last week with my girlfriends for a sunset cruise! The beautifully restored skipjack is the perfect outing for a girls night! Such a unique experience and a perfect way to make memories with your besties! I highly recommend the Annapolis maritime Museum and the Wilma Lee!

The crew and captain Rick were all very welcoming, knowledgeable and fun. We have been on many sunset cruises and have never had this amazing level of service and quality, especially for the price. We will definitely be back.

We attended as part of my sister’s bachelorette trip and the entire group agreed this was an incredible experience! The Captain and crew were incredibly friendly, courteous, and helped make the excursion so memorable! They built a fun atmosphere while tying in some history and knowledge of the Annapolis area! The weather and sunset were beautiful!

Wednesday Night Races Watch Party

Join us for a two-hour watch party of Annapolis’ weekly Wednesday Night Races, where you’ll have a front-row view of sailors competing in this quintessential Chesapeake Bay event! Enjoy complimentary snacks and beverages!

We did the Wednesday night cruise on the the Wilma Lee to watch the boat races, and it was such a fun experience! The crew was amazing-special thanks to Andrew, Mollie, Captain Rick, and the rest of the staff who made the night so enjoyable. Our group of 11 had the best time, and the atmosphere on the boat was fantastic.

This was such an amazing experience. The communication on when/where to arrive was excellent. The entire sailing crew was so friendly and very informative. We felt super safe the entire trip. 10/10 would recommend to anyone visiting Annapolis.

We had an excellent time! We went for my dad's 60th birthday and the crew was so fun and welcoming. Made the evening feel so special.

Wilma Lee Specialty Cruise

A Chilling Evening of Dark Secrets, Deadly Scandals, and Historic Crime

Step aboard the Wilma Lee, a historic skipjack steeped in Chesapeake Bay history, for a thrilling two-hour cruise that explores Annapolis’s most notorious true crime stories. With local storyteller Melissa Huston of Annapolis Ghost Tours leading the way, this adults-only evening brings waterfront whispers, real-life murder cases, and macabre maritime history to life. Your ticket includes culinary creations from Bread and Butter Kitchen with complimentary beverages.

Feel the thrill of mystery and intrigue as you glide through the historic waterways where these dark tales unfolded.

Private Charter

Book Wilma Lee for your next event and enjoy an authentic setting perfect for a variety of occasions – wedding, birthday celebration, anniversary, graduation, reunion, vow renewal, bachelor or bachelorette party, cocktail gathering, corporate team building, or a casual cruise on the water. Our 2-hour private charters, accommodate up to 35 passengers, making it ideal for your next private event or celebration.

History of Wilma Lee

The Wilma Lee is 47 feet on the deck, almost 75 feet overall, including the bowsprit and the davit. One of only a few remaining Chesapeake Bay Skipjacks, the Wilma Lee is a member of the last commercial sailing fleet in the United States as it is listed on the National Register of Historic Places.

Wilma Lee Public Cruises – FAQs

Duration

Heritage Tour, Sunset Cruise and Wednesday Night Races Watch Party are all 2 hours

Location

Heritage Tour and Wednesday Night Races Watch Party leave from Annapolis Maritime Museum Docks, 723 Second Street, Annapolis, MD 21403

Sunset Cruises leave from our Park Campus at 7300 Edgewood Road, Annapolis, MD 21403

IMPORTANT NOTE: On occasion, depending on events at the Museum and Park, we may switch the dock pickup location. Please check your messages and the website before you set off, to make sure you are going to the correct pickup dock.

Boarding: Begins 15 minutes before departure

Food and Beverages

Heritage Tour – Complimentary water is provided onboard, but feel free to bring your personal water bottle. You may bring your own single wrap sandwich but no shared food can be brought aboard.

Sunset Cruise and Wednesday Night Races Watch Party – These cruises include soft drinks, wine, beer or canned cocktails as well as packet snacks.

IMPORTANT NOTE: No outside alcohol is permitted onboard for public cruises, per our liquor license

What to bring

Your camera
Sunscreen, hat and sunglasses – there is NO shade onboard
a sense of adventure

Cancellation policy

We cruise rain or shine, but we will cancel two hours prior to departure for high winds or thunderstorms. We will contact you via text on the cell phone number provided. Cruises are subject to cancellation due to weather and unforeseen conditions and are fully refundable.

No refunds for guest cancellations or no-shows.

Gratuities are appreciated!

If you need assistance with your order, please email wilmalee@amaritime.org. We will respond during regular business hours, Monday through Friday from 8:00 AM to 5:00 PM.