Tour & Travel Agents and Operators in Annapolis, United States

"Whether you want to host a business reception, a bridal shower, a wedding itself, a sunset cruise with your beloved, or just want to spend a relaxing afternoon on the water in true elegance, A Classic Sailing Adventure can work with you to make sure that everything is sjust as you desire.

The schooner Patricia Divine can carry up to 25 passengers for day cruises and we have arrangements with several of the best caterers in the Annapolis area so that your specific choice of refreshments can be easily accommodated. For longer cruises, the Patricia Divine has sleeping accommodations for up to six and of course full amenities, including climate control and laundry.

A Classic Sailing Adventure operates out of Annapolis, Maryland, which is centrally located on the Chesapeake Bay. Directions

While many of our customers enjoy simply sailing on the beautiful waters of the Bay, others prefer to travel to and from some of the picturesque destinations on the Bay. St. Michael’s, Oxford, Solomon’s Island, and Rockhall are just some of the destinations that are within a day’s sail of Annapolis. And, of course, longer cruises can reach destinations along t"

Contact Info.:

Phone: (410) 224-8809
A Classic Sailing Adventure, Inc.
2708 Coriander Place
Edgewater, Maryland 21307

"Imagine...! offers you the opportunity to set sail aboard a seventy-six foot, gaff-rigged, wood schooner on the beautiful Chesapeake Bay. With her sleek hull and large sail area, the Schooner Imagine...! is specially designed to provide fast, comfortable cruising. Built in 1997 of cedar, fir, cypress, and mahogany, she can accommodate forty-eight passengers for day charters and up to ten guests for multi-day cruises.
One of Annapolis’ premiere charter boats, Imagine...! makes the perfect setting for your next corporate outing, family reunion, wedding, special event, or any other gathering. We also offer teambuilding programs with expert facilitators to ensure that your group returns to the office with more than just a sunburn, crabcakes and t-shirts. For the adventure of a lifetime join us in October for the Schooner Race. And keep an eye on our News & Events page to keep up-to-date on special charters such as photography workshops, singles cruises, charity events and other exciting opportunities. We hope you enjoy your visit to our website and we look forward to the possilbility of sailing with you this year on board Imagine...!.
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Contact Info.:

Phone: 410-216-9100
PO Box 1469
Annapolis, MD 21404-1469

"Woodwind Offers...

2-Hour Public Sailing Cruises
"Woodwind" sails up to four times daily throughout our summer season from the Annapolis Marriott Waterfront Hotel. Each trip is unique. All cruises sail by the United States Naval Academy and then into the Chesapeake Bay. Sailing under the Chesapeake Bay Bridge is a fabulous experience as are the breathtaking sunsets over the historic Annapolis skyline.

Let our captain and crew make your trip most enjoyable and memorable. Help hoist the sails (all 4 of them) or take a turn at the wheel. Our cash bar is stocked with beer and wine including a nice selection of local micro-brews.

The 74-foot, schooner "Woodwind" was custom designed and built specifically for sailing on the Chesapeake Bay. Woodwind is a replica of the classic, fast wooden schooners that were built as "yachts" in the early part of this century. Her handsome mahogany brightwork, gleaming chrome and roomy cockpit distinguish her from cargo carrying work vessels.


Sunset Sails & Entertainment

The sunset over the Annapolis skyline is breathtaking. The golden glow reflecting from the sails as the sun desce"

Contact Info.:

Phone: 410-263-7837
Schooner Woodwind
1930-A Lincoln Drive
Annapolis, MD 21401 USA

"For a perspective of Annapolis, Maryland you will never experience by land, be sure to try one or all of our 40-minute and 90-minute narrated boat tours. Tour the Annapolis Harbor, Severn River, Spa Creek, banks of the U.S. Naval academy, Chesapeake Bay Bridges, and historic Thomas Point Lighthouse. Check out our new Pirate Cruises and Lighthouse Cruises. Or, take one of our 7-1/2 hour Day on the bay Cruises to St. Michaels or Rock Hall. School field trips, group packages and destination planning are available.

For more than 30 years, Watermark Cruises has been providing visitors to Annapolis, Maryland with public group boat tours. We also specialize in private party charters including romantic weddings & receptions, stylish rehearsal dinners, impressive corporate entertaining, casual company outings, and festive anniversary & birthday celebrations. Watermark Cruises is Maryland’s largest, most diverse, company-owned and operated charter fleet and is the perfect solution to accommodate any banquet or event from 2 to 295 guests."

Contact Info.:

Phone: 410-268-7600
980 Awald Dr
Annapolis, MD 21403 USA

"Take the distinctive cuisine and service of a five star restaurant, place it on a handsomely appointed yacht in the midst of spectacular Chesapeake Bay scenery, and you’ll begin to understand the magic of Pintail Yachts. Since 1997, Annapolis-based Pintail Yachts has provided the enchantment behind thousands of events in the Baltimore and Annapolis area - from intimate weddings to lavish corporate parties.
When we began we set ourselves a daunting task: to provide the most spectacular dinner cruising service available in the Chesapeake Bay region. In an area famous for its lively water and the ships that move upon them, that was no small order.


Assembling a classic fleet of luxury yachts was a good start, and utilizing the stunning beauty of our region as a party setting didn’t hurt. But something else made our venture unique: our vision to make cruises of such extraordinary quality and value that we would be in competition with no one.

Pintail Yachts has hosted thousands of business and social group events during the last two decades. Here are just a few...

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Contact Info.:

Phone: 410-626-1888
312 Third Street
Suite 102
Annapolis, Maryland 21403

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