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Top Maryland Cruises, Sailing & Water Tours

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Maryland Tours

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Baltimore Inner Harbor Sail on Summer Wind

Enjoy the beautiful Inner Harbor of Baltimore on this 1.5-hour sailing experience. Relax on an authentic schooner and see the gorgeous views of the bustling …More

Likely to Sell Out
Likely to Sell Out
Baltimore, USA
4.7 (118)

Baltimore Inner Harbor Sail on Summer Wind

Enjoy the beautiful Inner Harbor of Baltimore on this 1.5-hour sailing experience. Relax on an authentic schooner and see the gorgeous views of the bustling...

1 hour 30 minutes • Free Cancellation
4.7 (118)
from
$65
Baltimore Inner Harbor Sightseeing Cruise

Explore Baltimore's Inner Harbor on a captivating 45-minute narrated sightseeing cruise. This journey unveils the rich history and vibrant culture of Charm City while gliding …More

Likely to Sell Out
Likely to Sell Out
Baltimore, USA
4.6 (24)

Baltimore Inner Harbor Sightseeing Cruise

Explore Baltimore's Inner Harbor on a captivating 45-minute narrated sightseeing cruise. This journey unveils the rich history and vibrant culture of Charm City while gliding...

45 minutes • Free Cancellation
4.6 (24)
from
$34
Assateague Island Cruise Departs from Ocean Pines

This boat trip provides the best way to see the famous Asseteague Island wild ponies. On this 2.5 hour trip that will depart from the …More

4.8 (48)

Assateague Island Cruise Departs from Ocean Pines

This boat trip provides the best way to see the famous Asseteague Island wild ponies. On this 2.5 hour trip that will depart from the...

2 hours • Free Cancellation
4.8 (48)
from
$40
Assateague Horses, Herons and Happy Hour Cruise

As we cruise to this enchanting island, keep your eyes peeled for the famous wild ponies. Did they swim here? Do they secretly moonlight as …More

Likely to Sell Out
Likely to Sell Out
Ocean City, USA
4.5 (20)

Assateague Horses, Herons and Happy Hour Cruise

As we cruise to this enchanting island, keep your eyes peeled for the famous wild ponies. Did they swim here? Do they secretly moonlight as...

1 hour 15 minutes • Free Cancellation
4.5 (20)
from
$50
Mount Vernon and The Millionaires, 2 hour Walking Tour

Mount Vernon Place: Considered the most beautiful of Baltimore neighborhoods, Mount Vernon Place was once home the more millionaire philanthropists than any other city in …More

Baltimore, USA
5.0 (22)

Mount Vernon and The Millionaires, 2 hour Walking Tour

Mount Vernon Place: Considered the most beautiful of Baltimore neighborhoods, Mount Vernon Place was once home the more millionaire philanthropists than any other city in...

2 hours • Free Cancellation
5.0 (22)
from
$30
Baltimore Evening Sail on the Summer Wind

Enjoy a beautiful time on the water while you nibble on cheese and sip delicious wine on this 1.5-hour sail. As you sail through beautiful …More

Baltimore, USA
5.0 (28)

Baltimore Evening Sail on the Summer Wind

Enjoy a beautiful time on the water while you nibble on cheese and sip delicious wine on this 1.5-hour sail. As you sail through beautiful...

1 hour 30 minutes • Free Cancellation
5.0 (28)
from
$75
Harborside Orange Crush Cruise

Try our new Harborside “Orange Crush” Cruise. Experience the bay behind Assateague Island in a unique way - with the original orange crush from the …More

5.0 (6)

Harborside Orange Crush Cruise

Try our new Harborside “Orange Crush” Cruise. Experience the bay behind Assateague Island in a unique way - with the original orange crush from the...

2 hours • Free Cancellation
5.0 (6)
from
$45
Annapolis Harbor and U.S. Naval Academy Cruise

Cruise through history on the Annapolis Harbor & USNA Cruise. This narrated cruise offers insights into the U.S. Naval Academy and Annapolis' rich maritime heritage …More

Likely to Sell Out
Likely to Sell Out
Annapolis, USA
4.9 (14)

Annapolis Harbor and U.S. Naval Academy Cruise

Cruise through history on the Annapolis Harbor & USNA Cruise. This narrated cruise offers insights into the U.S. Naval Academy and Annapolis' rich maritime heritage...

40 minutes • Free Cancellation
4.9 (14)
from
$34
City Cruises DC: Water Taxi One Day Pass

Skip the traffic and take the scenic route to your destination. Pass is valid for unlimited water taxi rides on a single date for one …More

Washington DC, USA
4.2 (70)

City Cruises DC: Water Taxi One Day Pass

Skip the traffic and take the scenic route to your destination. Pass is valid for unlimited water taxi rides on a single date for one...

35 minutes • Free Cancellation
4.2 (70)
from
$46
Kent Narrows Sunset Cruise

Experience an evening of beauty as we cruise into the golden hues of the sunset. All ages are welcome onboard, and for guests 21+, a …More

4.0 (6)

Kent Narrows Sunset Cruise

Experience an evening of beauty as we cruise into the golden hues of the sunset. All ages are welcome onboard, and for guests 21+, a...

1 hour 30 minutes • Free Cancellation
4.0 (6)
from
$42
Sailboat Cruise on Chesapeake Bay

Enjoy the peaceful sounds of the waves gently breaking off the hull of Eternal Hope as she glides through the waters of the bay, powered …More

Likely to Sell Out
Likely to Sell Out
5.0 (40)

Sailboat Cruise on Chesapeake Bay

Enjoy the peaceful sounds of the waves gently breaking off the hull of Eternal Hope as she glides through the waters of the bay, powered...

2 hours 30 minutes • Free Cancellation
5.0 (40)
from
$116
Baltimore History Sail on the Summer Wind

Learn about the maritime history of Baltimore and the Chesapeake Bay on this 1.5-hour sailing tour. Enjoy being on the water and listening to the …More

Baltimore, USA
4.9 (72)

Baltimore History Sail on the Summer Wind

Learn about the maritime history of Baltimore and the Chesapeake Bay on this 1.5-hour sailing tour. Enjoy being on the water and listening to the...

1 hour 30 minutes • Free Cancellation
4.9 (72)
from
$65
Baltimore Inner Harbor Sail on the Unforgettable

Enjoy the beautiful Inner Harbor of Baltimore on this 1.5-hour sailing experience. Relax on an authentic schooner and see the gorgeous views of the bustling …More

Likely to Sell Out
Likely to Sell Out
Baltimore, USA
4.8 (25)

Baltimore Inner Harbor Sail on the Unforgettable

Enjoy the beautiful Inner Harbor of Baltimore on this 1.5-hour sailing experience. Relax on an authentic schooner and see the gorgeous views of the bustling...

1 hour 30 minutes • Free Cancellation
4.8 (25)
from
$65
2-Hour Relaxing Chesapeake Day Sail on Lady Patty

Sail the serene waters of the Chesapeake Bay aboard the historic Lady Patty. This two-hour cruise offers a unique opportunity to unwind while taking in …More

5.0 (19)

2-Hour Relaxing Chesapeake Day Sail on Lady Patty

Sail the serene waters of the Chesapeake Bay aboard the historic Lady Patty. This two-hour cruise offers a unique opportunity to unwind while taking in...

2 hours • Free Cancellation
5.0 (19)
from
$160
2 Hour Chesapeake Day Sail on Catamaran Epiphany

Set sail on a 2-hour adventure aboard the modern catamaran, Epiphany, in the tranquil waters of St. Michaels, MD. Designed for comfort, this spacious vessel …More

5.0 (17)

2 Hour Chesapeake Day Sail on Catamaran Epiphany

Set sail on a 2-hour adventure aboard the modern catamaran, Epiphany, in the tranquil waters of St. Michaels, MD. Designed for comfort, this spacious vessel...

2 hours • Free Cancellation
5.0 (17)
from
$245
Sunset Cruise on Scenic Chesapeake Bay

Watching the sunset over the twin beaches on the Western Shores of the Chesapeake Bay! A great way to close out a summer day with …More

Likely to Sell Out
Likely to Sell Out
4.9 (10)

Sunset Cruise on Scenic Chesapeake Bay

Watching the sunset over the twin beaches on the Western Shores of the Chesapeake Bay! A great way to close out a summer day with...

2 hours 30 minutes • Free Cancellation
4.9 (10)
from
$139
Baltimore Inner Harbor Sunset Sail on Summer Wind

Experience the romance of sailing on this 1.5-hour sunset sail around the Inner Harbor. As the sun sinks into the water, enjoy gorgeous views of …More

Baltimore, USA
4.9 (58)

Baltimore Inner Harbor Sunset Sail on Summer Wind

Experience the romance of sailing on this 1.5-hour sunset sail around the Inner Harbor. As the sun sinks into the water, enjoy gorgeous views of...

1 hour 30 minutes • Free Cancellation
4.9 (58)
from
$75
Chesapeake Bay Private Cruise

This private cruise for up to 6 persons is great for family outings, friends in town, a girls or guys day out on the water, …More

Likely to Sell Out
Likely to Sell Out
5.0 (6)

Chesapeake Bay Private Cruise

This private cruise for up to 6 persons is great for family outings, friends in town, a girls or guys day out on the water,...

2 hours 30 minutes • Free Cancellation
5.0 (6)
from
$736
OC Bay Hopper Sunset Cruise Departs Downtown OC

The Bay in the evening slows down and gets calm and quiet. All you have to do is sit back, grab your favorite beverage, take …More

Likely to Sell Out
Likely to Sell Out
Ocean City, USA
5.0 (4)

OC Bay Hopper Sunset Cruise Departs Downtown OC

The Bay in the evening slows down and gets calm and quiet. All you have to do is sit back, grab your favorite beverage, take...

1 hour • Free Cancellation
5.0 (4)
from
$45
Themed and Special Event Cruise in Chesapeake Bay

This cruise is a unique way to celebrate that special event in your life while cruising on your very own private sailing yacht. You and …More

Likely to Sell Out
Likely to Sell Out
5.0 (1)

Themed and Special Event Cruise in Chesapeake Bay

This cruise is a unique way to celebrate that special event in your life while cruising on your very own private sailing yacht. You and...

2 hours 30 minutes • Free Cancellation
5.0 (1)
from
$790

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