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Browse Annapolis Boat Rentals

Page 2 of 361 listings

43 foot Captained Catalina Sailing Yacht Located In Rock Hall, Maryland
Sailing in Rock Hall · 6 guests

43 foot Captained Catalina Sailing Yacht Located In Rock Hall, Maryland

5.0
$140+/hour
Relaxing historic sailing experience in St. Michaels, Maryland - Half Day Sail
Sailing in Saint Michaels · 6 guests

Relaxing historic sailing experience in St. Michaels, Maryland - Half Day Sail

5.0
$325/hour
 SWEET & SALTY FOUNTAINE PAJOT HELIA 44 CATAMARAN
Sailing in Annapolis · 12 guests

SWEET & SALTY FOUNTAINE PAJOT HELIA 44 CATAMARAN

New
$400+/hour
Discover the Spirit of the Chesapeake Bay with our Nautical-Themed Photography
Events in Annapolis · 6 guests

Discover the Spirit of the Chesapeake Bay with our Nautical-Themed Photography

New
$255/hour
STARZ -Lagoon 42 Catamaran in Chesapeake Bay
Sailing in Annapolis · 13 guests

STARZ -Lagoon 42 Catamaran in Chesapeake Bay

New
$400+/hour
Fully Crewed Sailing Cruises Aboard 41' Sailboat in Rock Hall, MD
Sailing in Rock Hall · 4 guests

Fully Crewed Sailing Cruises Aboard 41' Sailboat in Rock Hall, MD

5.0
$150/hour
Relaxing Excitement of the Chesapeake Bay and tributaries on our Yacht
Events in Annapolis · 6 guests

Relaxing Excitement of the Chesapeake Bay and tributaries on our Yacht

New
$300/hour
Experience the Charm of St. Michaels Aboard the 41ft Sail Selina 2hr Boat Tour
Sailing in Saint Michaels · 6 guests

Experience the Charm of St. Michaels Aboard the 41ft Sail Selina 2hr Boat Tour

New
$350/hour
Cruise the South River on 46ft Meridian Sedan Bridge Yacht
Events in Annapolis · 6 guests

Cruise the South River on 46ft Meridian Sedan Bridge Yacht

New
$255+/hour
21′ KENCRAFT | Center Console | Located On The South River
Powerboats in Annapolis · 6 guests

21′ KENCRAFT | Center Console | Located On The South River

New
$125+/hour
Parker Southwestern | Seats 6 | 23'
Powerboats in Annapolis · 6 guests

Parker Southwestern | Seats 6 | 23'

New
$125+/hour
19' Hurricane (S) | Seats 6 | Ready For Adventure On The Chesapeake
Powerboats in Annapolis · 6 guests

19' Hurricane (S) | Seats 6 | Ready For Adventure On The Chesapeake

New
$125+/hour
30' Catamaran Tour Boat in Annapolis - BYOB Private Cruise - 6 Guests Capacity
Powerboats in Annapolis · 6 guests

30' Catamaran Tour Boat in Annapolis - BYOB Private Cruise - 6 Guests Capacity

New
$260/hour
Enjoy a Luxurious Boat Cruise on the Chesapeake Bay, Maryland
Events in North Beach · 8 guests

Enjoy a Luxurious Boat Cruise on the Chesapeake Bay, Maryland

5.0
$400/hour
32' Center Console - up to 6 Guests from Stevensville, MD
Powerboats in Stevensville · 6 guests

32' Center Console - up to 6 Guests from Stevensville, MD

5.0
$375/hour
19' Hurricane (S) | Seats 6 | Ready For Adventure On The Chesapeake
Powerboats in Annapolis · 6 guests

19' Hurricane (S) | Seats 6 | Ready For Adventure On The Chesapeake

New
$125+/hour
19' Hurricane (S) | Seats 6 | Ready For Adventure On The Chesapeake
Powerboats in Annapolis · 6 guests

19' Hurricane (S) | Seats 6 | Ready For Adventure On The Chesapeake

New
$125+/hour
Come take a cruise on the Annapolis Jet Boat
Powerboats in Annapolis · 11 guests

Come take a cruise on the Annapolis Jet Boat

New
$360/hour
 Sail in Style Aboard the 2024 Seawind 1160 Lite – Your Perfect Charter Escape
Sailing in Annapolis · 13 guests

Sail in Style Aboard the 2024 Seawind 1160 Lite – Your Perfect Charter Escape

New
$350+/hour
Cruise on the Shannon Brendan
Fishing in Annapolis · 6 guests

Cruise on the Shannon Brendan

New
$350/hour
Sail the Sea on the Pintita
Sailing in Annapolis · 20 guests

Sail the Sea on the Pintita

New
$500+/hour
26′ BENNINGTON PONTOON | Adventure Awaits | Seats 12
Powerboats in Annapolis · 12 guests

26′ BENNINGTON PONTOON | Adventure Awaits | Seats 12

New
$194+/hour
46′ CARMEN | Take Everybody With You! | Captain Included
Events in Annapolis · 30 guests

46′ CARMEN | Take Everybody With You! | Captain Included

New
$670+/hour
Maxum 30ft Yacht! Escape for a day on the Chesapeake
Events in Selby-on-the-Bay · 6 guests

Maxum 30ft Yacht! Escape for a day on the Chesapeake

New
$350/hour

Annapolis Reviews

  1. Pamela

    Pamela

    Relaxing historic sailing experience in St. Michaels, Maryland - Half Day Sail

    We booked this experience for my husbands birthday and it was PERFECT! The Selina II IS STUNNING, and Captain Iris and her crew were absolutely wonderful. Captain Matt was fantastic! He took such good care of us while we sailed across the Chesapeake Bay and celebrated with a couple of glasses of delicious champagne! Look no further and book the Selina II, you won’t regret it, it’s absolutely worth it !!

  2. LT

    Lloyd

    43 foot Captained Catalina Sailing Yacht Located In Rock Hall, Maryland

    Davis was our captain, he was great . Very informative and knowledgeable . We went on a 31/2 hour sail in the Chesapeake bay. Would definitely do it again

  3. MP

    Mohan

    Fully Crewed Sailing Cruises Aboard 41' Sailboat in Rock Hall, MD

    Captain Rob made the trip memorable with the beautiful views of the Chesapeake sunset and anecdotes of the area and his marine career.

  4. ac

    akhil

    Relaxing historic sailing experience in St. Michaels, Maryland - Half Day Sail

    Great trip, knowledgeable crew - was very accommodating with my family.

  5. Teresa

    Teresa

    Enjoy a Luxurious Boat Cruise on the Chesapeake Bay, Maryland

    We loved it, had a great time. Will definitely go again!