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Browse Annapolis Boat Rentals

5.0

(616 Reviews)

Page 2 of 2 • 46 listings

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

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

DOS MILAGROS Beneteau Oceanis 45 Sailing Yacht in Chesapeake Bay!

Sailing in Annapolis · 10 guests

DOS MILAGROS Beneteau Oceanis 45 Sailing Yacht in Chesapeake Bay!

New

$232+/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

50′ VIKING - Your Chartered Experience Awaits!

Events in Annapolis · 12 guests

50′ VIKING - Your Chartered Experience Awaits!

New

$841+/hour

Come take a cruise on the Annapolis Jet Boat

Powerboats in Kent Narrows · 11 guests

Come take a cruise on the Annapolis Jet Boat

New

$360/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

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

26’ CREST TRITOON | Excellent Pontoon | Seats 12

Powerboats in Annapolis · 12 guests

26’ CREST TRITOON | Excellent Pontoon | Seats 12

New

$194+/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

$280/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

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

Enjoy the best views of Annapolis, MD aboard this beautiful Lydia dinner yacht

Events in Annapolis · 128 guests

Enjoy the best views of Annapolis, MD aboard this beautiful Lydia dinner yacht

New

$480+/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

High Demand

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

Events in Annapolis · 30 guests

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

New

$670+/hour

VIKO S 35 Sailboat in Deale

Sailing in Deale · 6 guests

VIKO S 35 Sailboat in Deale

New

$298/hour

VIKO 30 Premium Sailing Yacht In Deale, MD

Sailing in Deale · 5 guests

VIKO 30 Premium Sailing Yacht In Deale, MD

New

$925/day

34ft Sailing Yacht in Annapolis, Maryland

Sailing in Annapolis · 4 guests

34ft Sailing Yacht in Annapolis, Maryland

New

$250/hour

STARZ -Lagoon 42 Catamaran in Chesapeake Bay

Sailing in Annapolis · 13 guests

STARZ -Lagoon 42 Catamaran in Chesapeake Bay

5.0

Snoozed - Active 02 Oct 2025

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

Snoozed - Active 25 Aug 2026

45' Catamaran Tour Boat in Annapolis - BYOB Private Cruise - 32 Guests Capacity

Powerboats in Annapolis · 32 guests

45' Catamaran Tour Boat in Annapolis - BYOB Private Cruise - 32 Guests Capacity

New

Snoozed - Active 25 Aug 2026

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Annapolis Reviews

JS
Jen

STARZ -Lagoon 42 Catamaran in Chesapeake Bay
I highly recommend Chronic Sailing! We did a 4 hour charter out of Annapolis as a bachelorette party. Captain Steve and Sarah were so accommodating and made our time so memorable. We are so appreciative. They made everything so easy- from booking to sailing and making memories with us. The STARZ catamaran boat was incredible! It fit our big group comfortably and gave us a little bit of luxury as we lounged and enjoyed on the bay. Again, this was a great experience for all of us and I would love to use them again!
MR
Matt

STARZ -Lagoon 42 Catamaran in Chesapeake Bay
Great experience and our family and friends had a wonderful time. Clean boat and fun crew to help us celebrate a special occasion. Highly recommend!
Teresa

Enjoy a Luxurious Boat Cruise on the Chesapeake Bay, Maryland
We loved it, had a great time. Will definitely go again!

Real reviews from happy Getmyboaters.

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