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Annapolis, Maryland Boat Rentals & Yacht Charters

5.0

(618 Reviews)

Page 2 of 2 • 47 listings

Take your Sailing Dream on Chesapeake Bay.

Sailing in Mayo · 6 guests

Take your Sailing Dream on Chesapeake Bay.

New

$175+/hour

Luxury Lagoon 42 Catamaran for 12 in Annapolis

Sailing in Annapolis · 12 guests

Luxury Lagoon 42 Catamaran for 12 in Annapolis

New

$335+/hour

New Yacht Charter Bali 5.4 Sailing Catamaran in Annapolis Maryland

Sailing in Annapolis · 13 guests

New Yacht Charter Bali 5.4 Sailing Catamaran in Annapolis Maryland

5.0

$1,100/hour

2022 Catspace 38 Sailing Catamaran in Chesapeake Bay

Sailing in Annapolis · 12 guests

2022 Catspace 38 Sailing Catamaran in Chesapeake Bay

New

$334+/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

Luxury 2022 Excess 11 Catamaran for 12 in Annapolis

Sailing in Annapolis · 12 guests

Luxury 2022 Excess 11 Catamaran for 12 in Annapolis

New

$335+/hour

Durfour 430 Sailing Yacht to Discover the Chesapeake Bay

Sailing in Annapolis · 12 guests

Durfour 430 Sailing Yacht to Discover the Chesapeake Bay

New

$210+/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

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

Cruise the Chesapeake on a Classic 46’ Deadrise – Up to 30 Guests

Powerboats in Edgewater · 20 guests

Cruise the Chesapeake on a Classic 46’ Deadrise – Up to 30 Guests

New

$600/hour

23ft Parker Center Console | Seats 6 | Edgewater, Maryland

Powerboats in Annapolis · 6 guests

23ft Parker Center Console | Seats 6 | Edgewater, Maryland

New

$125+/hour

Private Sail on 44ft Leopard Catamaran | 6 People | Gratuity & Tax Included

Sailing in Saint Michaels · 6 guests

Private Sail on 44ft Leopard Catamaran | 6 People | Gratuity & Tax Included

New

$585/hour

27' Godfrey Tritoon Pontoon Boat - Perfect for Cruising and Entertaining

Powerboats in Annapolis · 12 guests

27' Godfrey Tritoon Pontoon Boat - Perfect for Cruising and Entertaining

New

$175+/hour

High Demand

Meridian 541 Sedan Motor Yacht Ideal For Chesapeake Bay Cruising

Events in Annapolis · 12 guests

Meridian 541 Sedan Motor Yacht Ideal For Chesapeake Bay Cruising

New

$1,280/hour

Private Historic 1935 Ketch Sail | 13 People | Gratuity & Tax Included

Sailing in Saint Michaels · 13 guests

Private Historic 1935 Ketch Sail | 13 People | Gratuity & Tax Included

New

$645/hour

Private Sail Up to 13 Guests | 44ft Leopard Catamaran

Sailing in Saint Michaels · 13 guests

Private Sail Up to 13 Guests | 44ft Leopard Catamaran

New

$580/hour

Rent a 31ft Sailing Yacht In Rock Hall, MD

Sailing in Rock Hall · 4 guests

Rent a 31ft Sailing Yacht In Rock Hall, MD

New

$250/day

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

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

Snoozed - Active 02 Jul 2026

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

DC
Donte

New Yacht Charter Bali 5.4 Sailing Catamaran in Annapolis Maryland
From start to finish, the entire experience was seamless and professional. There was zero chaos—everything ran like clockwork. The crew was exceptional: friendly, attentive, and incredibly knowledgeable about the Chesapeake Bay and Annapolis. The yacht itself was spotless and in pristine condition. From the moment we arrived, the crew went above and beyond—helping us load in, beautifully setting up our catering, keeping our group refreshed with drinks and snacks, and later packing up leftovers and loading them into our car. Every detail was handled with care. If you’re considering a yacht rental, don’t hesitate—this experience was truly top-notch. We’re already looking forward to booking again!
WY
Weslie

New Yacht Charter Bali 5.4 Sailing Catamaran in Annapolis Maryland
Perfect Yacht. The pictures are 10000% accurate. We loved it.

Real reviews from happy Getmyboaters.

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