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Essex, Maryland Boat Rentals & Yacht Charters

Page 1 of 124 listings

Cruise the Chesapeake on Bay Lady
Powerboats in Essex · 5 guests

Cruise the Chesapeake on Bay Lady

New
$80+/hour
Welcome Aboard Optimystic! Create a beautiful memory on the water.
Sailing in Essex · 6 guests

Welcome Aboard Optimystic! Create a beautiful memory on the water.

5.0
$150/hour
38ft Seawind 1160 Luxury Sailing Catamaran in Essex, Maryland for 12 Guests
Sailing in Essex · 12 guests

38ft Seawind 1160 Luxury Sailing Catamaran in Essex, Maryland for 12 Guests

5.0
$799+/hour
STARCRAFT LUXURY PARTY PONTOON IS FINALLY HERE!!BEST OF BALTIMORE WINNER 2022...
Powerboats in Baltimore · 10 guests

STARCRAFT LUXURY PARTY PONTOON IS FINALLY HERE!!BEST OF BALTIMORE WINNER 2022...

5.0
$290/hour
 42ft Party Yacht Best of Baltimore 2024-25 Winner!
Events in Baltimore · 12 guests

42ft Party Yacht Best of Baltimore 2024-25 Winner!

5.0
$400/hour
House-Yacht for Relaxing on the Water in Quiet Luxury
Powerboats in Baltimore · 6 guests

House-Yacht for Relaxing on the Water in Quiet Luxury

New
$375/hour
Perfect 10-Seater Pontoon for Cruising DMV Waters - Annapolis, Baltimore, & D.C.
Powerboats in Baltimore · 10 guests

Perfect 10-Seater Pontoon for Cruising DMV Waters - Annapolis, Baltimore, & D.C.

New
$250/hour
Stunning 26FT Cabin Cruiser – Relax, Celebrate & Cruise Baltimore in Style
Powerboats in Baltimore · 6 guests

Stunning 26FT Cabin Cruiser – Relax, Celebrate & Cruise Baltimore in Style

5.0
$200/hour
22’ Bayliner Cruiser with Onboard Water and Toilet - 5 People
Powerboats in Dundalk · 8 guests

22’ Bayliner Cruiser with Onboard Water and Toilet - 5 People

New
$95/hour
Cruise the Inner Harbor and beyond on a Monterey 350 Sport Yacht
Powerboats in Baltimore · 6 guests

Cruise the Inner Harbor and beyond on a Monterey 350 Sport Yacht

5.0
$325/hour
Quest Sportsman 12 Jon Boat: Perfect for rivers and lakes in Baltimore Highlands
Fishing in Baltimore · 2 guests

Quest Sportsman 12 Jon Boat: Perfect for rivers and lakes in Baltimore Highlands

New
$50/hour
Fishing Charter in Pasadena, Maryland
Fishing in Riviera Beach · 6 guests

Fishing Charter in Pasadena, Maryland

5.0
$840/day
2016 Regal 31' Cruise The Inner Harbor, Annapolis, Hart Miller Island
Powerboats in Annapolis · 8 guests

2016 Regal 31' Cruise The Inner Harbor, Annapolis, Hart Miller Island

4.9
$225/hour
71’ Motor Yacht - $2500 4hrs l Captain Included l Perfect for Entertaining
Events in Annapolis · 12 guests

71’ Motor Yacht - $2500 4hrs l Captain Included l Perfect for Entertaining

New
$625/hour
2021 Tahoe T-16 Bowrider in Glen Burnie, Maryland
Powerboats in Severna Park · 4 guests

2021 Tahoe T-16 Bowrider in Glen Burnie, Maryland

5.0
$120/hour
42 foot Captained Catalina Sailing Yacht Located In Rock Hall, Maryland
Sailing in Rock Hall · 6 guests

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

5.0
$150+/hour
Beneteau Oceanis 50 Cruising Yacht in Rock Hall, Maryland
Sailing in Rock Hall · 6 guests

Beneteau Oceanis 50 Cruising Yacht in Rock Hall, Maryland

5.0
$150/hour
$1100 2hrs| 39ft Regal | 12 Guests | Annapolis
Events in Arnold · 12 guests

$1100 2hrs| 39ft Regal | 12 Guests | Annapolis

5.0
Superowner
$550/hour
Pro line Center Console Magothy River - Perfect for fishing, exploring, cruising
Powerboats in Arnold · 10 guests

Pro line Center Console Magothy River - Perfect for fishing, exploring, cruising

5.0
$80+/hour
Instant Book
34' Hunter Cruising Monohull In Rock Hall, Maryland United States
Sailing in Rock Hall · 4 guests

34' Hunter Cruising Monohull In Rock Hall, Maryland United States

4.6
$275+/night
34ft Sailing Yacht in Annapolis, Maryland
Sailing in Annapolis · 4 guests

34ft Sailing Yacht in Annapolis, Maryland

New
$250/hour
2020 Misty Harbor Tritoon for 12 people in Annapolis
Powerboats in Annapolis · 12 guests

2020 Misty Harbor Tritoon for 12 people in Annapolis

5.0
$250/hour
Cuddy Cabin/Walk Around bareboat fishing charter in Annapolis
Powerboats in Annapolis · 6 guests

Cuddy Cabin/Walk Around bareboat fishing charter in Annapolis

4.8
$95+/hour
Private Annapolis Sailing Experience on a Classic 37' Nauticat Ketch
Sailing in Annapolis · 6 guests

Private Annapolis Sailing Experience on a Classic 37' Nauticat Ketch

New
$150+/hour

Essex Reviews

  1. Geoffrey

    Geoffrey

    34' Hunter Cruising Monohull In Rock Hall, Maryland United States

    Icarus is a great boat and very well equipped. The sails and everything else on the vessel are in great shape and the fact it only draws 4' 6" is perfect for the Chesapeake. I spent a week on Icarus and everything worked well. The value of chartering Icarus is undeniable. I plan to charter Icarus again. Icarus has a lot of sail area, so if the winds are strong douse the headsail early.

  2. Sarah

    Sarah

    $1100 2hrs| 39ft Regal | 12 Guests | Annapolis

    An absolutely fantastic experience from start to finish! The captain was wonderful and the scenery was breathtaking, making for an unforgettable trip out on the water. The boat was spotless, the booking process was a breeze, and everything ran like clockwork — couldn’t recommend it more highly!

  3. LM

    Liz

    Welcome Aboard Optimystic! Create a beautiful memory on the water.

    Charles was an outstanding guide. Before the outing (which was a birthday gift for my fiancé) he even offered to pick up a cake so that it could be a surprise. He and his wife made us feel at home right away as if we were out just sailing with friends. It was a gorgeous late afternoon / sunset sail with the option of swimming and cooking on the boat. We didn't rush back. Riding on the bow was so relaxing. He took time explaining sailing tips to my fiancé and let him drive the boat for awhile. Communication was clear. We'd love to book again with Charles and Renee!

  4. RK

    Richard

    34' Hunter Cruising Monohull In Rock Hall, Maryland United States

    Our group of four had a great three days onboard the Icarus. The boat was easy to sail and operate. No problems motoring around in the marinas, steers easy in reverse too. Jim was a great host, very responsive and knowledgeable. Highly recommend his boat to sail the Chesapeake!

  5. hN

    hornella

    2016 Regal 31' Cruise The Inner Harbor, Annapolis, Hart Miller Island

    It was a good choice i’m really glad i booked with them. we had a good day on my birthday, Very fun and enjoyable, The captain was good and kind. Thank you so very much!

  6. MB

    Mary

    2021 Tahoe T-16 Bowrider in Glen Burnie, Maryland

    Sunmi was extremely attentive - he was on time, had the boat ready to, went through review of the boat and we were off. We had a blast!! The boat drives very well. Great for an afternoon on the Chesapeake!