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Saint Michaels, Maryland Boat Rentals - 2023

4.9(Average of 46,071 reviews in this area)
24 listings
Charter 41ft S/Y Selina II Sloop in St. Michaels, Maryland
Sailing in Chesapeake Bay · 6 guests

Charter 41ft S/Y Selina II Sloop in St. Michaels, Maryland

5.0
$349hour
Sunset Champagne Cruise on the Chesapeake Bay
Sailing in Chesapeake Bay · 6 guests

Sunset Champagne Cruise on the Chesapeake Bay

New
$399hour
Chesapeake Bay Rock Fishing Trip for 6 people with Captain Doug
Fishing in Potomac River · 6 guests

Chesapeake Bay Rock Fishing Trip for 6 people with Captain Doug

New
$750day
38' Center Console - up to 6 Guests from Stevensville, MD
Powerboats in Potomac River · 6 guests

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

5.0
$300hour
43ft Cruiser Express Yacht for Daily Charter on Chesapeake Bay, Annapolis, Rhodes River or South River
Events in Potomac River · 8 guests

43ft Cruiser Express Yacht for Daily Charter on Chesapeake Bay, Annapolis, Rhodes River or South River

5.0
$400hour
Sea Ray 450 Sundancer Luxury Cruising Yacht near Annapolis MD
Events in Potomac River · 13 guests

Sea Ray 450 Sundancer Luxury Cruising Yacht near Annapolis MD

5.0
$325hour
Captained Fishing Trips in Chesapeake Beach, Maryland
Fishing in Potomac River · 6 guests

Captained Fishing Trips in Chesapeake Beach, Maryland

New
$120hour
Charter 44' Orana Cruising Catamaran In Deale, Maryland
Sailing in Potomac River · 10 guests

Charter 44' Orana Cruising Catamaran In Deale, Maryland

5.0
$2,600day
Sea Ray Sundancer Cruising Yacht Charter in Annapolis
Events in Potomac River · 8 guests

Sea Ray Sundancer Cruising Yacht Charter in Annapolis

5.0
$250hour
Charter the 60' Sea Spirit Motor Yacht in Annapolis, Maryland
Events in Potomac River · 65 guests

Charter the 60' Sea Spirit Motor Yacht in Annapolis, Maryland

4.9
$3,600day
Beneteau 41ft Sailing Charter in Annapolis, Maryland
Sailing in Potomac River · 8 guests

Beneteau 41ft Sailing Charter in Annapolis, Maryland

5.0
$200hour
Cruising Monohull Sailing from Downtown Annapolis! Sunsets, daysails and stargazing!
Sailing in Potomac River · 6 guests

Cruising Monohull Sailing from Downtown Annapolis! Sunsets, daysails and stargazing!

New
$250hour
38' Hunter 376 Cruising Monohull in Annapolis, Maryland, USA
Sailing in Potomac River · 6 guests

38' Hunter 376 Cruising Monohull in Annapolis, Maryland, USA

5.0
Superowner
Best of 2022
$150hour
Blue Yamaha EX Jet Ski for rent
Water Sports in Potomac River · 2 guests

Blue Yamaha EX Jet Ski for rent

New
$125hour
2007 Seadoo Jet Boat for Rent
Powerboats in Potomac River · 4 guests

2007 Seadoo Jet Boat for Rent

New
$350hour
Seadoo Spark Trixx Jet Ski
Water Sports in Potomac River · 2 guests

Seadoo Spark Trixx Jet Ski

New
$125hour
Black Yamaha EX Jet Ski for Rent
Water Sports in Potomac River · 2 guests

Black Yamaha EX Jet Ski for Rent

New
$125hour
Green Yamaha EX Jet Ski for rent in Chesapeake Beach Maryland
Water Sports in Potomac River · 2 guests

Green Yamaha EX Jet Ski for rent in Chesapeake Beach Maryland

New
$125hour
34ft Sailing Yacht in Annapolis, Maryland
Sailing in Potomac River · 4 guests

34ft Sailing Yacht in Annapolis, Maryland

New
$300hour
Charter this 42ft Sailboat in Edgewater, Maryland for up to 6 persons and sail on beautiful Chesapeake Bay or take some Beginner or Advanced sailing lessons on a big boat.
Sailing in Potomac River · 6 guests

Charter this 42ft Sailboat in Edgewater, Maryland for up to 6 persons and sail on beautiful Chesapeake Bay or take some Beginner or Advanced sailing lessons on a big boat.

5.0
$175hour
Luxury yacht with Captain for 7 passengers to your Annapolis waterways
Events in Potomac River · 7 guests

Luxury yacht with Captain for 7 passengers to your Annapolis waterways

5.0
$50person
41' Lagoon Cruising Catamaran in Maryland, United States
Sailing in Potomac River · 12 guests

41' Lagoon Cruising Catamaran in Maryland, United States

5.0
Superowner
Best of 2022
$349hour
Seawind 1260 Cruising Catamaran Rental in Little Harbour, Bahamas
Sailing in Potomac River · 6 guests

Seawind 1260 Cruising Catamaran Rental in Little Harbour, Bahamas

5.0
$1,200day
''Imi Ola'' Seawind 1260 Cruising Catamaran Charter in Edgewater, Maryland
Sailing in Potomac River · 12 guests

''Imi Ola'' Seawind 1260 Cruising Catamaran Charter in Edgewater, Maryland

5.0
Superowner
$716hour

Saint Michaels Reviews

  1. Gina
    Gina
    41' Lagoon Cruising Catamaran in Maryland, United States

    Captain Jess, the catamaran, the outing, the sights, all of it EXCEEDED our group’s expectations (which were already high going in)!! We immediately felt comfortable and secure in Captain Jess upon initial meeting (especially because he quickly outlined safety rules first - green flag!) and the hours out on the water became the highlight of my sister’s bachelorette weekend - we will be forever grateful!

  2. Pamela
    Pamela
    Charter 41ft S/Y Selina II Sloop in St. Michaels, Maryland

    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 !!

  3. KK
    Kristen
    Sea Ray 450 Sundancer Luxury Cruising Yacht near Annapolis MD

    We chartered Imrul’s boat for a bachelorette party with 8 ladies and it was phenomenal! the captain and first mate are wonderful and so helpful, and we had a great time. Boat was clean and spacious and captain had great recommendations for where to go. Thank you so much !

  4. RG
    Ryan
    Sea Ray 450 Sundancer Luxury Cruising Yacht near Annapolis MD

    The boat was great and captain and crew were incredible! Had a bit of a departure delay but Imrul and our crew made sure we got our fully allotted time. Imrul was highly responsive to all requests and extremely professional. Highly recommend this gorgeous boat for a wonderful day out on the water.

  5. RR
    Rachel
    Sea Ray 450 Sundancer Luxury Cruising Yacht near Annapolis MD

    Thanks to Imrul and Capain Philip Robinson and "crew" for making our early father's day excursion a success! The day was glorious, the boat was wonderful and heading south to Mt. Vernon was a spectacular idea. Imrul was super responsive and accommodated all our crazy requests and answered all our questions. A great day was had by all!

  6. Danika
    Danika
    Charter 44' Orana Cruising Catamaran In Deale, Maryland

    We had the best time! Everything was perfect! Rob communicated well! The boat looked exactly like the pictures. It was enough space for my 10 guest party! We sailed out for 7hrs and it still didn’t feel like enough time! I’m so glad I went with this boat and will be using it again in the future. Best birthday ever!!!