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Saint Michaels, Maryland Boat Rentals - 2023

24 listings
Charter 41ft S/Y Selina II Sloop in St. Michaels, Maryland
Sailing in Saint Michaels · 6 guests

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

5.0
$250-$349hour
Sunset Champagne Cruise on the Chesapeake Bay
Sailing in Saint Michaels · 6 guests

Sunset Champagne Cruise on the Chesapeake Bay

New
$55person
46ft Chesapeake Motor Yacht Charter in Stevensville, Maryland
Fishing in Stevensville · 6 guests

46ft Chesapeake Motor Yacht Charter in Stevensville, Maryland

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

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

5.0
$300hour
Pershing 65 Power Mega Yacht Rental in Stevensville, Maryland
Events in Stevensville · 6 guests

Pershing 65 Power Mega Yacht Rental in Stevensville, Maryland

New
$550hour
29ft Everglades Center Console in Annapolis
Powerboats in Maryland · 6 guests

29ft Everglades Center Console in Annapolis

New
$450hour
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
$365hour
31' Chaparral 307 SSX Luxury Bowrider Rental in Edgewater, MD
Powerboats in Selby-on-the-Bay · 12 guests

31' Chaparral 307 SSX Luxury Bowrider Rental in Edgewater, MD

5.0
$250hour
43ft Cruiser Express Yacht for Daily Charter
Events in Selby-on-the-Bay · 8 guests

43ft Cruiser Express Yacht for Daily Charter

5.0
$400hour
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
$400hour
Experience the Serenity of Sailing SV Magic
Sailing in Mayo · 6 guests

Experience the Serenity of Sailing SV Magic

4.8
$165hour
Charter this 42ft Sailboat, for up 6 persons to enjoy the middle Chesapeake Bay
Sailing in Mayo · 6 guests

Charter this 42ft Sailboat, for up 6 persons to enjoy the middle Chesapeake Bay

5.0
$175hour
 VIKO S 35 Sailboat in Deale
Sailing in Deale · 6 guests

VIKO S 35 Sailboat in Deale

New
$298hour
Charter 44' Orana Cruising Catamaran In Deale, Maryland
Sailing in Deale · 10 guests

Charter 44' Orana Cruising Catamaran In Deale, Maryland

5.0
$2,600day
Catalina 445 Sailboat
Sailing in Deale · 6 guests

Catalina 445 Sailboat

New
$298hour
30ft Bowrider! Enjoy a day on the water around the Chesapeake Bay in Maryland!
Powerboats in Annapolis · 8 guests

30ft Bowrider! Enjoy a day on the water around the Chesapeake Bay in Maryland!

3.7
$170hour
Fully Crewed Annapolis Sailing Cruises
Sailing in Annapolis · 6 guests

Fully Crewed Annapolis Sailing Cruises

New
$175person
Come take a cruise on the Annapolis Jet Boat
Powerboats in Annapolis · 11 guests

Come take a cruise on the Annapolis Jet Boat

New
$500hour
Historical Annapolis Private Boat Cruise onboard a beautiful Swift Trawler!
Events in Annapolis · 6 guests

Historical Annapolis Private Boat Cruise onboard a beautiful Swift Trawler!

5.0
$250hour
Sail the Sea on the Pintita
Sailing in Annapolis · 20 guests

Sail the Sea on the Pintita

New
$500-$750hour
Luxury yacht with Captain for 8 passengers to your Annapolis waterways
Events in Annapolis · 8 guests

Luxury yacht with Captain for 8 passengers to your Annapolis waterways

5.0
$250hour
38' Hunter 376 Cruising Monohull in Annapolis, Maryland, USA
Sailing in Annapolis · 6 guests

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

5.0
Superowner
Best of 2023
$138-$150hour
34ft Sailing Yacht in Annapolis, Maryland
Sailing in Annapolis · 4 guests

34ft Sailing Yacht in Annapolis, Maryland

New
$300hour
41' Lagoon Catamaran in Maryland, United States
Sailing in Annapolis · 12 guests

41' Lagoon Catamaran in Maryland, United States

5.0
Superowner
Best of 2023
$320hour

Saint Michaels Reviews

  1. 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 !!

  2. BM
    Bernadette
    31' Chaparral 307 SSX Luxury Bowrider Rental in Edgewater, MD

    Capt Michael is amazing. His boat is beautiful and well maintained. He is friendly, professional and knows how to Captain. He was very flexible and understanding when we had a change of plans and dropped off some of our crew at another location. We highly recommend him for your fun day out on the bay and we will be booking him again!

  3. DL
    Debbie
    31' Chaparral 307 SSX Luxury Bowrider Rental in Edgewater, MD

    Everything went perfectly, from the time I initially reached out to the return back to the marina. Michael is an excellent captain, his boat is pristine in every way, and the trip was the best way imaginable to spend my daughters birthday with her 3 BFFs and their moms. I will be sure to consider Michael and his boat for another way to celebrate or spend a day on the water. He was flexible, communicative, knowledgeable, friendly, and willing to assure us all the best day ever. Can't be more grateful!

  4. GE
    Gerard
    Experience the Serenity of Sailing SV Magic

    Had a fantastic day sailing with Josh! He was great with communications and was ready to go when we got there. The boat is very comfortable and while we only did a 3 hour sail, the boat has a good galley and bathroom and would be great for a longer sail. The marina location is excellent and we were in the Chesapeake in 15 to 20 minutes. Josh was a great captain - we enjoyed chatting with him and he made us very comfortable. Highly recommended.

  5. WC
    Whitney
    Experience the Serenity of Sailing SV Magic

    We had an awesome trip with Josh. He was very flexible with timing and knowledgeable about sailing. We were able to take our engagement photos on Josh’s boat with his help and input on lighting/backgrounds. It was a wonderful experience we will never forget!

  6. WB
    Winnie
    Charter this 42ft Sailboat, for up 6 persons to enjoy the middle Chesapeake Bay

    Capt. Bill was so accommodating and great with his communication. We had an emergency and he was very understanding. He gave my nine year old great information about the boat and the waters. He and Jonathan were very kind during our charter. It was a great first sail for our family!