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Hillsmere Shores, Maryland Boat Rentals

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
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
Snoozed - Active 02 Jan 2025
Fully Crewed Annapolis Sailing Cruises
Sailing in Annapolis · 6 guests

Fully Crewed Annapolis Sailing Cruises

New
$175person
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
Snoozed - Active 02 Jun 2024
Sail the Sea on the Pintita
Sailing in Annapolis · 20 guests

Sail the Sea on the Pintita

New
$500-$750hour
Pristine Hooligan Departs from a Private Pier with a Captain and Fuel INCLUDED
Powerboats in Annapolis · 5 guests

Pristine Hooligan Departs from a Private Pier with a Captain and Fuel INCLUDED

New
$200hour
38' Hunter 376 Cruising Monohull in Annapolis, Maryland
Sailing in Annapolis · 6 guests

38' Hunter 376 Cruising Monohull in Annapolis, Maryland

5.0
Superowner
Best of 2023
$138-$150hour
Luxury SeaRay Yacht with Captain | Explore the Annapolis Waterways
Events in Annapolis · 8 guests

Luxury SeaRay Yacht with Captain | Explore the Annapolis Waterways

5.0
$250hour
41' Lagoon Catamaran in Maryland
Sailing in Annapolis · 12 guests

41' Lagoon Catamaran in Maryland

5.0
Superowner
Best of 2023
$390hour
50ft Catamaran Charter with Water Toys - Annapolis, MD
Sailing in Annapolis · 12 guests

50ft Catamaran Charter with Water Toys - Annapolis, MD

New
$425hour
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
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
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
Bentley 220 Cruise Pontoon for rent in Edgewater
Powerboats in Edgewater · 10 guests

Bentley 220 Cruise Pontoon for rent in Edgewater

New
$400hour
Relax in the Sun in Edgewater and Annapolis
Powerboats in Edgewater · 10 guests

Relax in the Sun in Edgewater and Annapolis

New
$200hour
Charter 42' Lagoon Catamaran in Annapolis, MD
Sailing in Edgewater · 12 guests

Charter 42' Lagoon Catamaran in Annapolis, MD

New
$400hour
Cruise on the Shannon Brendan
Fishing in Annapolis · 6 guests

Cruise on the Shannon Brendan

New
$350hour
Enjoy a Day on the Bay and Cruise the South River
Powerboats in Annapolis · 6 guests

Enjoy a Day on the Bay and Cruise the South River

New
$130-$150hour
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
Experience the Serenity of Sailing SV Magic
Sailing in Mayo · 6 guests

Experience the Serenity of Sailing SV Magic

4.8
$165hour
Just Repowered Cuddy Cabin/Walk Around bareboat fishing charter in Annapolis
Powerboats in Annapolis · 6 guests

Just Repowered Cuddy Cabin/Walk Around bareboat fishing charter in Annapolis

4.8
$95-$150hour
34ft Sailing Yacht in Annapolis, Maryland
Sailing in Annapolis · 4 guests

34ft Sailing Yacht in Annapolis, Maryland

New
$300hour
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
$375hour
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

Hillsmere Shores Reviews

  1. JR

    Josh

    38' Hunter 376 Cruising Monohull in Annapolis, Maryland

    Highly highly recommended! The boat is as advertised, but the real treat is spending time with Captain Alberto, and his wife Grace, who are such warm, loving, and knowledgeable people. They clearly know their boat inside and out, so you will never feel uncomfortable. But they also encourage guests to help running the boat and they have the knowledge to help everyone understand what is happening. Most importantly, they are simply fun to be around and a joy to talk to. I can't wait to sail with them again!

  2. BC

    Brian

    38' Hunter 376 Cruising Monohull in Annapolis, Maryland

    Across the board, a wonderful charter that exceeded expectations. It'd been some years since my wife and I had been on the water and what we expected was a day out refamiliarizing ourselves and just enjoying the Bay -- But Capt Alberto skillfully combined pleasurable sailing with private sailing lessons, a naval architecture primer, and boat buying 101. We can't wait to get back out on the water again with Alberto!

  3. Michael

    Michael

    38' Hunter 376 Cruising Monohull in Annapolis, Maryland

    We had an amazing experience today with Alberto and his lovely wife. The boat was beautiful. I’m interested in learning to sail and as soon as Alberto found that out he spent most of the day teaching me about sailing. He has deep knowledge and was very good at explaining things. They also both made us feel like good friends rather than customers. We will definitely sail again with them soon!

  4. JW

    Joe

    38' Hunter 376 Cruising Monohull in Annapolis, Maryland

    Captain Alberto and his wife, Grace, are such great hosts. They worked with us to reschedule because of a lightning storm. Communication was great. The boat is very nice and comfortable. We had a great time and learned a lot too. We will book with them again!

  5. MT

    Molly

    38' Hunter 376 Cruising Monohull in Annapolis, Maryland

    Fantastic experience! Alberto taught us how to sail and let us do as little or as much as we wanted to. We celebrated a friend’s birthday and this was the perfect mix of relaxing and doing something new. If you’re looking for an easy afternoon on the water with a few friends, this is the captain to book it with. 10/10 would recommend!

  6. JC

    Jim

    38' Hunter 376 Cruising Monohull in Annapolis, Maryland

    Capt Alberto and his wife Grace did a wonderful job on our trip on the Bay. Everything was on time, as advertised and they took great care to explain what was happening, particularly those in the group that were less comfortable with sailing. We will definitely book again. Thank you.