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Chesapeake Bay, US Boat Rentals & Yacht Charters

Page 5 of 10 • 229 listings

2022 Avalon Tritoon!
Powerboats in Virginia Beach · 10 guests

2022 Avalon Tritoon!

5.0
$199/hour
Cruise the beautiful Bay!!!
Powerboats in Deale · 6 guests

Cruise the beautiful Bay!!!

5.0
$200/hour
Charter 44' Orana Cruising Catamaran In Deale, Maryland
Sailing in Deale · 10 guests

Charter 44' Orana Cruising Catamaran In Deale, Maryland

5.0
$250+/hour
Luxury Sea Ray Yacht 320 Sundancer - $300Hr - 10 Guests + Complimentaries
Events in Washington · 10 guests

Luxury Sea Ray Yacht 320 Sundancer - $300Hr - 10 Guests + Complimentaries

New
$300/hour
40ft Regal 400 Commodore Yacht Charter for Celebrations and Parties
Events in Washington · 12 guests

40ft Regal 400 Commodore Yacht Charter for Celebrations and Parties

New
$350/hour
40ft Sea Ray SLX 400 Bowrider in Washington DC Potomac for Up to 12 Guests
Events in Washington · 13 guests

40ft Sea Ray SLX 400 Bowrider in Washington DC Potomac for Up to 12 Guests

5.0
$530/hour
Cruise The Annapolis Area Chesapeake on a Classic 46’ Downeast – Up to 25 Guests
Powerboats in Edgewater · 25 guests

Cruise The Annapolis Area Chesapeake on a Classic 46’ Downeast – Up to 25 Guests

5.0
$475+/hour
$300hr | 10 Guests | National Harbor + 30 Min Free
Events in Oxon Hill · 8 guests

$300hr | 10 Guests | National Harbor + 30 Min Free

New
Superowner
$300/hour
Enjoy the sights of Colonial Beach, VA ! Come boat with us!
Events in Colonial Beach · 6 guests

Enjoy the sights of Colonial Beach, VA ! Come boat with us!

5.0
$180/hour
Chaparral SSX 27ft - Captained Private Charter - Watersports Included!!
Powerboats in Edgewater · 6 guests

Chaparral SSX 27ft - Captained Private Charter - Watersports Included!!

5.0
$225/hour
The Big Kahuna 18 Passenger Tiki Boat
Powerboats in Cape May · 18 guests

The Big Kahuna 18 Passenger Tiki Boat

5.0
$250/hour
The Best Tiki/bar Cruise of the Summer in Dewey Beach
Powerboats in Dewey Beach · 18 guests

The Best Tiki/bar Cruise of the Summer in Dewey Beach

4.7
$450/hour
South Jersey Tiki Boat Wildwood Crest, NJ
Powerboats in Wildwood Crest · 12 guests

South Jersey Tiki Boat Wildwood Crest, NJ

5.0
$199/hour
New Yacht Charter Bali 5.4 Sailing Catamaran in Annapolis Maryland
Sailing in Annapolis · 12 guests

New Yacht Charter Bali 5.4 Sailing Catamaran in Annapolis Maryland

5.0
$1,100/hour
Ride on our 42 Passenger Navigator Boat! Full bar options!
Events in Washington · 49 guests

Ride on our 42 Passenger Navigator Boat! Full bar options!

5.0
Superowner
$865+/hour
$375hr | 12 Guests | Annapolis Area
Events in Edgewater · 12 guests

$375hr | 12 Guests | Annapolis Area

New
Superowner
$375/hour
$300hr  | 10 Guests | Occoquan & DC
Powerboats in Woodbridge · 10 guests

$300hr | 10 Guests | Occoquan & DC

New
Superowner
$300/hour
Instant Book
40' Robbins Deadrise Trawler Boat Rental in Rehoboth Beach, Delaware
Powerboats in Delaware · 6 guests

40' Robbins Deadrise Trawler Boat Rental in Rehoboth Beach, Delaware

5.0
$100+/hour
Sunset Boat Rides in Va Beach
Powerboats in Virginia Beach · 6 guests

Sunset Boat Rides in Va Beach

5.0
$225/hour
Sailing the DMV on a Welcraft. Offering professional service for all occasions.
Events in Washington · 12 guests

Sailing the DMV on a Welcraft. Offering professional service for all occasions.

5.0
$400/hour
Charter a Regal 400 Commodore Express Cruiser in Hampton for Up to 6 Guests
Powerboats in Hampton · 6 guests

Charter a Regal 400 Commodore Express Cruiser in Hampton for Up to 6 Guests

5.0
$250/hour
$275hr | 12 Guests | Bentley Pontoon
Powerboats in Washington · 13 guests

$275hr | 12 Guests | Bentley Pontoon

New
Superowner
$275/hour
River Runner 🚤 | Chaparral 260SSI – Cruise, Relax & Enjoy!
Powerboats in Arlington · 10 guests

River Runner 🚤 | Chaparral 260SSI – Cruise, Relax & Enjoy!

5.0
$200+/hour
Cruise DC and turn heads aboard the vintage 1985 Chris Craft, American Pie
Powerboats in Washington · 6 guests

Cruise DC and turn heads aboard the vintage 1985 Chris Craft, American Pie

5.0
$325/hour

Chesapeake Bay Reviews

  1. KS

    Kelly

    Charter a Regal 400 Commodore Express Cruiser in Hampton for Up to 6 Guests

    My husband and I had such a great time out with Chris and his first mate. We had very clear and quick communication from the first message and they were both friendly and professional day-of. He had an itinerary in mind that helped avoid overly choppy waters and gave us a nice tour of the area. We were super fortunate to find a pod of dolphins that came right up to the boat as well and Chris went above and beyond, staying out a few minutes extra, to allow us to experience seeing the up close. The boat had everything we needed and it was great to be able to lay out on the front sun deck and enjoy the beautiful weather. I would definitely go out again!

  2. LB

    Lauren

    The Best Tiki/bar Cruise of the Summer in Dewey Beach

    The tiki cruise out of Dewey was fun for both adults and kids! We had fun jumping into the bay. The floating mat for cruising and “surfing” was a highlight for the kids. The first mate and captain were top notch.

  3. SY

    Sarah

    Cruise The Annapolis Area Chesapeake on a Classic 46’ Downeast – Up to 25 Guests

    The boat and crew were perfect for a bachelorette party! Captain Steve and Sarah couldn’t have been nicer or cooler throughout the ride. They were very accommodating and were on top of communicating, especially with the possibility of bad weather. The day and process couldn’t have gone better!

  4. SM

    Shanickia

    Cruise The Annapolis Area Chesapeake on a Classic 46’ Downeast – Up to 25 Guests

    This experience couldn’t be better! We booked for my sisters 30th birthday.. and had an amazing time. We came with our own decor and food.. but Sarah made the vibes comfortable for us! Def a lit time!

  5. EC

    Emily

    Charter 44' Orana Cruising Catamaran In Deale, Maryland

    Had a group with me and they had a blast. Weather started as misty and then became wonderfully sunny along the way. Hoping to see some sea life but alas none waves were pretty choppy. Boat was wonderful.

  6. Liz

    Liz

    Cruise the beautiful Bay!!!

    Captain Steve was incredible. He made our two hour boat outing experience unforgettable. We stopped around monuments to snap some scenic photos and even when we got caught in some rain, we all were fully covered in the inside of the boat. We will certainly book again soon!!