We use cookies to improve your browsing experience.

And dolphins make us happy. Find out more about our cookies policy here.

Captain

Find The Best Boat Rentals in Chesapeake, Virginia.

Page 1 of 124 listings

22' Cape Craft 2200 DC Powerboat in Virginia Beach!
Powerboats in Virginia Beach · 6 guests

22' Cape Craft 2200 DC Powerboat in Virginia Beach!

5.0
$82-$100hour
38' Mini-Yacht!! - Large "Ultra Luxury" Adventure Boat in Virginia Beach!
Events in Virginia Beach · 13 guests

38' Mini-Yacht!! - Large "Ultra Luxury" Adventure Boat in Virginia Beach!

5.0
Superowner
$199-$299hour
Let's Go Sail in Gloucester Point, Virginia
Sailing in Gloucester Point · 6 guests

Let's Go Sail in Gloucester Point, Virginia

5.0
Superowner
$117-$125hour
Charter 32' Modern Hunter Sailboat In Gloucester, Point Virginia
Sailing in Gloucester Point · 6 guests

Charter 32' Modern Hunter Sailboat In Gloucester, Point Virginia

5.0
Superowner
$125hour
2022 Avalon Tritoon!!!!!!
Powerboats in Virginia Beach · 10 guests

2022 Avalon Tritoon!!!!!!

5.0
$199hour
38' Dawson Sportfish Motor Yacht Charter in Norfolk, Virginia
Fishing in Norfolk · 6 guests

38' Dawson Sportfish Motor Yacht Charter in Norfolk, Virginia

5.0
$450day
38' Mini-Yacht!! - Large "Ultra Luxury" Adventure Boat in Hampton, Virginia!
Events in Hampton · 13 guests

38' Mini-Yacht!! - Large "Ultra Luxury" Adventure Boat in Hampton, Virginia!

5.0
Superowner
$199-$299hour
Melges 24 - One Design Racing Experience Or Charter
Sailing in Hampton · 8 guests

Melges 24 - One Design Racing Experience Or Charter

5.0
Superowner
$200hour
Fishing Charter on 38' Dawson Sportfish Yacht in Norfolk, Virginia
Fishing in Norfolk · 6 guests

Fishing Charter on 38' Dawson Sportfish Yacht in Norfolk, Virginia

5.0
$94-$113hour
Custom Party Cruises & Fishing Trips in Virginia Beach
Events in Virginia Beach · 6 guests

Custom Party Cruises & Fishing Trips in Virginia Beach

5.0
$175-$185hour
Watersports Charter! Tubing · Wakeboarding · Waterskiing
Powerboats in Virginia Beach · 6 guests

Watersports Charter! Tubing · Wakeboarding · Waterskiing

5.0
$200-$250hour
Luxury Pontoon tours Serving Broad Bay Va Beach and Waterside Norfolk
Powerboats in Virginia Beach · 6 guests

Luxury Pontoon tours Serving Broad Bay Va Beach and Waterside Norfolk

5.0
$188hour
Inshore/Offshore Fishing Trip in Norfolk/VA Beach With Captain Lou
Fishing in Norfolk · 6 guests

Inshore/Offshore Fishing Trip in Norfolk/VA Beach With Captain Lou

5.0
$146-$250hour
Book this new, 6 person Suntracker Pontoon
Powerboats in Virginia Beach · 6 guests

Book this new, 6 person Suntracker Pontoon

5.0
$150hour
Family Yacht Sea Ray 340 in Virginia Beach area. Poquoson Va
Events in Poquoson · 9 guests

Family Yacht Sea Ray 340 in Virginia Beach area. Poquoson Va

5.0
$110hour
Proline 23ft Center Console Fishing Boat for Charter in Suffolk
Fishing in Hampton · 6 guests

Proline 23ft Center Console Fishing Boat for Charter in Suffolk

5.0
Snoozed - Active 02 Jan 2025
Sunset Boat Rides in Sandbridge (VA Beach)
Powerboats in Virginia Beach · 6 guests

Sunset Boat Rides in Sandbridge (VA Beach)

New
$250hour
26ft Sundeck with Bluetooth Stereo and Watersports for rent in Moyock
Powerboats in Moyock · 12 guests

26ft Sundeck with Bluetooth Stereo and Watersports for rent in Moyock

5.0
$120hour
Fish On! Rent Your 38ft Dawson Sportfish in Norfolk, VA
Sailing in Norfolk · 6 guests

Fish On! Rent Your 38ft Dawson Sportfish in Norfolk, VA

New
$725day
Fisherman’s Dream: 38ft Dawson Sportfish in Norfolk, VA!
Fishing in Norfolk · 6 guests

Fisherman’s Dream: 38ft Dawson Sportfish in Norfolk, VA!

New
$170hour
44ft ''Four Winds'' Fishing Yacht in Hampton, Virginia
Fishing in Hampton · 19 guests

44ft ''Four Winds'' Fishing Yacht in Hampton, Virginia

4.0
$225hour
Very Nice Sea Ray 185 Sport
Powerboats in Newport News · 7 guests

Very Nice Sea Ray 185 Sport

New
$75hour
23 Foot Grady White Gulfstream w/ twin Yamaha F150's
Powerboats in Virginia Beach · 6 guests

23 Foot Grady White Gulfstream w/ twin Yamaha F150's

New
Snoozed - Active 02 Sep 2024
Sail the Chesapeake Bay, Atlantic Coast or the Caribbean Islands in style! Charter this Jeanneau Sun Odyssey 509
Sailing in Deltaville · 8 guests

Sail the Chesapeake Bay, Atlantic Coast or the Caribbean Islands in style! Charter this Jeanneau Sun Odyssey 509

New
$524-$1,240day

Chesapeake Reviews

  1. AW

    ALEX

    22' Cape Craft 2200 DC Powerboat in Virginia Beach!

    Great experience with Max from beginning to end. Took 2 people and 1 dog to False Cape. Super communicative and happy to work with our schedule and requests. He was on time, the boat was nice and he was all around just a nice guy to talk with. No issues and would recommend a boat trip with Max to anyone!

  2. sophia

    sophia

    22' Cape Craft 2200 DC Powerboat in Virginia Beach!

    Max was the best boat captain! He was safe, knowledgeable, fun, and much more!!! He accommodated our group perfectly for my sisters Bachelorette! During our four hours we were able to see dolphins and much more around the bay. If your looking for a great captain and a fun time look no further and book with Max!

  3. AJ

    April

    38' Mini-Yacht!! - Large "Ultra Luxury" Adventure Boat in Virginia Beach!

    We had an amazing experience with our captain Ron today in Virginia Beach! He was very accommodating and continuously went out of his way to make sure we had a great time. He was very down to earth and super fun!! I highly recommend this company and can’t wait for the next venture!

  4. DH

    Dan

    Let's Go Sail in Gloucester Point, Virginia

    Bill was awesome. Very communicative leading up to the sail with weather, directions, and other logistical specifics. The trip left and returned on time, Bill was very knowledgeable about the boat and the area, let my wife and I take the helm several times and the boat was in great condition. Would totally sail with Cpt Bill again.

  5. CH

    Cyndi

    Charter 32' Modern Hunter Sailboat In Gloucester, Point Virginia

    My family of 5 had a wonderful day sailing with Bill to celebrate my husband's 40th birthday. Bill was very knowledgeable and excellent at explaining things to my children, even letting them each take the helm. We felt very at ease and safe our entire trip. I am already recommending him to friends.

  6. LN

    Linda

    Charter 32' Modern Hunter Sailboat In Gloucester, Point Virginia

    Mom, Dad, & three GROWN children went out on a wonderful outing with Captain Bill. He was a gracious host & his beautiful sailboat was spectacular! Enjoyed the experience immensely & seriously considering sailing lessons next spring. His boat was not only in immaculate condition but very comfortable for all five adults (plus the amiable captain). We were thrilled to see dolphins and hear about the area's history. We sailed 14.9 memorable miles. I gave a 5 star rating because the ratings don't go to 10. Honestly, how does one rate a great memory that lasts a lifetime? We weren't sure if the weather was going to be a wash out for a few days out, but Captain Bill kept in contact via email with weather updates and was extremely accommodating to what would work best for us. The weather wasn't what one would call picture perfect but I thought it was awesome having so much of the water to ourselves. We only saw one other sailboat. This was an exhilarating experience with a knowledgeable captain and I can't recommend him enough!