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Find Sailing Charters Near You

4.9
(5,031 Reviews)

Page 3 of 10240 listings

50ft Catamaran Charter with Water Toys - Annapolis, MD
Sailing in Annapolis · 12 guests

50ft Catamaran Charter with Water Toys - Annapolis, MD

5.0
$425/hour
38-ft Hunter 376 Sailing Adventure in Annapolis
Sailing in Annapolis · 6 guests

38-ft Hunter 376 Sailing Adventure in Annapolis

5.0
Superowner
$100+/hour
Instant Book
 Sail in Style Aboard the 2024 Seawind 1160 Lite – Your Perfect Charter Escape
Sailing in Annapolis · 13 guests

Sail in Style Aboard the 2024 Seawind 1160 Lite – Your Perfect Charter Escape

New
$350+/hour
STARZ -Lagoon 42 Catamaran in Chesapeake Bay
Sailing in Annapolis · 13 guests

STARZ -Lagoon 42 Catamaran in Chesapeake Bay

5.0
$400+/hour
SLOWDOWN - DUFOUR 430
Sailing in Annapolis · 12 guests

SLOWDOWN - DUFOUR 430

New
$250+/hour
 SWEET & SALTY FOUNTAINE PAJOT HELIA 44 CATAMARAN
Sailing in Annapolis · 12 guests

SWEET & SALTY FOUNTAINE PAJOT HELIA 44 CATAMARAN

5.0
$400+/hour
DOS MILAGROS Beneteau Oceanis 45 Sailing Yacht in Chesapeake Bay!
Sailing in Annapolis · 10 guests

DOS MILAGROS Beneteau Oceanis 45 Sailing Yacht in Chesapeake Bay!

New
$232+/hour
34ft Sailing Yacht in Annapolis, Maryland
Sailing in Annapolis · 4 guests

34ft Sailing Yacht in Annapolis, Maryland

New
$250/hour
43 foot Captained Catalina Sailing Yacht Located In Rock Hall, Maryland
Sailing in Rock Hall · 6 guests

43 foot Captained Catalina Sailing Yacht Located In Rock Hall, Maryland

5.0
$150+/hour
Beneteau Oceanis 50 Cruising Yacht in Rock Hall, Maryland
Sailing in Rock Hall · 6 guests

Beneteau Oceanis 50 Cruising Yacht in Rock Hall, Maryland

5.0
$150/hour
34' Hunter Cruising Monohull In Rock Hall, Maryland United States
Sailing in Rock Hall · 4 guests

34' Hunter Cruising Monohull In Rock Hall, Maryland United States

4.6
$275+/night
41’ Bristol Sailboat Charter in Solomons Island, MD
Sailing in Solomons · 6 guests

41’ Bristol Sailboat Charter in Solomons Island, MD

New
$90/hour
Relaxing historic sailing experience in St. Michaels, Maryland - Half Day Sail
Sailing in Saint Michaels · 6 guests

Relaxing historic sailing experience in St. Michaels, Maryland - Half Day Sail

5.0
$325/hour
Romantic Sunset Champagne Cruise on the Chesapeake Bay - 2 Hours
Sailing in Saint Michaels · 6 guests

Romantic Sunset Champagne Cruise on the Chesapeake Bay - 2 Hours

New
$400/hour
Experience the Charm of St. Michaels Aboard the 41ft Sail Selina 2hr Boat Tour
Sailing in Saint Michaels · 6 guests

Experience the Charm of St. Michaels Aboard the 41ft Sail Selina 2hr Boat Tour

New
$350/hour
Beautiful 24ft Bennington! Free Fuel, Delivery, Tube, And Life Vest!!!
Powerboats in South Carolina · 10 guests

Beautiful 24ft Bennington! Free Fuel, Delivery, Tube, And Life Vest!!!

5.0
$56/hour
Sailing Adventures on the Choptank River
Sailing in Cambridge · 6 guests

Sailing Adventures on the Choptank River

New
$100/hour
Chesapeake Bay Sailing (w/ Captain) - 33' Cape Dory - Kilmarnock, Virginia
Sailing in Kilmarnock · 4 guests

Chesapeake Bay Sailing (w/ Captain) - 33' Cape Dory - Kilmarnock, Virginia

5.0
$15+/hour
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+/hour
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
$125/hour
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+/day
Private Sailing Charters Aboard a 40ft Trimaran – Explore PEC by Wind
Sailing in Prince Edward · 12 guests

Private Sailing Charters Aboard a 40ft Trimaran – Explore PEC by Wind

4.9
Snoozed - Active 02 Nov 2025
Melges 24 - One Design Racing Experience
Sailing in Hampton · 5 guests

Melges 24 - One Design Racing Experience

5.0
Superowner
$100/hour
Bayliner Deck Boat Rental at Lake wallenpaupack!
Powerboats in Pennsylvania · 6 guests

Bayliner Deck Boat Rental at Lake wallenpaupack!

New
$115/hour

Local Sailing Reviews

  1. ML

    Martha

    50ft Catamaran Charter with Water Toys - Annapolis, MD

    We intentionally booked a late afternoon cruise around the Chesapeake so we would return around sunset to get great views and photos. Kristal was super responsive in preparing us and Captain Wayne and his 'first mate' Mish were super helpful with capturing the perfect photos. We would definitely book again!

  2. AP

    Andrea

    38-ft Hunter 376 Sailing Adventure in Annapolis

    This was our crew’s second trip with Capt Alberto and was a second great experience. Capt Alberto shares his passion for sailing and teaching sailing! Capt and Grace are incredibly kind and make a great day spent out on the bay!

  3. Lisa

    Lisa

    38-ft Hunter 376 Sailing Adventure in Annapolis

    Thank you so much Captain Alberto & Grace. We had a fabulous time and enjoyed learning about sailing. Thanks for trusting us to help steer and tack the boat. We had so much fun. You are a great teacher. We wish we could have stayed out longer.

  4. Joseph

    Joseph

    Beautiful 24ft Bennington! Free Fuel, Delivery, Tube, And Life Vest!!!

    Amazing communication, very friendly and transparent. I would rent again for sure

  5. JS

    Jen

    STARZ -Lagoon 42 Catamaran in Chesapeake Bay

    I highly recommend Chronic Sailing! We did a 4 hour charter out of Annapolis as a bachelorette party. Captain Steve and Sarah were so accommodating and made our time so memorable. We are so appreciative. They made everything so easy- from booking to sailing and making memories with us. The STARZ catamaran boat was incredible! It fit our big group comfortably and gave us a little bit of luxury as we lounged and enjoyed on the bay. Again, this was a great experience for all of us and I would love to use them again!

  6. Kasie

    Kasie

    38-ft Hunter 376 Sailing Adventure in Annapolis

    Wonderful Captain and wonderful boat! Plenty of shade above and below deck if the August heat becomes too much. We did the three hour tour, and it was a great half day length. We received a tour of downtown Annapolis and then Captain Alberto opened up the sails and we went on a beautiful ride down the river. It was fun and unique - even for those who have motor boat experience. Sailing is quintessential Annapolis and Captain Alberto was a great host.