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All listings near me

Find Sailing Charters Near You

4.9
(3,782 Reviews)

Page 2 of 10240 listings

Come Experience the ambient waters of the Potomac on the Sylvan MIRAGE Pontoon!
Powerboats in Washington · 6 guests

Come Experience the ambient waters of the Potomac on the Sylvan MIRAGE Pontoon!

5.0
$185/hour
Sail on the Potomac in Washington, DC aboard the 28ft Hunter Sailboat
Sailing in Washington · 6 guests

Sail on the Potomac in Washington, DC aboard the 28ft Hunter Sailboat

New
$280/hour
Fun time Jet Ski Rental at Lake Norman/Lake Wylie, SC near Charlotte, NC
Water Sports in Cornelius · 8 guests

Fun time Jet Ski Rental at Lake Norman/Lake Wylie, SC near Charlotte, NC

4.9
$84+/hour
SEARAY SLX400 | $800hr | 13 People
Events in Washington · 13 guests

SEARAY SLX400 | $800hr | 13 People

5.0
Superowner
Best of 2025
$800/hour
Instant Book
Captained Charter 30' Sailboat in Milwaukee, Wisconsin
Sailing in Milwaukee · 6 guests

Captained Charter 30' Sailboat in Milwaukee, Wisconsin

5.0
Snoozed - Active 02 Jan 2026
Luxury Stylish Poontoon
Powerboats in Cornelius · 8 guests

Luxury Stylish Poontoon

5.0
$150/hour
Hunter 216 Sailboat for rent in McKinley Marina, Milwaukee WI
Sailing in Milwaukee · 6 guests

Hunter 216 Sailboat for rent in McKinley Marina, Milwaukee WI

New
$120/hour
Charter this beautiful Catalina from Milwaukee, WI - Captain Included
Sailing in Milwaukee · 6 guests

Charter this beautiful Catalina from Milwaukee, WI - Captain Included

4.8
$150/hour
2022 Chaparral 23' SSI  - Get up to 6 captained up and down the Potomac River
Powerboats in Fort Washington · 6 guests

2022 Chaparral 23' SSI - Get up to 6 captained up and down the Potomac River

5.0
$150+/hour
CHEAP PONTOON BOAT RENTALS 8-12 PEOPLE
Water Sports in Huntersville · 12 guests

CHEAP PONTOON BOAT RENTALS 8-12 PEOPLE

New
$150/hour
Come Aboard and Sail Optimystic-Experience the breeze w/Lunch, Wine and Cheese
Sailing in Essex · 6 guests

Come Aboard and Sail Optimystic-Experience the breeze w/Lunch, Wine and Cheese

5.0
$150/hour
VIKO 30 Premium Sailing Yacht In Deale, MD
Sailing in Deale · 5 guests

VIKO 30 Premium Sailing Yacht In Deale, MD

New
$925/day
Take your Sailing Dream on Chesapeake Bay.  Rates reduced to for that dream!!
Sailing in Mayo · 6 guests

Take your Sailing Dream on Chesapeake Bay. Rates reduced to for that dream!!

5.0
$150+/hour
 VIKO S 35 Sailboat in Deale
Sailing in Deale · 6 guests

VIKO S 35 Sailboat in Deale

New
$298/hour
New Yacht Charter Bali 5.4 Sailing Catamaran in Annapolis Maryland
Sailing in Annapolis · 13 guests

New Yacht Charter Bali 5.4 Sailing Catamaran in Annapolis Maryland

5.0
$1,100/hour
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
 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

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. Elisabeth

    Elisabeth

    Come Aboard and Sail Optimystic-Experience the breeze w/Lunch, Wine and Cheese

    Charles & Renee were amazing! We booked last minute and enjoyed an awesome afternoon on The Optimystic in Chesapeake Bay!! We can’t wait to sail again!! Charles is an excellent Captain and host. A good teacher as well! Have an awesome winter!! See you in the Spring!! Charlie, Beth and Sam (Class of 2026) ⚓️⚓️⚓️

  3. Clinton

    Clinton

    Fun time Jet Ski Rental at Lake Norman/Lake Wylie, SC near Charlotte, NC

    Breyanna was AWESOME! Very accommodating! She went above, and beyond to ensure that our party had everything they needed for a great experience. I Look forward to working with her again. Next time we rent JetSki’s! Thank you Breyanna for making my birthday with my friends one to remember!

  4. Brandon

    Brandon

    Fun time Jet Ski Rental at Lake Norman/Lake Wylie, SC near Charlotte, NC

    Good time on the lake with two jet ski's. Drove around for awhile, hopped in the lake to cool off, jumped back on and explored the lake. Good summer day with the family. Read up on boating and lake rules and water safety before you go to keep yourself safe and the ski's in good shape. Stay in the open water, as Beyanna says

  5. JW

    Jessica

    Captained Charter 30' Sailboat in Milwaukee, Wisconsin

    Our group of six women celebrating girl's weekend had the most memorable and special outting on Scott's boat. He is very friendly, accomodating, generous, and easy going. His background as a Navy search and rescue swimmer coupled with his confident sailing abilites assured the group that safety was never an issue. He perfectly integrated into or out of our conversations, highlighting is flexible nature. We all highly recommend!

  6. SW

    SAJA

    Luxury Stylish Poontoon

    Our trip with Michael was fantastic! My family of 6 booked a trip with him on the 4th of July, and we had a great time relaxing on the water in his beautiful boat. He took us to some of the popular coves on Lake Norman until we finally settled on a sandbar. We parked and enjoyed the water with locals until our trip came to an end. 3 hours was the perfect amount of time for our group. We would certainly book with Michael again!