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Find Sailing Charters Near You

4.9(Average of 5,212 reviews in this area)
Learn more about sailing rentals and experiences
Page 1 of 10 (240 listings)
36ft Regal Luxury Yacht | $350 | 7 people
Events in Washington · 7 guests

36ft Regal Luxury Yacht | $350 | 7 people

New
Superowner
Best of 2022
$350hour
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
$175hour
Luxury Sailing Catamaran ⭐️⭐️⭐️⭐️⭐️
Events in Baltimore · 12 guests

Luxury Sailing Catamaran ⭐️⭐️⭐️⭐️⭐️

5.0
Superowner
Best of 2022
$349hour
30 ft sailboat with highly experienced Captain in Baltimore Inner Harbor
Sailing in Baltimore · 5 guests

30 ft sailboat with highly experienced Captain in Baltimore Inner Harbor

5.0
$150hour
Charter this 42ft Sailboat in Edgewater, Maryland for up to 6 persons MAXIMUM.  Take a sail on beautiful Chesapeake Bay or take some Beginner or Advanced sailing lessons on a big boat.
Sailing in Mayo · 6 guests

Charter this 42ft Sailboat in Edgewater, Maryland for up to 6 persons MAXIMUM. Take a sail on beautiful Chesapeake Bay or take some Beginner or Advanced sailing lessons on a big boat.

5.0
$175-200hour
Experience the Serenity of Sailing SV Magic
Sailing in Mayo · 6 guests

Experience the Serenity of Sailing SV Magic

4.7
$165hour
Catalina 445 Sailboat
Deale · 6 guests

Catalina 445 Sailboat

New
$298hour
Charter 44' Orana Cruising Catamaran In Deale, Maryland
Sailing in Deale · 10 guests

Charter 44' Orana Cruising Catamaran In Deale, Maryland

5.0
$2,600day
 VIKO S 35 Sailboat in Deale
Sailing in Deale · 6 guests

VIKO S 35 Sailboat in Deale

New
$298hour
41' Lagoon Catamaran in Maryland, United States
Sailing in Annapolis · 12 guests

41' Lagoon Catamaran in Maryland, United States

5.0
Superowner
Best of 2022
$320hour
38' Hunter 376 Cruising Monohull in Annapolis, Maryland, USA
Sailing in Annapolis · 6 guests

38' Hunter 376 Cruising Monohull in Annapolis, Maryland, USA

5.0
Superowner
Best of 2022
$138-150hour
46' Catamaran Charter with Water Toys - Annapolis, MD
Sailing in Annapolis · 8 guests

46' Catamaran Charter with Water Toys - Annapolis, MD

5.0
$213hour
Instant Book
New Yacht Charter 2022 Bali 5.4 Sailing Catamaran in Annapolis Maryland
Events in Annapolis · 12 guests

New Yacht Charter 2022 Bali 5.4 Sailing Catamaran in Annapolis Maryland

New
$1,100hour
Sail the Sea on the Pintita
Sailing in Annapolis · 20 guests

Sail the Sea on the Pintita

New
$500-750hour
Fully Crewed Annapolis Sailing Cruises
Sailing in Annapolis · 6 guests

Fully Crewed Annapolis Sailing Cruises

New
$175person
Sailing Adventure in Chesapeake Bay with 28ft Tartan Sailing Yacht!
Sailing in Annapolis · 4 guests

Sailing Adventure in Chesapeake Bay with 28ft Tartan Sailing Yacht!

5.0
$150hour
34ft Sailing Yacht in Annapolis, Maryland
Sailing in Annapolis · 4 guests

34ft Sailing Yacht in Annapolis, Maryland

New
$300hour
Sail out of Middle River onboard Hunter 41 AC Sailboat!!
Sailing in Essex · 6 guests

Sail out of Middle River onboard Hunter 41 AC Sailboat!!

5.0
$175hour
Catalina 425 Sailing Yacht in Rock Hall, Maryland
Sailing in Rock Hall · 6 guests

Catalina 425 Sailing Yacht in Rock Hall, Maryland

5.0
$150hour
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
Superowner
$150hour
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

4.5
$275-375night
Charter 41ft S/Y Selina II Sloop in St. Michaels, Maryland
Sailing in Saint Michaels · 6 guests

Charter 41ft S/Y Selina II Sloop in St. Michaels, Maryland

5.0
$250-350hour
Sunset Champagne Cruise on the Chesapeake Bay
Sailing in Saint Michaels · 6 guests

Sunset Champagne Cruise on the Chesapeake Bay

New
$399-400hour
41’ Bristol Sailboat Charter in Solomons Island, MD
Sailing in Solomons · 6 guests

41’ Bristol Sailboat Charter in Solomons Island, MD

New
$90hour

Set sail with GetMyBoat - enjoy a sailing charter.

Hit the open water in style on a sailing charter. Sailing charters with a professional captain are a relaxing way to get on the water and travel by wind power. A sunset sailing cruise, cocktail cruise, or other sailing adventure can make for the perfect experience on a lake or the ocean. Most larger sailboats (typically 18+ feet) also use an engine for longer sailing trips. GetMyBoat has all types of sailing charters and you can build a custom itinerary to plan the sailing holiday of your dreams. From hourly, half-day, full-day or overnight sailing excursions, you are sure to create memories that will last a lifetime.

Using GetMyBoat to rent your next sailboat.

Experiencing the water has never been easier thanks to GetMyBoat. GetMyBoat allows you to quickly search, compare prices, submit rental inquiries, and pay for your rental or charter from the convenience of your phone or computer. We offer a secure platform for renters to facilitate a seamless rental transaction. For boat owners, we connect millions of renters to their boat and provide the security and safety checks on each rental transaction.

Search for the perfect experience now and book your dream day out on the water.

Things to consider when booking a sailboat rental or charter.

  • Sailboats range in size and carrying capacity, so check with the captain to make sure the boat you pick will meet your needs.
  • If you want to learn some sailing techniques, ask about instruction or lessons while you're onboard.
  • Any doubts about booking your sailing adventure? No problem! Simply message the captain and ask any questions you may have.

Local Sailing Reviews

  1. JR
    Josh
    38' Hunter 376 Cruising Monohull in Annapolis, Maryland, USA

    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. MS
    Monique
    46' Catamaran Charter with Water Toys - Annapolis, MD

    Deren & Kristal were excellent hosts! We had a lovely day sailing the Chesapeake. They were very communicative and timely with their responses and were flexible with our parties needs and wants. What an excellent experience! Would highly recommend their boat.

  3. ZC
    Zee
    30 ft sailboat with highly experienced Captain in Baltimore Inner Harbor

    Captain John gave our group a very memorable and relaxing evening on the water! He made us feel welcome and right at home, was very knowledgeable, and made sure we all truly enjoyed our outing. 10 out of 10 recommend!

  4. LR
    Loretta
    Beneteau Oceanis 50 Cruising Yacht in Rock Hall, Maryland

    What a gorgeous day on the water aboard Sol Searcher! Captain Joe was an awesome host for our day! Peaceful, serene and exactly what we were hoping for to bring the summer to a close. What a lovely world we have to enjoy when we step away from the hustle of life and take the opportunity to take in all that it has to offer. Thank you Capt’n Joe for a wonderful sailing experience. Until we meet again, Loretta and Greg

  5. WC
    Whitney
    Experience the Serenity of Sailing SV Magic

    We had an awesome trip with Josh. He was very flexible with timing and knowledgeable about sailing. We were able to take our engagement photos on Josh’s boat with his help and input on lighting/backgrounds. It was a wonderful experience we will never forget!

  6. JW
    Julie
    46' Catamaran Charter with Water Toys - Annapolis, MD

    Incredible! Deren and Krystal made our experience phenomenal. From start to finish they were fun and professional. The boat is a stunner! We felt like royalty. My son celebrated his 8th birthday in style with all the toys and had a blast. We will be using them again next year.

Boating Guide - Sailing

Set sail with GetMyBoat - enjoy a sailing charter.

Hit the open water in style on a sailing charter. Sailing charters with a professional captain are a relaxing way to get on the water and travel by wind power. A sunset sailing cruise, cocktail cruise, or other sailing adventure can make for the perfect experience on a lake or the ocean. Most larger sailboats (typically 18+ feet) also use an engine for longer sailing trips. GetMyBoat has all types of sailing charters and you can build a custom itinerary to plan the sailing holiday of your dreams. From hourly, half-day, full-day or overnight sailing excursions, you are sure to create memories that will last a lifetime.

Using GetMyBoat to rent your next sailboat.

Experiencing the water has never been easier thanks to GetMyBoat. GetMyBoat allows you to quickly search, compare prices, submit rental inquiries, and pay for your rental or charter from the convenience of your phone or computer. We offer a secure platform for renters to facilitate a seamless rental transaction. For boat owners, we connect millions of renters to their boat and provide the security and safety checks on each rental transaction.

Search for the perfect experience now and book your dream day out on the water.

Things to consider when booking a sailboat rental or charter.

  • Sailboats range in size and carrying capacity, so check with the captain to make sure the boat you pick will meet your needs.
  • If you want to learn some sailing techniques, ask about instruction or lessons while you're onboard.
  • Any doubts about booking your sailing adventure? No problem! Simply message the captain and ask any questions you may have.

GetMyBoat has 240 listings for Sailing experiences in this location with 5,212 reviews.

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