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Find Sailing Charters Near You

4.9(Average of 4,164 reviews in this area)
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
Charter 42' Lagoon Catamaran in Annapolis, MD
Sailing in Edgewater · 12 guests

Charter 42' Lagoon Catamaran in Annapolis, MD

New
$400hour
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.
Sailing in Mayo · 6 guests

Charter this 42ft Sailboat in Edgewater, Maryland for up to 6 persons MAXIMUM.

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

Experience the Serenity of Sailing SV Magic

4.8
$165hour
Catalina 445 Sailboat
Sailing in 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
New Yacht Charter 2022 Bali 5.4 Sailing Catamaran in Annapolis Maryland
Sailing 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
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-$349hour
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
Starratt & Jenks Morgan 45ft Sailing Charter in Havre de Grace, MD - USCG Licensed Captain
Sailing in Havre de Grace · 6 guests

Starratt & Jenks Morgan 45ft Sailing Charter in Havre de Grace, MD - USCG Licensed Captain

New
$200hour

Local Sailing Reviews

  1. GF
    George
    34' Hunter Cruising Monohull In Rock Hall, Maryland United States

    Great value! Excellent sailing gear!! If you are an experienced sailor with at least one other person, you won't find a better value for day or overnight sailing near Annapolis. I will definitely be renting this boat again either with my family for the day or some buddies overnight. Took Icarus on a two night late-October trip from Rock Hall, overnight in Annapolis then St. Michaels with a couple buddies. James made the process VERY easy - very communicative and willing to go the extra mile for our convenience. This Hunter 34 sails really well (especially upwind.) It is set up that one experienced sailor and one other person can easily manage it. Comfort-wise it is probably better dockside on shore power in order to be able to utilize the cabin climate control system and power outlets for charging your phones (bring portable chargers if you won't be on shore power.) Returning the boat into the slip was a little tricky and James offered to be there to "coach us" in but we managed it on our own. The diesel was very reliable and fuel efficient - recommend you listen very carefully to James when he explains how to start it because can be a little tricky (as of Oct 2023.) Recommend you bring a handheld (or phone) GPS because as of Oct 23 the GPS is in the cabin. Bottom line - this is a great value - don't hesitate to book!!

  2. GE
    Gerard
    Experience the Serenity of Sailing SV Magic

    Had a fantastic day sailing with Josh! He was great with communications and was ready to go when we got there. The boat is very comfortable and while we only did a 3 hour sail, the boat has a good galley and bathroom and would be great for a longer sail. The marina location is excellent and we were in the Chesapeake in 15 to 20 minutes. Josh was a great captain - we enjoyed chatting with him and he made us very comfortable. Highly recommended.

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

    Captain David was amazing, all around including flexibility, punctuality, service. The vessel was clean and comfortable for my party. I would give him 10 stars and I will recommend him for any time of events.

  4. 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!

  5. Adam
    Adam
    Beneteau Oceanis 50 Cruising Yacht in Rock Hall, Maryland

    Excellent time out on the water for my wedding anniversary . Relaxing at times and also cruised around when the wind picked up. Saw many cool sights and lighthouses.

  6. 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!