Best Sailboat Rentals Near Annapolis

Name: 54' Luxury Yacht – Perfect for Family, Friends & Business Outings
Rating: 5.0

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Labor Day Weekend Boat Rentals

Our top sailboat rentals

Rent a Catamaran catamaran in Annapolis, MD near me

$831+ /hour

Annapolis, MD

5.0 (18 bookings)

54' Luxury Yacht – Perfect for Family, Friends & Business Outings

3 - 8 hours Captained

Up to 12 passengers

$469+ /hour

Annapolis, MD

5.0 (35 bookings)

46' Catamaran Charter with Water Toys - Annapolis, MD

3 - 8 hours Captained

Up to 12 passengers

Rent a Hunter cruiser in Essex, MD near me

$166+ /hour

Essex, MD

5.0 (2 bookings)

Sail Away on Optimystic

2 - 8 hours Captained

Up to 6 passengers

$167+ /hour

Galesville, MD

5.0 (10 bookings)

Das Boot Custom Sailing Charters

4 - 6 hours Captained

Up to 8 passengers

$334+ /hour

Annapolis, MD

2018 Fountaine Pajot Helia 44

4 - 8 hours Captain optional

Up to 12 passengers

$341+ /hour

Annapolis, MD

Shared Adventure

4 - 8 hours Captained

Up to 12 passengers

$175+ /hour

Rock Hall, MD

"Shardana" - 42' Sailboat with Captain

3 - 8 hours Captained

Up to 6 passengers

$203+ /hour

Annapolis, MD

5.0 (9 bookings)

Sail away on the Chesapeake Bay with Chessie from Annapolis!⛵️

2 - 8 hours Captained

Up to 6 passengers

$275+ /hour

Deale, MD

4.8 (26 bookings)

Stable, comfortable & fast - sleeps 8 w/4 baths!

4 - 8 hours Captained

Up to 10 passengers

$256+ /hour

Annapolis, MD

Slowdown Dufour 430

4 - 8 hours Captained

Up to 10 passengers

$256+ /hour

Annapolis, MD

2013 Catalina 445

4 - 8 hours Captained

Up to 10 passengers

$78+ /hour

Easton, MD

Boston Whaler Harpoon 5.2 Sailboat

6 - 8 hours Captain optional

Up to 4 passengers

$141+ /hour

Annapolis, MD

5.0 (14 bookings)

Experience sailing in the heart of Annapolis md

4 - 8 hours Captained

Up to 6 passengers

$244+ /hour

Annapolis, MD

DOS MILAGROS - Beneteau Oceanis 45

4 - 8 hours Captained

Up to 11 passengers

Top sailboat rentals reviews in Annapolis, MD

300,822

Customers Reviews

4.95

Avg. Rating

5/5 stars

Sail away on the...

Great experience renting this boat. Clean, well provisioned, just as described. Would definitely rent again.

Rohit

Aug 2025
5/5 stars

46' Catamaran...

I can't say enough positive things about Captain Dave and his First Mate, Krystal. It was a reunion day with my...

Joel

Aug 2025
5/5 stars

46' Catamaran...

We enjoyed ourselves! A great time was had. I will be renting again. Thank you!

Darien

Jul 2025
5/5 stars

Experience...

Thank you Alberto! Was wonderful sailing with you and your wife today. The weather was beautiful and we learnt a lot...

Aparajita

Jun 2025
5/5 stars

46' Catamaran...

Late writing this review (sorry!) but our group had an amazing experience! The boat was clean and had everything we...

Lauren

Jun 2025
5/5 stars

Experience...

Boat was in excellent condition.

Oliver

Oct 2024
5/5 stars

46' Catamaran...

We rented this boat for my sister's bachelorette party and had the BEST time! Seriously it was the highlight of the...

Brittany

Sep 2024
5/5 stars

46' Catamaran...

My group had the best time with Windsong Charters. Everything was exactly as described and we had a wonderful day....

Patricia

Sep 2024
5/5 stars

46' Catamaran...

The boat was super spacious and filled with an array of water toys that were a crowd favorite at my sister’s...

Rachel

Sep 2024
5/5 stars

Experience...

Laura

Aug 2024
5/5 stars

46' Catamaran...

Amazing boat, perf for our bachelorette party of 9. Put simply, it was just a total blast. And cutest seafaring dogs...

Catherine

Aug 2024
5/5 stars

46' Catamaran...

I had an incredible time on the 50' catamaran! It offered ample space for everyone, including those less comfortable...

Mohamed

Aug 2024

How to rent a sailboat in Annapolis?

Find the perfect boat

Enter your desired location and date to explore our fleet of sailboats.

Select a captain

Choose to drive yourself or select a USCG licensed captain.

Book with ease

Connect with your boat owner and complete your booking online.

Set sail

Enjoy your day on the water with friends and family!

Why Boatsetter?

As the global leader in peer-to-peer boat rentals, Boatsetter offers an easy, safe and accessible way to experience on-the-water adventure. With boat rentals in 600+ locations, finding a boat is easy and with the option to tap into the largest network of USCG licensed captains, boating experience is not required.

Get out on the water worry-free, knowing our insurance covers every boating trip

Choosing the right boat rental platform is essential to your peace of mind while on the water. That's why we've gone the extra mile to focus on safety through our exclusive partnership with GEICO Marine and BoatUS. As the first and only boat rental marketplace to offer insurance on every peer-to-peer rental, you are protected during all rentals with insurance coverage and on-water assistance through TowBoatUS.

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Got questions?

Frequently asked questions

How much does it cost to rent a boat?

The cost to rent a boat depends on whether you are renting for a half-day or a full day, the boat features and the boat size can impact your boat rental price. Rental prices can range from $200 to $1,000 plus depending on the boat rental itself and the length of time of the rental.

How many people can fit on the boat rental?

The number of people who can fit on boat rental largely depends on the boat’s size and how many life jackets are on board. Currently the coast guard allows a maximum of 10-12 people on a Boatsetter boat rental.

How old do you have to be to rent a boat?

You must be 18 years old to rent a captained boat and 25 years old if you would like to rent a bareboat charter.

Do I need a boating license to rent a boat?

Boating license requirements vary from state to state. As a renter, you are responsible for understanding local state requirements.

How much does it cost to rent a boat for the day?

The cost of renting a boat for the day on average ranges from $200 to $1200. The cost to rent a boat varies depending on the size of the boat and the length of time that you will be using the boat.