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38-ft Hunter 376 Sailing Adventure in Annapolis

Annapolis Sailing Charter: Experience the Chesapeake Bay on a 38-ft Hunter 376

Name: 38-ft Hunter 376 Sailing Adventure in Annapolis
Brand: Hunter
Price: 100 USD
Availability: OnlineOnly
Rating: 5.00 (222 reviews)

With Captain

100% refund within 5 days of your trip

5.0(222 reviews) ·

320 bookings

the United States,Maryland,Annapolis,Sailing

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Relaxed, scenic sails on the Chesapeake with a warm, welcoming crew. Guests describe magical outings, from romantic moments to hands-on sailing lessons.

Comfortable cruising sailboat set up for easy, stable bay sailing, giving guests space to relax while still getting involved in the sailing experience.

Guests repeatedly praise the captain couple as kind, flexible, and skilled teachers who share their passion for sailing and make outings feel personal and special.

Renters say this listing is great for:

Date NightsFamily TimeSunset CruisingSightseeing

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AI Overview

Owner's Description

ABOUT THE TRIP Set sail on the scenic Chesapeake Bay aboard NewLife, a 38-ft Hunter cruising monohull, perfect for up to six guests. Whether you're seeking a romantic sunset cruise, a family adventure, or a peaceful day on the water, this experience has something for everyone. Captain Alberto ensures every guest feels like a welcome adventurer, offering expert guidance and a warm, relaxed atmosphere. ABOUT THE BOAT NewLife, a Hunter sailboat, is built for both comfort and performance. The bright, airy interior features cozy private berths, while the spacious cockpit and deck provide plenty of room to relax and enjoy the sail—whether you're a seasoned sailor or stepping aboard for the first time. WHAT'S INCLUDED Your booking includes the vessel, a licensed captain, and crew fees. NewLife is clean, well-maintained, and fully equipped for your next sailing adventure. WHAT'S NOT INCLUDED Meals, beverages, and optional activities can be arranged directly with Captain Alberto. Gratuities are not included but are always appreciated. OTHER THINGS TO KNOW Trip details can be tailored with Captain Alberto after booking to ensure a personalized experience. A former Annapolis Sailing School instructor and a U.S. Coast Guard Licensed Master (100 Ton), Captain Alberto has sailed waters from Long Island Sound to the Florida Keys, Bahamas, Virgin Islands, and even the coast of Patagonia, Argentina—bringing world-class expertise and genuine hospitality to every charter.

Capt Alberto

320 total bookings

Superowner

Capacity: 6 guests

Sailing: Cruising Monohull

Reviews

5.0 (222 reviews)

Listing Accuracy
Awesome
Departure & Return
Awesome
Vessel & Equipment
Awesome
Communication
Awesome
Value
Awesome
Itinerary & Experience
Awesome

261 photos have been added by reviewers who booked this listing.

AH
Alexandra

Alberto and Grace were the perfect team. They are kind, knowledgeable, respectful, communicative, safe and I would recommend them to anyone. This was our first time sailing in Annapolis, and we could not have asked for a better experience. We hope to share future experiences with them. Everything was perfect.
BF
Bruce

This was our 2nd sail with Capt Alberto. He is super friendly and easy to talk with. And he invites his guests to take an active role in sailing, or to just kick back and relax if they prefer. Great experiences for our family.
CR
Chawin

Captain Alberto and Grace are wonderful hosts and guides. They have a wealth of sailing and life experience to share during your trip. They were very flexible with us during a proposal event.
AP
Andrea

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!
Lisa

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.

Capt Alberto

320 total bookings

Superowner

I am excited to be a part of the GetMyBoat movement in making boats more accessible and affordable to others. I hope to get out on the water more and help boating grow!