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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 (247 reviews)

With Captain

100% refund within 5 days of your trip

5.0(247 reviews) ·

353 bookings

the United States,Maryland,Annapolis,Sailing

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Relaxed, scenic sails on the Chesapeake with hands-on sailing, easy conversation, and a welcoming vibe that works equally well for friends and families.

Comfortable cruising sailboat with plenty of space to relax, smooth on the water and consistently praised by guests as a great platform for learning and bay touring.

Attentive, kind hosts known for thoughtful care, clear communication, flexible rescheduling, and patient sailing instruction that puts first-timers at ease.

Renters say this listing is great for:

Family TimeDate NightsSightseeingSunset Cruising

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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

353 total bookings

Superowner

Capacity: 6 guests

Sailing: Cruising Monohull

Reviews

5.0 (247 reviews)

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

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

AR
Alison

We had such a fun experience with Captain Alberto and Grace. They were delightful company and the sailing was beautiful! Getting to steer and learn the ropes was an extra perk.
SL
Saskia

Captain Alberto and his wife provided a lovely sailing experience for myself and my elderly parents, and were so kind to help both of my parents on and off the boat with great care-- even assisting them to get back to our car. We really enjoyed our time out on the bay
LH
Laura

Alberto and his wife were absolutely wonderful hosts. They were welcoming, attentive, and made sure every detail of our sailing trip felt effortless. We had the most perfect day on the water, beautiful views, great company, and an experience we’ll remember for a long time. Highly recommend their boat and hospitality.
PS
Patricia

Alberto was great about communicating and flexible when we had to reschedule due to bad weather the first time. He and his wife hosted us, balancing chatting and talking with them and having our own time as friends. Definitely recommend and would book again
DR
Doug

Outstanding evening on the Chesapeake with Captain Alberto! Excellent Captain who taught as we went. The kids really enjoyed their first sailing experience!

Capt Alberto

353 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!