Cookies!

We use cookies to improve your browsing experience. By continuing to browse or closing this banner, you agree to our use of cookies. Find out more about our cookies policy here.

38-ft Hunter 376 Sailing Adventure in Annapolis38-ft Hunter 376 Sailing Adventure in Annapolis38-ft Hunter 376 Sailing Adventure in Annapolis38-ft Hunter 376 Sailing Adventure in Annapolis

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

With Captain

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

Capt Alberto

301 total bookings
Superowner
Capacity
6 guests
Sailing
Cruising Monohull

Reviews

5.0 (212 reviews)
  • Listing Accuracy

    Awesome
  • Departure & Return

    Awesome
  • Vessel & Equipment

    Awesome
  • Communication

    Awesome
  • Value

    Awesome
  • Itinerary & Experience

    Awesome
  1. 38-ft Hunter 376 Sailing Adventure in Annapolis
  2. 38-ft Hunter 376 Sailing Adventure in Annapolis
  3. 38-ft Hunter 376 Sailing Adventure in Annapolis
  4. 38-ft Hunter 376 Sailing Adventure in Annapolis
  5. 38-ft Hunter 376 Sailing Adventure in Annapolis
  6. 38-ft Hunter 376 Sailing Adventure in Annapolis
  7. 38-ft Hunter 376 Sailing Adventure in Annapolis
  8. 38-ft Hunter 376 Sailing Adventure in Annapolis
  9. 38-ft Hunter 376 Sailing Adventure in Annapolis
  10. 38-ft Hunter 376 Sailing Adventure in Annapolis
  11. 38-ft Hunter 376 Sailing Adventure in Annapolis
  12. 38-ft Hunter 376 Sailing Adventure in Annapolis
240 photos have been added by reviewers who booked this listing.
  1. Lisa
    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.

  2. Kasie
    Kasie

    Wonderful Captain and wonderful boat! Plenty of shade above and below deck if the August heat becomes too much. We did the three hour tour, and it was a great half day length. We received a tour of downtown Annapolis and then Captain Alberto opened up the sails and we went on a beautiful ride down the river. It was fun and unique - even for those who have motor boat experience. Sailing is quintessential Annapolis and Captain Alberto was a great host.

  3. Bobby
    Bobby

    We went out for an afternoon sail with Capt Alberto and had an amazing time. We were blessed with a beautiful sunny day with perfect wind. Capt Alberto shared interesting stories and taught us a good bit about sailing along the way. Highly recommend!

  4. LP

    Laura

    Captain Alberto and his wife are absolute jewels! We sailed with them a couple of years ago and were excited to have this time with them today. They are friendly, professional and just such a joy to be around. Will be seeing them again soon, for sure!

  5. AE

    Amer

    Great, fun, safe sailing trip with Captain Alberto. Very knowledgeable and entertaining. Very welcoming and kept it safe. Excellent and safe trip idea for families. Highly recommended.

Capt Alberto

Capt Alberto

301 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!

Features & Details

Make
Hunter
Model
376
Length
38ft
Year
2020
  • Life jackets/required safety gear
  • Single Engine
  • Bimini
  • Wheel steering
  • Music System
  • Cabin

Approximate Location

You’ll get directions to the departure location when you make a booking.

The boat's approximate location on a map
Approximate Location

Cancellation Policy

Full refund up to 5 days prior.

Similar Listings

50ft Catamaran Charter with Water Toys - Annapolis, MD
Sailing in Annapolis · 12 guests

50ft Catamaran Charter with Water Toys - Annapolis, MD

5.0
$325/hour
Take your Sailing Dream on Chesapeake Bay.  Rates reduced to for that dream!!
Sailing in Mayo · 6 guests

Take your Sailing Dream on Chesapeake Bay. Rates reduced to for that dream!!

5.0
$150+/hour
 SWEET & SALTY FOUNTAINE PAJOT HELIA 44 CATAMARAN
Sailing in Annapolis · 12 guests

SWEET & SALTY FOUNTAINE PAJOT HELIA 44 CATAMARAN

5.0
$400+/hour
JEHM of the SEA 2014 CATALINA 445 Sailboat for Amazing Day in Chesapeake Bay!
Sailing in Annapolis · 12 guests

JEHM of the SEA 2014 CATALINA 445 Sailboat for Amazing Day in Chesapeake Bay!

5.0
$250+/hour
Charter 42' Lagoon Catamaran in Annapolis, MD
Sailing in Edgewater · 12 guests

Charter 42' Lagoon Catamaran in Annapolis, MD

5.0
$425/hour
  • Expiring SoonThis date becomes unavailable for instant booking in less than 1 day.
  • High DemandSeveral others are asking about this available date.
With Captain
  • Hourly Trips
  • Multi-Day Trips
  • With Captain Only