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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

  • Expiring Soon

    This date becomes unavailable for instant booking in less than 1 day.

  • Limited availability

    Some departure times on this date are still available.

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

308 total bookings
Superowner
Capacity
6 guests
Sailing
Cruising Monohull

Reviews

5.0 (215 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
242 photos have been added by reviewers who booked this listing.
  1. AK

    Ashley

    What a great time with Alberto and his wife…the sweetest couple! We really enjoyed it!

  2. 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!

  3. 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.

  4. 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.

  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

308 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

  • Hunter
  • 376
  • Capacity: 6 people max

Safety Equipment

Anchor & Rode
Bilge Pumps
Carbon Monoxide Detectors
Emergency Steering
Fire Extinguishers
First Aid Kit
Flares
Life Jackets (1)
Life-Saving Appliances
Medical Supplies
Navigation Lights
Navigation Equipment
Sound Signals
Tool Kit
VHF Radio

Operating Equipment

AIS
Autopilot
Dinghy/Tender
GPS ChartPlotter
Depth Sounder

Guest Amenities

Coffee Maker
Cooler
Fridge
Kitchen Utensils
Pillows & Blankets
Shower
Sink
Sun Protection
Toilets (1)
Towels
Wine Fridge

Leisure & Entertainment Equipment

Bar
Bluetooth
Floats
Sound System
Indoor dinning Area
Outdoor Dinning Area
Outdoor Sun Bed

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

Free cancellation up to 5 days before your trip.

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  • Expiring SoonThis date becomes unavailable for instant booking in less than 1 day.
  • Limited availabilitySome departure times on this date are still available.
With Captain
  • Hourly Trips
  • Multi-Day Trips
  • With Captain Only