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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

100% refund within 5 days of your trip
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    This date is available.

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

Capt Alberto

342 total bookings
Superowner
Capacity
6 guests
Sailing
Cruising Monohull

Reviews

5.0 (230 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
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  11. 38-ft Hunter 376 Sailing Adventure in Annapolis
  12. 38-ft Hunter 376 Sailing Adventure in Annapolis
270 photos have been added by reviewers who booked this listing.
  1. MS

    Mary Beth

    Excellent trip! Friendly and experienced Captain and first mate! My family and I had a lovely time on a beautiful day! Book today - you will be happy you did!

  2. Erika
    Erika

    We had such a great time! The boat was perfect and Alberto and his wife were great hosts. It’s a good sized boat, kid-friendly (they had kids life jackets), and the cabin was spacious with plenty of room to eat.

  3. AV

    Ariel

    We had a lovely experience out on the bay. Captain Alberto let my husband steer the boat & put the kiddos to work as well. We were able to play & relax as well while out on the water. Very family credibly experience and lovely to get to know the captain & his wife! Overall 5 stars for a sailing experience on the bay!

  4. LT

    Libby

    Wonderful sunset sail either Captain Alberto. Everything was perfect!

  5. JH

    Julie

    A great day on the bay with Alberto and Grace. They are lovely and wonderful hosts—and a super safe and accommodating Captain/ First Mate!!

Capt Alberto

Capt Alberto

342 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

Departure Location

The boat's approximate location on a map

You’ll get helpful information for your departure after your booking is confirmed.

Street Address For Arrival

Street Address For Arrival

7366-7364 Edgewood Road
Annapolis, Maryland, 21403
United States
Departure Location

Departure Location

Same as Street Address

Cancellation Policy

Free cancellation up to 5 days before your trip.

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With Captain
  • Hourly Trips
  • Multi-Day Trips
  • With Captain Only