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St. Michaels Sailing Charters

Sunset and private sails through the stunning Chesapeake waters
(4 reviews)
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5.0 out of 5 stars (based on 4 reviews)
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Laura Bell
CEO / Founder
Number of Tours
6
Number of Reviews
(4 reviews)
Rating
5.0
5.0 out of 5 stars (based on 275 reviews)
Excellent99%
Very good1%
Average0%
Poor0%
Terrible0%
Response Rate
94%

About

St. Michaels Sailing Charters offers exceptional sailing experiences from the scenic waters of St. Michaels, Maryland, providing guests with a memorable blend of relaxation, adventure, and local maritime charm. Whether you’re seeking a romantic sunset cruise, a private charter for family and friends, or a customized sailing excursion on the Chesapeake Bay, their experienced crew delivers top-notch service and personalized attention from start to finish.

Guests aboard St. Michaels Sailing Charters enjoy spacious, comfortable vessels and knowledgeable captains who share insights about the Bay’s history, ecology, and hidden gems along the coastline. Perfect for celebrations, date nights, sightseeing, or simply enjoying the water and breeze, these charters are tailored to your group’s preferences and interests.

From serene sunset sails to adventure-filled outings, St. Michaels Sailing Charters creates unforgettable experiences that showcase the beauty of the Chesapeake Bay while providing a relaxing escape on the water.

Tours and adventures by Local Legends Tours

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Chesapeake Bay Sunset Champagne Sail on Lady Patty

(3 reviews)

Free Cancellation

  • 2 hours

Sail the Chesapeake Bay on a 2-hour sunset cruise aboard the historic Lady Patty. Enjoy champagne, scenic river views, and a relaxing, romantic atmosphere guided by knowledgeable crew.

From: $115.00 per person
Book Now
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Chesapeake Bay Sunset Champagne Sail on Epiphany

(3 reviews)

Free Cancellation

  • 2 hours

Enjoy a Champagne Sunset Sail aboard the Epiphany catamaran on Chesapeake Bay. Sip drinks, take in stunning river and bay views, and relax in a scenic, romantic evening cruise with expert crew.

$195.00 per person
Book Now
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St. Michaels Wine Tasting Cruise on Epiphany

(3 reviews)

Free Cancellation

  • 2 hours

Enjoy a relaxing wine tasting cruise aboard the Epiphany catamaran on Chesapeake Bay. Sip curated wines, admire scenic harbor views, and unwind with friendly crew on tranquil waters.

From: $195.00 per person
Book Now
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Review Summary

5.0
5.0 out of 5 stars (based on 4 reviews)
Excellent100%
Very good0%
Average0%
Poor0%
Terrible0%

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Hands down the best way to see Maryland!

February 11, 2026

Hands down the best way to see Maryland! We had such a fabulous time on the water in such a beautiful boat. Diane is amazing! She went out of here way to make sure it was a memorial event and Captain Scott knew all the best places for the perfect views. We will definitely be back next time we visit. Thank you both so much!

Tamara Lawrence

Amazing time with amazing hosts for my boyfriend's birthday!

February 11, 2026

surprised my boyfriend with a sunset cruise with St. Michael’s Sailing Charters for his birthday. We had such an amazing time! Laura and GM were amazing hosts and we felt truly pampered. The catamaran is stunning and so comfortable. I highly recommend it!

Jennifer Fowler

Perfect Evening on the Chesapeake Bay

February 11, 2026

Our sunset cruise was amazing! Captain Scott and First Mate Diane were truly the best – we felt like we were with family the whole time! Truly an enjoyable evening! I highly recommend this cruise and this team! If you are looking for a beautiful enjoyable time book this! It was a memorable time, one we will not forget! Thank you for a lovely evening in St Michael.

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Kathy Hennessy

The Best Way to Experience St. Michaels

February 11, 2026

We had a fantastic experience with Captain Scott and First Mate Diane on St. Michael’s Sailing Charters on board the Epiphany during a wedding weekend getaway with our family of six. The catamaran was beautiful, spacious, clean, and perfect for cruising the Chesapeake Bay.

Captain Scott was professional, knowledgeable, and shared great insight about the area, making the tour both relaxing and informative. First Mate Diane was incredibly warm and welcoming from the moment we stepped on board.

It was our first time in St. Michael’s, and seeing the region by water was the perfect way to take in the charm and natural beauty of the Bay. A wonderful memory for all of us. We highly recommend this experience to anyone visiting the area!

Angeli Breen

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Frequently asked questions

St. Michaels Sailing Charters offers private sailing trips including sunset cruises, daytime sails, romantic outings, family excursions, and fully customized charters on the Chesapeake Bay.
Charter lengths vary, with most experiences ranging from 2 to 4 hours, depending on the package selected. Custom durations may also be available upon request.
All sailing experiences are private charters, meaning the boat is exclusively reserved for your group.
No experience is required. Your licensed captain handles all navigation and sailing while you relax and enjoy the experience.
Guests are encouraged to bring sunscreen, sunglasses, soft-soled shoes, and light layers. You may also bring snacks or beverages, depending on the charter guidelines.
Absolutely! St. Michaels Sailing Charters is perfect for anniversaries, proposals, birthdays, corporate outings, and small celebrations, with customizable options to make your sail memorable.

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