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Destination Cruises: A Private Yacht Adventure on the Bay

More than just a nice boat ride! Here's what recent Private Charter Guests said:

Watermark is outstanding. The entire team went above and beyond to make this cruise extra special. Thank you for all your great work! ~Sarah O'Malley

Everything went extremely well. Service was outstanding, food as well, captain and crew were very helpful and polite. Could not have been any better. ~Edmund T. Wooldridge

Take your own private cruise to…well, here are some ideas out of Annapolis & Baltimore:

1. St. Michaels. One of the favorites is the Cruise to St. Michaels…the town that fooled the British (but not the rest of us!). With amazing restaurants, wonderful shopping, and a walkable, quaint "seaport." this is a really relaxing way to take your office out and about. We can help you with your Crab Feast or other delicious dining options when you get there…FUN!

Suggested Itinerary: Depart at 9:30am from Annapolis, arrive in St. Michaels 11:30am, Lunch 12-1:30pm, free time to wander until 2:45pm, Depart St. Michaels for arrival in Annapolis at 5:15pm.

Suggested yachts: Lady Sarah and Cabaret II

2. Cantler's. Cruise to Cantler’s for a classic Crab Feast! Just an hour cruise from Annapolis, this is a locals' favorite for cracking crabs! Take this weekday-getaway and make it an event with a cruise up Mill Creek to Cantler’s. We wait dockside for your group to finish the feast. Then come back aboard for a casual cruise back to Annapolis with music and chill atmosphere. Awesome!

Suggested Itinerary: Depart at noon for Cantler’s with a 1pm arrival. Nosh until 2:30pm. Casual cruise back with views of the Bay Bridge, USNA, Severn River Bridge and more. Arrive back to Annapolis at 3:45pm.

Suggested yachts: Cabaret II and Lady Sarah (for groups of 10-15 people, try it aboard Miss Anne!)

3. Lighthouses! Take a tour of lighthouses out of Annapolis. Iconic Thomas Point Light, Sandy Point Light and Baltimore Harbor Light…toss in a cruise under the spans of the Chesapeake Bay Bridges and you have a really memorable experience for your group. Bring the photos on!! Add in a knowledgeable tour guide for fun facts to know and tell…more memories! A buffet lunch from an award winning caterer tops off the day.

Suggested Itinerary: Depart at 11:00am from Annapolis serving lunch after passing under the Bay Bridge. The Baltimore Light, Sandy Point Light and Thomas Point Light visited over the next 2 hours, arriving back in Annapolis at 2:45pm.

Suggested yachts: Lady Sarah or, for groups up to 200 guests, Catherine Marie

4. Baltimore! Cruise aboard Annapolitan II to Nick’s Crab House for a mouth-watering selection of locals' favorites or a crab feast! This casual cruise includes views of Baltimore including both history and port activities. After the meal, catch the City Lights as they light up the skyline…a treat for all.

Suggested Itinerary: Depart Baltimore Finger Piers at 5:30pm for a 1 hour cruise to Nick’s. Enjoy the feast and then board around 8:00pm for a casual cruise back to the Inner Harbor arriving back to the dock at 9:15pm.

Suggested yacht: Annapolitan II (up to 50 people)

5. Baltimore Cruise to Nowhere. This is a destination cruise to nowhere with everything you need right on board. Cocktails start the cruise with passed appetizers as you cruise out of Inner Harbor heading toward the Key Bridge. Dinner is served either buffet or seated from an award winning caterer with an open bar to keep the conversation lively. The DJ plays topside with room for dancing as you cruise back to Inner Harbor dockage. A special treat for everyone.

Suggested Itinerary: Depart Inner Harbor at 7:00pm for a 4 hour cruise to nowhere. Arrive back to dock at 10:45pm

Suggested yacht: Raven (up to 149 people)

Cruise with Watermark year-round! Our Holiday Charters are booking now for Lights Parade in Annapolis and New Year’s Eve in Baltimore and Annapolis. Plan a Friday or Saturday evening cruise for your company party. The Chesapeake Bay is always fun on a private yacht charter with Watermark.


Photo Credits: Top two photos by Webster Wright. Annapolitan II (red boat) photo by JT Frenaye.