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You're in good hands

Book your trip with confidence — We only work with the best local guides that know the area like the back of their hand.

About Your Trip

Type

Boat Cruise, Booze Cruise

Skill Levels

Beginner, Intermediate, Advanced

Weather

You won’t lose your deposit if the trip is canceled due to weather.

About Your Trip

Spend the afternoon cruising Annapolis and the Chesapeake Bay on a private 2.5-hour charter for up to 6 passengers.

Your captain will show you some of the area's most recognizable sights from the water, with the opportunity to cruise past places like Ego Alley, the Naval Academy, Spa Creek, and Thomas Point Lighthouse. It's a great option for sightseeing, celebrations, or simply enjoying an afternoon on the Bay with friends and family.

You'll cruise aboard a classic 35' Maryland-built Chesapeake Bay deadrise with a covered deck area, indoor cabin, and private marine restroom. A charcuterie spread, light snacks, bottled water, and cold drinks are provided, and you're welcome to bring additional food and alcoholic beverages of your own. Cooler space and ice are available onboard.

Trips depart at 1:00 PM from Nautilus Point Marina in Annapolis. Please arrive 15 minutes before departure.

Grab a cold drink, settle in, and enjoy an afternoon exploring the Chesapeake!

Amenities

Type

Boat Cruise, Booze Cruise

Skill Levels

Beginner, Intermediate, Advanced

Beer

Feel free to enjoy responsibly, but please no glass.

Boat Restroom

This boat has a restroom.

Weather

You won’t lose your deposit if the trip is canceled due to weather.

Kid Friendly

This trip can cater to small children.

Flexible Cancelation

This trip can be canceled up to 7 days before the trip.

Disability Friendly

This trip is not suited for those with disabilities.

Lunch

Please provide your own food / snacks.

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Pricing Matrix

	2 hours
1 Person	$950.00
2 People	$950.00
3 People	$950.00
4 People	$950.00
5 People	$950.00
6 People	$950.00

Pay 50% of the price as a deposit today, with the balance due on the day of the trip.

About Your Guide

Rob C.

Independent Guide

About Your Guide

Rob C.

Independent Guide

Captain Rob and Captain Bill grew up near the headwaters of the Chesapeake Bay, spending their lives around the rivers and waters that make Maryland such a special place to explore by boat.

Rob eventually made his way to the Annapolis area, where he spent years exploring the middle Chesapeake, from the South River and Annapolis to Kent Island, West River, and beyond. His time fishing, crabbing, and boating throughout the Bay eventually led him to earn his captain's license and begin sharing these waters with others.

Bill brings extensive experience of his own, with time spent aboard both powerboats and sailboats. His adventures have taken him throughout the Chesapeake, along the East Coast, and into the Caribbean.

Both captains hold USCG 50-ton Master's licenses along with additional boating safety and instruction certifications. Safety is always at the forefront, but they also love sharing the history, scenery, and local knowledge of the Chesapeake with their guests.

Whether you're celebrating a special occasion, sightseeing around Annapolis, or simply looking for a relaxing day on the water, Rob and Bill are ready to welcome you aboard!

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Start Location & Lodging Options

Annapolis, Maryland

About Your Boat

Boat photo for Annapolis Afternoon Cruise

1/6

Boat Type: Down East Cruiser
Boat Manufacturer: Markley
Boat Length: 35'
Boat Restroom: Yes

About Your Boat

Boat Type: Down East Cruiser
Boat Manufacturer: Markley
Boat Length: 35'
Boat Restroom: Yes

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Trip Details & Amenities

Type

Boat Cruise, Booze Cruise

Skill Levels

Beginner, Intermediate, Advanced

Beer

Feel free to enjoy responsibly, but please no glass.

Boat Restroom

This boat has a restroom.

Weather

You won't lose your deposit if the trip is canceled due to weather.

Kid Friendly

This trip can cater to small children.

Flexible Cancelation

This trip can be canceled up to 7 days before the trip.

Disability Friendly

This trip is not suited for those with disabilities.

Lunch

Please provide your own food / snacks.

Everything Else to Know

Everything is included, but we also recommend bringing sunglasses, sunscreen, weather-appropriate clothing, and anything else you might want on the trip.

We use a cashless autopay system. We'll send you a boarding pass, and on the day of the trip, your guide will scan your boarding pass to automatically transfer the remaining balance. The only cash needed is to tip your guide (we recommend 20%).

Cancel for free up to 7 days before the trip and receive credit back to your account. Cancelling within 7 of the trip will forfeit your deposit to the guide. Day-of cancellations and no-shows will be charged the full balance of the trip to their card.

In the event of inclement weather you'll be covered by out 100% Weather Guarantee and will not lose your deposit.

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First Time Booking with Us?

Captain Experiences is home to thousands of quality, vetted fishing, hunting, and other outdoor sports guides across the US and beyond. Our mission is to Unlock the Outdoors by making it quick and easy to book the trip of a lifetime every time with our Damn Good Guides.

We vet our guides and only partner with the best of the best. Our guides do their very best to keep you safe, show you a great time, and send you home with a memorable experience shared with family and friends.

Once you've paid your deposit at checkout, we'll send you a QR Code boarding pass. Just show your guide your boarding pass on the day of the trip, they'll scan it, the remaining balance will transfer automatically, and you'll be all set to get out there. Just make sure you bring a cash tip for the guide!

In the event of inclement weather, our guides will check the conditions and make the final call on whether its safe to go on the trip. If they decide the trip needs to be postponed, we'll work closely with you to reschedule or provide a credit for the full deposit, which can be applied to any of our trips in the US and beyond.

Each trip's price is determined by the guide and reflects all associated costs. A significant factor in pricing is often the type of boat and the corresponding fuel expenses. Additional costs may include leases, marina or slip fees, and the expenses involved in providing and maintaining the necessary gear for your trip.

After booking your trip, we'll connect you directly with your guide to discuss additional details. In the meantime, our team is here to answer any questions via email, text, or phone.