Annapolis, Maryland
Your Private Boat Experience Awaits
Custom trips on Spa Creek, Annapolis Harbor, and the Chesapeake Bay — with a USCG-licensed Master Captain.
A different kind of boat experience
Not a Tour Boat. Your Boat.
This isn't a crowded party boat or a scripted harbor tour. When you book with us, you get the whole boat — just your group, your agenda, and a USCG Master-credentialed captain who knows these waters.
Whether you want to sail the Chesapeake, cruise Spa Creek and Ego Alley, anchor and swim, pull up to a waterfront restaurant by boat, or simply enjoy a quiet afternoon on the water — we'll tailor the outing to you. The experience is low-key and personal, never rushed.
Guests are welcome to bring food and drinks or arrange for catering prior to your trip. We'll work around the weather, the conditions, and whatever sounds good to your group.
USCG Master
Credentialed Captain
Who you'll be sailing with
Captain Steve
I'm a USCG Master-credentialed captain based in Annapolis, and I've spent years on these waters — Spa Creek, the Severn River, and the many peaceful creeks and charming ports of call on the Chesapeake Bay. I know the anchorages, the best spots for different activities, and the waterfront restaurants worth arriving at by boat.
My goal is simple: give you a safe, comfortable, and genuinely memorable time on the water. I keep things relaxed and personal. No crowds, no scripts, no rushing. Just a good day on the Bay with those who appreciate it.
I operate two boats — a classic Nauticat 331 pilothouse ketch for sailing and longer outings, and a nimble 12-foot AB Oceanus RIB for shorter harbor cruises. Whatever you have in mind, we can make it work. Special requests welcome!
Choose your vessel
Two Ways to Get on the Water
Choose the experience that fits your group and your day.
Sailing, cruising, and longer outings
Nauticat 331 — Classic Pilothouse Ketch
Step aboard a classic Nauticat 331 for a private sailing experience in Annapolis. This comfortable pilothouse sailboat is ideal for a relaxed harbor cruise, sightseeing around Spa Creek and the Severn River, sailing the Chesapeake Bay, or a quiet time on the water with friends or family.
The pilothouse design gives you the option to be inside or outside — offering a comfortable, dry option when the weather doesn't cooperate, and A/C relief on hot days. The shaded cockpit, classic teak character, and movable cushioned seats make for a genuinely comfortable outing. Guests are welcome to bring food and drinks. Plates, cups, utensils, a cooler with ice, and a small gas BBQ grill are available. Catering can also be arranged.
Short, affordable, and fun harbor rides
AB Oceanus RIB — Harbor Cruiser
Step aboard a nimble 12-foot AB Oceanus RIB for a private, relaxed cruise through the heart of Annapolis. Perfect for 1–4 guests, this quick harbor ride offers an intimate, personalized way to experience Spa Creek, the lively Ego Alley, and the iconic Annapolis waterfront.
Piloted by a USCG Master-credentialed captain, the RIB blends safety and agility — carving close to moored yachts, waterfront homes, and scenic shoreline vistas while remaining dry, comfortable, and secure. Onboard: Bluetooth stereo, a cooler for drinks and snacks, and an anchor for when you want to pause and enjoy the atmosphere. Pets, children (with properly fitted life vests), and light refreshments are all welcome.
Private Annapolis boat charter
What Would You Like to Do?
Scenic Harbor Cruise
Take in the iconic Annapolis skyline, the Naval Academy, and the historic waterfront from the water. Perfect for first-timers or anyone who wants to see Annapolis at its best.
Sunset Outing
There's nothing quite like a Chesapeake Bay sunset from the water. We'll time the trip to catch the golden hour and find the perfect spot to watch the sky change.
Anchored Picnic
Drop anchor in a quiet cove, put out the swim ladder, and enjoy the afternoon. Bring your own food and drinks — we'll find the spot.
Casual Celebration
Birthdays, anniversaries, proposals, graduations — the boat is a great venue. Intimate, memorable, and completely private.
Family Experience
Kids love being on the water. We keep it safe, fun, and relaxed — a great way to introduce the family to life on the Bay.
Custom Trip
Have something specific in mind? A lighthouse run, a crab feast at anchor, a photography outing? Tell us what you're imagining and we'll make it work.
Every trip is private and customized. These are just starting points.
Chesapeake Bay private cruise
Estimated Pricing
Rates vary by trip length, group size, season and booking site. Contact Steve or your preferred booking site for an exact quote. Special requests and requests for flexibility welcome.
2 Hours
Starting at $500
Perfect for a quick harbor cruise or sunset outing. Up to 6 guests on the Nauticat, up to 4 on the RIB.
4 Hours
Starting at $850
Our most popular option — enough time to anchor, swim, and explore. Up to 6 guests.
Full Day
Starting at $1,500
A full day on the Bay. Bring lunch, explore multiple destinations, make a real day of it.
Prices are estimates. Final pricing confirmed at booking. Dockage, food/drinks, and gratuity not included.
The boats & the experience
Life on the Water
Our charter boat in Annapolis Harbor
Sunset cruise on the Chesapeake Bay
Evening on the water in Annapolis
Out on the Bay with Captain Steve
On the water near Annapolis
Aboard the charter boat
Chesapeake Bay sailing
Boat interior — comfortable below deck
Helm and cockpit
Galley kitchen below deck
On deck underway
Beautiful day on the Bay
Sailing the Chesapeake
On the water near Annapolis
Life aboard the Lynx
Chesapeake Bay adventure
Out on the Bay
Annapolis waterfront
Sailing on the Severn
On deck relaxing
Chesapeake Bay views
Harbor cruise
Sailing the Bay
On the water
Annapolis from the water
Beautiful Chesapeake day
Spa Creek drawbridge
Sailing underway
On the Bay
Chesapeake sailing
Annapolis harbor
Out on the water
Sailing the Chesapeake
On deck
On deck underway
Beautiful day on the Bay
Sailing the Chesapeake
On the water near Annapolis
Life aboard the Lynx
Chesapeake Bay adventure
Out on the Bay with Captain Steve
Fireworks over Annapolis harbor from the boat
Young guest at the helm on the Chesapeake Bay
Guest experiences
What Guests Are Saying
"This was my first Boatsetter chartered experience and Captain Steve really set the bar high!! He truly went above and beyond. I brought my family to include my 3 and 5 year old boys with a goal of taking them sailing for the first time and check out the Annapolis 4th of July fireworks from the water — and he just hit it out of the park! He thoughtfully (and without being asked) gathered a tentative agenda and it was perfect. A genuinely kind person who loves to sail. HIGHLY RECOMMEND A++"
Mark
July 2026 · Boatsetter
Safety & credentials
Your Safety Is the Priority
USCG-Licensed Master Captain
Fully Insured & Inspected
Local Chesapeake Bay Expert
Every trip departs with a full safety briefing, properly maintained safety equipment, and a captain who holds a USCG Master Captain license. The boat is fully insured and inspected. You're in good hands.
Everything you need to know
Frequently Asked Questions
Flexible on weather — your comfort and safety come first. We'll work with you on rescheduling if conditions aren't right.
Annapolis sunset cruise & more
Let's Plan Your Trip
Have a question or ready to book? Reach out directly — Steve responds quickly.