Chesapeake Bay Boat Tours to check out!
Nothing beats the pure thrill of sailing with the wind in your hair and spending a day in the great outdoors with your nearest and dearest. However, with so many incredible Chesapeake Bay boat tours on offer, choosing one is not for the faint-hearted!
Chesapeake Bay Boat Tours
Although it is true that there are numerous unique Chesapeake Bay boat tours in the region that cater to various personal tastes and price points, some are simply outstanding. So, if you want to know Chesapeake Bay’s best-kept boat tour secrets – read on! Also check out some fo the best chesapeake beaches to visit with your family.
1. M/V Bay Breeze
Conveniently located in the picturesque Upper Chesapeake Bay’s Schaefer’s Canal House, the M/V Bay Breeze offers a wide variety of fun sightseeing, Blue Crab cruises, and tours of the scenic Chesapeake Bay area.
Renowned for hosting outstanding special family events and fun sunset booze cruises, with 26 comfortable seats and spectacular views from every angle, it’s no wonder that the M/V Bay Breeze is in such high demand! Consequently, it’s one of the best Chesapeake Bay boat tours!
2. Chesapeake City Water Tours
Located in the postcard-pretty “Canal Town” in South Chesapeake City, Maryland, dates to the 1800s, Chesapeake City Water Tours, surrounded by quirky waterfront restaurants and shops, has built a well-deserved reputation for being one of the top tour operators in the region.
Chesapeake City Water Tours has several fun tours to choose from, ranging from Daily Sightseeing Tours, Ultimate Sunset Cruises, and Wine and Craft Beer Tastings to private parties with live music and their legendary Rum and Reggae Cruises.
Guest can arrange private charters for special events like birthdays and weddings on any of their fleet of party boats. Their largest Catamaran can comfortably seat 48 guests, and a wide range of amenities like a full bar, festive LED lighting, and surround-sound stereo.
So, if you are looking for a Chesapeake Bay boat tour for your next birthday bash, or a party boat, these fun city water tours are the best!
3. M/V Summer Breeze
Situated in the stunning Havre De Grace, Maryland, which is one of the most beautiful areas in the Northeast, including the idyllic Susquehanna Rivers, the M/V Summer Breeze is a family-friendly boat tour operator that showcases the Upper Chesapeake Bay at its finest!
Apart from offering families a fun day out, the M/V Summer Breeze, which can comfortably seat up to 49 passengers, also prides itself on its warm and inviting atmosphere and being able to offer educational tours, with a wealth of local knowledge about this pristine area.
However, the M/V Summer Breeze can also cater to a wide range of private special family events, corporate outings, wedding rehearsals, and sunset booze cruises, and it is hands down one of the
of the best Chesapeake Bay boat tours in the area.
4. Sail Selina
If you have always dreamed about sailing on a luxurious sailing yacht, Sail Selina is a dream come true and one of the finest Chesapeake Bay boat tours for sailing enthusiasts with a taste for adventure!
Located in the picturesque St. Michaels Harbour Inn and Marina, guests have a choice between testing their sailing skills and being part of the crew or sitting back and enjoying the sheer thrill of sailing and immersing themselves in the Eastern Shore scenery.
The immaculate Selina II yacht is a “thing of beauty” with pristine mahogany cabinetry and perfect shiny polished brass accessories that are the epitome of old-world elegance and can comfortably seat only six guests.
The 2-hour Chesapeake Bay boat tour, under the expert stewardship of Captain Iris and her experienced crew, departs at the Harbour Inn and Marina, from where it meanders past the Chesapeake Bay Maritime Museum all the way to the Miles River, where it opens its sales.
The Sail Selina tour also ventures past areas with fantastic wildlife like Bald Eagles, porpoises, and Osprey; although those sightings are rare surprises, you just might be in luck!
Captain Iris provides a personalized tour of the scenic St. Michaels waterfront and its long and illustrious history, including the fascinating and adventurous past of the iconic Selina II yacht.
Furthermore, Sail Selina also offers romantic 2-hour Chesapeake Bay Champagne Sunset Sail cruises, which are the perfect setting for marriage proposals, wedding anniversary celebrations, and other special celebrations.
Guests are treated to a huge variety of sunset treats, including champagne, pinot grigio, Shiraz, un-oaked chardonnay, craft beer from leading Maryland artisanal breweries, refreshing sodas, including delicious hors-d’oeuvres while watching a spectacular sunset.
5. Family Fishing Adventures
The award-winning Family Fishing Adventures, located in the scenic Annapolis City Marina, is a one-of-a-kind, educational fishing boat tour for kids and one of the most fun Chesapeake Bay boat tours for your little ones!
Hosted by proud owners Chris Hendershot and Samantha Polizzi, this one-and-a-half-hour tour onboard the fun Sea Dragon boat was started to teach kids about how to sustainably catch fish and crabs while still preserving Chesapeake Bay’s fragile ecology.
Boat tours depart the marina four times a day, and kids can learn how to read a map, fishing, and crabbing skills, including magical immersive encounters with Chesapeake Bay’s incredibly diverse marine wildlife like minnows, fish, and slippery eels.
This unique fishing tour also offers kids the opportunity to try their luck at fishing with light tackle kits and experience what it’s like to hoist up crab traps. So, there’s genuinely no doubt it will be a cherished childhood memory!
Check out some great places to go fishing in Maryland.
6. Schooner Woodwind Annapolis Sailing Cruises
The family-owned, iconic 74-foot wooden schooners sets sail from the Annapolis Waterfront Hotel and provide guests with the unique and thrilling experience of taking their turn at the ship’s wheel and hoisting the ship’s four sails.
The Schooner Woodwind Annapolis Sailing company offers daily, sunset, specialty, and holiday-themed cruises onboard the Woodwind and the Woodwind II schooners, which are replicas of yachts built in the 1900s and were custom-built and designed to sail on the Chesapeake Bay at speed.
The gleaming mahogany regal wooden schooners feature elegant chrome finishes with roomy glamorous cockpits that resemble a lost era, so guests can simply sit back and relax in comfort.
While there are various great cruises to choose from, the 2-hour public sailing cruises are the most popular, with a fully stocked bar and a wide range of refreshing wine, craft beer, and other refreshing beverages on a hot sunny day.
Visitors can catch sight of the impressive United States Naval Academy, scenic Annapolis Harbor, the skyline, and picturesque the Chesapeake Bay, including the idyllic Severn River.
Depending on the wind’s direction, other potential cruise highlights include sailing past the statuesque Chesapeake Bay Bridge, pristine Kent Island, and the historic Thomas Point Lighthouse.
Other potential sites include seeing competing regattas in the bay and scenic local wildlife like swooping Ospreys and other birds that frequent this area which is renowned for its outstanding natural beauty.
7. Watermark Cruises and Tours
The critically acclaimed, family-owned Watermark Cruises and Tours company has several excellent sightseeing cruises from Annapolis and Baltimore to choose from, which have received rave customer reviews for being one of the best Chesapeake Bay boat tours in the region.
Their Annapolis cruises range from 40 minutes sightseeing cruises to daylong, 7 ½ hours daylong cruises from the Chesapeake Bay to the historic town of St. Michaels, which is situated on Maryland’s Eastern Shore, and across the Chesapeake Bay.
The 90-minuted narrated Thomas Point Lighthouse Cruise is also a popular choice, especially for visitors with limited time to view the fascinating National Historic Landmark. Again, however, it is an incredibly popular cruise, so book well in advance, especially in peak summer seasons.
8. Classic Sail Charters
If you are looking for a more exclusive and luxurious cruise – look no further! Classic Sail Charters is perfect for couples or small groups of up to six people who are looking for a private 2–3-hour sailing adventure or the Chesapeake Bay, and potentially Annapolis.
Classic Sail Charter’s well-equipped and comfortable yacht, the Licentia, offers guests the opportunity to enjoy one of the world’s finest sailing areas or to brush up on their rusty sailing skills with refresher courses.
Apart from the standard short cruises of Chesapeake Bay, guests also have the option to book
a full day’s sailing experience in the largest estuary in the world and enjoy the abundant marine wildlife along the way.
Another really great option if you have enough time (and cash to burn) is the two days Classic Sail Charters, Overnight Adventure, which is a once-in-a-lifetime opportunity to sleep on board your very own private chartered yacht.
However, if you are planning a sailing vacation onboard this luxurious yacht, it would be wise to make a booking ahead of time. The award-winning Classic Sail Charters are incredibly popular due to their luxury amenities and world-class service.
9. Skipjack H.M. Krentz
The award-winning Skipjack H.M. Krentz sailing charters are moored in the Chesapeake Bay Maritime Museum in St. Michaels, and they offer daily fun cruises between April and October each year.
Cruising on the historic H.M. Krentz boat is a unique experience and one of the most historic Chesapeake Bay boat tours as it is one of the few remaining authentic 1950s skipjacks that were custom designed and built to dredge oysters in Maryland’s icy winters.
Guest can either enjoy fully catered cruises with bespoke picnics, appetizers, and cocktails or bring their own refreshments onboard to enjoy the unforgettable sights and sounds of the Chesapeake Bay area and learn more about its incredibly rich history.
10. Choptank Riverboat Co
The incredible Choptank Riverboat company offers visitors a unique opportunity to explore Maryland’s Eastern Shoreline on an iconic replica of a turn-of-the-century paddle-wheeler boat from April through to December each year.
Guests can embark at the (interestingly named) Suicide Bridge Restaurant and choose between venturing out on The Dorothy & Megan or The Choptank River Queen in all her 80-foot elegant splendor.
Visitors can enjoy breathtaking views of the idyllic river in enclosed cozy seating with air-conditioning and heating on the paddle-wheeler’s lower deck or enjoy fresh air in the ship’s semi-enclosed upper deck area.
There are various fun cruises on offer that are all fully catered by the Suicide Bridge Restaurant, which provides a delicious array of lunches and dinners, including the Eastern Shore’s freshest seafood specialties.
Choptank Riverboat Co also offers fun special events like murder mysteries and delicious crab feasts where you need a big appetite!
Traveling onboard one of these iconic boats is hands down one of the most fantastic Chesapeake Bay boat tours for history buffs who want to experience what sailing on an old vessel was like back in time.
11. Miss Arielle Charters
Anchored in the idyllic Tilghman Island, Dogwood Harbor, a historic little fishing community, look no further than Miss Arielle Charters! It offers guests the unique experience of trying their hand at traditional crab trot lining in the picturesque Choptank River and Harris Creek in an iconic skipjack oystering vessel.
Apart from teaching visitors all the tricks of the crab fishing trade, Captain Murphy is a great storyteller and has a wealth of knowledge about Chesapeake Bay’s colorful past.
But the best part of chartering a cruise on this unique boat is that you can take a bushel of crabs home for a delicious dinner and have the option to have them steamed and prepared before you head home, and let’s face it – nothing beats the joy of fresh seafood!
Final thoughts on Chesapeake Bay Boat Tours
With so many diverse Chesapeake Bay boat tours to choose from showcasing the world’s largest estuary at its finest, visitors to this picturesque area are genuinely spoilt for choice. Also, check out some great places to rent boats in Maryland.
So, whether you want to sail on your own private luxury yacht or let your hair down on a Rum and Reggae Cruise – Chesapeake Bay is the place to be!
