The Chesapeake Bay - crab country and home to over 5,000 of protected coastline at our disposal to voyage onward through America’s sailing capital. With sprawling nature along the water’s edge, there are predictable winds and protected harbors within easy reach in nearly every corner of the Bay. We sail to historic and scenic ports, enjoy the nightlight of downtown Baltimore, enjoy some of the best seaside restaurants in North America, and best of all, the Chesapeake Bay is in our own backyard!
Beginning summer 2020, Sailing Collective has put the Chesapeake Bay as one of our top Journeys with dozen of quality sailboats options available at a variety of travel budgets. The Chesapeake Bay Journey is a perfect summer vacation perfect for families or a private group of friends.
Price range for a private crewed charter for 5 to 7 nights | $13,000 to $19,000 (all-inclusive)
The season begins July 1st and we will organize sailing charters in the Chesapeake Bay through September. Each journey is crewed by a Sailing Collective captain and chef who will adhere to all Covid-19 cautionary measures prior to and during the voyage. Please contact us for more information.
• 40’ to 58’ monohull accomodating up to 6 guests in 3 private cabins | 40’ to 48’ catamarans accommodating up to 6 guests in 4 private cabins. If there are more than 6 people in your group, ask us about our Flotilla options - two or more boats sailing together during the itinerary. Cost for a private charte depends on the boat and availability.
Included in the total trip cost:
• Private captain and chef
• Travel support to help customize and guide your group's journey
• Delicious family style meals with breakfasts, 6 lunches, 3 dinners and snacks aboard, all prepared by your private chef
• Marina fees, dockage, and moorings for overnight anchorages
• Boat incidentals including fuel, water, local taxes, etc.
• And of course unabashed adventure and epic memories!
50% due at booking, remaining balance due 30 days prior to departure
Before booking, please review CANCELLATIONS/CHANGES, INSURANCE, AND CONDUCT policy on the booking page.
Born and raised in Key West, FL, Capt. Lilly has lived her life surrounded by saltwater. With over 20 years of boating experience, Lilly learned to operate her own boat - navigating it through the narrow channels and over the shallow waters of the Florida Keys backcountry years before she could drive a car. At 15 she sailed from Key West to Boston. Lilly is an avid angler and free diver, loves to surf, hike, and explore the many gifts Hawaii has to offer. In her lifetime of experience on the water Lilly has matured into a skilled boat handler with an emphasis on the safety of her crew and passengers, and a gift for sharing her love of the ocean. After graduating from the University of Florida, Lilly moved aboard a 125-ft gaff-rigged schooner that she crewed seasonally from Key West to Boston. In the Caribbean, Lilly worked with a fleet of boats including large catamarans and schooners. She has managed the fractional ownership business SailTime and the American Sailing Association School in Virginia Beach, where she maintained, operated, and taught sailing aboard a fleet of boats. She currently holds a 100-ton GRT Master Captains License with Sail and Tow endorsements and her teaching certification through the American Sailing Association.
Despite my tiny frame, I am an eater and food is always on my mind! I love every element of the food experience, from shopping the finest the farmers market has to provide to the preparation of an exquisite meal. A hostess at heart, it is the sensual and intimate aspect of dining that remains most important to me. I always keep in mind that overall indulgence is exemplified through flawless service and genuine hospitality. I believe that food has the capacity to fascinate and surprise, and I am not one to resist sharing my discoveries with any innocent bystander who has a set of ears, an open mind, and an empty stomach. biglittlenyc.com/flannery IG: flannerykk
Spencer's sailing career began early on the rough waters of New Jersey's Lake Hopatcong. After a skeptical first year at age 7, he eventually found his sea legs and started to gain recognition in the racing circuit. Spencer sailed in the PHRF Race Series as well as 420s and placed 13th in the US Nationals. Spencer continued competitive sailing until he started at New York Maritime College. In College he discovered the joys of noncompetetive recreational sailing while earning his degree in Marine Business and Commerce. Spencer has sailed on the T.S. Empire State to more than fourteen different countries and is a certified rescue diver with more than seventy dives in five different countries. When he's not manning the helm, Spencer can be found slinging cocktails behind the stick of one of New York's favorite outdoor bars...which also happens to be on a boat.
Gabrielle is passionate about the intersection of food, shared-experience and nutrition. The origin, quality and seasonality of the ingredients are essential to her methodology, and she strives to use her cooking to connect people and open diners up to new flavors and sensations. Her style is a mix of home-cooking, experimentation, and ethnic flare. She attended Natural Gourmet Institute, where she learned to cook for people with dietary restrictions and transform culinary techniques into health-supportive recipes and menus. Additionally, she worked at Blue Hill, where she was trained in the highest level of farm-to-table food preparation and presentation. From there, she moved on to Pietro, where she was the Sous-Chef, and delved into the nuances of Sardinian-Italian cuisine. Most recently she made a pilgrimage to Lebanon where she investigated her heritage through the lease of food, by spending time cooking with women from various regions of the country at Tawlet, Beirut.
The Chesapeake Bay is the largest bay in the United States with its estuary located between Mayland and Virginia. The mouth of the Bay along the southern points are marked by Cape Henry and Cape Charles. Known for its beautify and bounty, the Bay is made up of brackish water with many freshwater rivers that run from the mouth of the river north of Baltimore. A close look and you may spot bottlenose dolphins, Atlantic sturgeon, ospreys, great blue herons, and peregrine falcons throughout the waterway. To reach Annapolis base in Maryland, fly into Baltimore Washington International Airport (BWI) or Washington Dulles International Airport (IAD). As part of our Covid-19 protection recommendations, we recommend all guests drive to the marina location where there is complimentary parking.
Rock Hall | Baltimore Inner Harbor | Chester River | Whitehall Bay | St. Michael's | Wye Island | Herrington Harbor | Oxford | St. Leonard's Creek | Solomons Island
Pusser's Caribbean Grille | Dry 85 | Stan & Joe's | Iron Rooster | The Point Crab House & Grill
Port Annapolis Marina
7074 Bembe Beach Rd
Annapolis, MD 21403
Embark: 3:00 pm on the first day of the charter
Disembark: 5:00 pm on the final day of the charter
Baltimore Washington International Airport (BWI) or Washington Dulles International Airport (IAD)
TRANSPORATION FROM AIRPORT TO MARINA
We can arrange airport transfers on request and Baltimore Washington International Airport is a 40-minute taxi ride away, while Dulles airport is one hour and 20 minutes away by car.
PASSPORTS AND VISAS
Since this trip is only travels in the USA you will not need your passport. Please bring a valid ID.
During summer in the Chesapeak Bay you will experience many sunny days with a nice refreshing breeze. Average daytime highs are 80s to 90s F overnight low 70s F. You will experience some overcast weather with morning fog that burns off in the afternoon.
July and August is the prime season for boating in the Chesapeake Bay. Sunrise in July is 530 am and sunset is not until 930pm which makes for nice long summer days and beautiful sunsets after dinner. The summer water temperature average is 70 degrees F which can be very refreshing on a hot summers day.
Sailing Collective will provision your journey with local foods and produce. Cooking Aboard: Your Sailing Collective chef/crew is incredibly talented and can handle the group's needs with ease. We are all about participation and learning, so if you'd like to help, just ask and we'll get you involved! Collective groups may choose to dine out more times than scheduled if the group or individuals choose.
Included in provisioning package: 7 Breakfasts, 6 Lunches, 3 Dinners, Light Snacks, Water, Coffee & Tea
Not included in provisioning package: Soft Drinks, Alcohol, Wine, Beer, etc.
Dietary Restrictions: Important to notify your Sailing Collective representative of any dietary restrictions ahead of time and fill out details in Guest Form
Recommended $300 – $600 in spending money depending on spending habits.
Additional food and beverages including alcohol.
All expenses on shore including meals and drinks.
Flights and transportation to and from the marina location.
Tipping captain and crew is welcomed, 10-20% is customary in the industry
Collapsible bags in place of large rigid suitcases are advised for ease of transport on and off the boat. Loading and unloading from the dingy can be a wet activity, a pair of shoes such as flip flops that you can get wet if we are landing on a beach.
During days on the water, you’ll want to be wearing light and comfortable clothing. As the vast majority of your time will be spent outside, prepare for elements - bring a light rain coat just in case, a hat to shield yourself from the sun, and a set of warm clothing. Throughout the week we may dine out at a nice restaurant, so bring gear that you’ll look nice in and suits your style. Loading and unloading from the dingy can be a wet activity, a pair of shoes that you can get wet is recommended.
Day 1: Begin by sailing to Herrington Harbour. Herrington Harbour South and sister marina Herrington Harbour North are both located on the western shore of the Chesapeake Bay and offer overnight slips, several restaurants and lounges, and a wide range of amenities. Due to Herrington Harbour South’s popularity, it’s best to make reservations. We recommend Mango’s Bar & Grill for beautiful waterfront dining in a classy but laid-back atmosphere.
Day 2: Sail to Oxford, located on the eastern shore and bordered on three sides by the Tred Avon River and Town Creek. The community make visitors feel like old friends and works hard to maintain a serene, boater-friendly atmosphere. It boasts a walkable downtown with plenty of shops, restaurants, and attractions.
Day 3: Cambridge lies about 13 miles from the mouth of the Choptank River. It was settled in 1684, and is one of the oldest towns in Maryland. Known for its elegant 19th-century homes and maritime museums. Highlights include Richardson Maritime Museum, Meredith House with its Heritage Museum and Gardens, the Skipjack Nathan, Sailwinds Park, and the Choptank River Fishing Pier. Cambridge Creek offers ample protected anchorage.
Day 4: St. Leonard Creek is considered one of the most beautiful areas on the Patuxent River. This five-mile-long creek on the river’s north shore features marshes, rolling hills and wooded bluffs. At the mouth of Johns Creek is Vera’s White Sands Beach Club. Decorated with South Sea treasures culled from international voyages, Vera’s is a wonderful marina that welcomes all cruisers.
Day 5: Solomon’s Island is a charming island town between the Patuxent River and Chesapeake Bay. Solomon’s is a fishing village, alive with work-boats and fishing fleet, but offers numerous dining options, shopping, and special events. Be sure to visit The Tiki Bar and order a Mai-Tai, it’s the first completely open air bar in southern Maryland. The bar’s annual opening is a tradition, drawing crowds near 10,000.
Day 6: Another quaint waterfront village, St. Michael’s sits on a bucolic peninsula. It was an important shipbuilding center, known for its Baltimore Clippers – the fastest sailing vessels of their time. Today, the town is a popular yachting center and home to Chesapeake Bay Maritime Museum.
Day 7: It’ll take 5-7 hours to sail back to base – the Chesapeake will always welcome you back! (Text by DYC)
The Dufour 410 is a beautiful redesign from the previous and also elegant 405. She is low and sleek with attractive, contemporary styling that leaves aside unnecessary frills. The cockpit is well laid out for ease of handling. The interior is designed for live aboard comfort in style.
The Dufour 460 is modern, with straightforward lines and the strong and appealing design characteristic for Dufour Yachts. It offers a unique cruising concept for comfortable and secure live-aboard, blue-water cruising, yet still offers a dynamic sailing performance combined with the Dufour’s renowned style and elegance.
One of Sailing Collective's favorite monohulls, the 53 built by Jeanneau, is perfect for larger groups and families, looking for a combination of sailing performance and comfort. Above and below deck, her layout allows for plenty of room for socializing, but also offers practicality and performance where required. Headroom: Entry to Cabins: 6' 1" Galley and Cabins: 6' 5" Headroom at helm: 6' 6" The Jeanneau 53 is a pleasure to sail and is responsive to touch, her electric winches and bow thrusters make her surprisingly easy to handle.
The Lagoon 42 is the sublime successor to the best selling 421.Italian design legends Nauta have created stunning curved wood finishes which deliver supreme elegance and outstanding functionality. Defined by sleek curves and a ground breaking single level cockpit… this boat offers limitless possibilities for an enviable on water lifestyle. The three-cabin "owners edition has a master suite that takes up one entire side of the boat and offers an unusually luxurious accommodation for a sailboat.
There’s no shortage of gathering spaces for small-group conversations or even a solitary escape when it’s time to get away from the pack on this spacious catamaran. Forward are two cushioned lounges that unfold onto the trampoline, forming double sunpads with a place for drinks in between. Aft, the cockpit will accommodate six for dinner, two more on the side lounge and four across the transom seat. Up top, eight can keep the helmsman company, even if one is en repose on the starboard lounge.
Explore photos from our past journeys