St. Michaels Sailing Charters Food Options

We’ve partnered with three local food providers to offer a variety of catering options prepared fresh and delivered directly to your sailboat at the time of your charter. Whether you’re looking for casual boxed lunches for a daytime sail, elegant appetizers and grazing boards for entertaining, or full-service catering for a private event, each menu offers something unique to complement your time on the water. Browse the options below to find the dining experience that best fits your charter.

Village Shoppe | Fresh Boxed Lunches

Perfect for daytime sails, corporate outings, and casual cruises, The Village Shoppe offers fresh boxed lunches designed for easy onboard dining while enjoying time on the Chesapeake Bay. Each boxed lunch includes a sandwich selection, chef’s choice side salad, potato chips, and dessert.

*Orders must be placed 72 hours prior to charters.

Standard Boxed Lunches – $25 per person

Sandwiches served with chef’s choice salad of the day, potato chips, cookie or brownie.

Chicken Salad Croissant
Diced chicken breast with red onions, celery, and mayonnaise served on a flaky croissant with lettuce and tomato.

Egg Salad Sandwich
Traditional egg salad served with lettuce and tomato on wheat bread.

Ham Salad Sandwich
Black forest ham salad with lettuce and tomato on a soft potato roll.

The American
Smoked turkey or ham with lettuce, tomato, pickles, dijon mustard, served on a sub roll.

The Italian
Pepperoni, hard salami, tavern ham, provolone, lettuce, tomato, sweet and hot peppers, mayonnaise, and oil & vinegar on a sub roll.

The Birdie
Smoked turkey breast with pimento cheese on wheat bread.

Sample side salads include: Dill potato salad, lemon orzo salad, vegetarian pasta salad, cucumber salad, or chickpea salad. Chef will select the side salad.

Sample sweets include: Fudge brownie, blonde brownie, chocolate chip cookie, sugar cookie, or oatmeal raisin cookie. Nut-free desserts only. Chef will select the dessert item.

Premium Boxed Lunches – $33 per person

Sandwiches served with chef’s choice salad of the day, potato chips, cookie or brownie.

Roast Beef Sliders
House-roasted beef top round with sliced red onions and horseradish cream on a brioche roll.

Banh Mi
Vietnamese marinated chicken breast with cucumbers, pickled vegetables, and ginger aioli on a sub roll.

Mediterranean Vegetable
Garlic hummus, cucumbers, red peppers, carrots, red onions, kalamata olives, feta, arugula, and basil aioli on sourdough bread.

Sample side salads include: Dill potato salad, lemon orzo salad, vegetarian pasta salad, cucumber salad, or chickpea salad. Chef will select the side salad.

Sample sweets include: Fudge brownie, blonde brownie, chocolate chip cookie, sugar cookie, or oatmeal raisin cookie. Nut-free desserts only. Chef will select the dessert item.

Royal Oak Catering | Appetizers, Small Plates & Meals

Royal Oak Catering specializes in beautifully styled grazing boards, upscale appetizers, and elevated catering experiences designed for entertaining aboard our sailing yachts. Their menus focus on fresh ingredients, Chesapeake-inspired flavors, and elegant presentation perfect for sharing while relaxing on the water.

*Orders must be placed 7 days prior to charters.

Appetizers & Light Bites

Cheese & Charcuterie Board – $39 per person
An assortment of artisan cheeses, cured meats, jams, nuts, olives, and fresh fruit, served with crackers and flatbread.

Mediterranean Mezze Grazing Board — $39 per person
A vibrant selection of marinated vegetables, olives, cheeses, hummus, and nuts, served with crackers and pita bread.

Mini Maryland Crab Cakes — $46 per person
Classic Maryland-style crab cakes served with lemon aioli on a bed of bibb lettuce with heirloom tomatoes.

Chocolate-Dipped Strawberries — $26 (6 pieces)
A simple, elegant treat perfect for celebrations or a sweet addition to your sail.

Salmon Caviar & House-Made Potato Crisps — $49 (2 oz tin)
Served with crème fraîche and lemon zest for a refined, indulgent experience.

Paddlefish Caviar & House-Made Potato Crisps — $77 (1 oz tin)
Served with crème fraîche and lemon zest for a refined, indulgent experience.

Lunch Options

Assorted Deli Sandwiches & Wraps — $33 per person
Turkey, ham, and roast beef with lettuce, tomato, and mayo, served with chips, fruit, and a cookie.

Dinner Selections

*One entrée selection per group

Tier 1 — $85 per person

Maryland Jumbo Lump Crab Cakes
Served with French green beans and pommes purée

Tenderloin of Beef with Red Wine Demi-Glace
Served with heirloom carrots and herb roasted fingerling potatoes

Pan-Seared Scallops
With white wine and lemon butter sauce, served with summer squash and garlic mashed potatoes

Tier 2 — $68 per person

Fried Chicken Dinner
With biscuits, coleslaw, and pasta salad

Pulled Pork BBQ
Served with rolls, salad, and coleslaw

Sliced Flank Steak with Chimichurri
Served with Chesapeake corn salad and rolls

Brunch & Morning Options

Tea Party Selection — $33 per person
Assorted tea sandwiches including ham salad, egg salad, and cucumber with cream cheese.

Breakfast Sandwich Platter — $33 per person
Sausage or bacon with egg and cheese on an English muffin, served with hash browns and fruit.

Bagels with Lox & Cream Cheese — $37 per person
Served with fresh seasonal fruit.

Pastry Selection — $33 per person
Danish, muffins, and croissants served with seasonal fruit.

Quiche Selection — $39 per person
Served with a light salad or fresh fruit.

Hambleton House | Large Group & Private Charter Catering

Hambleton House offers chef-prepared meals and thoughtfully curated menus for guests seeking a more substantial onboard dining experience. From brunch favorites to full dinners, these menus pair beautifully with a relaxing day on the water.

*Available for group of 6 or more. Orders must be placed 7 days prior to charters. 

The Coastal Picnic — $46 per person

A relaxed, Chesapeake-inspired spread designed for easy sharing on the water.

• Artisan cheese board with local cheeses, fig jam, and honey

• Charcuterie with cured meats, olives, and house-roasted nuts

• Crackers and sliced baguette

The Chesapeake Elevated — $72 per person

An expanded coastal experience featuring signature Chesapeake flavors. Includes everything in the Coastal Picnic, plus:

• Jumbo lump crab parfaits with citrus aioli

• Chilled Old Bay shrimp skewers with lemon

• Classic deviled eggs with fresh herbs

• House-baked seasonal cookies

The Sunset Sail Experience — $98 per person

A celebratory, elevated offering perfect for special occasions and sunset cruises. Includes everything in the Coastal Picnic and Chesapeake Elevated, plus:

Choose Two Sandwich Selections:

• Honey-Cured Ham with Gruyère & Roasted Tomato
  Honey-cured ham layered with Gruyère, roasted tomato, and avocado buttermilk ranch on seeded brioche.

• Italian Meats with Provolone & Sun-Dried Tomato Spread
  Capicola, mortadella, and salami with provolone and Parmesan Reggiano, finished with roasted garlic aioli and a sun-dried tomato pepper spread on a pine-nut crisp.

• Chicken Salad with Garlic-Celery Mayo
  Classic chicken salad with roasted garlic–celery mayonnaise and fresh parsley, served on sourdough toast.

• Vegetable Sliders with Hummus & Avocado
  A vibrant mix of lemon-tahini hummus, shredded carrots, alfalfa sprouts, cucumbers, and bell peppers with avocado spread on an olive oil brioche bun.

• Roasted Turkey with Cheddar & Apple
  Roasted turkey breast with Chesapeake Gold cheddar, crisp Honeycrisp apple, garlic mayo, and butter lettuce.

Sandwiches are prepared in half portions for easy sharing and cooler placement, designed to remain stable and refined throughout your sail.

How It Works

This offering is available exclusively for private charters. Advance notice is required to ensure availability and proper preparation. All packages are delivered directly to your vessel, fully assembled and ready to enjoy, with no onboard preparation needed.

Plan Your Perfect Day on the Water

Pre-order your onboard dining in advance to ensure availability and allow our team to prepare everything for your trip. Whether you’re looking for light snacks or a full meal, we’ll help create a seamless and memorable experience.

Food Cancellation Policy

Catering must be arranged in advance. Final selections and guest counts are required prior to your charter date.

All food and catering orders are prepared specifically for your charter through our local catering partners and require advance ordering and preparation.

Village Shoppe boxed lunches and Royal Oak Catering orders may be canceled or modified up to 48 hours prior to your charter departure time for a full refund. Cancellations made within 48 hours of the charter are non-refundable.

Hambleton House Catering orders may be canceled or modified up to 72 hours prior to your charter departure time for a full refund. Cancellations made within 72 hours of the charter are non-refundable.

Contact us to add catering to your charter. We’re happy to help you plan the perfect experience.

☎ 410-849-9864
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