Lobster Roll 18.00

A lightly toasted split top roll filled with tender, sweet chunks of cooked cold water lobster tossed in a coating of mayonnaise containing a dash of lemon zest and secret ingredients

Peel and Eat Shrimp 14.00

Peel your own ½ pound of shrimp cooked with old bay seasoning and served with our housemade cocktail sauce

Shrimp Cocktail 15.00

for those that don’t want to get their fingers dirty

Wings12.00

These premium chicken wings have a kick. Fried so they’re nice and crispy, then we coat them with our yummy secret sauce & serve them with celery sticks

Conch Fritters 14.00

fresh conch, blended in a special batter, deep fried and served with cocktail sauce ( a true Florida staple)

Charcuterie Plate 18.00

a delicious selection of cured meats, gourmet cheeses, olives, and fruit all selected by our chef to compliment each other

Chips and Housemade Salsa or Queso dip 7.00

Fresh Grouper Appetizer

Caught locally, and delivered daily: Our grouper is hand cut and prepared by our chef’s, then lightly breaded, deep fried to a golden brown and served with lemon & our house made tartar

Market Price

Soup of the Day

Cup 6.00 | Bowl 8.00

Willie's Wings11.00

These premium chicken wings have a kick. Fried so they’re nice and crispy then we coat them with our yummy secret sauce & serve them with celery sticks

Ale Battered Onion Rings 9.00

Thick, white onion slices coated with beer batter, deep fried and served with our house made jalapeno-ranch dressing

House Made Soup7.00

Prepared by our chefs daily, ask for today’s selection

Mini Burgers11.00

Three mini burgers topped with American cheese and served on toasted mini buns

Fresh Grouper Fingers

Caught locally, and delivered daily: our grouper is hand cut and prepared by our chefs, then lightly breaded, deep fried to a golden brown and served with lemon & our house made tartar

Market Price

Fried Green Tomatoes8.00

A southern tradition, hand breaded and fried to perfection, served with our house made jalapeno ranch dressing (no one else makes them like we do)

Fire House Chili6.00

Gluten Free

Made with angus beef, onions, three types of beans, tomatoes, and other fresh garden ingredients, this house made specialty is topped with onion & cheddar cheese

Caboose Fries6.00

A basket full of our house fries, cooked to a perfect golden brown

Chili Cheese Fries9.00

House fries loaded with our house made chili and topped with cheddar cheese

Buffalo Blue Cheese Fries9.00

Our fries coated with buffalo wing sauce and blue cheese crumbles

Philly Cheese Fries10.00

Fries loaded with tender steak, garden fresh peppers, onions, and a generous portion of cheddar cheese sauce

Conch Fritters12.00

Fresh conch, blended in a special batter, deep fried and served with cocktail sauce (a true Florida staple)

Traditional Caesar11.00

Florida grown fresh romaine, shredded parmesan cheese, and homemade croutons tossed in our caesar dressing  

Caboose Cobb14.00

Gluten Free

A fresh blend of mixed greens, topped with a sliced hard-boiled egg, garden fresh cucumber, tomato, applewood smoked bacon, fresh avocado, & blue cheese crumbles

Crab Cake Salad18.00

Our house made crab cake is loaded with wild caught lump blue crab, and claw meat, hand pattied and served over a mix of fresh greens, onion, cucumbers, carrots, and tomato & served with a mango vinaigrette dressing

Soup & Salad11.00

A bowl of our chef’s daily special soup and your choice of a garden or Caesar salad

Garden Salad10.00

Gluten Free

Mixed greens, tomato, carrots, onion and cucumber

Taco Salad13.00

Crispy tortilla chips topped with chili, onion, cheddar cheese, lettuce, tomato, nacho cheese, our house made salsa fresca & sour cream

Cranberry Walnut15.00

Gluten Free

A fresh blend of mixed greens, walnuts, sun dried cranberries, red onion, and feta cheese served with a cranberry citrus vinaigrette

Crab Cake Sandwich18.00

Our fresh made crab cake (loaded with lump blue crab and claw meat) with fresh lettuce, tomato, & our house made Dijon mustard sauce on grilled rye bread

Depot Burger14.00

A juicy, hand pattied, ground chuck burger from Florida grown cattle on a fresh kaiser with crisp lettuce and tomato

Add Cheese 1.00 | Add Bacon 2.00

Fresh Grouper Sandwich

Fresh gulf grouper, hand breaded and lightly fried, on a kaiser with crisp lettuce, tomato, and served with housemade tartar

Market Price

Grilled or Cajun Grilled add 1.00

TBA16.00

Thin sliced turkey breast, applewood smoked bacon, lettuce, tomato, avocado, & mayo on honey wheat

Reuben16.00

Choice of classic corned beef or turkey on grilled rye with housemade thousand island dressing, Swiss cheese & sauerkraut

Tuna Salad Sandwich15.00

Chunk white albacore tossed with our house made seasoned mayo with lettuce and tomato on honey wheat

BLT13.00

A generous portion of applewood smoked bacon, vine ripe tomato, crisp lettuce, & mayo on toasted white bread

Add brie 1.00

Half & Half13.00

Half a turkey, chicken salad, or tuna sandwich on wheat with a bowl of house made soup or choice of side garden or Caesar salad

Grilled Cheese10.00

American cheese with applewood smoked bacon & fresh sliced tomato on white bread

Hot Dog9.00

Quarter pound all beef hebrew national

Add kraut, chili or cheese 1.00 each

Chili Cheese Onion Dog11.00

Our quarter pound all beef hebrew national with chili, cheese, and onions

Cuban Panini15.00

Herb roasted pork loin, ham, swiss, mustard & pickles on grilled panini

Caboose Chicken Club17.00

Fresh grilled chicken breast, applewood smoked bacon, American cheese, crisp lettuce and tomato on a fresh kaiser roll

Boca Steak Sandwich16.00

“Philly-style” tender strips of beef grilled with peppers & onions, topped with our cheddar cheese sauce and served on a fresh, toasted hoagie roll

Cranberry Walnut Chicken Salad Sandwich16.00

A house recipe! Tender chicken, cranberries, walnuts, onion, celery, crisp lettuce and tomato on honey wheat

*Boca Grande Wrap

Lightly breaded and fried, fresh grouper, black beans, yellow rice, lettuce & tomato in a fresh tortilla, served with our house made tartar

Market Price

Thanksgiving Wrap13.00

Thin sliced turkey, cranberry sauce, lettuce & stuffing in a fresh flour tortilla

Grilled Shrimp Wrap18.00

Fresh, wild caught shrimp, marinated artichokes, roasted red peppers & onions with crisp lettuce in a fresh flour tortilla (no substitutions)

Chicken Caesar Wrap14.00

Tender grilled chicken, crisp romaine, with a Caesar dressing in a fresh flour tortilla

Railroad Wrap15.00

Tender grilled chicken, black beans, yellow rice, lettuce and tomato in a fresh flour tortilla (no substitutions)

Crispy Shrimp17.00

A generous portion of fresh, wild caught shrimp lightly breaded by hand and fried to a golden brown

Chicken Fingers15.00

Succulent chicken breast tenders hand breaded and fried to a perfect golden brown

Fresh Grouper Fingers

Fresh “and we do mean fresh, it’s delivered daily and prepared by our chefs” local grouper, lightly breaded and fried golden brown, served with our house made tartar sauce.

Market Price

Grouper and Shrimp Combo Basket

Fresh, local grouper, lightly breaded and fried golden brown, and wild caught shrimp lightly breaded by hand and fried golden brown served with our house made tartar sauce

Market Price

Tomato Brie Wrap 16.00

Fresh tomato and brie with pears, avocados, cucumbers, mixed greens and citrus aioli in a flour tortilla

Heirlooms and Burrata 17.00

Fresh burrata mozzarella with heirloom tomatoes, watermelon radish, almonds, mixed greens, basil oil and balsamic reduction

The Greek Wrap 16.00

Tomato, feta, olives, cucumber, roasted peppers and artichokes, banana peppers and hummus

Vegan Whole Grain And Mushroom Burger 14.00

House made with whole grains and wild mushrooms with ginger soy seasoned slaw and spicy vegan mayo on a Kaiser bun

Vegan Cold Plate15.00

Edamame, roasted beets, heirloom tomatoes, sweety drop peppers, olives, walnuts, cucumbers, grapefruit, avocado, watermelon radish and balsamic reduction

Vegan Garden Vegetable Wrap 12.00

A medley of fresh garden vegetables with mango vinaigrette dressing in a fresh flour tortilla

Vegan Black Beans over Yellow Rice 11.00

With salsa fresca

Key Lime Pie7.00

Our house made specialty.

Chef’s Daily Creation

Ask your server for today’s selection

Ice Cream

Our Ice Cream is made on the premises using 16% cream. That’s why it’s so rich and creamy. Ask your server for today’s selection, made by your request

*Southern Fried Green Tomato and Crab Cake Combo10.00

Our hand breaded, fried to perfection, green tomato slices served with our house made ranch dressing.

House Made Soup

Made fresh daily by our chef’s using the freshest, locally grown ingredients, ask for today’s selection

Cup 6.00 | Bowl 8.00

*Fresh Grouper Fingers

Delivered fresh daily, locally caught grouper prepared by our chef’s, hand breaded and fried golden brown, served with a lemon wedge & our house made tartar

Market Price 

Conch Fritters14.00

Fresh conch blended in a special batter, deep fried and served with our house made cocktail sauce (a true Florida staple)

Chef Shakespeare's Fried Calamari15.00

Hand breaded and pan fried calamari sautéed with banana peppers.

Caboose Thai Shrimp17.00

Fresh, wild caught gulf shrimp, panko breaded and flash fried, then lightly coated in our house made thai chili aoli

Crab Cake 12.00

One of our house made crab cakes, loaded with lump blue crab, claw meat and served with our house made tartar sauce.

*Shrimp and Grits32.00

Our take on a southern tradition. Wild caught Gulf Shrimp lightly seasoned, and grilled, served with our house made cheddar cheese grit cakes (Jacques’ recipe) and topped with a lite sherry cream sauce (a new favorite)

Half Portion 24.00

Suggested Wine: Pinot Grigio, Chardonnay

NY Strip Steak 12 oz 36.00

Angus beef hand cut by our chef’s, then rubbed with our secret blend of seasonings and grilled to order with carmelized red onions Served with your choice of rice or potato and garden fresh seasonal vegetables

Suggested Wine: Syrah, Merlot, Cabernet, Red Zinfandel

Seafood Pot Pie30.00

Tender pieces of fresh, locally caught grouper, wild caught gulf shrimp, blue crab, and a fresh garden medley of celery, onions, and carrots cooked until tender in a tomato saffron broth topped with a puff pastry crust

Half Portion 25.00

Suggested Wine: Pinot Grigio, Chardonnay, Pinot Noir

*Crispy Duck36.00

(A house favorite) Half a succulent farm raised duck, cooked to perfection and served with an orange teriyaki sauce and your choice of rice or potato and fresh garden vegetables

Suggested Wine: Pinot Noir

Mediterranean Chicken29.00

Fresh, hormone free, grilled chicken breast marinated in a blend of balsamic, olive oil and our special combination of seasonings, prepared with fresh garlic, villagio marzano tomatoes, baby spinach, and feta cheese over

Gluten Free penne pasta

Suggested Wine: Pinot Grigio

Grouper Tacos33.00

We use the freshest fish available, tequila lime slaw, tomato, queso, and salsa fresca served with a side of black beans and rice

Suggested Wine: Pinot Grigio, Chardonnay

*Fresh Grouper35.00

Cajun grilled, fried, or sautéed with lemon & white wine, served with your choice of rice or potato and fresh garden vegetables

Suggested Wine: Sauvignon Blanc, Riesling

Seafood Crepes 35.00

A delectable selection of lobster, shrimp, crab, and grouper tossed in a basil crème sauce

Half Portion: 19.00

Suggested Wine: Pinot Grigio, Chardonnay

Chicken Pot Pie25.00

Tender pieces of succulent chicken, fresh sweet peas, and carrots, topped with a puff pastry crust

Half Portion 19.00

Suggested Wine: Pinot Grigio

Jose Gaspar’s Black Beans & Rice 15.00

A generous portion served with salsa fresca 

With Grilled Chicken Breast 21.00 | With Fresh Fish 25.00  | With Sriracha Shimp 21.00

Fresh Grouper Sandwich23.00

Gulf Grouper, locally caught, lightly coated with breading by hand and fried golden brown, served on a Kaiser with lettuce and tomato with our house made tartar on the side

Grilled add 1.00 | Cajun add 1.00

Depot Burger16.00

Half pound of juicy ground chuck on a fresh Kaiser with lettuce and tomato served with our caboose fries

Add cheese or bacon each 1.00

Beyond Veggie Burger available 17.00

Heart of Iceberg12.00

Crisp iceberg wedge with fresh tomato slices, bleu cheese crumbles, smokehouse bacon crumbles, and our house made bleu cheese dressing

Side 8.00

Caboose Cobb16.00

A blend of fresh romaine and iceberg lettuce, radicchio, garden fresh tomato, a sliced hardboiled egg, bacon, avocado, cucumbers, and bleu cheese crumbles

Side 10.00

With Grilled Chicken Breast 20.00 | With Grilled Shrimp 22.00 | With Fresh Fish 26.00

Traditional Caesar14.00

Romaine lettuce and shaved parmesan cheese tossed in a creamy Caesar dressing

Side 7.00

With Grilled Chicken Breast 18.00 | With Grilled Gulf Shrimp 21.00 | With Fresh Fish 26.00

Cranberry Walnut16.00

A fresh mix of romaine and iceberg lettuce, radicchio, walnuts, sun dried cranberries, red onion, and feta cheese served with a cranberry citrus vinaigrette

Side 10.00

With Grilled Chicken Breast 20.00 | With Grilled Gulf Shrimp 22.00 | With Fresh Fish 26.00

Chicken Fingers10.00

3 Tender pieces of all white meat grilled or fried golden brown

Fresh Catch Fingers14.00

3 Fried or grilled fingers of our fresh catch of the day

Grilled Cheese Sandwich8.00

American cheese on white bread or whole wheat

Hamburger9.00

2 All beef mini burgers cooked to perfection

Add cheese for 1.00

Hot Dog8.00

2 All beef mini hot dogs.

Macaroni and Cheese8.00

Fried Shrimp11.00

Fresh gulf shrimp fried or grilled to a golden brown

Peanut Butter & Jelly6.00

Creamy peanut butter and grape jelly on white bread or whole wheat

Peanut Butter & Jelly6.00

Creamy peanut butter and grape jelly on white bread.

Peanut Butter & Jelly6.00

Creamy peanut butter and grape jelly on white bread.

Spaghetti Marinara10.00

Our marinara sauce served over spaghetti.

Chicken Fingers10.00

Tender pieces of all white meat fried to a golden brown.

Fresh Grouper Fingers

3 Fried fingers of our fresh catch of the day.

Market Price

Grilled Cheese Sandwich7.00

American cheese on white bread.

Buttered Noodles9.00

Spaghetti noodles lightly buttered.

Hamburger8.00

2 All beef mini burgers cooked to perfection.

Add cheese for 1.00

Macaroni and Cheese9.00

Kraft® brand.

Fried Shrimp12.00

Fresh gulf shrimp fried to a golden brown.

Sodas

Pepsi, diet pepsi, sierra mist, lemonade, mountain dew, root beer, dr pepper.

Free Refills

Iced Tea

Sweet or unsweetened.

Free Refills

Flavored teas

Choice of mango, cherry, blackberry, or raspberry.

1 Refill

Flavored Lemonades

Choice of mango, cherry, blackberry, or raspberry.

1 Refill

Canned Ginger Ale

No Refills

Fruit Smoothies

When available small or large mango, strawberry, pina colada, or lemonade.

Domestic

Bud, Bud Light, Mich Ultra, Miller Lite, Coors Lite, Yuengling, St Paulie NA.

Imports & Premiums

Heineken, Corona, Sam Adams, Blue Moon, Corona Light, Stella.

Microbrews

Keywest Sunset Ale, Holy Mackeral (when available).

Draft Microbrews

Amberbock, Landshark, ask your server about our special selection.

Pitchers Available

Woodbridge Chardonnay

Woodbridge Pinot Grigio

Woodbridge White Zinfindel

Beaulieu Cabernet

Columbia Crest Merlo

Sangria

The Pullman 10.00

Absolut Vodka, Blue Curacao, Lemonade

The Cowcatcher12.00

Patron, Blue Curacao, Lime Juice, Lemon Juice, Club Soda

Boca Baby12.00

Captain Morgan, Absolut, Malibu Rum , splash of Orange Juice, Pineapple Juice, and Pina Colada mix

Malibu Bay Breeze10.00

Malibu Rum, Cranberry Juice, and Pineapple Juice

All American Lemonade11.00

Tito’s Handmade Vodka, Lemonade and a Lemon 

Sunshine Punch11.00

Bacardi Rum, Orange Juice, Cranberry Juice, Lime Juice Grenadine Syrup and an orange slice

Classic Margarita12.00

Patron Silver Tequila, sour mix, orange triple sec 

Whiskey Sour11.00

Crown Royal Canadian Whiskey and sour mix

Gin Collins10.00

Bombay Gin, sour mix, soda water, and a cherry

Ocean Breeze10.00

Absolut Vodka, Orange Juice, Cranberry Juice

Hibiscus7.00

Mimosa7.00

Bloody Mary 12.00

Seagrams 7 & 7 9.00