Wine Dine and Play: Woody's Waterside Island Rum and Grill

Woody's Waterside Island Rum and Grill

The Woody's Waterside restaurant is located in St. James City on Pine Island, Florida offering bar and grill foods in a laid back space with a unique buoy sign recreating the Key West sign.

A Notch Above The Bar And Grill
St. James City, Pine Island, Florida
Cuisine Style: Bar and Grill
Average Price: $
Overall Rating: 3/5
Dined: October 2019

By Sean Overpeck (CFE)
**A full article and index glossary of restaurants, wines, recipes and travel for 
Wine Dine and Play are in the pages section above, or by following these links:

Woody's Waterside Zomato rating:

Woody's Waterside Menu, Reviews, Photos, Location and Info - Zomato 

Woody's Waterside Culinary Team:
Big "D" & Eric

We came across Woody's Waterside while looking around St. James City on the southern end of Pine Island. We were staying in Matlacha and had visited most of the restaurants there plus a few in Cape Coral so it was the greater Pine Islands turn. The restaurant is a laid back with lots of televisions indoors and a large bar catering to the sports crowd, while outside on the patio you could enjoy views of the Monroe Canal which leads out into the Pine Island sound and greater Gulf of Mexico. The main tourist attraction is a recreation of Key West’s “southernmost point” buoy except this one reads #Drunken most point in the USA with a milage marker of 245 to Cuba instead of 90 miles like the Key West sign. 

At the southern end of the island of Key West Florida is a buoy signifying the southernmost point in the USA, and 90 miles to Cuba. Here at Woody's Waterside on Pine Island in St. James City, Florida they have the same buoy with the drunken most point in USA.
Woody's Waterside / Drunken most point in the USA

Woody’s Waterside has two locations, with the second in Cape Coral, named after the family dog Woodrow Wilson (not the former American President) but a purebred yellow Labrador. Their food focus is on fresh Gulf Seafood and burgers, plus other favorites.  

The patio of Woody's Waterside restaurant in St. James City, Florida faces a canal that leads to the Gulf of Mexico with wonderful views of Pine Island
Woody's Waterside / Patio

Woody's Waterside Menu:
    • Woody's Bar Apps & Shareables
    • Homemade Soups
    • Homemade Sides
    • Signature Salads
    • Woody's Original Classics... Sandwiches, Wraps & BBQ
    • Woody's Craft Burgers
    • Fresh Local Seafood... Sandwiches, Baskets & Tacos
    • Evening Entrees
    • Desserts

We started with a few cocktails with my wife enjoying the Hazy Lil Thing, followed by a Milagro Tequila cocktail while I had the Homies Bloody Mary. The flavor profile had good amounts of spice, enough to frown out the vodka which was a good thing but almost too much to drown out other key tasting items. The Worcestershire and lemon or lime should come through with a hint, but on this drink, it did not. The symphony of spice from celery and pepper was not there but it was still a good afternoon drink for a hot October day.

We came only for drinks and to see the location but ended up sharing an appetizer of interest from the menu anyway called the smoked deviled eggs, made on-sight in their smoker and topped with a house-made bacon jam. The flavors of sweet and savory from the jam, plus the rich texture of the egg whip were amazing, and something I’d love to duplicate in the future for parties. It was just enough to nibble on as we were not hungry, but it did whet our appetites to return one day again to have other items and a second review to follow on to this one.

The deviled eggs at Woody's Waterside in St. James City, Florida is topped with a bacon jam and full of great flavor
Woody's Waterside / Deviled Eggs

We did not have dessert during this visit

But check out some of these wonderful selections from Wine Dine and Play: 

Please see these guidelines for Tipping in Restaurants and on following proper etiquette, customs, cultures, and avoiding assumptions when you dine out.

Other noteworthy “Bar and Grill” cuisine articles and restaurants similar to Woody's Waterside:
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Beaches Restaurant and Bar Casual beach fare at PDX International, Portland, Oregon
Beef ‘O’ Brady’s A family-friendly chain restaurant based in Florida, reviewed from St. Petersburg
BJ’s Restaurant and Brewhouse Chain (180+) for pub grub and brewed beer; reviewed in Pinellas Park, Florida
Bongos Bar and Grille Eclectic beachfront bistro, Cuban and American cuisine, in St. Pete Beach, Florida
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Boulevard Burgers Second review of this burger joint for the carnivore connoisseur in St Pete Beach, Florida 
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Ferg’s Sports Bar and Grill Casual pub grub sports bar in St. Petersburg, Florida
Hamburger Mary’s A San Fransisco Burger joint chain started in 1972 with 19 locations reviewed in Clearwater, Florida
Jungle Prada Tavern American Bar/Tavern next to the Narvaez historical site in St. Petersburg, Florida
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Miller’s Ale House Casual Floribbean and American pub chain; reviewed in Brandon, Florida
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See the whole list by visiting “The Wine Dine and Play Article Glossary

Other Pine Island and Matlacha restaurants, and articles on Wine Dine and Play:

Waterfront Italian restaurant in a unique artsy town
Matlacha, Florida, USA
A healthy Asian alternative to other local restaurants
Matlacha, Florida, USA
2nd review of the Italian restaurant
Matlacha, Florida, USA
Breakfast plus coffee beans from around the world
Matlacha, Florida, USA
A Marina with seafood stand, market, and gulf view dining
Matlacha, Florida, USA
Seafood with the essence of place
Matlacha, Florida, USA

A few Florida restaurant favorites:

Small shop for good sushi
Cape Coral, Florida USA
Relaxed hangout serving German Grub
Brandon, Florida USA
Third-floor terrace seafood-centric New American dining
Bradenton Beach, Florida, USA

See the whole list by visiting “The Wine Dine and Play Article Glossary by country

Final notes, review basics, observations, and more pictures:

Most reviews are subjective, depending on the writer; but they should also be responsible, and respectfully written, upholding the truth, and accurately conveying the experience to the best of the writer's knowledge, even if it includes metaphors the restaurant may not like to read about. My ratings are by the stars I award (from 0 to 5). The rating is calculated on a point accumulation of six separate factors based on individual experience. They include wine and other beverage selections, plate presentation, customer service, restaurant or café ambience, food quality, and wow factor. 
To see more details of this rating list, read this article:

Overall from this experience and the score factors outlined in the ‘about page’ section, based on my individual experience and rating, I give Woody's Waterside 3 out of 5 stars, meaning that they exceeded my expectations and were far above the average dining experience of most restaurants.

Scores are detailed in the factor chart below:

Formula Factor Conclusions and Overall Ratings for Woody’s Waterside
Max Points Possible:
Total Points Awarded:
Total Points deducted:
Food quality
Plate presentation
Customer service
Alcohol and other beverages
Total regular points awarded
Total percentage — less the Bonus


“Wow” factor BONUS
Total bonus percentage


Total percentage and bonus for a final star rating


Stars Awarded (see chart below)
- 0 - 5

**A full break down and explanation of the observations and point disbursement is available in the linked article above. To receive a detailed copy of your score, feel free to contact me at any time and I will provide it to you.**


Overall Star Rating:
3 of 5 Stars: 
82% Rating with a 0 point “wow” bonus
Exceeded My Expectations In A Dining Experience
Corkage fees:
Woody's Waterside does not list any corkage fee’s however, most American restaurants charge $25.00 per bottle
Casual dining
Cuisine Style at Woody's Waterside:
Bar and Grille
Allergen or dietary accommodations: 
Gluten-free choices, Low Carb Choices, Pescatarian, Vegetarian Options
Not Required
Accepted, but not guaranteed
Dress code:
Casual attire

It’s Florida, everybody wears flip-flops!
Child policy:

The Restaurants reviewed on this site may have a kids menu or cater to them; however, for full enjoyment of food and wine, it is recommended that kids not to be in attendance, unless they have been trained in proper etiquette. 
If not then:
Hire a Babysitter! 
Woody's WatersideExperiences:
A place for foodies, Modern, Trendy, Hotspot, Great bar, Great outdoor dining, Good for special occasions, Scenic views, Tourist grabber, and a Neighborhood Gem.
Cash, Visa, MasterCard, Discover, American Express
Woody's Waterside has a private lot
The restaurants reviewed on this site may have Wi-Fi, but do not require you to go online, because the excitement of the food and wine alone will keep you too entertained instead of checking your social media and emails.
Noise level:
Woody's Waterside is a non-smoking restaurant with a non-smoking patio   
Patio or terrace:

Food Prices 
(excludes, alcohol, taxes & 20% gratuity’s)

$£€¥ -                Under 50.00 (inexpensive)
$£€¥ x 2 -          51.00- 99.00 (moderate)
$£€¥ x 3 -          Over 100.00 (pricey)
$£€¥ x 4 -          Over 200.00 (expensive)
$£€¥ x 5 -          Over 400.00 (very expensive)

**Currencies reflect the world’s major travelers, restaurant, or wine connoisseur’s**

United States Dollar (USD)
Great Britain Pound Sterling (GBP)
Canadian Dollar (CAN)
Chinese Yuan (CNY)  
European Union (EUR)

 Alcohol prices:

$30.00 USD

Woody's Waterside:

3051 Stringfellow Road
St James City, Florida 

Contact Information: 

Restaurant website:
Maître d or host:
+1 239-283-5555
Website Contact:

Email Us:

Serving hours:
Eastern Standard Time
(GMT, Zulu, or UTC - 5:00)
Sun - Thur
11:00 am - 9:00 pm
Fri - Sat
11:00 am - 10:00 pm

Social Media 
Accolades for Woody's Waterside:
Woody's Waterside Facebook link                
Woody's Waterside on Twitter (@woodyswaterside)

The world’s best restaurants is a subjective list of who is writing it and changes on a regular basis. The Wine Dine and Play best experiences are based on my highest rated stared restaurants, meaning that the visit was an outstanding or extraordinary experience. From cafés, chains, mom + pops, hole in the walls, to fine dining including a few Michelin spots. Visit the Top 100 page to see the entire list.

A few to tease you with…
Farm-to-Table Southern bites spot Sandy Springs, Georgia, USA
Fine-dining waterfront spot for grilled fish and steaks
Indian Shores, Florida, USA
Native American Cuisine w/Barbacoa Grilling
Tampa, Florida, USA

Other Woody's Waterside Pictures:

The bar and dining room to Woody's Waterside in St. James City, Florida on Pine Island is catered to the sports fan with a good menu that goes beyond bar food.
Woody's Waterside / Bar

“Culinary perfection consists not in doing extraordinary things, 
But in doing ordinary things extraordinarily well.”
-Angelique Arnauld (1591-1661)

Who is John Galt?


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