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Biloxi & Ocean Springs 4-Day Weekend Itinerary (Sept 26–29, 2025) — Beaches, Art, Beer & Oktoberfest

Viewed by 115 travelers

Day 1: Arrival Night

Biloxi, USA on September 26, 2025

7:00PM

Arrive & Check-in — IP Casino Resort

Arrive at IP Casino Resort, check in and drop luggage; use the front desk concierge for any restaurant/show reservations. This sets your base on the Biloxi beachside for easy access to attractions.
USD0, 0h30m

7:30PM

Settle in / Explore Hotel Amenities

Unpack and relax or check out the hotel pool, spa, and casino floor to get oriented; many amenities are open late but verify individual hours with the hotel.
USD0, 1h0m

9:00PM

Dinner — Felix's Oysters

Classic Gulf Coast seafood spot; try oysters Rockefeller or fried shrimp for an authentic local meal and waterfront atmosphere (confirm seating/wait times).
USD25, 1h30m

9:00PM

Alternative Dinner — The Reef

Casual ocean-view seafood with a relaxed vibe if you prefer a quieter spot with sunset views.
USD30, 1h30m

9:00PM

Alternative Dinner — Mary Mahoney’s Old French House

Historic restaurant offering classic Southern seafood in an atmospheric setting; reserve in advance for a table.
USD40, 1h30m

10:30PM

Evening Stroll or Hotel Live Entertainment

Take a relaxed walk along the Biloxi beachfront or catch live entertainment at IP Casino (check the hotel events schedule for show times and cover charges).
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11:00PM

Return to Hotel / Rest

Head back to the room to rest and prepare for a full day tomorrow.
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Day 2: Arts, Beer & Live Show

Biloxi & Gulfport, USA on September 27, 2025

8:00AM

Breakfast — The Greenhouse on Porter

Start with fresh pastries and Southern breakfast options in a bright café; arrive early to avoid the mid-morning rush.
USD15, 1h0m

9:00AM

Biloxi Lighthouse & Visitor Center

Quick visit to the historic Biloxi Lighthouse and nearby visitor center to learn coastal history and grab maps; check current visitor center hours (commonly morning–afternoon).
USD5, 0h45m

10:00AM

Ohr-O’Keefe Museum of Art

Explore Frank Gehry-influenced architecture and George Ohr pottery exhibits; rotating exhibitions make each visit unique (museum hours often start ~10:00AM — confirm before you go).
USD12, 2h0m

12:30PM

Lunch — Lady May

Casual lunch specializing in Gulf seafood and po’boys; a solid midday stop for fresh fish and local flavors.
USD20, 1h0m

2:00PM

Beer Tasting — Chandeleur Brewing Company (Gulfport)

Drive (~20–30 minutes) to Gulfport for a tasting flight of IPAs, stouts and seasonal brews; check brewery hours (many open midday into evening).
USD15, 1h30m

4:30PM

Happy Hour — Shaggy's Biloxi Beach

Return to Biloxi for discounted drinks and gulf views during happy hour — a nice pre-dinner break (happy hour times commonly late afternoon).
USD10, 1h0m

6:30PM

Dinner Option — Patio 44

Upscale seafood and steakhouse with a refined menu; great for a special evening meal (reservations recommended).
USD45, 1h30m

6:30PM

Dinner Option — The Reef

Casual oceanfront dinner if you want fresh seafood without formality.
USD30, 1h30m

6:30PM

Dinner Option — Mary Mahoney’s Old French House

Historic, classic Southern seafood with elegant ambiance for a memorable evening.
USD40, 1h30m

8:30PM

Live Music / Show — Studio A, IP Casino

Catch an evening concert or show at Studio A; check the IP Casino events calendar for exact show time and ticket prices.
USD25, 1h30m

10:30PM

Optional — Evening Casino Stroll or Beach Walk

If energy remains, try your luck at the casino or take a calming beach walk under the stars.
USD0, 0h30m

Day 3: Bay St. Louis & Ocean Springs

Biloxi, Bay St. Louis & Ocean Springs, USA on September 28, 2025

8:00AM

Breakfast — The Ruby Slipper Café

Hearty Southern breakfast favorites and brunch classics to fuel a full day of exploring; expect a popular morning crowd on weekends.
USD18, 1h0m

9:00AM

Apartment Visit — Southern Avenue, Biloxi

Spend extended time touring and settling into your Biloxi apartment — inspect, measure, or relax; budget extra time for any follow-up tasks.
USD0, 1h30m

10:30AM

Drive to Old Town Bay St. Louis

Depart Biloxi and drive west along the coast to Old Town Bay St. Louis (scenic coastal route) to explore shops and the historic district.
USD0, 1h0m

11:30AM

Explore Old Town Bay St. Louis

Stroll art galleries, boutiques, and the waterfront in this charming town — great for picking up unique gifts and prints.
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12:00PM

Lunch — Shaggy's Biloxi Beach (listed as final plan)

Casual seafood basket or fish tacos; the itinerary lists Shaggy’s at noon as a flexible midday option (confirm drive time if you prefer to eat in Bay St. Louis instead).
USD20, 1h0m

2:00PM

St. Louis Oktoberfest — Bay St. Louis

Enjoy German food, music and festival atmosphere at Bay St. Louis’ Oktoberfest (festival hours typically afternoon — confirm event schedule ahead).
USD10, 1h30m

4:00PM

Downtown Ocean Springs — Galleries & Shops

Return east to Ocean Springs and visit Studio 7, Saenger Galleries, Cox & Co., Crescent City Studio, Glazed & Amazed, Old Town Traders and The Local Market along Washington Ave & Government St; many galleries close by 5:00–6:00PM so time accordingly.
USD0, 1h30m

5:30PM

Dessert — Quakes Ice Cream

Grab a shake or sundae for a sweet break before evening activities.
USD8, 0h15m

6:00PM

Happy Hour — Neon Moon, Ocean Springs

Catch a drink during Neon Moon’s happy hour (noted $1 off drinks until 7PM) and enjoy a local bar vibe before heading back to Biloxi.
USD8, 0h30m

6:30PM

Optional — Ocean Springs Waterfront Walk or Extra Shopping

Take a relaxed waterfront stroll or return to a favorite shop for last-minute purchases; evening gallery hours may be limited so this is a good time to enjoy the waterfront.
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7:30PM

Return to Biloxi

Drive back to your IP Casino base and freshen up for dinner or evening entertainment.
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8:00PM

Optional — Sunset Beach Stroll or Live Music at IP Casino Chill Ultra Lounge

Finish the day with a sunset walk on Biloxi Beach or enjoy live music at the hotel lounge (check performance schedules).
USD0, 1h30m

9:30PM

Return to Hotel

Head back to the room to rest after a full day of festival and shopping.
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Day 4: Pack & Depart

Biloxi, USA on September 29, 2025

7:30AM

Breakfast — Cafe Beignet, Biloxi

Classic breakfast and beignets to finish your weekend on a sweet note; early morning service is ideal for travelers checking out the same day.
USD12, 1h0m

8:30AM

Return to Hotel, Pack & Check-out

Return to IP Casino Resort to finish packing, check out and settle any incidental charges with the front desk.
USD0, 1h0m

9:30AM

Optional — Biloxi Beach Walk or Nearby Shops

Take a final walk on Biloxi Beach or swing by nearby shops for souvenirs if your schedule allows.
USD0, 0h30m

9:30AM

Optional — Beauvoir (Jefferson Davis Home & Presidential Library)

If time allows, visit Beauvoir for a short tour of the grounds and museum (confirm opening hours — many historic sites open mid-morning). Choose either the beach walk or Beauvoir depending on timing.
USD12, 1h0m

11:00AM

Depart Biloxi

Check local traffic and head out; safe travels home or to your next destination.
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