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Home / Trips / Upcoming

Jul 14, 2027 to Jul 20, 2027

Full trip pageAdd to calendar (.ics)

Essentials

  • Destination: Walt Disney World Resort, Orlando, Florida (Epcot, Hollywood Studios, Animal Kingdom, Magic Kingdom, Typhoon Lagoon).
  • Optimal Travel Dates: 2027-07-14 to 2027-07-20 (Summer night park hours, Disney H2O Glow After Hours, and Deluxe extended evenings).
  • Travel Party: 2 adults (4 dogs stay home with dedicated Rover care in Cudahy).
  • Target Budget Range: $4,508 to $5,022 per person ($9,016 to $10,044 total party cost).
  • Hotel Starting Point: Disney's Riviera Resort, 1080 Esplanade Ave, Lake Buena Vista, FL 32830.
  • Hotel Pet Policy: $0 resort pet fee (dogs stay home in Cudahy).
  • Home Pet Care (If Pets Stay Home): Rover.com Cudahy Pet Sitting Search estimates $130 to $170 per night ($780 to $1,020 total for 6 nights).

Day by Day

Day 1: Wednesday, Jul 14, 2027: Milwaukee Departure, Nonstop Flight to Orlando & Riviera Rooftop Dinner

  • 6:15 AM CDT to 6:45 AM CDT Uber to Milwaukee Airport (5300 S Howell Ave, Milwaukee, WI 53207) Milwaukee Mitchell International Airport
  • 6:45 AM CDT to 8:15 AM CDT MKE Airport Buffer & Security
  • 8:15 AM CDT to 12:00 PM EDT Nonstop Flight to Orlando
  • 12:00 PM EDT to 1:00 PM EDT MCO Baggage Claim Buffer (1 Jeff Fuqua Blvd, Orlando, FL 32827) Orlando International Airport
  • 1:00 PM to 1:45 PM Uber Transfer to Riviera (1080 Esplanade Ave, Lake Buena Vista, FL 32830) Disney's Riviera Resort
  • 2:00 PM to 5:30 PM Riviera Unpack & Pool Time
  • 6:00 PM to 8:30 PM Topolino's Terrace Rooftop Dinner Topolino's Terrace
  • 9:00 PM to 11:00 PM Epcot Extended Evening Hours EPCOT

Day 2: Thursday, Jul 15, 2027: Hollywood Studios Thrills & Galaxy's Edge

  • 8:00 AM to 8:30 AM Skyliner to Studios (351 S Studio Dr, Lake Buena Vista, FL 32830) Disney's Hollywood Studios
  • 8:30 AM to 1:00 PM Star Wars: Galaxy's Edge Rise of the Resistance
  • 1:00 PM to 4:00 PM Rides & Live Stunts Tower of Terror
  • 4:30 PM to 6:30 PM Riviera Afternoon Break
  • 7:00 PM to 9:30 PM Fantasmic! & Dinner The Hollywood Brown Derby

Day 3: Friday, Jul 16, 2027: Animal Kingdom Morning Safari, Pandora & Evening Disney H2O Glow Nights

  • 7:00 AM to 7:30 AM Bus to Animal Kingdom (551 Rainforest Rd, Lake Buena Vista, FL 32830) Disney's Animal Kingdom
  • 7:30 AM to 11:30 AM Pandora Flight & Safari
  • 11:30 AM to 1:30 PM Lunch at Tiffins Tiffins Restaurant
  • 1:30 PM to 4:00 PM Everest & Lion King Expedition Everest
  • 4:30 PM to 6:00 PM Riviera Rest & Prep
  • 6:00 PM to 11:00 PM Disney H2O Glow After Hours (1145 E Buena Vista Dr, Orlando, FL 32830) Disney's Typhoon Lagoon Water Park

Day 4: Saturday, Jul 17, 2027: Epcot World Showcase, Guardians of the Galaxy & Via Napoli Pizza

  • 8:00 AM to 8:30 AM Skyliner to Epcot (200 Epcot Center Dr, Lake Buena Vista, FL 32830) Epcot
  • 8:30 AM to 12:30 PM Morning Rides & Cosmic Rewind Guardians of the Galaxy: Cosmic Rewind
  • 12:30 PM to 2:30 PM Pizza Lunch at Via Napoli Via Napoli Ristorante e Pizzeria
  • 2:30 PM to 5:30 PM World Showcase Stroll & Drinks
  • 6:00 PM to 9:00 PM Le Cellier Dinner & Luminous Fireworks Le Cellier Steakhouse
  • 9:15 PM to 9:45 PM Skyliner Return

Day 5: Sunday, Jul 18, 2027: Magic Kingdom Mountains, Fantasy & Fireworks

  • 7:45 AM to 8:20 AM Bus to Magic Kingdom (1180 Seven Seas Dr, Lake Buena Vista, FL 32830) Magic Kingdom
  • 8:30 AM to 1:00 PM Fantasyland & Tomorrowland TRON Lightcycle / Run
  • 1:00 PM to 3:30 PM Pirates & Big Thunder Pirates of the Caribbean
  • 4:00 PM to 6:00 PM Midday Rest Window
  • 6:30 PM to 9:30 PM Happily Ever After Fireworks Happily Ever After

Day 6: Monday, Jul 19, 2027: Resort Rest, Pool Cabana, Disney Springs Craft Beers & Cocktails

  • 9:00 AM to 11:30 AM Late Sleep & Fresh Pastries Le Petit Cafe
  • 11:30 AM to 3:30 PM Pool Lounging Bar Riva
  • 4:00 PM to 6:30 PM City Works Craft Beer Taproom (1486 Buena Vista Dr, Lake Buena Vista, FL 32830) Disney Springs
  • 6:30 PM to 9:30 PM Waterfront Cocktails & Dining Summer House on the Lake
  • 10:00 PM to 12:00 AM Magic Kingdom Extended Evening Hours Magic Kingdom

Day 7: Tuesday, Jul 20, 2027: Farewell Breakfast, Return Flight to Milwaukee & Home

  • 8:30 AM to 10:00 AM Breakfast & Check Out Primo Piatto
  • 10:45 AM to 11:30 AM Airport Uber Ride (1 Jeff Fuqua Blvd, Orlando, FL 32827) Orlando International Airport
  • 1:30 PM EDT to 3:45 PM CDT Nonstop Flight to Milwaukee (5300 S Howell Ave, Milwaukee, WI 53207) Milwaukee Mitchell International Airport
  • 4:15 PM CDT to 4:45 PM CDT Uber Home to Cudahy

Costs

Expense Category / Line ItemProvider / VenueExact Unit Price / RateTotal Cost RangeVerified Booking / Info Link
Nonstop Flights (2 Adults)Commercial Airlines MKE to MCO$380 / adult round-trip$760 to $760MKE Mitchell Airport
Milwaukee Airport Uber (2 Trips)Cudahy to MKE Rideshare$15 to $18 each way$30 to $36MKE Mitchell Airport Parking
Orlando Airport Uber (2 Trips)MCO to Riviera Rideshare$32 to $38 each way$64 to $76Orlando Airport Transit
Deluxe Resort Lodging (6 Nights)Disney's Riviera Resort$620 / night$3,720 to $3,720Disney Riviera Resort
4-Day Theme Park Tickets (2 Adults)Walt Disney World Theme Parks$580 / adult 4-day pass$1,160 to $1,160Walt Disney World Tickets
Lightning Lane Multi PassWalt Disney World Digital App$28 / person / day (4 days)$224 to $224Walt Disney World Pass
Disney H2O Glow After Hours (2 Adults)Disney's Typhoon Lagoon Water Park$89 / adult event ticket$178 to $178Disney H2O Glow After Hours
Fine Dining & Signature MealsTopolino's Terrace, Tiffins, The Boathouse, Le Cellier$110 to $150 / person / day$1,540 to $2,100Walt Disney World Dining
Quick Service, Craft Beer & LunchesVia Napoli, City Works, Primo Piatto, Bar Riva$40 to $55 / person / day$560 to $770Walt Disney World Dining
Home Pet Care (4 Dogs in Cudahy)Rover.com Cudahy Pet Sitting Search$130 to $170 / night$780 to $1,020Rover Cudahy Pet Sitting
TOTAL (All-In Vacation Expenses for Party of 2)Flights + MKE Uber + Orlando Uber + Resort + Tickets + Lightning Lane + H2O Glow + Dining + Rover$4,508 to $5,022 / person$9,016 to $10,044 totalWalt Disney World

Ross Rondeau

Principal Enterprise Architect & Systems Strategist. Helping organizations build scalable, compliant, and cost-effective technology platforms.

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