5 Over-the-Top Vacation Surprises

Sure, onsite playgrounds and free milk and cookies score big with families on vacation, but what about making a truly memorable impression? From a “Candy Man on Call” to an In-Room Princess or Pirate Party, consider these super surprises, destined to give your loved ones an over-the-top vacation experience.

1. Candy Man on Call
What’s even better than room service for dinner? Take your Windy City visit to the next — and delicious — level at The Ritz-Carlton Chicago, where a “Candy Man” delivers sweet dreams with a traveling cart full of treats.

Decked out in a crisp red and white jacket and accessorized with a dapper bow tie, the hotel “Candy Man” (or Candy Lady) arrives at your room with a mouth-watering selection of sweet, sour, gummy and chocolate treats. Kids are invited to fill a bag free of charge.

Visits are available between 3 and 6 p.m., so you can schedule a surprise special delivery (and the inevitable “sugar rush”) well in advance of slumber time! To help the transition to bedtime, kids can enjoy their treats in their own colorful in-room tent, set up by the hotel’s staff upon request.

2. Free Goldfish
Famous for its pet friendliness, the hip Kimpton chain of boutique hotels does a great job of delivering popular perks for families, from trendy (animal print robes and Wii games) to practical (complimentary high chairs and play yards). When taking the family pet along isn’t possible, Kimpton extends a hospitable hand, with a lending program that offers both in-room amusement and anxiety reduction. At over 20 Kimpton locations, from Miami to Seattle, guests have the option of borrowing a low-maintenance pet for the night through the company’s “Guppy Love” program. Betta fish — Kimpton’s preferred pets — are proven to calm nerves and are cared for by hotel staff. Guests can enjoy the benefits of ownership without the typical duties — no walking, feeding or cleaning up required!

3. Flash Mob
Want to say “Happy Sweet Sixteen!” or “I’m Glad you Married Me!” in a really “moving” and enduring fashion? For a truly over-the-top way to celebrate the special day, consider the “Flash Mob” package at Marco Island Marriott Beach Resort in Southwest Florida. At the award-winning beachfront resort, which features a kid’s club, water sports and plenty of pampering opportunities for both kids and grown-ups, you can schedule an unforgettable customized group dance surprise. The package, available to both business groups (“Mobbed at Marco”) and leisure guests (“Marco Island Flash”), includes a choreographer to teach the dance, as well as a videographer to film it. Customers are invited to post videos of their event online.

According to promoters, those who manage to gather a major social media following will be invited back for a complimentary return visit. There is no minimum number of participants required. The property will customize the package based upon the customer’s needs.

4. Personal Pixie
Are you hoping to commemorate a special occasion with a magical and mysterious surprise? Take your loved ones on the “trip” of a lifetime with a personalized theme park quest created by Orlando’s Presentations: Gifts of a Lifetime.

Using details you provide, the company will craft a custom hunt for a special birthday, anniversary, holiday or family event. Hired “pixies” hide clues for the scavenger-style searches, which average one to two hours in duration and can take place in an area theme park or special location of your choice.

Customers have the option of incorporating an item of significance or special gift in their event. Guests of honor must be five years or older. The average cost is $325 to $375 and theme park admission is not included.

For those with more time and a smaller budget, Masters of the Hunt offers “Do-it-Yourself” scavenger hunts for $7 to $57 each. You purchase a pre-planned itinerary, which you can implement according to your needs. Kid-friendly choices include a “Beach Treasure Hunt,” “Princess Hunt” and “Pirate Treasure Hunt.” For teens, “The Great Race,” “Music Treasure Hunt,” and “Hollywood Treasure Hunt” are engaging options. The helpful staff will make suggestions and assist you in finding the best option for your family.

5. In-Room Pirate or Princess Party
Meeting Disney royalty is at the top of just about every aspiring young princess’s list, and Disney World is rolling out the red carpet with a stately in-room offering that takes the term “royal treatment” to new heights. For guests of onsite resorts, Disney Floral & Gifts offers “Presenting Your Royal Princess,” a gilded package featuring an array of regal gifts, including a rhinestone-studded tiara, a special princess door sash, rose petals scattered throughout the room and a certificate proclaiming royal status, signed by The Fairy Godmother herself.

The package is offered in three varieties: Child (ages 3 to 6), Junior (ages 7 to 13) and Adult (ages 13 and up). Depending on the recipient’s age, the package may also include a princess sash or backpack to wear, a princess necklace or bracelet, make-up or perfume, a princess balloon, and a gem-studded rose bouquet. It’s perfect for special occasions, from graduations to Sweet 16’s.

For boys, the “Me Pirate Adventure” package is a fitting welcome for any young buccaneer. The in-room adventure includes pirate-inspired decorations and a scavenger hunt, which leads to a special chest of hidden treasure! In addition to a sash that goes over the resort room door, the package includes a personalized note from Captain Jack, a pirate flag, netting, a skeleton with “glowing” eyes and a souvenir pirate disguise.

Delivery, which includes in-room decorating, is available to Disney resort guests. A 48-hour advance notice is requested.

At Disneyland in California, Disney Dream Makers will deck out a resort room for those who order one of a number of special kid-friendly surprises. Current offerings, which greet guests upon arrival, include “Mickey and Pals Big Birthday Wish,” a birthday celebration themed to Disney’s “Fab Five” characters, and “Mickey’s Grand Welcome,” a perfect way to commemorate a first stay or a first trip to Disneyland.

The in-room parties are available to guests of Disneyland’s three resort hotels: Disney’s Grand California Hotel & Spa, Disneyland Hotel and Disney’s Paradise Pier Hotel. A 72-hour advance notice is requested. More in-room offerings and an online site detailing the offerings are in the works.

More from Family Vacation Critic:
10 Best Hotel Amenities for Kids
5 Super Services for Vacation Rentals

Written by Jackie Perrin
Jackie has covered the best of family travel for over a decade, providing insider tips for newspapers, magazines and online sites. At home and on the go, she manages a crew of companions, from tot to teen.