Elaine Olstadt

Middleton, WI

Family Vacations

Enjoy the world with your family!

My Travel Specialties

Family Vacations

I specialize in Family Vacations of all types.  Spring break, holidays, graduations, extend family trips,  high adventure,  theme parks, beaches- whatever type of travel you would love to do with your family.  I have been an travel agent for 30 years and have been going on family vacations my husband,...
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Travel Consultant

I have been a travel agent for over 30 years. I have earned my CTA certification, lifetime Gold level status as a Certified Sandals Specialist, graduate of Disney College of Knowledge & Master agent for AM Resorts. I have been to the Caribbean over 40 times- including 23 times Jamaica, Mexico over...
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Customer Testimonials

Family Vacation Mexico

The vacation was EXCELLENT!!! It’s not often in life that you go into a vacation with a set expectations, then have those expectations exceeded in nearly every way possible. I have wanted so bad to go to a warm sunny beach when its super cold in Wisconsin. This trip was a fulfillment of enjoying that experience.
Ryan, Jackson, Spencer and Paige

Punta Cana

The vacation from start to end was flawless and AMAZING! We were at Breathless. It was beautiful. We enjoyed the fact that the resort wasn't huge and we were able to walk around from here to there comfortably. We dined at each restaurant with the exception of the French. Our service in all aspects was great, All the staff were wonderful and friendly and very helpful if needed. The evening shows were wonderful and super fun to watch. Over all, the trip was simply amazing. We enjoyed every minute. Neither one of us have a single complaint or concern. Thank you so much for helping us. Without you, this trip would have never happened. THANK YOU!
LH, Madison, WI


Love, Love, Loved IT!!! Room was great. We loved the Patios and Palms the best. The restaurants Lemon Grass and Feathers were good. We snorkeled and did the Catamaran boat. We chose to stay on the resort and totally enjoy it. The weather was fabulous! It only rained twice for about 5 minutes. Once during the day and once at night. The island is so beautiful and the people are absolutely great to be with. We got to know a few. Loved the beach!!! We will go back, but am looking at other places like St. Thomas and Grand Camions. Thank you for all your help. I would totally recommend this place. I could go on and tell you more but this email is getting long enough.
DF, Wisconsin

Disney World

The trip was amazing. Your ears must have been ringing the whole week. We were always talking about our fast passes and glad that you were able to help us with them. I don’t think I would have changed a thing about this trip. It was nice to have the beach day and Sea World in the middle of the trip. I am telling people that want to go to Disney that they should get in touch with you. How was your trip? Thanks again Elaine for all your help to plan our trip.
DI, Sun Prairie, WI

Riviera Maya Mexco

Our trip was wonderful, especially the Valentin. We really liked the restaurants at night, especially the surf n turf one near the beach and the Japanese one. Our room was great, and we loved the pool! The beach was wonderful too. The service overall was by far the best - every restaurant, bar, pool, beach area, etc. Everyone was so friendly and helpful, it was very relaxing. Our guide was fantastic and so knowledgeable - and the traditional Mayan food they served after zip lining/snorkeling at Jungle Maya was amazing!! All in all, a fabulous trip. I'm so glad we went!! Thanks again for all your help!
S, Minneapolis, MN

St. Thomas

The flights were great. Our rooms were close together which made me very happy. The restaurants were all very good, my daughter did just fine with the food allergy. We did a few excursions and my daughter went snorkeling. We went to St. Johns to a wonderful beech. The resort we stayed at had 104 steps down to the pool which gave us good exercise, a shuttle was available if needed. I highly recommend the Sugar Bay Resort. The private beach was a little rocky but nothing to be upset about. The weather was just perfect. We will use your EXCELLENT service again when we are ready for our next vacation.
JS, Sun Prairie, WI

Sandals La Toc St. Lucia

We had a great vacation and we really enjoyed the resort. Our room had a great view and was conveniently located to everything. Food was really good, sushi, jerk chicken, Italian, Neptunes. Loved the beach and paddle boarding. We were never bored. Our flights were all on time and without incident. WallyPark was great. Thanks again for all of your help. It was a great time!
SW, Sun Prairie, WI

My Reviews

15 of 25 people found this review helpful
By  DSW  from  Sun Prairie WI
Traveled to  Jamaica ~ Caribbean
I would recommend this agent to my family and friends
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Destination Expert:

  • Caribbean
  • Dominican Republic
  • Jamaica
  • Mexico
  • St. Lucia
  • Turks and Caicos Islands
  • Maui Island

Travel Specialist:

  • All Inclusive
  • Family Vacations
  • Honeymoons
  • Destination Weddings
  • Couples & Romance

Top Travel Partners:

  • Disney


  • CTA
  • Gold Level Sandals Specialist
  • AM Resorts Master Agent
  • Authorized Disney Vacation Planner
  • CTA
  • Jamaica Travel Specialist
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