Trip to Anywhere

Experiences Beyond YOUR Reach...

Participating in different activities, cultures and ventures is one of the best reasons to travel! While being spontaneous on vacation seems ideal in theory, when it comes to choosing certain experiences, planning them beforehand is always in your best interest.

Here are some of the best reasons to book your experiences/shore excursions with Olsen-O'Leary

1.Your payment is made here and you know where you money is going.

  • When you book a shore excursion or experience internationally over the internet, either spontaneously or before you go, you do not always know exactly where your credit card information is going, or who's hands it may pass through on the way there. We securely process payments stateside and pay our vendors directly, third parties never even have access to your information.

2. We can get you the best deals, don't be tricked by tourist-traps and inflated, arbitrary pricing.

  • By booking excursions and experiences at the time you book your vacation, we can usually get you discounts and perks that are reserved for agents by our vendors. Plus, there are often even better deals for booking more than one activity. Jumping on a local tour at the last minute will definitely be much more expensive. Additionally, we have access to booking private tours and experiences for activities that cannot be accessed via internet booking sites.

3. Planning with us before you go ensures that your valuable vacation time is not wasted or mismanaged.

  • Imagine this scenario: You signed up (and paid) for cooking class on the last night of your vacation. That day you notice a historical castle tour that you've been eyeing all week has an opening, so you hop on—however, it ends up going longer than you anticipated and you’re late getting to the cooking class, or even miss it altogether. Your first thought may be "oh, I wouldn't do that!" however, if you are visiting somewhere for the first and maybe only time, you never know the emotional decisions you may make.
  • Your travel consultant could have gotten you tickets (and maybe even a private tour) for the castle on another day and saved you the hassle and anguish. Furthermore, during the planning stages, we can discuss the many available options for your destination so you are aware of the choices available and won't miss any opportunities that may interest you.

4. You know what you’re signing up for before you get there.

  • You won’t be surprised by the quality (or lack) of service, equipment or location. Our agents and/or clients have seen it, and know what you can expect. There is a reason they're called "tourist traps"—they are supposed to look amazing and trigger spontaneous purchases and participation!
  • Also, it is important to be wary of reviews, both good and bad. While people typically “review” to rant about a bad experience, not all raving reviews are straightforward either—watch out for key words like sponsored and partner (as well as the indicative hashtags like #ad, #spon, etc.) for obvious reasons, the truth may be sugarcoated, especially if someone is getting paid (or gifted a free stay) for writing it.

5. We can manage the expectations and limitations of each member of your traveling party, so that you are able to reasonably, and enjoyably, participate in everything that you want.

  • Your family has booked an escorted tour to see that Instagram-worthy view and waterfall. You didn’t realize you’d be riding 4 miles on serpentine roads to get there, and your daughter suffers from terrible motion sickness from your party being seated at the back of the van. Now she is miserable, you feel terrible that she's miserable, and you still have to make it back down-yikes! Booking before you go can ensure these issues can be prevented, either by securing a seat for her at the front, or finding a comparable solution or different tour.
  • It is our job to cover those type of bases and bring to your attention issues that may not cross your mind in the excitement of planning a fun vacation.

Here are some of the unique experiences & excursions that we have booked in the past:

Swimming with whale sharks

Sand boarding and dune hiking


Harry Potter Studio Set Tour

Fly Fishing

National Geographic Endorsed adventures/up close & personal photography tours

Front row seats for the Carnivale parades in Rio

Character meals and activities for kids

Winery and Brewery tours & tastings

Jeep safaris and off-roading excursions

Community Service, Volunteering and Relief Efforts

For inquiries about planning an upcoming trip & any experiences you may be interested in give us a call at 412-963-7272 or send us an email at!

Photo credits: 1. "SnorkelingWhaleshark"by Quo Vadis Dive Resortis licensed under CC BY-NC-SA 4.0, 2. "Woman Sandboarding1"by Namastê... ॐis licensed under CC BY-NC-SA 4.0, 3. "Parabuteo_unicinctus_-falconry_show-8a"by Stephan Richteris licensed under CC BY-NC-SA 4., 4. "Carnaval 2014 - Rio de Janeiro"by Nicolas de Camaretis licensed under CC BY-NC-SA 4.0, 5. "The Making of Harry Potter"byDave Catchpoleis licensed underCC BY-NC-SA 4.0, 6. "Carnaval 2014 - Rio de Janeiro"by Nicolas de Camaretis licensed under CC BY-NC-SA 4.0, 7. "Allagash Tour Tasting-1" by Allagash Brewing, 8. "Punta Cana Just Safari - Jeep Safari Adventure"byPunta Cana Just Safariis licensed underCC BY-NC-SA 4.0

Start Your Trip Today