Pittsburgh Travel Advisor for Luxury & Custom Trips

I’m Anna Harrison, owner of Travel Observations and a luxury travel advisor based in Carnegie, just outside Pittsburgh. I design customized trips, river and small-ship cruises, safaris, rail journeys, and guided tours for travelers who want their trip planned well — and I work with clients across the country, not only locally.

If you’re in the Pittsburgh area and looking for someone to plan a meaningful trip, being nearby has real advantages. But the biggest one isn’t proximity — it’s that you get an advisor who knows the places you’re actually going, handles the logistics so you don’t have to, and can meet you in person when it makes sense.

What working with a local advisor actually looks like

Most of my planning happens remotely — by phone, email, and video — which means the process is easy whether you’re in Mt. Lebanon or across the country. I use planning tools that let you review itineraries, hotel options, and documents online, so nothing depends on being in the same room.

If you’d like to hear from travelers I’ve worked with, you can read their reviews on my Virtuoso advisor profile.

Where being local comes in is the relationship. Once we have a working relationship, I’m happy to meet in person — to hand off final documents before a big trip, or to hear how it went when you’re back. I don’t push to meet before we’ve established a working relationship, and I don’t require it at all; it’s simply an option Pittsburgh-area clients have if they’d like it. Plenty of my local clients and I have never met face-to-face, and their trips are planned just as thoroughly.

What I plan

I don’t start with a product and sell it to you. I start with how you like to travel and match you to the right kind of trip — which might be a fully customized private itinerary, or might be a cruise, safari, or guided tour you hadn’t considered. What I plan:

• Customized private itineraries — hotels, private transfers and guides, and a well-paced route, fully coordinated
• River and small-ship cruises — matching you to the right line, ship, and cabin (one of my specialties)
• African safaris — planned with specialist partners on the ground
• Luxury rail journeys — from the Rocky Mountaineer to Europe’s great train routes
• Premium escorted and guided tours — when a well-run group trip is the better fit
• Hotel-only bookings — expert hotel selection with preferred-partner amenities for independent travelers

I have particular depth in Portugal (I was raised there and hold dual citizenship) and Alaska (I’ve traveled it many times), along with Italy, France, the UK, and river cruise routes throughout Europe.

Flying internationally from Pittsburgh

Nonstop from Pittsburgh to Europe

PIT’s transatlantic service has grown, and a few nonstops make parts of Europe especially easy from home:

• London (Heathrow) — British Airways flies this year-round, daily. Beyond London itself, Heathrow is one of the strongest hubs for onward connections across Europe.
• Dublin — Aer Lingus added nonstop service in 2026, operating four times a week for most of the year. Two real perks: you clear US customs and immigration in Dublin before your flight home, so you skip the customs line back at PIT — and Dublin connects onward to cities across Europe and the UK, including Paris, Rome, Amsterdam, and Edinburgh.
• Reykjavík — Icelandair runs seasonal summer service to Iceland, which is both a destination in its own right and a convenient stopover hub for onward flights into Europe.

One genuinely useful thing about working with a local advisor: I plan around Pittsburgh International (PIT) all the time, and routing matters more than most travelers expect.

PIT has grown its nonstop network, but for most overseas trips you’ll still connect — often through a East Coast hub, or occasionally onward from PIT’s seasonal transatlantic service. That has practical consequences I build into every itinerary:

• Build in a travel day. For Europe, you’ll typically arrive the day after you depart. I plan your first hotel night and arrival transfer accordingly, so you’re not scrambling jet-lagged.
• Connections aren’t all equal. Some routings leave you a tight, stressful transfer; others give you a comfortable buffer or a better-timed arrival. I look at this before booking, not after.
• Sometimes a positioning night makes sense. For an early international departure or a trip where missing the first day would be costly, an overnight near your connecting hub can be worth it. I’ll tell you when it is and when it’s overkill.
• Alaska from Pittsburgh is its own routing puzzle — it’s a long travel day, and how you sequence the flights, a cruise embarkation, and any Denali land time makes a real difference. This is one of the places my Alaska experience saves you the most trouble.

Airfare isn’t typically included in what I book, but I can arrange it for $150 per ticket if you’d like me to handle the routing along with everything else.

Why clients here work with me

• Genuine expertise in where you’re going — not a catalog, but places I know firsthand
• Recommendations built around you — I narrow overwhelming choices down to a clear, well-reasoned set rather than handing you more options to sort through
• Preferred-partner amenities — as a Virtuoso-affiliated advisor, I can often add perks at hotels you won’t get booking direct
• Honest guidance — I’ll tell you when something isn’t the right fit, when a budget won’t stretch to cover everything, and exactly why I’m recommending what I’m recommending
• Recognition I’ve earned — named to Condé Nast Traveler’s Top Travel Specialists list (2024, 2025, 2026) and quoted on travel in The New York Times and The Washington Post

Frequently asked questions

Do I need to meet with you in person? No. Most of my planning happens remotely, and plenty of my local clients and I have never met face-to-face. If you’re in the Pittsburgh area and we’ve built a working relationship, I’m glad to meet — to drop off final documents or hear about your trip afterward — but it’s an option, not a requirement.

Can you plan my trip if I’m not in Pittsburgh? Yes. I work with clients across the country. The process is designed to work smoothly no matter where you are.

What kind of trips do you plan? Customized private itineraries, river and small-ship cruises, safaris, luxury rail journeys, and premium guided tours — mainly in Europe, Portugal, Alaska, and Africa, though I plan trips worldwide. I focus on matching you to the right travel style, not selling one type of trip.

What’s the best way to fly to Europe from Pittsburgh? It depends on your destination and dates, since most overseas trips from PIT involve a connection. I look at routing and timing for every itinerary and build in the travel day, buffer, or positioning night that makes sense for your trip.

What does a trip cost? As a general starting point, plan on roughly $5,000 per person per week, excluding international airfare. Where a trip lands from there depends on your travel style, the season, and how you like to travel. I’m positioned on value — thoughtful planning and seamless logistics — not on being the most expensive option.

Let’s talk about your trip

If you’re in the Pittsburgh area — or anywhere — and thinking about a trip, the best next step is to fill out my trip request form with a few details about what you have in mind. From there we’ll set up a call to see if I’m the right fit.