November 6-15, 2027
Limited to just 14 travelers
This nine-night Kenya safari is designed for travelers who want incredible wildlife, beautiful accommodations, thoughtful planning, and a comfortable pace.
We’ll explore Nairobi, Ol Pejeta Conservancy, Lake Naivasha, and the Masai Mara—with three nights in the Mara to truly experience it. Highlights include Big Five game drives, the world’s remaining Northern White Rhinos, conservation visits, local culture, bush breakfasts, sundowners, and an optional sunrise hot-air-balloon safari (I’m doing it!).
The trip includes accommodations, most meals, domestic flights, custom 4x4 Land Cruisers, professional guides, transfers, Kenya eVisa processing, and many experiences.
$10,950 per person, double occupancy. International airfare, travel protection, gratuities, and some additional expenses are not included.
I’ve intentionally kept the group small, and several spots were reserved during early access. The remaining rooms are now open. If Africa is on your bucket list, take a look at the itinerary—and reach out with any questions about the safari or whether this trip is right for you.
Conclude your Kenyan adventure with an unforgettable stay at one of the world's most iconic boutique properties. Steeped in old world charm and surrounded by lush gardens, Giraffe Manor offers an intimate and enchanting experience unlike any other. Share breakfast with the resident Rothschild's giraffes, unwind amidst timeless elegance, and indulge in exceptional hospitality before enjoying a leisurely final day in Nairobi. Thoughtfully designed to blend luxury, wildlife, and relaxation, this exclusive extension is the perfect finale to your journey through Magical Kenya.
$2399 per person
Includes private transfers, meals, drinks and laundry services.
Escorted by Erin
Travel to Ireland for this unforgettable 8-day journey through Ireland’s stunning west and south. Highlights include a jaunting car ride in Killarney, the dramatic Cliffs of Moher, Blarney Castle, and the charming streets of Galway and Kilkenny. Visit historic pubs like Sean’s Bar, tour the House of Waterford Crystal, and savor whiskey at the Pearse Lyons Distillery. With luxury hotels, scenic drives, and exclusive cultural experiences, this small-group tour offers a perfect blend of history, beauty, and authentic Irish charm.
Prices - $3495 per person double occupancy.
Single Room supplement $1095
Easy Pace Italy is a 10-day guided tour beginning March 14, 2027, visiting Rome, Florence, Pisa, and Venice. The itinerary includes fast-track entry to the Vatican Museums and Sistine Chapel, a guided visit to the Colosseum, time at leisure in Rome, Florence sightseeing including Michelangelo’s David (choice-based), a leatherwork demonstration, wine and olive oil tasting in Tuscany, Pisa’s Leaning Tower, and private boat sightseeing in Venice. The tour ends with a departure transfer from Venice.
Insight Vacations operates premium guided tours with smaller group sizes, professional Travel Directors, centrally located hotels, porterage included, and many meals included in the itinerary. This trip includes 9 nights in hotels, daily breakfast, select lunches and dinners, guided sightseeing, and luxury coach transportation.
Wake up each morning to a new Caribbean island, spend your days exploring secluded beaches and turquoise waters, and end each evening in some of the region's most exclusive ports.
Join me and my family on this unforgettable 7-night luxury yacht voyage.
Emerald Sakara, 50 rooms
What's Included
All inclusive Experience
- Airport transfers • Luxury yacht accommodations
- All meals, wine, beer, soft drinks & select cocktails
- Included shore excursions • Wi-Fi • Gratuities
Exclusive O'Leary Travel Pricing
- Oceanview Staterooms from $4,002 per person
- Balcony Suites from $4,993 per person
- Yacht Suites from $7,737 per person
*Special group pricing is available for guests who pay in full within 30 days of booking after making their deposit.
I love family travel, solo travel and couples travel- here are some of the places I have been and some suggestions for you! I have been to Alaska, Ecuador, Europe and more.... I love luxury- but you can also find me on a hike in the cloud forest! I live in Lambertville New Hope and love to provide travel concierge services for those looking for a weekend getaway from NYC or PHILLY
These are affiliate links for suppliers I have used and trust
Day Tours & Cruise Excursions
Looking for unforgettable excursions?
Browse and book handpicked tours and activities around the world with Project Expedition— perfect for customizing your travel experience!
Day Tours and Cruise Excursions
Enhance your trip with unforgettable experiences!
Discover top-rated tours, skip-the-line tickets, and unique activities worldwide with Viator — book ahead and travel smarter.
Luxury Escorted Tours & Cruises
Travel effortlessly with Tauck’s award-winning tours.
From exclusive access to expert-guided experiences, Tauck offers luxury journeys that go beyond the ordinary. Explore expertly crafted, all-inclusive journeys.
Multi Gen
Norwegian Cruise Line (NCL) is known for its vibrant and flexible cruising experience, offering a range of options for travelers seeking adventure and relaxation. With a focus on "Freestyle Cruising," NCL provides guests with the freedom to choose their dining, entertainment, and activities on their own schedule. Their fleet features a variety of amenities, from diverse dining venues and innovative entertainment to family-friendly options and luxurious accommodations. Norwegian Cruise Line aims to deliver a fun and customizable cruise experience for all types of travelers.
4o mini
For Adults Only
Virgin Voyages is a cruise line offering a modern, adults-only experience with a focus on contemporary design, innovative amenities, and personalized service. Their ships feature a range of stylish accommodations, diverse dining options, and entertainment that caters to a sophisticated crowd. With an emphasis on relaxation, adventure, and luxury, Virgin Voyages aims to redefine cruising for a new generation of travelers
Luxury Small Ship
Explora Journeys is a luxury cruise line that offers an elegant and immersive travel experience for discerning explorers. Their ships blend sophisticated design with exceptional comfort, providing guests with spacious accommodations, gourmet dining, and personalized service. Focusing on enriching itineraries, Explor Journeys aims to deliver a seamless journey that combines cultural discovery with refined relaxation.
I'll walk you through my room at Equinox NYC so you can know before you go. Its a great hotel with a lot of health based extras (and additions at a cost - including IV drips !!!!!!)
Check out the opportunity to enjoy a stress free family trip.
O'Leary Travel is ready to help you book and travel to places that meet your child's specific needs.
All Inclusive Luxury for Families
We’ve elevated the experience at Beaches Negril with 100% all-new rooms and suites, as well as a sweeping array of enhancements throughout the resort. Beaches Negril captures the essence of a laid-back paradise along with the elegance of a luxury all inclusive resort
Pro Tip
Go to the dollar store/target/amazon and buy little gifts for your young child. WRAP them in wrapping paper and give them one at a time on the airplane or trip!
Where Magic Meets the Sea
From the moment you step on board to your last wave goodbye, a Disney cruise includes almost everything you could hope for—larger-than-life entertainment, outstanding dining, spacious accommodations, dazzling destinations and more—with most experiences included in the price of your cruise.
If you are out of the box, and prefer to avoid already arranged cruises and all inclusive resorts for a change- O'Leary Travel offers a fee based travel planning so you don't have to think about the research and detail. I will do a personalized intake that allows me to understand your needs, provide you with a fee quote and start planning!