Mike O’Sullivan is an independent travel advisor affiliated with Travelmation, LLC.
Travel guides

Useful answers before you choose the trip.

Practical guidance for comparing vacations, avoiding common planning mistakes, and understanding which details deserve your attention.

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Disney vacations

Planning Your First Disney World Trip: Where to Start

A decision-first guide to dates, trip length, resorts, tickets, priorities, and pacing.

READ THE GUIDE →
Cruises

Cruise Planning Checklist: What to Decide Before You Book

Work through the experience, ship, itinerary, cabin, costs, and logistics before choosing a sailing.

READ THE GUIDE →
All-inclusive resorts

How to Choose an All-Inclusive Resort

Compare destinations, resort styles, rooms, inclusions, logistics, and total trip costs.

READ THE GUIDE →
Cruises from New York & New Jersey

Best Cruise Options from New York and New Jersey: How to Choose the Right Sailing

Compare local terminals, itinerary styles, ships, cabins, transportation, and the full vacation cost.

COMPARE LOCAL CRUISE OPTIONS →
Disney resort comparison

Disney World Resort Comparison for First-Time Families: How to Choose Where to Stay

Compare resort categories, room needs, park access, transportation, amenities, and your family’s budget.

COMPARE DISNEY RESORT OPTIONS →
Disney family vacations

Disney World vs. Disney Cruise for Families: Which Vacation Is Right for You?

Compare park days and ship days, room arrangements, family interests, logistics, and the complete vacation cost.

COMPARE THE OPTIONS →
Cruise and resort comparison

Cruise vs. All-Inclusive Resort: Which Vacation Is Right for You?

Compare cruises and all-inclusive resorts by total cost, daily pace, destinations, rooms, and the vacation experience you actually want.

COMPARE THE OPTIONS →
Sports team travel

Sports Team Hotel Blocks: A Guide for Coaches, Team Managers & Parents

Compare tournament hotels, estimate rooms by night, and understand what your team is agreeing to before families book.

Read the sports hotel block guide →
Multigenerational vacations

How to Plan a Multigenerational Family Vacation Without the Stress

Work through dates, budgets, room arrangements, and shared activities for a family trip that works across generations.

Read the family vacation guide →

What makes these guides different

Each guide focuses on the choices that shape a trip: what to compare, which tradeoffs matter, and what to verify before booking. When you want help applying that to your plans, I can help narrow the options.

For help coordinating a tournament or an extended-family vacation, explore my group travel planning service.

Travel details can change. I verify current policies, schedules, inclusions, and operating information while planning your trip.

Have a trip in mind already?

You do not need to finish all the research first. Share the basics and let’s narrow the choices together.

START PLANNING