Where to Start: How to Choose the Right Type of Vacation for Your Travel Style

Because the best trip isn’t just about the destination—it’s about the experience you want to have.

Feeling Stuck Before You Even Start Planning?

With social media feeds full of dreamy destinations, trending resorts, and "must-do" lists, it's easy to get overwhelmed when planning your next trip. One day it’s a Mediterranean cruise that catches your eye, the next it’s a jungle bungalow in Costa Rica.

So, how do you choose what kind of vacation is actually right for you?

Many people don’t realize how specific their preferences are until we start digging in. The first thing I usually ask clients is simple: “What do you want to get out of this vacation?” Do you want to relax and be left alone? Chase every adventure available? Sip cocktails on the beach without lifting a finger?

Let’s walk through the most popular vacation styles—and how to know which one fits you best.

4 Popular Vacation Styles—and Who They’re Best For

Cruises

Best for: Travelers who want to see multiple destinations without the hassle of packing and unpacking.

Why people love it: Cruises offer a mix of relaxation, entertainment, and adventure—all from the same floating hotel.

Pros:

• Visit multiple destinations in one trip

• Unpack once

• Built-in dining, entertainment, and excursions

• Options for all budgets

Cons:

• Limited time in each port

• Extra planning needed for excursions

• Can feel crowded during peak season

Great Destinations: Alaska, Mediterranean, Caribbean, Northern Europe

Pro Tip: I specialize in cruising and can help match you with the right line, itinerary, and pre/post-cruise experiences.

All-Inclusive Resorts

Best for: Travelers who want a no-hassle, stay-in-one-place vacation with everything included.

Why people love it: Meals, drinks, activities—all covered. You show up, check in, and let go.

Pros:

• Easy budgeting (most costs included)

• Great for couples or groups

• Many adults-only options are available

Cons:

• Limited exploration unless planned separately

• Quality varies by resort and brand

Great Destinations: Mexico, Jamaica, St. Lucia, Dominican Republic, Turks & Caicos

Escorted or Group Tours

Best for: Travelers who want structure, expert guides, and zero logistics stress.

Why people love it: These tours dive deep into the culture and include everything from hotels to sightseeing to local experiences.

Pros:

• Great for first-time international travelers or solo adventurers

• Pre-arranged access to exclusive experiences

• Perfect for special-interest travel (food, history, nature)

Cons:

• Less personal flexibility

• Can be fast-paced

Great Destinations: Europe, Japan, South America, U.S. National Parks

Examples: Tauck, Grand Circle, Adventures by Disney, Trafalgar

Custom / Independent Itineraries

Best for: Travelers who want a trip that’s 100% tailored to them

Why people love it: Every detail reflects your travel style—from boutique hotels to off-the-beaten-path finds

Pros:

• Ultimate flexibility and personalization

• Deeper cultural immersion

• Great for honeymoons, anniversaries, or bucket list adventures

Cons:

• Requires more upfront planning

• Can be overwhelming without expert help

Great Destinations: Italy, France, Iceland, Hawaii, New Zealand

I specialize in building custom itineraries that balance freedom and expert planning—so you never feel overbooked or underwhelmed.

How to Choose the Right Vacation for You

Here are some key questions to help you discover what kind of travel truly fits your personality:

Personal Preferences

• How structured do I want my days?

  • Am I okay with a set itinerary, or do I want the freedom to explore?

• Do I want to unpack once—or am I okay moving around?

  • Cruises and all-inclusives are great for “one and done” travelers.

• What level of luxury or comfort do I want to experience?

  • Boutique hotels? Budget-friendly? Five-star indulgence?

• Do I want an adults-only environment or something family-friendly?

• Do I prefer all-inclusive pricing, or do I like choosing restaurants and activities as I go?

• Am I most excited by adventure, culture, relaxation, or food?

• How social do I want the experience to be?

  • Am I energized by meeting new people or do I prefer quiet time?

• How confident do I feel navigating a foreign country or planning complex logistics?

Budget & Practicality

• What’s my realistic travel budget—and what does that need to include?

  • Flights, accommodations, food, excursions, insurance, tips?

• How far am I willing to travel—and for how long?

• Am I celebrating something special—like a honeymoon, anniversary, or milestone?

  • These occasions can shape everything from destination to style.

Bonus Reflection

• Would I be disappointed if I didn’t visit multiple places—or do I prefer soaking in one destination deeply?

There’s no wrong answer—just the right fit for you. That’s exactly where I come in: I ask the right questions, listen closely, and help you design a trip that perfectly matches your goals, personality, and preferences.

Common Mistakes When Choosing the Wrong Type of Trip

1. Over-planning when you really needed to unwind

• Choosing a jam-packed itinerary when all you needed was a hammock and a book.

2. Picking an all-inclusive… and then getting bored by Day 3

• If you’re naturally adventurous, staying in one place can leave you restless.

3. Booking a cruise without understanding the ports or ship vibe

• The wrong cruise line or cabin can turn an amazing itinerary into a frustrating experience.

4. Leaving no room for rest

• Trying to squeeze in “everything” can leave you more tired after vacation than before it.

5. Going with what’s trendy, not what fits

• Just because Iceland or Tulum is all over Instagram doesn’t mean it fits your vibe or budget.

6. Not knowing the atmosphere

• Family-friendly vs. adults-only matters—especially when you’re expecting peace and quiet.

7. Forgetting to plan for flight times and jet lag

• No one wants to miss a cruise departure or sleepwalk through Paris.

8. Budgeting only for the sticker price

• Excursions, transfers, tips, and insurance add up—and can be stressful if unplanned.

Why Work With a Travel Advisor?

As a Travel Advisor, I help you sort through the noise. By asking the right questions and understanding your priorities, I match you with the travel style that truly suits you—not what the internet says you “should” do.

And because I’ve personally experienced cruises, resorts, guided tours, and custom adventures, I offer real insight—not generic search results.

Still Unsure What’s Right for You?

That’s exactly what I’m here for. Whether you’re craving relaxation, culture, or a little bit of everything, I’ll help design a trip that feels perfectly you.

Let's start planning!