Top Baby Boomer Destinations (And Travel Insurance Considerations for Each)

May 5, 2017 - Kate

Last Updated On

For avid travelers and anyone in the workforce, really, retirement is an era in our lives to really look forward to. After decades of hard work, in retirement we’re finally able to kick back and relax, and have the availability to do it.

But with a world as big as ours, it can be difficult, not to mention time consuming, to choose a destination. To think through your best choices, first consider your reasons for traveling. For example, are you seeking adventure or a relaxing vacation by the beach? Do you want to unplug or explore the nightlife of a new city?

Recent travel trend research shows that Baby Boomers remain one of the most active travel demographics. According to AARP’s 2025 Travel Trends survey, 70% of adults age 50 and older planned to travel in 2025, surpassing pre-pandemic travel levels. Many travelers in this age group continue to prioritize meaningful experiences, international destinations, and longer trips that make the most of retirement flexibility.

Based on Yonder traveler data, three destinations that have been particularly popular among baby boomer-aged travelers are Israel, the British Virgin Islands, and the United Kingdom.

Table of Contents

• What Many Baby Boomers Prioritize In Retirement Travel
• Questions To Ask Before Choosing Your Next Retirement Trip
• Exploring History & Culture: Israel
• Once-in-a Lifetime Luxury Experience: British Virgin Islands
• Independent International Exploration: United Kingdom
• What Many Baby Boomers Don’t Consider Until It’s Too Late
• Why Travel Insurance Matters More As Retirement Travel Increases

What Many Baby Boomers Prioritize In Retirement Travel

Retirement Travel Priority	Why It Matters
Meaningful Experiences	Many retirees prioritize memorable trips over simply checking destinations off a list.
Longer Stays	More flexibility allows travelers to spend additional time in each destination.
Multigenerational Travel	Retirement often creates opportunities to travel with children and grandchildren.
Comfort & Convenience	Ease of transportation and accommodations become more important.
Smaller Group Experiences	Many travelers prefer more personalized experiences.
Slower-Paced Exploration	Flexibility often becomes more valuable than seeing everything.

Here’s how Yonder’s top three destinations amongst Baby Boomer customers relates to these priorities:

• Israel aligns with meaningful experiences

• BVI aligns with smaller-group luxury travel

• UK aligns with flexible exploration

Questions To Ask Before Choosing Your Next Retirement Trip

How Much Structure Do You Want?

Some travelers love organized tours and detailed itineraries, while others prefer the freedom to explore independently.

• Israel often appeals to travelers who enjoy guided experiences and structured sightseeing.

• The United Kingdom tends to work well for travelers who enjoy building their own itinerary.

• Yacht charters in the British Virgin Islands often fall somewhere in between, offering flexibility within a planned route.

Are You Traveling With Family?

The logistics of traveling with adult children and grandchildren can look very different than planning a trip for two.

• The British Virgin Islands can work well for multigenerational travel because travelers share accommodations and activities.

• Israel is often better suited for smaller groups interested in history and cultural exploration.

• The United Kingdom offers flexibility for families who may want to split up during the day and reunite later.

How Much Travel Complexity Are You Comfortable With?

Some destinations require more moving pieces than others.

• Israel itineraries often involve multiple cities, guided tours, and long-haul flights.

• Yacht charters may involve charter schedules, weather considerations, and multiple transportation connections.

• The United Kingdom can often be explored at a slower pace using rail networks and centralized accommodations.

Exploring History & Culture: Israel

What’s the number one type of trip Baby Boomers take? The bucket list trip. You’ve been waiting all your life for this trip and now you have the time for it!

For many Baby Boomers, that means destinations rich in history, culture, and once-in-a-lifetime experiences. Based on Yonder traveler trends, Israel continues to be a popular destination among travelers in the baby boomer age group.

From the ancient streets of Jerusalem to the beaches of Tel Aviv and the dramatic landscapes surrounding the Dead Sea, Israel offers a unique blend of history, religion, food, and adventure. It’s the kind of destination where every day can look completely different from the one before. 

Why Boomers Love Israel

• Rich historical and religious significance

• Guided tours available throughout the country

• Easy to combine with nearby destinations

• Appeals to travelers seeking meaningful experiences

To prepare for a safe trip, check out our Israel Travel Safety guide.

Travel Insurance Considerations

Trips to Israel often involve long-haul international flights, guided tours, multiple hotel stays, and significant prepaid expenses. Many travelers also combine Israel with visits to neighboring destinations like Egypt and Jordan. This creates more complex itineraries that can be difficult and expensive to rearrange if plans change unexpectedly.

Travel Insurance Benefits To Prioritize

Yonder’s travel insurance experts recommend prioritizing the following benefits for Boomers taking trips to Israel.

Benefit	Priority
Trip Cancellation and Trip Interruption	High to protect more expensive trip costs
Emergency Medical Coverage	High to reimburse potential medical bills from emergencies
Medical Evacuation Coverage	High to coordinate evacuations to more appropriate medical facilities
Travel Delay Coverage	Medium to reimburse extra hotel and meal costs if delayed
Baggage Protection	Medium to repair or replace lost or stolen personal belongings

Expert Tip: For travelers planning a multi-city itinerary, it’s especially important to review interruption and delay benefits before departure.

Once-in-a Lifetime Luxury Experience: British Virgin Islands

Some travelers dream about seeing the world from a cruise ship. Others dream about exploring it from the deck of a private yacht. For many Yonder travelers, the British Virgin Islands remain one of the most popular destinations for sailing vacations and yacht charters. Read our Yacht Charter Planning guide if you’re new to private sailing and need some help getting started.

Known for crystal-clear water, secluded coves, and island-hopping adventures, the British Virgin Islands offer a more intimate and flexible way to experience the Caribbean. Many Boomer travelers opt to make their charter trips multigenerational and include their children and grandchildren in the fun.

Why the BVI Appeals to Boomer Travelers

• Smaller-group travel experiences compared to large resorts and cruise ships

• The flexibility to explore multiple islands at your own pace

• Opportunities for multigenerational vacations with children and grandchildren

• Relaxed, uncrowded Caribbean experiences Private yacht charters that combine adventure, comfort, and luxury

• Easy access to snorkeling, sailing, beaches, and waterfront dining

Travel Insurance Considerations

Unlike a traditional resort vacation, yacht charters often involve substantial prepaid deposits, island-to-island logistics, and itineraries that depend heavily on weather conditions. Missing a flight or experiencing a travel delay can have a much larger impact when a charter departure is scheduled for a specific day and location.

Travel Insurance Benefits To Prioritize

Yonder’s charter insurance experts recommend these most-asked-about benefits for anyone taking a private sailing in the BVI. Learn more about important travel insurance benefits in our British Virgin Islands Travel Insurance guide.

Benefit	Priority
Trip Cancellation and Trip Interruption	High to protect more expensive charter costs
Medical Evacuation Coverage	High since medical care between islands is limited
Travel Delay Coverage	Medium to reimburse extra hotel and meal costs if delayed to or from charter

Expert Tip: Medical evacuation is particularly important for sailing vacations because travelers may spend significant time away from larger medical facilities.

Independent International Exploration: United Kingdom

Retirement often brings a new kind of freedom: the ability to travel without rushing. That’s one reason the United Kingdom remains a favorite destination among Yonder travelers in the Baby Boomer generation.

Whether you’re exploring London, touring the Scottish Highlands, visiting historic castles, or taking a train through the English countryside, the UK offers countless opportunities for independent travel.

Why The UK Appeals To Baby Boomers

• English-speaking destinations that are easy to navigate independently

• Rich history, architecture, and cultural attractions

• Extensive rail networks that make multi-city travel convenient

• A mix of vibrant cities, countryside villages, castles, and historic landmarks

• Flexible itineraries that can be customized around personal interests

• Comfortable travel experiences that balance familiarity with international exploration

Travel Insurance Considerations

Many UK itineraries involve multiple cities, rail travel, guided excursions, and extended stays. While these trips are often less complex than cruises or yacht charters, delays, cancellations, baggage issues, and unexpected medical expenses can still create costly disruptions.

Travel Insurance Benefits To Prioritize

Benefit	Priority
Trip Cancellation and Trip Interruption	Medium to protect all your different nonrefundable bookings
Emergency Medical Coverage	Medium to reimburse potential medical bills from illness or injury during trip
Travel Delay Coverage	High to reimburse costly extra hotel and meal costs if delayed
Baggage Delay Coverage	High to reimburse extra clothing and toiletries if bags are delayed

Travelers planning extended stays should also carefully review policy maximum trip lengths and coverage limits before purchasing a plan. 

What Many Baby Boomers Don’t Consider Until It’s Too Late

Choosing a destination is exciting. Planning the details that make the trip run smoothly? Not always as fun. But many of the biggest travel headaches happen because travelers overlook small details before departure.

Here are a few things worth thinking about before booking your next adventure.

Passport Expiration Requirements

Many countries require your passport to remain valid for at least six months beyond your travel dates. Waiting until the last minute to check expiration dates can quickly derail international travel plans. Here’s what to know about renewing your passport.

Long-Haul Flight Fatigue

A 10-hour flight may have sounded easier twenty years ago. Many retirement travelers find that building in an extra day to rest before starting a busy itinerary makes the entire trip more enjoyable.

Multi-City Transportation Logistics

The more destinations you add, the more moving pieces you create. Flights, trains, ferries, cruises, transfers, and tours all need to work together. A delay in one part of the itinerary can create unexpected challenges throughout the trip.

Emergency Contacts And Important Documents

Before traveling internationally, make sure family members know your itinerary and have copies of important travel information. Keeping digital copies of passports, travel confirmations, and emergency contact information can also be helpful if something goes wrong. Check out Yonder’s traveling overseas packing list so you don’t forget other important items on your trip.

Accessing Healthcare Abroad

Many travelers don’t research local healthcare options until they need them. Before departure, it’s worth understanding where nearby hospitals, clinics, or pharmacies are located, especially for longer trips or travelers managing ongoing medical needs. The CDC Traveler’s Health resource can help you understand a destination’s safety risks, vaccines needed, and other health tips when traveling.

The True Cost Of A Trip

One of the easiest mistakes to make is focusing only on airfare and accommodations. Excursions, transportation, guided tours, dining, cruise packages, and other travel expenses can add up quickly. Understanding how to calculate your total trip cost can help you plan more confidently and avoid surprises later.

Slower Travel Often Creates Better Experiences

Many experienced travelers discover that seeing fewer places in greater depth creates a more enjoyable trip than trying to fit everything into one itinerary. Building in flexibility can make travel feel less rushed and more rewarding.

The best retirement trips aren’t always the ones with the longest itineraries. They’re often the ones that leave enough room to enjoy the experience along the way. 

Why Travel Insurance Matters More As Retirement Travel Increases

Many Baby Boomers are taking longer trips, traveling internationally more frequently, and investing more money into bucket-list experiences than they did earlier in life. As trip costs increase, so does the potential financial impact of cancellations, interruptions, medical emergencies, and travel delays.

While every traveler has different needs, many retirees prioritize:

• Comprehensive coverage

• Emergency medical benefits

• Medical evacuation coverage

• Protection for significant prepaid travel expenses

Understanding which benefits matter most can help travelers choose coverage that aligns with both their destination and travel style.

For a deeper look at coverage options, visit our guide to senior travel insurance.

 

Tags: travel planning