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Planning Dream Vacations for Grandparents and Grandchildren

April 08, 2025 |
Last updated on June 03, 2025
Family Vacation Packages

There are two truths no one can deny: everybody loves to go on vacation and grandparents love to spoil their grandchildren. When the two combine, parents, grandparents and grandkids are all happy! Going on vacation together is a perfect way for grandparents to connect with the younger generation and create memories that will last a lifetime. From experiencing breathtaking views to spotting wildlife alongside reefs or mountainsides, here are some of the best vacations for grandparents and grandchildren to embark on together.

Dream Vacation Cruise Ideas for Families
Looking to plan a dream getaway that offers a mix of adventure and relaxation for all ages? A river cruise through Europe’s most iconic rivers, like the Danube or Rhine, is the perfect option for families. With scenic views of castles, quaint villages, and lush landscapes, these cruises make it easy to visit multiple destinations in comfort. Onboard, families can enjoy spacious cabins, kid-friendly activities, and themed excursions like treasure hunts or visits to historical sites. Whether exploring grand cities or quiet towns, a river cruise provides a relaxing and enriching experience for everyone.

Hawaiian Islands
There isn’t a person, from those who prefer toy race cars to those who like a crossword, who wouldn’t love visiting Hawaii. Dream Vacations can help secure different types of trips to Hawaii so you can explore, from kid-friendly resorts to island-hopping cruises. Kids can have fun on the Big Island, feasting on delicious food and trying their hand at surfing, or visiting Maui or Kauai to explore volcanic peaks or swim alongside sea turtles. Hawaii has a little bit of something for everyone, where its stunning landscapes and unique experiences are sure to enthrall all generations.

The Caribbean
No matter how many times you go to the Caribbean, you can always find a new adventure to embark upon or spot to relax in the sun next to crystal clear water. The Caribbean has some of the best all inclusive resorts in the world. From themed resorts specifically for kids to beachside resorts ideal for the whole family, it’s hard to deny a week away in a tropical paradise. The Caribbean includes many destinations, including the Bahamas, Dominican Republic, Barbados, Bermuda, Puerto Rico, Jamaica, Belize and many more hidden gems. Caribbean cruises are also a great way to visit multiple countries and must-see destinations.

Mediterranean Cruises
The Mediterranean is known for its rich culture, tasty food and stunning landscapes—it’s perfect for those seeking sun and vibrant cities. Mediterranean cruises are a good way to explore the region’s highlights and visit multiple countries, including Spain, France, Italy, Greece, Turkey, Croatia and more. If you’d like to pose with the Tower of Pisa or watch progress of the work continuously being done to the legendary Sagrada Familia, you can bring your grandchildren to some of the greatest historical sites in the world. Many family cruises have specialty kids programs and entertainment, including teen lounges, kids-only parties, themed nights, sports and adventure courts, babysitting, movie nights and Broadway-style shows.

Alaskan Cruises
If you’re looking for a little adventure, Alaskan cruises can be the perfect middle ground for grandparents and grandchildren. Activities can include lumberjack shows, whale watching, helicopter rides and glacier viewing. Visiting Alaska is a major bucket list for many adults, and kids will have a unique adventure to tell everyone at school when they get home. Royal Caribbean and Princess are just a couple of the cruise lines that operate family cruise deals for Alaska, with most sailings from mid-spring to early fall.

Book Your Dream Vacation Today!
These are just some of the dream vacations for grandparents and grandchildren on which you can embark. Connect with your local Dream Vacations Travel Advisor to book your family a cruise or resort vacation – it will be a vacation you won’t soon forget!