Big families mean big adventure, and this summer, we have the perfect destinations to make your family vacation one to never forget. With sunny, seaside locations, exciting city activities, and relaxing accommodations, Independent Collection Hotels & Resorts are the ideal choice for multi-generational travel. From the littlest ones in your family to the most seasoned travelers, there’s a world of summer fun to discover. Ready to hit the road?

Dive into Discovery in Boston

Dive into a world of endless discovery when you and your family stay at The Whitney Hotel Boston this summer. This gem tucked away in Boston’s beloved Beacon Hill neighborhood offers a calming retreat for families of all kinds. Even the four-legged members of the family are welcome to join this city escape.

Allow the personality of the neighborhood to guide your adventures, whether you opt for a serene stroll alongside the iconic Victorian row houses to enjoy Boston’s temperate summer weather or set out for a day of family fun at the Museum of Science.

Want to make your stay extra special for kids of all ages? Discover The Whitney’s LEGO Discovery Center Package. Not only does this package include overnight accommodations and an exciting LEGO-themed welcome gift for your child, but it also includes a full American breakfast at their on-site restaurant Peregrine, and tickets to the Lego Discovery Center. As the little ones take in the sights of over two million LEGO bricks, who says you can’t tap into your childlike side as well?

When you’re ready for some rest after a day of fun, discover inviting guest rooms or townhome-style suites, offering the comforts of home with a touch of Boston flair.

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Take a Splash in the Florida Keys

There’s no better place to truly make yourself at home than Bayside Villas by Islander Resort. This sunny property offers an exquisite waterfront escape that every generation will want to return to, summer after summer. As you settle into your individual space, each villa offers an ideal home base for exploring the magic of the Florida Keys.

When you step into your villa,  you’ll discover room enough for eight, incredible ocean views, a full kitchen, and multiple beds — perfectly suited for groups and families. As you settle into tropical rest, you’ll find a deep sense of slow-paced relaxation on your villa patio, perfect for some quality time with family or even some alone time before the day’s adventures start.

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You don’t have to pile into a car or public transport to witness the area’s famous sunsets either. You can simply step outside, surrounded by your favorite people. Beyond the villa, parents of young kids will love convenient options around the property like poolside changing rooms in the Bayside pool area. Not only are these features practical, but they also ensure that everyone in your group is taken care of, so the whole family can focus on enjoying time together. 

When you’re ready to experience more exciting warm-weather activities, head over to the oceanside property at Islander Resort. From there, you can discover everything from water sports to on-site dining. As you sit together under the glow of a Florida sunset, living your best island life, you’ll quickly want this destination to be a family tradition!

Live in the Present Moment in Annapolis

Welcome to your maritime summer getaway, and not in an “aye, aye, captain!” sort of way either (unless that’s what you’re looking for). Annapolis is a charming and slow-paced locale, offering an inviting and tranquil option for families wanting to experience the beauty of the present moment together.

Annapolis Waterfront Hotel offers proximity to the beauty of the Chesapeake Bay in one of America’s most walkable towns. From sailing to strolling the historic streets of downtown, this hotel is your gateway to the city.

This idyllic destination offers a refreshing change of scenery for the whole family, taking you beyond the ordinary summer vacation. Stay in the hotel’s newly redesigned guest rooms, complete with nautical details, bay views, and thoughtful amenities, creating the perfect environment to rest and enjoy.

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You’ll find plenty of fun things to do in downtown Annapolis, with eclectic boutiques, one-of-a-kind boat shows, spectacular restaurants, and beautiful 18th-century architecture just steps away. Take it all in as you treat yourself to waterfront dining, set out on a harbor cruise, take sailing lessons, or rent a paddleboard.

Curious travelers will find plenty of excitement in Annapolis, starting with the nearby Naval Academy. Explore the campus and admire spectacular Beaux-Arts architecture and monuments commemorating naval events.

Likewise, history is around every corner in Annapolis, and there’s no better way to discover the stories that make up the city than a historic tour. You’ll find a range of tours suited to all sorts of interests, from walking tours to trolleys and minibusses, giving active families a chance to exercise while still offering options that are more accessible to elderly family members.

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After days spent exploring, if anyone in the group is tired from all the travel, why not spend a leisurely afternoon in one of Annapolis’s beautiful parks? Quiet Waters Park or Sandy Point State Park are great spots to enjoy a book, a blanket, and the opportunity to soak up a bit of the summer sun. For your next multi-generational trip, Annapolis awaits as a destination to make priceless memories by the Chesapeake Bay.

Plan a Family Escape to Miami Beach 

For fun-seeking families, a visit to Cadillac Hotel & Beach Club in Miami Beach offers a vibrant escape to remember. And for those who love a European escape, don’t worry, as the hotel brings a touch of European charm to the sunny shores of Florida.

Cadillac’s European approach doesn’t just apply to aesthetics and cuisine — it’s also apparent in their offering of kid-friendly activities. The whole hotel has been designed to allow families to spend quality time together instead of creating hard lines of separation between kid and adult areas. That said, should children need a space of their own, there is a designated beach play area, signature toys, and a family pool available.

Let the beach do the heavy lifting when it comes to planning family activities as you’ll have direct access to Miami’s glistening shores. Featuring an entire block of pristine shoreline, Miami Beach beckons just steps from your accommodations, offering full towel and beach service, two complimentary beach chairs, and umbrellas available for rental. Not much of a beach person? Two sparkling outdoor pools and an inviting hot tub are also yours to enjoy.

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There’s no appetite like a post-beach or pool day appetite, and lucky for you, delicious bites and drinks are always within reach at Bungalow by the Sea or Il Merkato. Bungalow by the Sea is an oceanside palapa featuring a seafood-inspired menu along with refreshing wines, cocktails, and more. If you’re more of a packed lunch type of beachgoer, then Il Merkato is the spot for you. Equal parts coffee bar, gelateria, and a social gathering place, Il Merkato is a modern Miami Beach twist on a traditional Italian market.

No summer holiday would be complete without some relaxing time to yourself. Consider a visit to the al fresco K’AIma Spa at Cadillac to indulge in custom-created spa journeys that infuse European refinement within Miami’s stunning landscapes.

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If a day spent exploring sounds more like your idea of family fun, then consider Miami Beach your personal playground. Cadillac is ideally located on Collins Avenue, putting you at the center of some of Miami’s most exciting bars, restaurants, and shops. Alternatively, explore delicious on-site dining with Donna Mare, the Lobby Bar, or even a night-in with room service.

No matter how you spend your stay, a memorable and fun-filled summer vacation awaits you and your family at Cadillac.

Find Serenity for All Ages in Santa Monica

There’s no denying that Los Angeles embodies a certain allure, drawing thousands to its vibrant shores every summer. But what if we told you that you and your family could experience all the excitement of Los Angeles without giving up the comforts of a serene stay? All of this and more is possible when you plan your next multi-generational trip at The Ambrose Hotel.

Set out together to discover Santa Monica Pier, only steps away from the hotel. See it all on foot or take advantage of the hotel’s Beach Cruiser Bikes for a family spin around the neighborhood.

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Likewise, if older or less mobile members of the family experience challenges getting around, take advantage of the Tesla house car, comfortably transporting guests in style to destinations within three miles of the hotel. The Ambrose is also proud to offer a senior rate, providing guests 65 and above with 10% off their accommodations.

After a day of seeing the sights together, Santa Monica Sips daily tastings are available for the adults in the family, so you don’t have to venture beyond the hotel to unwind with a drink. It’s the perfect way to toast to memories made as a family before retiring to your modern and revitalized rooms.

Discover Thoughtful Details in Philadelphia

For a sophisticated getaway that the whole family will love, consider a stay at The Rittenhouse Hotel. As the only Forbes Five-Star hotel in Philadelphia, this standout destination in the heart of Center City is the perfect place to book your next summer getaway.

Explore nearby kid-friendly attractions like The Academy of Natural Sciences, The Franklin Institute, and the Please Touch Museum, a safe space for kids to discover a whole new way to play. Whether you’re looking for indoor options to cool off from the heat or you want to give your kids a learning activity, Philadelphia is filled with opportunities for kids to make memories.

That said, kids aren’t the only ones who will love a stay at The Rittenhouse. The elegant rooms and suites provide everything needed for the family to truly relax. The hotel staff will be happy to configure your room in a way that makes sense for your unique family, ensuring that both kids and adults can utilize their space in a way that suits their specific needs.

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Speaking of truly relaxing, The Rittenhouse Spa & Club is the perfect place to unwind, offering guests a masterclass in the art of luxury wellness. The choice is yours — get pampered with high-end nail and hair treatments, spend an afternoon on the sunny outdoor patio, or splash around with your kids in the indoor heated pool.

You don’t need to leave the hotel to have enriching experiences that the whole family can enjoy. Families can spend the day together over tea at the Mary Cassatt Tea Room, pasta-making classes at Scarpetta, or a delicious brunch at Lacroix. The Rittenhouse offers a wide array of interesting events, no matter your age or interests.

Beyond engaging events, The Rittenhouse also features several sophisticated restaurants and bars, making it easy for adults to sneak away for a romantic date night. The hotel team is committed to offering a family-friendly environment, offering perks such as complimentary in-room movies for teens, local books for young children, and amenities provided just for infants.

Celebrate Time Spent Together

With so many destinations to explore, where will your summer adventures take you? Discover these Independent Collection properties up close for a stress-free stay, allowing you and your family to enjoy unforgettable moments this season. From villas that bring you closer to one another on Florida’s shores to relaxing stays in Annapolis, there’s something for every member of the family to discover.