
Ashley Whipple
Based in Rochester, NY
Speaks English, Spanish
Ashley Whipple
Ask me about
My Story
I’m a mom of two adventurous boys, a list-maker at heart, and a traveler who believes the best memories are made exploring together. I create seamless, stress-free trips filled with adventure, hidden gems, and unforgettable moments for families, couples, and groups.
My Travel Style
I design trips for families, couples, and groups that balance adventure with downtime and must-see sights with hidden gems. I take care of the details so you can simply enjoy—whether that means laughing with your kids, sharing a romantic dinner, or exploring a new city with friends. Every journey is tailored to your pace and interests, making it both seamless and unforgettable.
My reviews (12)
Paul M.
7 days ago
Ashley is my absolute go-to for travel. The moment I send a request, she is back to me with curated, high-quality options that perfectly match my preferences. She recently planned a NYC trip for me and my teenage daughter, and her recommendation to stay at the SoHo Grand was a game-changer—it put us just minutes away from every shop my daughter wanted to visit. If you want to remove the hassle from planning and guarantee a seamless trip, just ask Ashley.
Sierra L.
2 months ago
Ashley was phenomenal! We ask her to plan a very last minute trip to WY to visit Grand Teton and Yellowstone. Ashley moved very quickly while still planning out such a thoughtful itinerary that was the perfect balance between adventure and R&R. Her recommendations for hotels, food, things to do, and guided tours were all spot on! Ashley made taking a vacation fun without the stress of planning & booking. I would highly recommend Ashley to my closest friends and family! We will definitely be reaching out to Ashley for our future trips!
Chelsea N.
2 months ago
ashley got us some perks we never would have known about ! personable and incredibly easy to work with.
Hannah A.
3 months ago
Ashley is phenomenal. She makes herself available for her clients when they need her and is very patient. Ashley wants to make the experience for her client very enjoyable and she is a pressure free resource. She talks things through and helps her client make informed decisions. I HIGHLY recommend working with Ashley and look forward to booking our next trip with her!
Lindsay M.
5 months ago
Ashley was the best! Easy to work with. On top of every detail and very responsive. I would highly recommend using her for any and all travel needs.
Paul M.
7 days ago
Ashley is my absolute go-to for travel. The moment I send a request, she is back to me with curated, high-quality options that perfectly match my preferences. She recently planned a NYC trip for me and my teenage daughter, and her recommendation to stay at the SoHo Grand was a game-changer—it put us just minutes away from every shop my daughter wanted to visit. If you want to remove the hassle from planning and guarantee a seamless trip, just ask Ashley.
Sierra L.
2 months ago
Ashley was phenomenal! We ask her to plan a very last minute trip to WY to visit Grand Teton and Yellowstone. Ashley moved very quickly while still planning out such a thoughtful itinerary that was the perfect balance between adventure and R&R. Her recommendations for hotels, food, things to do, and guided tours were all spot on! Ashley made taking a vacation fun without the stress of planning & booking. I would highly recommend Ashley to my closest friends and family! We will definitely be reaching out to Ashley for our future trips!
Chelsea N.
2 months ago
ashley got us some perks we never would have known about ! personable and incredibly easy to work with.
Hannah A.
3 months ago
Ashley is phenomenal. She makes herself available for her clients when they need her and is very patient. Ashley wants to make the experience for her client very enjoyable and she is a pressure free resource. She talks things through and helps her client make informed decisions. I HIGHLY recommend working with Ashley and look forward to booking our next trip with her!
My travel ideas (15)

Epic Family Adventure in the National Parks: Cuyahoga in Fall
Cuyahoga Valley National Park was the fifth national park my family visited, and it turned out to be the perfect fall weekend escape. With its mix of boardwalks, waterfalls, wildlife, and easy trails, this park is incredibly accessible for families with young children. Whether you’re local to the Midwest or flying into Cleveland for a quick getaway, CVNP offers just the right amount of adventure without overwhelming little legs. In this guide, I’m sharing a full weekend itinerary that mirrors how we structured our own trip in October. It’s paced intentionally for families with slow mornings, realistic driving times, plenty of sensory-friendly nature experiences, and enough “wow” moments to get everyone excited for your next national park adventure.

Epic Family Adventure in the National Parks: Cuyahoga in Fall
Cuyahoga Valley National Park was the fifth national park my family visited, and it turned out to be the perfect fall weekend escape. With its mix of boardwalks, waterfalls, wildlife, and easy trails, this park is incredibly accessible for families with young children. Whether you’re local to the Midwest or flying into Cleveland for a quick getaway, CVNP offers just the right amount of adventure without overwhelming little legs. In this guide, I’m sharing a full weekend itinerary that mirrors how we structured our own trip in October. It’s paced intentionally for families with slow mornings, realistic driving times, plenty of sensory-friendly nature experiences, and enough “wow” moments to get everyone excited for your next national park adventure.

Hyatt Regency Lake Tahoe Site Visit: Perfect for Families, Outdoor Fun & Multi-Gen Getaways
Located on the shores of North Lake Tahoe in Incline Village, the Hyatt Regency Lake Tahoe Resort, Spa and Casino combines rustic alpine charm with modern resort amenities. It’s one of the area’s most well-known properties and although it is undergoing an extensive renovation to its beach area, I would not hesitate to recommend a visit to this property. My family spent a week at this property over the summer and we are already planning our trip back! For families planning a Lake Tahoe getaway, it’s worth understanding what’s available now and what exciting changes are on the horizon.

Hyatt Regency Lake Tahoe Site Visit: Perfect for Families, Outdoor Fun & Multi-Gen Getaways
Located on the shores of North Lake Tahoe in Incline Village, the Hyatt Regency Lake Tahoe Resort, Spa and Casino combines rustic alpine charm with modern resort amenities. It’s one of the area’s most well-known properties and although it is undergoing an extensive renovation to its beach area, I would not hesitate to recommend a visit to this property. My family spent a week at this property over the summer and we are already planning our trip back! For families planning a Lake Tahoe getaway, it’s worth understanding what’s available now and what exciting changes are on the horizon.

Big Apple, Big League: A 10th Birthday with Yankees & NYC Adventures
In my family, we started the tradition of celebrating our boys’ 10th birthdays with a special trip—just for them. For my oldest son, there was no question where he wanted to go: New York City, with a Yankees game at the heart of the adventure. It was his very first visit to NYC, so we set out to do all the quintessential “first-time” experiences, from the Empire State Building to strolling Central Park. What made it even more memorable was pairing the game with a Yankees Stadium tour, giving him a whole day of baseball magic before cheering on his team. Between iconic sights, unforgettable birthday moments, and a few sweet treats, this trip was the perfect blend of a milestone celebration and a classic New York adventure.

Big Apple, Big League: A 10th Birthday with Yankees & NYC Adventures
In my family, we started the tradition of celebrating our boys’ 10th birthdays with a special trip—just for them. For my oldest son, there was no question where he wanted to go: New York City, with a Yankees game at the heart of the adventure. It was his very first visit to NYC, so we set out to do all the quintessential “first-time” experiences, from the Empire State Building to strolling Central Park. What made it even more memorable was pairing the game with a Yankees Stadium tour, giving him a whole day of baseball magic before cheering on his team. Between iconic sights, unforgettable birthday moments, and a few sweet treats, this trip was the perfect blend of a milestone celebration and a classic New York adventure.

Family Adventure in Scotland: Castles, Coasts & Highland Charm
Scotland’s blend of history, dramatic landscapes, and welcoming towns makes it a wonderful family destination. For us, this was the second part of a larger Ireland and Scotland adventure, but it also works beautifully as a standalone trip. Families can follow this five-day loop through Edinburgh, St. Andrews, Aberdeen, and Inverness before returning to the capital, or expand it into a longer Scotland-focused itinerary. From castle ruins and legendary lochs to seaside villages, each stop brings something new—all at a pace that works with kids in tow. Trust me, our boys were 1 and 3 on this trip, so I get it! We found the Scottish Highlands to be pure magic and can’t wait to plan a return trip now that our boys are older.

Family Adventure in Scotland: Castles, Coasts & Highland Charm
Scotland’s blend of history, dramatic landscapes, and welcoming towns makes it a wonderful family destination. For us, this was the second part of a larger Ireland and Scotland adventure, but it also works beautifully as a standalone trip. Families can follow this five-day loop through Edinburgh, St. Andrews, Aberdeen, and Inverness before returning to the capital, or expand it into a longer Scotland-focused itinerary. From castle ruins and legendary lochs to seaside villages, each stop brings something new—all at a pace that works with kids in tow. Trust me, our boys were 1 and 3 on this trip, so I get it! We found the Scottish Highlands to be pure magic and can’t wait to plan a return trip now that our boys are older.

Castles, Cliffs & Fairy Tales: A Magical Family Road Trip Through Ireland
Ireland is a country filled with history, natural beauty, and warm hospitality—and it makes for an unforgettable family trip. From ancient castles and dramatic cliffs to kayaking on quiet lakes, each day brings something new for parents and kids alike. My extended family and I took this trip when my boys were 1 and 3 years old, so this eight-day itinerary balances sightseeing, outdoor adventures, and cultural experiences. Following this itinerary will allow your family to explore Ireland at a comfortable pace.

Castles, Cliffs & Fairy Tales: A Magical Family Road Trip Through Ireland
Ireland is a country filled with history, natural beauty, and warm hospitality—and it makes for an unforgettable family trip. From ancient castles and dramatic cliffs to kayaking on quiet lakes, each day brings something new for parents and kids alike. My extended family and I took this trip when my boys were 1 and 3 years old, so this eight-day itinerary balances sightseeing, outdoor adventures, and cultural experiences. Following this itinerary will allow your family to explore Ireland at a comfortable pace.

Family-Friendly Lake Tahoe: A Guide to Summer Fun
Lake Tahoe is often known as a premier ski destination, but it shines just as bright in summer. Our family spent a week enjoying all that the lake and surrounding Sierra Nevada mountains have to offer: sparkling water adventures, kid-friendly hikes, and charming towns filled with history and good food. With its mix of relaxation and adventure, Tahoe makes the perfect family-friendly summer getaway.

Family-Friendly Lake Tahoe: A Guide to Summer Fun
Lake Tahoe is often known as a premier ski destination, but it shines just as bright in summer. Our family spent a week enjoying all that the lake and surrounding Sierra Nevada mountains have to offer: sparkling water adventures, kid-friendly hikes, and charming towns filled with history and good food. With its mix of relaxation and adventure, Tahoe makes the perfect family-friendly summer getaway.

Epic Family Adventure in the National Parks: Lassen Volcanic, Redwood & Crater Lake
This summer, my family embarked on a road trip through Northern California and Oregon to explore three of the West Coast’s most stunning national parks. Each stop brought something completely new—steaming geothermal features, ancient redwoods towering overhead, and the sapphire-blue depths of Crater Lake. Traveling with kids, we found the balance of shorter hikes, scenic drives, and playful downtime made the adventure not only doable but truly unforgettable. Whether you’re traveling with kids or just looking for a mix of outdoor beauty and family-friendly activities, this route is packed with variety and wonder.

Epic Family Adventure in the National Parks: Lassen Volcanic, Redwood & Crater Lake
This summer, my family embarked on a road trip through Northern California and Oregon to explore three of the West Coast’s most stunning national parks. Each stop brought something completely new—steaming geothermal features, ancient redwoods towering overhead, and the sapphire-blue depths of Crater Lake. Traveling with kids, we found the balance of shorter hikes, scenic drives, and playful downtime made the adventure not only doable but truly unforgettable. Whether you’re traveling with kids or just looking for a mix of outdoor beauty and family-friendly activities, this route is packed with variety and wonder.

Epic Family Adventure in the National Parks: Zion, Bryce Canyon, and Arches 9-Day Itinerary
This Utah road trip was my family’s introduction to the US National Parks out west. Once we experienced just how varied and amazing our landscape is in the United States, we were hooked and have now been to seven more parks! However, few places offer the wild magic and cinematic landscapes of Utah’s “Mighty Five”. For families looking to strike the perfect balance between adventure and ease, this thoughtfully paced 9-day itinerary stitches together the best of Utah’s treasures—from the red rock cathedrals of Zion to the whimsical hoodoos of Bryce Canyon and the gravity-defying arches of Moab, all capped with culture and comfort in Salt Lake City. Here’s how to turn Utah’s untamed beauty into the family road trip of a lifetime.

Epic Family Adventure in the National Parks: Zion, Bryce Canyon, and Arches 9-Day Itinerary
This Utah road trip was my family’s introduction to the US National Parks out west. Once we experienced just how varied and amazing our landscape is in the United States, we were hooked and have now been to seven more parks! However, few places offer the wild magic and cinematic landscapes of Utah’s “Mighty Five”. For families looking to strike the perfect balance between adventure and ease, this thoughtfully paced 9-day itinerary stitches together the best of Utah’s treasures—from the red rock cathedrals of Zion to the whimsical hoodoos of Bryce Canyon and the gravity-defying arches of Moab, all capped with culture and comfort in Salt Lake City. Here’s how to turn Utah’s untamed beauty into the family road trip of a lifetime.

Epic Family Adventure in the National Parks: Yellowstone & Grand Teton Eight-Day Itinerary
When I think of the trip that had my family feeling the most in tune with rugged, untouched nature and exciting wildlife encounters, there is only one place that comes to mind: the greater Yellowstone ecosystem. From steaming geysers and vast glacial lakes to wildlife encounters and starlit serenity, this eight-day journey through Bozeman, Yellowstone, and the Tetons is the ultimate family escape—crafted for curious young minds and parents who crave both discovery and downtime. If you want the perfect blend of gorgeous vistas, plentiful wildlife, geothermal activity, and exciting hikes, then look no further than Yellowstone and Grand Teton National Parks.

Epic Family Adventure in the National Parks: Yellowstone & Grand Teton Eight-Day Itinerary
When I think of the trip that had my family feeling the most in tune with rugged, untouched nature and exciting wildlife encounters, there is only one place that comes to mind: the greater Yellowstone ecosystem. From steaming geysers and vast glacial lakes to wildlife encounters and starlit serenity, this eight-day journey through Bozeman, Yellowstone, and the Tetons is the ultimate family escape—crafted for curious young minds and parents who crave both discovery and downtime. If you want the perfect blend of gorgeous vistas, plentiful wildlife, geothermal activity, and exciting hikes, then look no further than Yellowstone and Grand Teton National Parks.

Get off the Beaten Path With Your Family: Zagreb, Ljubljana, and Venice
If you’re looking for family-friendly destinations without all the crowds that normally plague European capital cities, then look no further than Zagreb and Ljubljana. Don’t get me wrong, there’s a reason London, Paris, and Rome are perennial favorites for travelers around the world. However, my husband and I were searching for somewhere more under the radar, and Zagreb and Ljubljana delivered. We had such a pleasant experience while traveling throughout Croatia, Slovenia, and Italy with our then two- and four-year-old boys. I encourage you to think outside the box and consider Zagreb and Ljubljana for your next family trip!

Get off the Beaten Path With Your Family: Zagreb, Ljubljana, and Venice
If you’re looking for family-friendly destinations without all the crowds that normally plague European capital cities, then look no further than Zagreb and Ljubljana. Don’t get me wrong, there’s a reason London, Paris, and Rome are perennial favorites for travelers around the world. However, my husband and I were searching for somewhere more under the radar, and Zagreb and Ljubljana delivered. We had such a pleasant experience while traveling throughout Croatia, Slovenia, and Italy with our then two- and four-year-old boys. I encourage you to think outside the box and consider Zagreb and Ljubljana for your next family trip!

Poland’s Christmas Markets: A Festive Family Trip Through 4 Cities
After years of talking about visiting the Christmas markets in Europe, my family finally decided to make this trip a reality. We were a large family group of 15 people spanning the ages of six months all the way to 60 years, so we needed to prioritize budget and ease of travel. While we researched all the popular and more well-known markets in Germany, France, and beyond, we were on the hunt for a more budget-friendly and under-the-radar destination. We kept coming back to Poland and finally decided it was the perfect place for us. We had an amazing time exploring this often-overlooked country and we can’t wait to head back in other seasons to explore all that Poland has to offer.

Poland’s Christmas Markets: A Festive Family Trip Through 4 Cities
After years of talking about visiting the Christmas markets in Europe, my family finally decided to make this trip a reality. We were a large family group of 15 people spanning the ages of six months all the way to 60 years, so we needed to prioritize budget and ease of travel. While we researched all the popular and more well-known markets in Germany, France, and beyond, we were on the hunt for a more budget-friendly and under-the-radar destination. We kept coming back to Poland and finally decided it was the perfect place for us. We had an amazing time exploring this often-overlooked country and we can’t wait to head back in other seasons to explore all that Poland has to offer.

Family Cruise on the Royal Caribbean Freedom of the Seas: 8 Days of Sun and Fun
When I was planning a beach trip for my large family group of 15 people, it was proving hard to please everyone — that’s where a cruise comes in! Cruising to sunny islands on the Freedom of the Seas means a ship full of endless activities with a bunch of different ports thrown in. This is the perfect solution when you have a large group of people traveling together. We didn’t have to worry about anyone being bored or not being able to find some way to entertain themselves. So if you have been thinking about a cruise for your family, read on and see how it can be the perfect solution for you too!

Family Cruise on the Royal Caribbean Freedom of the Seas: 8 Days of Sun and Fun
When I was planning a beach trip for my large family group of 15 people, it was proving hard to please everyone — that’s where a cruise comes in! Cruising to sunny islands on the Freedom of the Seas means a ship full of endless activities with a bunch of different ports thrown in. This is the perfect solution when you have a large group of people traveling together. We didn’t have to worry about anyone being bored or not being able to find some way to entertain themselves. So if you have been thinking about a cruise for your family, read on and see how it can be the perfect solution for you too!

The Perfect Family-Friendly Colorado Road Trip Itinerary: Rocky Mountain National Park and Beyond
Colorado is a beautiful state that offers something for everyone in the family during all four seasons. My family loved our summer road trip through four different cities and I highly recommend adding Rocky Mountain National Park to your list of “must-see” places in the US. If you love outdoor activities, hiking, horseback riding, white-water rafting and adventure, this is the perfect itinerary for you!

The Perfect Family-Friendly Colorado Road Trip Itinerary: Rocky Mountain National Park and Beyond
Colorado is a beautiful state that offers something for everyone in the family during all four seasons. My family loved our summer road trip through four different cities and I highly recommend adding Rocky Mountain National Park to your list of “must-see” places in the US. If you love outdoor activities, hiking, horseback riding, white-water rafting and adventure, this is the perfect itinerary for you!

Breckenridge Beyond Skiing: 6 Family-Friendly Winter Activities for Non-Skiers
An idyllic town nestled almost 9,600 feet high in the Rocky Mountains, Breckenridge boasts a long list of outdoor activities for every season. My family fell in love with Breck during our summer road trip through the Rockies but weren’t sure we’d ever go back in the winter since none of us ski. When presented with the opportunity to stay with some friends in Breckenridge over the winter break, we jumped at the chance to see what one of our favorite mountain towns could offer us as non-skiers. Spoiler alert: we were not disappointed!

Breckenridge Beyond Skiing: 6 Family-Friendly Winter Activities for Non-Skiers
An idyllic town nestled almost 9,600 feet high in the Rocky Mountains, Breckenridge boasts a long list of outdoor activities for every season. My family fell in love with Breck during our summer road trip through the Rockies but weren’t sure we’d ever go back in the winter since none of us ski. When presented with the opportunity to stay with some friends in Breckenridge over the winter break, we jumped at the chance to see what one of our favorite mountain towns could offer us as non-skiers. Spoiler alert: we were not disappointed!

Amsterdam, Bruges and Brussels: A Family-Friendly 8 Day Itinerary Your Kids Will Love
A family trip to the Netherlands and Belgium will exceed all your expectations. From the array of colorful tulips to the multitude of museums to a chocolate-making class — there is something for everyone. You will be impressed by the rich cultural offerings, walkability of the cities and the diverse food offerings available throughout both countries. The activities we found to entertain our two young boys are experiences they still talk about today! Whether you're traveling with children like we were or as a solo, couple or group travelers, this eight-day itinerary is fully customizable to your unique tastes and needs.

Amsterdam, Bruges and Brussels: A Family-Friendly 8 Day Itinerary Your Kids Will Love
A family trip to the Netherlands and Belgium will exceed all your expectations. From the array of colorful tulips to the multitude of museums to a chocolate-making class — there is something for everyone. You will be impressed by the rich cultural offerings, walkability of the cities and the diverse food offerings available throughout both countries. The activities we found to entertain our two young boys are experiences they still talk about today! Whether you're traveling with children like we were or as a solo, couple or group travelers, this eight-day itinerary is fully customizable to your unique tastes and needs.

Epic Family Adventure in the National Parks: Cuyahoga in Fall
Cuyahoga Valley National Park was the fifth national park my family visited, and it turned out to be the perfect fall weekend escape. With its mix of boardwalks, waterfalls, wildlife, and easy trails, this park is incredibly accessible for families with young children. Whether you’re local to the Midwest or flying into Cleveland for a quick getaway, CVNP offers just the right amount of adventure without overwhelming little legs. In this guide, I’m sharing a full weekend itinerary that mirrors how we structured our own trip in October. It’s paced intentionally for families with slow mornings, realistic driving times, plenty of sensory-friendly nature experiences, and enough “wow” moments to get everyone excited for your next national park adventure.

Epic Family Adventure in the National Parks: Cuyahoga in Fall
Cuyahoga Valley National Park was the fifth national park my family visited, and it turned out to be the perfect fall weekend escape. With its mix of boardwalks, waterfalls, wildlife, and easy trails, this park is incredibly accessible for families with young children. Whether you’re local to the Midwest or flying into Cleveland for a quick getaway, CVNP offers just the right amount of adventure without overwhelming little legs. In this guide, I’m sharing a full weekend itinerary that mirrors how we structured our own trip in October. It’s paced intentionally for families with slow mornings, realistic driving times, plenty of sensory-friendly nature experiences, and enough “wow” moments to get everyone excited for your next national park adventure.

Hyatt Regency Lake Tahoe Site Visit: Perfect for Families, Outdoor Fun & Multi-Gen Getaways
Located on the shores of North Lake Tahoe in Incline Village, the Hyatt Regency Lake Tahoe Resort, Spa and Casino combines rustic alpine charm with modern resort amenities. It’s one of the area’s most well-known properties and although it is undergoing an extensive renovation to its beach area, I would not hesitate to recommend a visit to this property. My family spent a week at this property over the summer and we are already planning our trip back! For families planning a Lake Tahoe getaway, it’s worth understanding what’s available now and what exciting changes are on the horizon.

Hyatt Regency Lake Tahoe Site Visit: Perfect for Families, Outdoor Fun & Multi-Gen Getaways
Located on the shores of North Lake Tahoe in Incline Village, the Hyatt Regency Lake Tahoe Resort, Spa and Casino combines rustic alpine charm with modern resort amenities. It’s one of the area’s most well-known properties and although it is undergoing an extensive renovation to its beach area, I would not hesitate to recommend a visit to this property. My family spent a week at this property over the summer and we are already planning our trip back! For families planning a Lake Tahoe getaway, it’s worth understanding what’s available now and what exciting changes are on the horizon.

Big Apple, Big League: A 10th Birthday with Yankees & NYC Adventures
In my family, we started the tradition of celebrating our boys’ 10th birthdays with a special trip—just for them. For my oldest son, there was no question where he wanted to go: New York City, with a Yankees game at the heart of the adventure. It was his very first visit to NYC, so we set out to do all the quintessential “first-time” experiences, from the Empire State Building to strolling Central Park. What made it even more memorable was pairing the game with a Yankees Stadium tour, giving him a whole day of baseball magic before cheering on his team. Between iconic sights, unforgettable birthday moments, and a few sweet treats, this trip was the perfect blend of a milestone celebration and a classic New York adventure.

Big Apple, Big League: A 10th Birthday with Yankees & NYC Adventures
In my family, we started the tradition of celebrating our boys’ 10th birthdays with a special trip—just for them. For my oldest son, there was no question where he wanted to go: New York City, with a Yankees game at the heart of the adventure. It was his very first visit to NYC, so we set out to do all the quintessential “first-time” experiences, from the Empire State Building to strolling Central Park. What made it even more memorable was pairing the game with a Yankees Stadium tour, giving him a whole day of baseball magic before cheering on his team. Between iconic sights, unforgettable birthday moments, and a few sweet treats, this trip was the perfect blend of a milestone celebration and a classic New York adventure.
My travel photos




