Michelle Cassidy
She/Her
Based in Philadelphia, PA
Michelle Cassidy
Ask me about
My Story
I love designing travel experiences that feel both effortless and unforgettable. From milestone celebrations to multi-city adventures, or securing exclusive perks at partner hotels, my goal is to make every journey seamless and joyful. Clients value my communication, attention to detail, and ability to anticipate what will make each trip truly special.
Travel Style
My travel style varies because I want to see everything the world has to offer. From relaxing poolside in St. Barths with my husband to glamping under the stars in the Sahara Desert with friends, I'm here for all of it!
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Reviews (82)
Sharon D.
24 days ago
Michelle is a real pleasure to work with, very professional.
Stephanie T.
a month ago
Michelle is incredible and has changed my whole approach to travel. She is incredibly thoughtful and brilliant. She has planned 3 trips for us including one international trip where we had no basis of knowledge for the trip. We meet and I give her some highlights of the desires and goals for my trip and she consistently hits it out of the park in terms of exceeding my expectations. My only concern is that I will never be able to book a trip without her because she has set our trip planning standard so high! I am very particular about my trips and she somehow impresses me more every time. Additionally, she is highly responsive and willing to go above and beyond in terms of last minute changes, requests, and reaching out directly to hotel contacts to ensure our trips are phenomenal. I recommend her to all of my friends and cannot wait to book my next trip with her!
Sara S.
a month ago
If you are even thinking about booking a trip and not using Michelle as your travel advisor, please pause and reconsider, because she is truly in a league of her own.
From the very beginning, Michelle was incredibly communicative. I never once felt unsure, forgotten, or left waiting. Every question I had was answered quickly and clearly, and she stayed so on top of every detail that I felt completely held the entire time. She didn’t just book a trip, she supported the whole experience. Even helping us with additional taxi transportation, she went above and beyond to make sure everything was seamless and stress free.
What really sets Michelle apart is how deeply she listens. She took the time to understand what kind of holiday we actually wanted, not just dates and a destination, but the feeling we were looking for. Because of that, she picked the perfect resort for us. It felt so aligned, so thoughtful, and so intentional, like the trip was curated specifically for us rather than pulled from a generic list.
Throughout the trip, Michelle checked in on me in a way that felt genuinely caring. Not in a salesy or transactional way, but in a “I truly want you to have the best time” way. She made me feel supported and honestly loved, which is something you do not often experience when working with someone in the travel space.
On top of all of that, she got us an incredible deal with amazing perks, which somehow felt like the cherry on top of an already perfect experience. Luxury, ease, care, and value all wrapped into one.
Michelle is the kind of travel advisor you keep for life. Once you work with her, you will never want to plan a trip without her again. She is thoughtful, intuitive, detail oriented, and truly exceptional at what she does. I cannot recommend her highly enough!
Jen G.
2 months ago
Michelle picked this hotel for our girls night out and it did not disappoint! Free breakfast, upgraded rooms, and such an easy booking process!
Billy R.
2 months ago
Michelle is amazing. Attentive, and timely to help curate the perfect staycation/birthday for my wife. Can’t wait to book our next adventure
Sharon D.
24 days ago
Michelle is a real pleasure to work with, very professional.
Stephanie T.
a month ago
Michelle is incredible and has changed my whole approach to travel. She is incredibly thoughtful and brilliant. She has planned 3 trips for us including one international trip where we had no basis of knowledge for the trip. We meet and I give her some highlights of the desires and goals for my trip and she consistently hits it out of the park in terms of exceeding my expectations. My only concern is that I will never be able to book a trip without her because she has set our trip planning standard so high! I am very particular about my trips and she somehow impresses me more every time. Additionally, she is highly responsive and willing to go above and beyond in terms of last minute changes, requests, and reaching out directly to hotel contacts to ensure our trips are phenomenal. I recommend her to all of my friends and cannot wait to book my next trip with her!
Sara S.
a month ago
If you are even thinking about booking a trip and not using Michelle as your travel advisor, please pause and reconsider, because she is truly in a league of her own.
From the very beginning, Michelle was incredibly communicative. I never once felt unsure, forgotten, or left waiting. Every question I had was answered quickly and clearly, and she stayed so on top of every detail that I felt completely held the entire time. She didn’t just book a trip, she supported the whole experience. Even helping us with additional taxi transportation, she went above and beyond to make sure everything was seamless and stress free.
What really sets Michelle apart is how deeply she listens. She took the time to understand what kind of holiday we actually wanted, not just dates and a destination, but the feeling we were looking for. Because of that, she picked the perfect resort for us. It felt so aligned, so thoughtful, and so intentional, like the trip was curated specifically for us rather than pulled from a generic list.
Throughout the trip, Michelle checked in on me in a way that felt genuinely caring. Not in a salesy or transactional way, but in a “I truly want you to have the best time” way. She made me feel supported and honestly loved, which is something you do not often experience when working with someone in the travel space.
On top of all of that, she got us an incredible deal with amazing perks, which somehow felt like the cherry on top of an already perfect experience. Luxury, ease, care, and value all wrapped into one.
Michelle is the kind of travel advisor you keep for life. Once you work with her, you will never want to plan a trip without her again. She is thoughtful, intuitive, detail oriented, and truly exceptional at what she does. I cannot recommend her highly enough!
Jen G.
2 months ago
Michelle picked this hotel for our girls night out and it did not disappoint! Free breakfast, upgraded rooms, and such an easy booking process!
Travel ideas (8)
Unforgettable Moments: 10 Days in Northern Italy
My husband and I celebrated our 10th wedding anniversary with a beautiful 10-day journey through Northern Italy. From historic cities and iconic art to rolling hills, thermal baths, and some of the best food we’ve ever tasted, the trip was filled with unforgettable moments. This itinerary is ideal for anyone who wants to explore multiple regions without sacrificing time to relax, savor, and soak it all in.
Unforgettable Moments: 10 Days in Northern Italy
My husband and I celebrated our 10th wedding anniversary with a beautiful 10-day journey through Northern Italy. From historic cities and iconic art to rolling hills, thermal baths, and some of the best food we’ve ever tasted, the trip was filled with unforgettable moments. This itinerary is ideal for anyone who wants to explore multiple regions without sacrificing time to relax, savor, and soak it all in.
Where to Eat, Stay and Play in Anguilla
As someone who is absolutely obsessed with St. Barths, I’ve always wanted to experience Anguilla firsthand. The islands are often paired together for trips due to their close proximity, but they are extremely different. St. Barths is a French island and is great for people who like a balance of relaxation and high energy. There’s a social, fun vibe, ideal for couples and group trips. Anguilla, on the other hand, is a British territory that offers more of a laid-back Caribbean experience. Yes, there is still fun to be had, but the focus of Anguilla is relaxation. Think gorgeous white sand beaches as far as the eye can see, resorts that cater to every need, and a true escape from everyday life. It’s ideal for honeymoons, romantic getaways, and families. Both islands experience peak travel during the festive season, and both go quiet from mid-August through mid-October, which is hurricane season.
Where to Eat, Stay and Play in Anguilla
As someone who is absolutely obsessed with St. Barths, I’ve always wanted to experience Anguilla firsthand. The islands are often paired together for trips due to their close proximity, but they are extremely different. St. Barths is a French island and is great for people who like a balance of relaxation and high energy. There’s a social, fun vibe, ideal for couples and group trips. Anguilla, on the other hand, is a British territory that offers more of a laid-back Caribbean experience. Yes, there is still fun to be had, but the focus of Anguilla is relaxation. Think gorgeous white sand beaches as far as the eye can see, resorts that cater to every need, and a true escape from everyday life. It’s ideal for honeymoons, romantic getaways, and families. Both islands experience peak travel during the festive season, and both go quiet from mid-August through mid-October, which is hurricane season.
Where to Eat, Stay and Play in Holbox
Getting to Holbox requires a little bit of work, but this slice of paradise is well worth it. Fly to Cancun, take a two-hour shuttle to Chiquilá, then a short ferry and finally, a golf cart taxi to your final destination. You’ll be welcomed by soft sand beaches with calm, clear water. Plus excellent restaurants, shopping and star-filled skies.
Where to Eat, Stay and Play in Holbox
Getting to Holbox requires a little bit of work, but this slice of paradise is well worth it. Fly to Cancun, take a two-hour shuttle to Chiquilá, then a short ferry and finally, a golf cart taxi to your final destination. You’ll be welcomed by soft sand beaches with calm, clear water. Plus excellent restaurants, shopping and star-filled skies.
The Belle of Broad Street: Philadelphia’s Bellevue Hotel
The Bellevue Hotel is back, and it was worth the wait. Now part of The Unbound Collection by Hyatt, this glorious Philadelphia institution has been modernized while still retaining its historic charm.
The Belle of Broad Street: Philadelphia’s Bellevue Hotel
The Bellevue Hotel is back, and it was worth the wait. Now part of The Unbound Collection by Hyatt, this glorious Philadelphia institution has been modernized while still retaining its historic charm.
A Winter Week in Scandinavia
If you’ve ever dreamed of chasing the Northern Lights, spending cozy days curled up with a book while watching the snow fall and visiting gorgeous historical cities, Scandinavia is hard to beat. Starting and ending in Oslo, this weeklong itinerary hits the highlights of Scandinavia in the winter months.
A Winter Week in Scandinavia
If you’ve ever dreamed of chasing the Northern Lights, spending cozy days curled up with a book while watching the snow fall and visiting gorgeous historical cities, Scandinavia is hard to beat. Starting and ending in Oslo, this weeklong itinerary hits the highlights of Scandinavia in the winter months.
Where to Eat, Stay and Play in St. Barths
St. Barths holds a special place in my heart; it was the location of my honeymoon, a milestone birthday trip and romantic vacations with my husband. I instantly fell in love with the vibe – French and sophisticated mixed with the laid-back chill of the Caribbean. If you like bougie vacations filled with fine dining, stunning beaches and a lot of fun, St. Barths is the destination for you!
Where to Eat, Stay and Play in St. Barths
St. Barths holds a special place in my heart; it was the location of my honeymoon, a milestone birthday trip and romantic vacations with my husband. I instantly fell in love with the vibe – French and sophisticated mixed with the laid-back chill of the Caribbean. If you like bougie vacations filled with fine dining, stunning beaches and a lot of fun, St. Barths is the destination for you!
A Long Weekend in San Miguel de Allende
Located four hours north of Mexico City by bus or car, San Miguel de Allende is well worth the trip. Walk the cobblestone streets of the UNESCO World Heritage Site and discover fantastic restaurants, cafes, art galleries and shops. After witnessing a magical sunset from a rooftop bar, you’ll see why so many people have relocated to this enchanting city in central Mexico.
A Long Weekend in San Miguel de Allende
Located four hours north of Mexico City by bus or car, San Miguel de Allende is well worth the trip. Walk the cobblestone streets of the UNESCO World Heritage Site and discover fantastic restaurants, cafes, art galleries and shops. After witnessing a magical sunset from a rooftop bar, you’ll see why so many people have relocated to this enchanting city in central Mexico.
The Best Boutique Hotels in Costa Rica’s Arenal and Guanacaste Regions
Intimate, unique, and with a focus on design, boutique hotels are perfect for vacationers in search of rest and relaxation. Though they may not offer the same amenities as some of the larger brands, the attention to detail and service provide a personal touch that guests may not find at big resorts. Read on for some of my top picks for boutique hotels in Costa Rica’s Arenal and Guanacaste regions.
The Best Boutique Hotels in Costa Rica’s Arenal and Guanacaste Regions
Intimate, unique, and with a focus on design, boutique hotels are perfect for vacationers in search of rest and relaxation. Though they may not offer the same amenities as some of the larger brands, the attention to detail and service provide a personal touch that guests may not find at big resorts. Read on for some of my top picks for boutique hotels in Costa Rica’s Arenal and Guanacaste regions.
Unforgettable Moments: 10 Days in Northern Italy
My husband and I celebrated our 10th wedding anniversary with a beautiful 10-day journey through Northern Italy. From historic cities and iconic art to rolling hills, thermal baths, and some of the best food we’ve ever tasted, the trip was filled with unforgettable moments. This itinerary is ideal for anyone who wants to explore multiple regions without sacrificing time to relax, savor, and soak it all in.
Unforgettable Moments: 10 Days in Northern Italy
My husband and I celebrated our 10th wedding anniversary with a beautiful 10-day journey through Northern Italy. From historic cities and iconic art to rolling hills, thermal baths, and some of the best food we’ve ever tasted, the trip was filled with unforgettable moments. This itinerary is ideal for anyone who wants to explore multiple regions without sacrificing time to relax, savor, and soak it all in.
Where to Eat, Stay and Play in Anguilla
As someone who is absolutely obsessed with St. Barths, I’ve always wanted to experience Anguilla firsthand. The islands are often paired together for trips due to their close proximity, but they are extremely different. St. Barths is a French island and is great for people who like a balance of relaxation and high energy. There’s a social, fun vibe, ideal for couples and group trips. Anguilla, on the other hand, is a British territory that offers more of a laid-back Caribbean experience. Yes, there is still fun to be had, but the focus of Anguilla is relaxation. Think gorgeous white sand beaches as far as the eye can see, resorts that cater to every need, and a true escape from everyday life. It’s ideal for honeymoons, romantic getaways, and families. Both islands experience peak travel during the festive season, and both go quiet from mid-August through mid-October, which is hurricane season.
Where to Eat, Stay and Play in Anguilla
As someone who is absolutely obsessed with St. Barths, I’ve always wanted to experience Anguilla firsthand. The islands are often paired together for trips due to their close proximity, but they are extremely different. St. Barths is a French island and is great for people who like a balance of relaxation and high energy. There’s a social, fun vibe, ideal for couples and group trips. Anguilla, on the other hand, is a British territory that offers more of a laid-back Caribbean experience. Yes, there is still fun to be had, but the focus of Anguilla is relaxation. Think gorgeous white sand beaches as far as the eye can see, resorts that cater to every need, and a true escape from everyday life. It’s ideal for honeymoons, romantic getaways, and families. Both islands experience peak travel during the festive season, and both go quiet from mid-August through mid-October, which is hurricane season.
Where to Eat, Stay and Play in Holbox
Getting to Holbox requires a little bit of work, but this slice of paradise is well worth it. Fly to Cancun, take a two-hour shuttle to Chiquilá, then a short ferry and finally, a golf cart taxi to your final destination. You’ll be welcomed by soft sand beaches with calm, clear water. Plus excellent restaurants, shopping and star-filled skies.
Where to Eat, Stay and Play in Holbox
Getting to Holbox requires a little bit of work, but this slice of paradise is well worth it. Fly to Cancun, take a two-hour shuttle to Chiquilá, then a short ferry and finally, a golf cart taxi to your final destination. You’ll be welcomed by soft sand beaches with calm, clear water. Plus excellent restaurants, shopping and star-filled skies.
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