Michelle Cassidy

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.

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.

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 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.

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.

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!

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.

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.