26 Comments

Thank you Hillary! This was inspiring and you ask the best questions a la Second Life. Endless respect for your interview skills and curated guest list. Brava!

Expand full comment

❤️❤️❤️❤️❤️

Expand full comment

Just want to share that I’m currently packing for my summer holiday, and what did I do to prepare?? I went through your articles for tips on travel and what you’ve packed. Your articles are my bible. Thank you!! ❤️

Expand full comment

I love this!!!!

Expand full comment

Thank you - what a wonderful interview! Any thoughts on Caribbean islands/hotels to check out?

Expand full comment

Yes please! Or winter break trips with tweens who mostly still want water parks but parents who want something a bit more upscale.

Expand full comment

Hi Amy! Warm weather or cold? Domestic or international?

Expand full comment

March timeframe (limited by school break schedule) coming from the nyc area airports. Ideally no longer than 5hr flights. My kiddo haaaaates bugs so Costa Rica is likely out. Already done Bahamas, T&C and Jamaica. Prefer to avoid Mexico. Thank you!!

Expand full comment

While not my personal favorite Aruba has very few, if any, bugs and there's heaps to do for families! Florida is always a great option for families from a resort perspective and easily accessible from NY.

Expand full comment

Hello! Yes! I love Jamaica. Goldeneye for the vibes and the Cliff Hotel for younger families. The staff here are great with kids. I’m also personally fond of St Lucia and Sugar Beach on the fancier end of things.

I haven’t been myself but Cobbler’s Cove (Barbados) looks super cute and is repped by a friend I trust, so I’m sure it’s great.

Expand full comment

This was a goldmine of info! Thank you!

Expand full comment

Loved this read!

Expand full comment

This was amazing! Thank you!

Expand full comment

The way I yelped when I saw the st Regis Venice show up! We are staying there for a night en route to Slovenia this August. I was excited already excited but this has raised the level. We did Portugal last year and I couldn’t agree more on the affordability and how utterly delightful it is. I’m itching to get back to the Douro Valley and Balearic Islands but just keep running out of time (my employer does require me to do some work and not just take PTO endlessly 😂)

Echoing that this should be a quarterly convo! Also - which of all the European holiday markets is your favorite?

Expand full comment

I am SO excited to read this! If you want to send me an email via my IG account I can put in a good word for you.

For holiday markets Prague is pretty epic.

Expand full comment

LOVED this article and topic, my favorite one yet! So much great Summer travel intel and ideas for future travel. Can we have more columns featuring Rebecca?!

Expand full comment

I love this! I feel like it would be fun to do a winter holidays version and/or spring version too!

Expand full comment

Thank you!

Expand full comment

Am just today returning home from a 3 (not nearly long enough!) night stay at Stanly Ranch in Napa and cannot give it any less than a glowing review! It's stunning, secluded, private, service is fantastic and yet it is casual and carefree. Food at its restaurant (The Bear) was so amazing we ate there two nights out of three! I'm flying home feeling indulged and very relaxed!

Expand full comment

I'm so glad to read this!

Expand full comment

Your travel insights are absolutely invaluable! I'm so inspired by your recommendations for off-the-beaten-path destinations like Liguria and the lesser-known Cycladic Islands. Your tips on avoiding US connecting flights and the emphasis on booking ahead for popular spots are spot on. I'm definitely adding those hidden gems and boutique hotels to my travel list. Thank you for sharing your expertise and making travel planning feel exciting and accessible, even last-minute!

Expand full comment

Thank you for your kind comments! Happy traveling!

Expand full comment

Absolutely loved this one! Look forward to your messages, always. Thank you!

Expand full comment

Loved this but wish I could afford $1.5k per night 💔😭

Expand full comment

Hi Emily! I always try to share options for most budgets. Take a look at Genova/Liguria, Morocco or traveling in low season. I also mentioned the best lowest cost Four Seasons in America. The best (read: lowest) rates are usually found last minute and/or low season. Hope that helps!

Expand full comment

Thank you! Will check it out

Expand full comment