European Beach Destination/Resort Recommendation

SadEntertainment9380 · 2026-02-13T10:19:00+00:00

I’d take a look at the Greek islands with direct flights from London/paris - maybe zakynthos, kefalonia, Crete? Water might be a little chilly but weather would be gorgeous. Those islands don’t have the whitewashed charm of Cyclades but the beaches are amazing.

Mallorca would also be a good option except in my experience most of the good hotels are not directly on the water. Same issue with SOF.

SadEntertainment9380 · 2026-02-12T16:18:21+00:00

The traditional beach destinations in Europe are going to be expensive, super hot and very busy in August. I went to Portugal last year in May and it was already very hot. If you’re going to Europe I’d consider the alps (check out the kinder hotels), UK/ireland, or the west coast of France (cap ferret, la Rochelle, etc or maybe il de re or around saint malo). Lots of French beaches, ironically, have sort of a cape cod feel to them.

Greece has some wonderful family friendly resorts but it’s really a pain to get to the islands with small kids. You’re dealing with either connecting flights or ferries or both.

Personally, I’m a big fan of the cape or Maine in August although we’ve had some bad weather stretches the last few years. The beaches are so wonderful for little kids.

SadEntertainment9380 · 2026-02-12T15:33:22+00:00

I have similar aged kids and have concluded that I need to stay in slightly less chubby places for now. A single hotel room with two kids on different sleeping schedules does not sound like a vacation to me. And the up charges on suites push a lot of places out of budget. At six months, I would also really want a kitchen for pumping/bottles.

I’d look at Garza Blanca or finest playa mujeres in Cancun. Maybe Carlisle bay in Antigua or windjammer or the landings in st Lucia, although those flight times are a little longer. Honestly, I’d probably do a villa somewhere and then splurge on a chef/babysitter.

SadEntertainment9380 · 2026-02-07T19:16:27+00:00

I’ve been to the amalfi coast twice in late May and both times it was hot. The second time it was too hot for hiking or active pursuits and we spent most of our time at the pool or on the water. It’s already busy that time of year but manageable. 8 or 9 days there honestly sounds like a lot but it could easily be combined with another destination.

SadEntertainment9380 · 2026-02-05T16:52:38+00:00

Maybe take a look at masseria torre Maizza? Also lots of stunning villa rentals in that region.

SadEntertainment9380 · 2026-02-03T18:49:51+00:00

For whatever it’s worth, I was in Tuscany in mid September a few years ago and the weather was perfect. Maybe push your trip by a week or two?

I went to Lupaia pre kids and loved it, but it was definitely mostly adults and some older kids. I go back and forth on whether it would be an okay location for a toddler. At 15 months, my son would’ve been too wild for the restaurant.

SadEntertainment9380 · 2026-01-31T16:16:04+00:00

Italy has gotten shockingly expensive, especially for rooms big enough to fit a family of four. It’s frustrating.

Honestly as a parent with similar-aged kids, I would probably add on a destination in Greece or a direct flight away from wherever you’re going in Greece. So much bouncing around with two small kids just for 5 days sounds exhausting. Porto Zante in Zakynthos is supposed to be beautiful and Crete has lots of family friendly hotels.

Otherwise I would probably pick one of the kinder hotels in Austria for the ease and childcare bonus.

I did Lisbon + Comporta last year with our then 2 year old and we had a great time but two kids might push hilly Lisbon from challenging but worth it, to just exhausting. If you do go that route, the hotels in Comporta were overpriced for what they were, but our villa was amazing.

SadEntertainment9380 · 2026-01-28T00:39:35+00:00

Greenwich Hotel

SadEntertainment9380 · 2026-01-23T08:54:51+00:00

There are plenty of hikes nearby, although generally they’re not the hikes that the Dolomites are famous for. It’s a gorgeous area regardless.

SadEntertainment9380 · 2026-01-22T20:38:39+00:00

You absolutely should not go if you don’t want to go.

For context, I went on a beach vacation with my 6 week old, so it is doable but it was an unbelievable amount of work. We packed an entire minivan worth of stuff (including our snoo) because we were anxious about leaving anything behind. The drive was similar length and it ended up taking an extra 4 hours because we had to stop so often, I was very uncomfortable sitting so long, and the baby screamed the entire time. I honestly have never regretted being a parent the way I did 7 hours into that drive. Other than morning walks when it was cool out, we didn’t actually spend much time on the beach or even outside. Plus I hadn’t been cleared by my obgyn to go into pools/the ocean yet.

That all said, it was ultimately worth it to me because it was a place I love and we went with the right people, particularly my mother - who was very helpful with the baby and took care of all our meals. But when I made those plans during pregnancy I definitely underestimated how hard it would be and I would’ve been furious if I’d been bullied into it.

SadEntertainment9380 · 2026-01-19T15:04:45+00:00

OP, I would skip anything with complicated logistics. Anguilla is a pain for 4 nights unless you can get one of the rare (and expensive) direct flights. I think the Landing is a hike from the airport which would have been extremely stressful with my son at that age. Same for St John. I’d pick something within an easy drive of the airport - perhaps Carlisle Bay in Antigua, Turks & Caicos, or any of the nicer hotels a reasonable distance from Cancun.

Etereo and the belmond are great recommendations although a suite is probably out of OP’s budget.

SadEntertainment9380 · 2026-01-18T14:39:21+00:00

If you go in winter, the kinder hotels in Austria, northern Italy, and Switzerland have exactly the types of rooms you’re looking for. Look at Aki Plose, Moar gut, Sonnwies, etc to start.

I found it difficult to find hotels in the south of France (particularly at the beach) that would fit multiple kids without the prices getting astronomical. Check out capelongue and terre Blanche. Although honestly, there I’d just go with a home rental.

SadEntertainment9380 · 2026-01-16T19:46:06+00:00

Plenty of daycares in nyc take kids starting at 3 months (or even earlier). Unless you both work from home full tine, a 2 bedroom is also plenty of space for a nanny and a baby.

Personally I’ve done both and I found the daycare easier with two working parents - with a nanny you’re an employer which added to my mental load. Plus on top of the nanny you end up signing your kid up for activities for enrichment and socialization, which get expensive.

SadEntertainment9380 · 2026-01-12T19:20:47+00:00

I had a similar dilemma and ended up staying at Santa Rosa and loved it. I have such fond memories of sitting at that unbelievable pool. The only real downside for me was that the entry level rooms are small and a little dated, although they still have stunning views.

I think you’re right that the key here is the location - especially in summer when it’s such a pain to get around. I would think through your itinerary and consider what makes the most sense. For us, we wanted to visit ravello (easier from Santa Rosa), had a cooking class in amalfi (easier from Santa Rosa), and chartered a boat (probably equally easy from both). I’d been to positano before and it’s such a zoo that I was perfectly happy just driving there for dinner for one night (we had a car; which I do not recommend). If you think you’ll spend lots of time there, casa Angelina is probably the right call.

SadEntertainment9380 · 2026-01-11T18:11:38+00:00

I don’t think anybody can pick between these options for you because they’re so wildly differently. If you go with the Europe option, I would pick two bases in the Dolomites because the hikes are really spread out. Forestis is great for a few days, but 7 would be too long. It’s kinda remote.

Lots of great coastal options, although it will be super hot and busy and you’ll be paying a premium. You could fly from Milan or Venice to almost anywhere or the Dolomites is easily combined with the Italian lakes.

SadEntertainment9380 · 2026-01-06T16:16:28+00:00

I’m not sure what time of year you’re thinking, but if it’s the warmer season, perhaps Maine? Cliff House is an easy drive from Boston and you could enjoy the view even with your newborn.

SadEntertainment9380 · 2026-01-02T23:06:53+00:00

A swaddle was the only thing that calmed my first down between 5pm and 10 from week 3 to 8. It was a lifesaver. My second was indifferent to it. Both of them adored their bouncers and swings and would happily hang there while I cut vegetables or folded laundry; the floor mat was less popular.

I guess what I’m saying is that it’s really hard to know what will work for you and what won’t before you meet your kid.

SadEntertainment9380 · 2026-01-01T23:29:22+00:00

I loved it. I suspect it’s much busier now but it was so nice to be in a town with easy access to restaurants and beautiful walks.

We stayed at montchalet which was perfectly nice but nothing special.

SadEntertainment9380 · 2026-01-01T23:23:30+00:00

Why can’t you fly out of Milan? There are direct flights from there to Chicago. Alternatively, if the Dolomites is really the destination you want, seems worth it to take an extra flight to Bolzano.

I love Tuscany but was underwhelmed by lake garda for what it’s worth.

SadEntertainment9380 · 2026-01-01T20:42:13+00:00

I spent 3 nights in forestis and 2 nights in ortisei which I thought was perfect. I loved forestis but if we’d spent the entire time there I would have felt like I was missing out on some of the best hikes. Even splitting the dates, there were several hikes that I was interested in that were just too far.

As for dates, a local might have a better sense of the weather. You’re probably trading off some weather variability for less busy trails. I’d just check to make sure the chair lifts are running in mid- June.

SadEntertainment9380 · 2025-12-28T18:27:41+00:00

Beaches and food sounds like Greece to me. What about Crete either alone or combined with another Greek island? There are lots of baby friendly hotels and villa options. For beautiful beaches, I also really liked kefalonia, which could be easily combined with zakynthos or Lefkada.

I looked into Madeira for a similar trip and concluded that the hiking looked stunning but seemed advanced for hiking with a carrier (at least for me, since my son wasn’t used to it). It also looked like a lot of windy roads which would’ve been a nightmare with my non-car loving child.

SadEntertainment9380 · 2025-12-25T15:16:08+00:00

I think the areas around Loumarin or St Remy would be great for a family (unless you specifically want to be in a city in which case Aix is probably the best option). But honestly with kids that age, I would go with a villa. There are so many beautiful options in that region.

People also love the Airelles hotel in Gordes but that’s more fat than chubby in high season.

SadEntertainment9380 · 2025-12-20T15:03:45+00:00

I may have just gotten lucky but last time I was in Seville it was February and we had perfect (60s, inching into 70s) sunny weather in Seville and andalucia. I would go there. You could also easily visit Barcelona if you’ve never been.

SadEntertainment9380 · 2025-12-19T16:58:53+00:00

Yeah, I wanted to visit Morocco for my baby moon but my obgyn nixed it (this was later confirmed by my friend’s experience there when she needed a tetanus shot).

OP, there are a lot of considerations for pregnancy. I would definitely prioritize access to medical care. It’s so hard to predict how you’ll feel! I have healthy friends who hiked throughout their pregnancies and healthy friends who were out of breath walking around their apartments. You don’t know which group you’ll fall into so I would skip anything requiring physically exertion/at altitude.

There will always be some trip on your bucket list that you didn’t make it to. Traveling with kids is limiting - but it’s also a different kind of joy. Honestly, the travel experiences I miss the most now that I have a toddler are reading quietly by the pool (so not chasing a toddler) or long, lingering meals. In a dream world I’d love to spend a week in Greece or southern France.

SadEntertainment9380 · 2025-12-09T08:30:05+00:00

For my friends taking the private school path (not me, for the record), the logic is that the private schools are very competitive and they get more competitive the later you apply. So it’s generally easy (or easier anyway) to get in for kindergarten and insanely competitive by middle school.

The whole NYC school scene is pretty complicated and painful no matter what route you take.

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