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Up Up And Away ✈️ My favorites from around the world
29
items My husband and I go to a new place every wedding anniversary. This list showcases some of our favorite travel spots we've discovered over the years.
Map
Sections
12
Travel Essentials
Boston & Martha's Vineyard
Hilton Head, SC
Shelter Island, NY
Maine
Hawaii
Travel Essentials
No matter where we go these are the things I'm always taking with me.
I love these bags! We have one for every family member (so 5 total!) They are all a different color so everyone can easily know which is theirs. They are the perfect size for a weekend trip or 4-5 day trip. Really amazing brand and great quality prod... Bonus is you are shopping small!
Walker Family Goods | Inspiring Families to Travel Simple
A good book is always a must when traveling. I tend to love self-improvement and small business books but truly whatever floats your boat.
The Power of Moments: Why Certain Experiences
A good (and comfortable) set of headphones. Just basic traveling 101 really.
Headphones & Speakers - All Accessories - Apple
Boston & Martha's Vineyard
This was our 13th anniversary trip and we visited in 2023
This was an upgrade for us, we don't usually stay in this high-end of a hotel but it was really nice and I love the slippers and turn down service they provide every night. The room was very clean and beautifully designed.
The Langham, Boston
We grabbed coffee here multiple times and a few bakery items too! I can't believe this place is a chain. It feels so highend and small business like. The service was great, the breakfast was on point and the decor was amazing. Oh and great coffee!
Tatte Bakery and Cafe
Worth the hype 100%. The pizza was good, like really good.
Regina Pizzeria
Hilton Head, SC
This was our 12th anniversary trip and we visited in 2022
We did not stay here ($$$$$) but you can take a day trip, walk the grounds, eat at the restaurants and shop. It's absolutely drop dead gorgeous and a great place to dream ✨💭💕
Montage Palmetto Bluff
This was the first place we stopped in Hilton Head and boy did we get lucky. This was a great spot to eat for breakfast, lunch or dinner. Really great food and a cute atmosphere.
Nectar Farm Kitchen
Not in Hilton Head (sorry) but we flew out of Savannah so this was a pit-stop before the airport. Oh man did this hit the spot. So incredibly good I might even just fly to Savannah just to go here again.
Flying Monk Noodle Bar
Shelter Island, NY
This was our 7th wedding anniversary and we visited in 2017
Our hotel on Shelter Island. Cute but small rooms. Clean which is important.
The Chequit
Perfect breakfast spot and really good!
Estia's Little Kitchen
Maine
This was our 11th anniversary trip and we visited in 2021
Beautiful and clean hotel in downtown Portland. Beautiful space and great breakfast and coffee in the morning.
The Press Hotel, Autograph Collection
I discovered this in Portland and wow oh wow it was good. My personal favorite is the Vanilla
Cocojune
A classic place to stop while downtown. The line gets long so go EARLY!
The Holy Donut | Gourmet Potato Donuts | Portland, Maine
Our B&B in Camden, MA. Lovely owners and cute place.
Captain Swift Inn
Hawaii
This was our 5th anniversary and by far our favorite trip to date. We visited in 2015
This is a great introductory to the islands and the culture, specifically if it's your first time visiting Hawaii. It's fun, interactive and really informative. It's great for all ages, particularly families.
Polynesian Cultural Center
The name says it all. I don't think I've seen a better sunset anywhere in my life than here.
Sunset Beach Park
If this place is still open, go. It's a great find, local and easy breezy.
MACKY'S SWEET SHRIMP TRUCK - CLOSED - Yelp
Charleston, SC
This was our 6th wedding anniversary and we visited in 2016
Iconic and must if you are in the area and can snag a reservation. No questions about it, just go!
Husk
The first time I ever had Jeni's Ice cream was in Charleston and it was so good that we later sent Christmas presents to everyone that year with Jeni's shipped directly to them. Highly recommend!
Jeni's Splendid Ice Creams
Again it's iconic and if you are in the area you should see it.
Angel Oak Tree
Middleburg, VA
During the height of the pandemic in 2020 we hit our 10th wedding anniversary. We kept our travels close to home and landed an hour and half out from where we live in the beautiful horse country of Virginia.
This is where we stayed and it was very charming. All the rooms are different so pictures can't really show you what it was like. Very romantic though.
The Red Fox Inn & Tavern
Favorite store in Middleburg. Perfect home furnishings and gifts for everyone you know
Creme de la Creme
gorgeous beyond gorgeous and truly a treat to visit (even if it was just for dinner)
Salamander Middleburg Resort & Spa
Denver & Vail, CO
This was our 8th wedding anniversary and we visited in 2018
This was our Denver hotel downtown. It was clean, hip and a very comfortable stay
Kimpton Hotel Born
What a beautiful reward after a great intermediate hike. This place was beautiful and so worth the early rise. You have to go at the crack of dawn otherwise you may not get a parking spot where you start the hike. Highly recommend, it is totally worth it!
Hanging Lake
Key West, FL
This was our 9th anniversary trip and we visited in 2019
Key West was our least favorite anniversary trip. The drinking town scene just isn't for us. But this is where we stayed and it was lovely.
The Perry Hotel & Marina Key West
California - Highway 1
This was our 4th wedding anniversary and we visited in 2014
A beautiful small town that you can drive through if you are making the Highway 1 drive. Close to Pebble Beach and lots of fun shops
Carmel-by-the-Sea
Camping
We try and go camping at least once a year as a family. Our kids look forward to it and I think its a great teaching opportunity for them. A good camping trip can really humble you. We don't really rough it but we also don't go glamping. A happy bala...
Perfect to hang at the top of the tent and it has different brightness levels which is nice.
FLY2SKY Portable LED Tent Light 4 Pack