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Up Up And Away ✈️ My favorites from around the world

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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.
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Travel Essentials

No matter where we go these are the things I'm always taking with me.

 
Allison Powell profile picture
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
 
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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
 
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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

 
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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
 
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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

 
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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
 
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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
 
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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

 
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Our hotel on Shelter Island. Cute but small rooms. Clean which is important. 
The Chequit
 
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Perfect breakfast spot and really good! 
Estia's Little Kitchen

Maine

This was our 11th anniversary trip and we visited in 2021

 
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Beautiful and clean hotel in downtown Portland. Beautiful space and great breakfast and coffee in the morning.
The Press Hotel, Autograph Collection
 
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I discovered this in Portland and wow oh wow it was good. My personal favorite is the Vanilla
Cocojune
 
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A classic place to stop while downtown. The line gets long so go EARLY!
The Holy Donut | Gourmet Potato Donuts | Portland, Maine
 
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Our B&B in Camden, MA. Lovely owners and cute place. 
Captain Swift Inn
 
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I dream about this food all the time. I wish I could experience this Thai food again. It was heavenly. The best I've ever had.
Long Grain Restaurant | Camden, Maine

Hawaii

This was our 5th anniversary and by far our favorite trip to date. We visited in 2015

 
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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
 
Allison Powell profile picture
The name says it all.  I don't think I've seen a better sunset anywhere in my life than here.
Sunset Beach Park
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Allison Powell profile picture
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

 
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Iconic and must if you are in the area and can snag a reservation. No questions about it, just go!
Husk
 
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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
 
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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.
 
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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
 
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Favorite store in Middleburg. Perfect home furnishings and gifts for everyone you know
Creme de la Creme
 
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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

 
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This was our Denver hotel downtown. It was clean, hip and a very comfortable stay
Kimpton Hotel Born
 
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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

 
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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

 
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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... 

 
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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

The Great Smoky Mountains & Gatlinburg, TN

This was our 2024 family vacation destination and we had some highs and lows. Here's all the best I would recommend to my friends. 

 
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This is the house we stayed in and it was well worth it. More expensive than others in the area but we are particular about a clean and updated house. It had a great view and was very well stocked. It fit our family of 5 perfectly.
Alpine Abode Luxury Rentals in Gatlinburg TN
 
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1,000% worth it. This was the highlight of our trip. We did this on my husbands 40th birthday and it was amazing. We had a 6 seater with our 3 kids with us (ages 4, 7,& 9) it was so fun. Thrilling, long, beautiful views and unexpected surprises. ...
UTV Rentals - Off-Road Gatlinburg
 
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Good food, crowded but moved quickly. Burgers are their thing. Fries are good too.
Local Goat - New American Restaurant Pigeon Forge
 
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We ate here on the way out of town and wish we had come sooner. We didn't get to walk around the shops nearby and it looked really nice. Food was good and you could tell homemade. Biscuts…OMG so good!
The Old Mill Restaurant
 
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The first hike we did as a family and it was a hit. Super easy for even our 4 year old to do and the reward was exceptional…now we can say we walked behind a waterfall. 10 out of 10 would recommend.
Grotto Falls - Great Smoky Mountains National Park (U.S. National ...
 
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Another waterfall hike, this one a little further but still manageable (even with a 4 year old). Beautiful surroundings and easy trail to follow.
Laurel Falls Trail
 
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This place is off the charts. Expensive for a milkshake but its a work of art really. You only need one and can split it between a whole family. Fun for the kids for sure!
The Crazy Mason Milkshake Bar Gatlinburg
 
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This was fun and all our kids could do it. The water was low on the day we went, we all agreed it would have been a 10 out of 10 with higher water levels. We got stuck a bit over some rocks but still relaxing and a great way to change up the Smoky Mo...
Smoky Mountain River Rat Main Tubing Outpost
 
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If you have someone that doesn't like to hike this is for you. The road can get congested (one lane and one way only) but you do see some wildlife and it is very pretty.
Cades Cove Scenic Loop

NYC 🗽🏙️

For our 14th Anniversary we didn't have a ton of time to go somewhere far away. We opted for NYC which is an easy 3 hour train ride from Baltimore. Technically we've been to NYC before but not just the two of us. This trip was fun because we could go... 

 
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I went with a list of some of the best “one bite” pizza ratings. This was our first one (right in the train food hall) and it was by far our favorite. The sauce was so perfect and the crust was thin but crispy. 10/10
Sauce Pizzeria - Moynihan Food Hall
 
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Yes it's a hole in the wall and yes it fills up. Does the lady at the register sort of yell at you, maybe. But the fried pork and chive dumplings are worth it! Cheap, delicious with the chili oil and worth the trip to Chinatown.
Super Taste
 
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Home of the rainbow bagel but they have really good bagels and tons of cream cheese options. High quality. Line is out the door but moves quickly. Worth it.
Liberty Bagels Midtown
 
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We went for drinks and sat at the bar. Good options, decent happy hour with some little bite options that were pretty good. Moody bar, good people, worth the visit.
Cask Bar & Kitchen
 
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Another place on the “one bite” pizza tour. This was pretty good. I'd give it an 8.5/10. I really liked the crust. Service was great, very attentive.
Angelo's Coal Oven Pizzeria
 
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This is literally a hole in the wall. Cash only, very little that meets the eye. But good and CHEAP!  Go for the experience and a cheap good meal. It's worth it.
Fried Dumpling
 
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Great cocktails! Great service and pretty hotel bar. Got in without a reservation but does seem to get crowded.
Lobby Bar at The Hotel Chelsea
 
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Fancy breakfast/brunch. We sat outside which was nice but I really love the inside decor if you can snag a seat. It's French so service can and will be slow if you want it to be. We didn't mind. Get the chocolate chip cookie (but its not on the menu)...
La Mercerie
 
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Clean and great views. It is SO close to the Empire State Building. Some rooms have a view but if you don't you can go to the rooftop bar and see it really well. Staff was friendly and helpful. Worth the price.
Arlo NoMad
 
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We wanted to visit the Sleeping Beauty exhibit but the wait was too long. Worth the trip though and the gift shop is extensive so even if you just go there it is nice.
The Metropolitan Museum of Art
 
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Tickets are a little pricey but we enjoyed ourselves. You can definitely find deals on tickets. It's a fun interactive museum that is self paced.
Mercer Labs
 
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A fun (and FREE) evening at the Little Island. They have a paid concert in the summer but the free one is just as nice. The landscaping is exquisite and they have food and beverages on the island too for purchase. Just to go walk around is good even ...
Little Island