Experiencing The Proposal in Sitka

Posted by Maike Prewett on

Categories: Arts and Culture

When I arrived in Sitka, my friends and family all wanted to know the same thing: was it just like in The Proposal 

This 2009 romantic comedy was the main cultural reference point relating to Sitka, and everyone seemed to know it. It wasn’t until my flight home for Christmas, however, that I finally had the chance to sit down and watch The Proposal for the first time. 

While most of the movie was filmed on the East Coast, there are still many ways to experience the magic of The Proposal in Sitka(Although I can’t speak to your chances for romance.) 

1. Stay on an island

The house in The Proposal is a gorgeous cedar-shingled stone house located on an island in Sitka Sound. Although you won’t find the house in question here (it’s in Massachusetts), there are still many jaw-dropping island properties that you can stay in – or even purchase!  

Several of our luxury lodges are located on their own private islands, where you’ll receive customized service from highly trained staff. Ask about add ons like multi-day saltwater fishing packages or even a personalized float plane tour over the Tongass National Forest! You can learn more on our Lodges page. 

Looking for a home away from home? If you book a stay at Sitka Lighthouse, you’ll have both a replica lighthouse (with luxurious accommodations) and a one acre private island to yourself. It’s about a five minute boat ride from town, but still feels remote and peaceful. Climb up to the top floor to enjoy the panoramic view through 360 degree windows, or soak in the outdoor hot tub.  

Want something closer to land? Bart Island, a rental available through Sitka Travel, is connected to the mainland by a small foot bridge. The property includes access to kayaks, bikes, and a private dock; it can comfortably accommodate up to eight people. You can even hire a private chef to cook a delicious, multi-course meal for you and your group.

Located just a five minute boat ride from town, the Sitka Lighthouse was featured in Netflix’s The World’s Most Amazing Vacation Rentals

2. Watch a performance by the Naa Kahidi Dancers 

One of the movie’s more memorable scenes involves Betty White’s character, Grandma Annie, performing dances in a black and red robe in the forest behind her home.  Though you’re not likely to catch a local dancing in the woods, you can see a performance by Sitka’s Naa Kahidi Dancers, a Tlingit dance troupe that performs from May to September.

I would highly recommend viewing one of their shows to learn more about Tlingit culture and history. You will have the chance to see many generations of performers representing different Tlingit clans and houses and, at the end of every show, audience members even have the chance to join in for one final song.  


Through a guided tour with Sitka Tribal Tours, you can learn more about the living culture and history found here in Sitka.

The Naa Kahidi Dancers perform during the summer at the Sheet’ka Kwaan Tribal Community House

3. Take a picture with St. Michael’s Cathedral

Throughout the movie, you can see several shots of the iconic St. Michael’s Cathedral in the background. The original building, built in 1848, was destroyed in a 1966 fire, but the current building is a reconstruction holding many of the original Russian Orthodox artefacts.  

The cathedral has weekly services, and is also open for tours. There are some truly beautiful pieces inside, from elaborate oil paintings to gilt religious iconography. This cathedral is open on limited days and hours, so check with the Visitor Information Center for more information.

Featured in several shots in the movie, St. Michael’s Orthodox Cathedral was originally built in the 19th century

4. Experience Sitka’s local nightlife

Sitka is home to 8,500 people – so can you expect the world’s most active nightlife? Maybe not, but we’ve still got some great options depending on your mood. The Pioneer Bar is a popular fishermen’s bar, located across the street from ANB Harbor, visited by both fishermen and non-fishermen alike. Down the street, Ernie’s Old Time Saloon is a beloved saloon known for its wild karaoke nights. The Bayview Pub, meanwhile, is the perfect stop for food, drinks, and a round of pool.

The Bayview Pub has 20+ bars on tap

5. Meet the real Ramon

If you’ve seen the movie, I’m sure you remember Ramon – an omnipresent, larger-than-life character played by Oscar Nuñez. Ramon is a Jack-of-all-trades, reappearing throughout the movie as a caterer, exotic dancer, clerk, and wedding officiant.  

What many people don’t know, however, is that Ramon is based off of a real person. The real Ramon works as a bartender at the Westmark Sitka Hotel’s Kadataan Lounge, where he’s been a fixture among the community for over sixteen years.  

When I meet Ramon for the first time, I’m immediately struck by his inviting and playful personality. He has this great way of connecting people, experiences, and making you feel welcome.

Stop by the Westmark Hotel to meet the original Ramon

“You wanted to talk about The Proposal, right? Did you know the movie’s writer actually came here?” he asks, while serving a chilled draft beer. “He wanted to connect with the local community, so he spent a summer in Sitka. The Paxtons were hosting him, so they brought him into the Westmark 3-4 times a week, and that’s how we met.” (Paxton is a name you might recognize from the movie, and the family name was inspired by former city administrator and mayor Gary Paxton. You might even run into him and his wife in town!)

Ramon found out that he was famous after the film was released. The Westmark is situated next to the Colosseum Theater, and after the first showing a steady stream of audience members flooded the Westmark’s restaurant to share the news. 

“Everyone kept telling me I was in the movie, but I didn’t even know what movie,” Ramon laughs. “Many people come through Sitka to make movies – Animal Planet, National Geographic, Discovery Channel, they’ve all been here. A lot of them will stay in the hotel so I get to meet them and sometimes go on hikes with them.”

Ramon flips through his phone, showing me different pictures posing with visitors. In every photo, he’s beaming. 


 Is there a proposal in your future? You can make the shot-gun wedding that we saw in The Proposal a reality, with a destination wedding your family will talk about for year’s to come. Sitka has flower shops, gourmet bakers, and event planners. In the State of Alaska, you can have anyone become your marriage commissioner for a day if they apply in advance. Visit our Getting Married page for more information.

Any other details from The Proposal that you noticed during your visit? Share them on Facebook or Instagram with the hashtag #visitsitka! 

Sitka is the perfect choice for your romantic destination wedding

About The Author

Maike Prewett

Maike Prewett is the Visitor Services and Community Coordinator at Visit Sitka. Maike Prewett grew up in Colorado and moved to Alaska after living in China for six years. She was a member of New York University Shanghai’s third graduating class and explored her love of storytelling through the Interactive Media Arts program there. While she worked with Visit Sitka she participated in the Alaska Fellows Program, a nine-month residential fellowship program nurturing the next generation of Alaska- based leaders. She stayed on with Visit Sitka as the Visitor Services and Community Coordinator for a year following her fellowship.

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