The holidays feel a little different when you live on a sailboat full-time. Instead of snowdrifts and fireplaces, we get twinkling masts, waterfront parades, and festive coastal towns that know how to celebrate Christmas in their own salty way.
Whether you’re cruising the ICW, exploring tropical islands, or chasing adventure up north, these are my Top 5 Coastal Towns for Liveaboards to Spend the Holidays — chosen specifically for cruiser-friendly amenities, holiday spirit, and memorable experiences on the water.
1. Beaufort, North Carolina: Classic Coastal Christmas
Beaufort holds a special place in my heart. Last year, my family and I were anchored nearby when we watched the Christmas Flotilla glide through Taylor’s Creek — boats of every size glowing with lights, reflections dancing on the water. It felt like something out of a coastal storybook.
Why cruisers love it:
- Easy anchorage and marina access
- Walkable historic waterfront
- The Olde Fashioned Holiday Market
- Friendly locals and a warm, welcoming feel
If you want small-town charm wrapped in nautical sparkle, Beaufort is a perfect holiday stop. If you’re near Beaufort, NC around Christmas this year and you’re interested in attending, you can find more information here.
2. Key West, Florida: A Tropical Christmas Wonderland
Imagine palm trees strung with Christmas lights, carolers in sandals, and boats decorated like floating gingerbread houses. That’s Key West during the holidays.
The highlight of the season is the Schooner Wharf Lighted Boat Parade, and it’s iconic. Whether you join the flotilla or dinghy over to watch, the whole island radiates festive energy.
Why cruisers love it:
- Tons of marinas and moorings
- Huge boating community
- Endless holiday events, concerts, and markets
- Warm, sunny December weather
If you want a “Merry & Bright” season with rum cocktails and ocean breezes, this is your place.
Kennebunkport, Maine: A Cozy New England Coastal Christmas
For cruisers who prefer sweaters over swimsuits in December, Kennebunkport delivers the ultimate New England holiday vibe. Their famous Christmas Prelude includes tree lightings, festive markets, fireworks, and Santa arriving by lobster boat — a tradition you won’t find anywhere else. This activity is part of a much larger event, which you can find here.
Why cruisers love it:
- Nautical holiday traditions
- Beautiful harbor and waterfront
- Hot cocoa, cozy shops, and a small-town feel
- A peaceful break from the typical sailing-route crowds
A note for cruisers: This stop is best for those comfortable with cold-weather living aboard or who winter in a marina with solid amenities.
4. Cocoa Beach, Florida: Quirky, Warm, and Full of Coastal Spirit
Cocoa Beach takes holiday fun to the next level with Surfing Santas, where hundreds of surfers dressed as Santa paddle out on Christmas Eve. It’s chaotic, hilarious, and unforgettable.
Why cruisers love it:
- Laid-back liveaboard-friendly town
- Easy anchorage and marina access
- Close to beaches and holiday events
- Warm, sunny weather perfect for outdoor festivities
If your family loves fun, color, and a touch of Florida quirkiness, Cocoa Beach is a blast during the holidays.
5. Southeast Alaska: A Magical Northern Holiday for Adventurous Cruisers
Yes — you read that right. Southeast Alaska might not be the first place that comes to mind for holiday cruising, but those who spend winters there swear it’s pure magic. Think snow-dusted mountains framing quiet harbors, Christmas lights reflecting off glassy inlets, and tight-knit coastal towns that welcome boaters like locals.
Popular towns for holiday liveaboards include Sitka, Juneau, Ketchikan, and Petersburg. Each one offers small-town charm, incredibly festive decorations, and a sense of peace you can’t find anywhere else.
Why cruisers love it:
- Stunning, peaceful winter scenery
- Strong community vibe — locals look out for each other
- Holiday markets, boat parades, tree lightings, and cultural celebrations
- Cozy marinas perfect for hunkering down with heaters and hot cocoa
This region is best for experienced cruisers prepared for cold-weather liveaboard life, but if you’re up for the adventure, Southeast Alaska delivers one of the most unique holiday seasons you’ll ever experience on the water.
Final Thoughts
Spending the holidays on a sailboat is already its own kind of magic — but picking the right coastal town makes the season unforgettable. Whether you’re chasing sunshine, looking for cozy winter charm, or dreaming of a quiet anchorage beneath snow-capped peaks, these five destinations offer something truly special for liveaboards.
What are some of your favorite coastal towns to spend the holidays in? Let me know in the comments! And be sure to subscribe to receive email updates!
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