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Where to Travel This October

Where to Travel This October

Shoulder season got you feeling the end-of-summertime blues?

Your friends might be unpacking their chunky sweaters and brown scarves, but if you’re like us, you know that boat season is always better than boot season. 
You’re probably asking yourself, how can I convince my travel partner to go on one last epic trip before we officially swarm the entrance with winter coats? Or maybe you’re wondering what tropical destination will get the crew on board for your upcoming group trip?
Get ready to cozy up with your favorite travel booking site as we’ve got 5 vacation-ready destinations that will have you forgetting about saisons and ciders, and get you back to sippin’ mai tais poolside. Here are our favorite October getaways to kick off your second summer celebrations:


Mexico is calling, and when it does, you always answer. This country is brimming with vibrant culture, pristine beaches, and activities for everyone to enjoy. We’re partial to the eastern part of the peninsula in Quintana Roo, Riviera Maya and the beaches and luxe resorts of Mayakoba. However, Mexico is full of warm destinations this time of year for any type of trip.
From the Riviera Maya to Baja California, the finest resorts to luxe group villas, we’ve got you covered with daytime swimwear for him and her, and stylish linen shirts and vacation dresses for date night at Flora Farms. We’ve also kept the kids in mind with matching swim and resort wear for the whole family.  


Maybe you’re still waiting for that renewed passport to come in the mail and you’re looking for a stateside getaway trip with the ladies. Or your travel partner is more the Stay at Home Somm type, hoping for a trip filled with Cabernets, Pinot Grigios, and fine dining. There’s no better time to visit the world-renowned Napa Valley than October. With a seasonably warm climate for you to break out those designer swim trunks and bikinis by the pool during the day and don your finest wine-inspired long sleeve shirts and sundresses for the tasting room and fancy dinner when the temps drop. A true Indian Summer destination where you get the ideal climate without the dramatic high and low temps.
Where else can you be enjoying your poolside cabana with a chilled glass of rosè and exploring miles of lush vineyards all in the same day? A trip like this needs a versatile wardrobe, and thankfully, we’ve got you covered. Check out our blog on what to wear to Napa as a guy and what to pack for the girls trip to Napa, and while you’re at it, check out our favorite places to go wine tasting.


While you likely won’t find a more peaceful setting than a rainy breeze in Bali, you probably prefer the drier weather. Lucky for us, October marks the end of Bali’s dry season, so now is your chance to experience the beautiful country where it all started for KF, without spending the entire trip in your poncho.
Rent yourself any of the luxurious villas across the island, unpack his and her matching outfits and you’re instantly in vacation mode. Keep the flannels at home, stick to the swimwear, shirts made in Bali, and bathing suit cover ups as your everyday essentials.


Welcome to a place where you can throw on a Hawaiian shirt or a cheeky bikini with a cover up and be all set for the day. Let’s face it, there’s never a bad time to visit Hawaii, but October is oh-so-perfect for any type of trip, whether you prefer the comforts of your hotel pool in Waikiki, hiking the lush trails along the coast of Maui, or cruising along the scenic roads of the North Shore.
Save room in your carry on and stick with the essentials: obviously Hawaiian shirts (referred to more commonly as aloha shirts on the island), maybe some matching swimwear for him and her to let everyone know you’re on vacation mode. Set that watch to 5 o’clock and leave the battery at home; the rest will fall into place.  And if you’re looking for some vacation golf, we already did the full rundown on the best places to golf in Oahu, Hawaii.
Wherever you’re headed in this fall, we’ve got you covered. And just remember, you can always bring the vacation to you. Feel free to reach out to our Customer Concierge for more travel ideas and style tips.
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