After a week sailing around Guadeloupe, I’m back in Denver, cooking, and getting posts ready before I head out on another trip next week. Summer is officially here and things are picking up — which I love. I’m an early riser, so the long, dark winter mornings never worked for me. Right now the sun is coming up and the birds are singing, and I’m feeling grateful for warm, long days.
Let’s talk about what I wore on the TradeWinds trip. We took a red-eye from Denver to Miami, then a morning flight to Guadeloupe. Because I’d just gotten a spray tan at Glamour Bar, I avoided wearing leggings on the plane to prevent rubbing it off. Instead I chose a long-sleeve, super-soft dress that was comfortable for travel. I also packed a scarf that doubled as a blanket on the overnight flight — lifesaver.
{ Dress (40% off) | Hat | Sneakers }
One evening while exploring Guadeloupe we stumbled on a stunning beach and enjoyed champagne at sunset. Definitely a highlight. I loved a particular swimsuit I packed because it’s affordable, comfortable, and the bottoms flatter the shape nicely. I found the same style in white and black, which made it easy to mix and match.
{ Bikini Top | Bikini Bottom | Hat | Earrings | Sunglasses }
I bought a few cover-ups before the trip and was surprised how pricey many of them are. One under-$100 cover-up quickly became my go-to — it’s lightweight, breathable, and easy to throw on after the water. I wore it almost every day because it kept me comfortable and cool.
{ Bikini Top | Bikini Bottom | Cover-up | Sunglasses | Earrings }
I reached for another bikini several times because the cut feels so comfortable. On the way home I realized I’d forgotten a bra, so I wore the bikini top on the flight — practical and comfortable. I also picked up a travel-friendly hat before the trip that packed well: sturdy enough to keep its shape, but flexible enough to avoid crushing in transit.
{ Bikini Top | Bikini Bottom | Earrings | Hat | Sunglasses }
This bright, colorful cover-up was perfect for a day with excursions when I wanted extra sun protection. It’s cheerful and lightweight, and the hat I paired with it provided excellent shade. Between hats and sunscreen, my face stayed protected even if my legs got a little sun while sailing.
{ Bikini Top | Bikini Bottom | Cover-up | Hat | Earrings | Sunglasses | Sandals }
Whenever I think I’ve found a favorite bikini, another one comes along that feels even better. One suit I packed has a supportive top that stays in place and seamless bottoms that avoid any awkward lines — incredibly flattering and comfortable for active days on the water.
{ Bikini Top | Bikini Bottom | Hat | Earrings }
On one evening we had dinner in Terre-de-Haut at a charming restaurant called Couleurs du monde, and that was the first night I wore “real” clothes in several days. I packed a lightweight dress that worked perfectly for dinner — easy to pack, comfortable, and breezy. Since it was low in stock, I also suggested similar options.
{ Dress | Sandals | Bandana }
Finally, I brought one more favorite bikini with a cute cutout and bow detail on the top — such a fun, feminine suit. I wish I had worn it more and I’ll likely pack it for my upcoming trips to Palm Springs and Houston. It’s an easy pick for summer.
{ Bikini Top | Bikini Bottom | Sunglasses | Earrings }
A few followers asked how I pack a carry-on for a longer trip. For sailing with TradeWinds, guests unpack on board and the crew stores suitcases to free up cabin space. I always travel with a reliable hard-sided carry-on and packing cubes to organize everything. Hard-sided luggage helps ensure your bag fits in the overhead, and packing cubes squeeze more into your suitcase while keeping items easy to find.
For a sailing trip, you really only need swimsuits, cover-ups, tennis shoes, sandals, and a couple casual outfits for exploring — so you can fit multiple looks into a single carry-on. Packing cubes genuinely make a difference: they maximize space and keep items sorted so nothing has to be spread across the bed to find it.
Everything Else That Made it Into My Suitcase
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Hope this gives you inspiration for your upcoming vacation wardrobe. This post includes some affiliate links and I may earn compensation from purchases, but all opinions are my own. That support helps keep the blog running — thank you!