What to Wear During the Day on an October Mediterranean Cruise: Stylish & Weather-Ready
Cruise week continues as I share a few photos from my excursion in Montenegro plus outfits which are perfect daytime outings, including what I wore. Packing for a Mediterranean cruise in October requires a bit more thought than the peak summer months. While the weather is still pleasant, it can be more unpredictable, ranging from warm, sunny days to cooler, breezier moments as you venture between cities and islands. You'll need versatile outfits that keep you stylish while adapting to the shifting conditions. Here's how to plan your daytime wardrobe for an October Mediterranean cruise, where layering, comfort, and chic simplicity reign supreme.
TL;DR
Beth shares what to wear on a Mediterranean cruise
The outfits are shoppable via text and image widgets
Plus, find a shoppable collages at the end of the post
What to Wear During the Day on an October Mediterranean Cruise: Stylish & Weather-Ready
layering is key
October in the Mediterranean is a transition season—mornings and evenings can be crisp, while afternoons still feel warm, especially when the sun is out. The secret to staying comfortable is mastering the art of layering.
Think lightweight tops, such as cotton or silk blouses, paired with cardigans or lightweight jackets. A denim jacket or a soft sweater is perfect for layering over a dress or top when the temperatures dip.
Style Tip: Pack pieces you can easily mix and match. A neutral cardigan or light jacket can be worn multiple times over different outfits, saving space in your suitcase while keeping you warm.
Shop the Outfit
Long Sleeve Striped Dress | Leather Espadrilles (old, similar here, here, and here) | Black Leather Tote
nautical-inspired looks
If you’re on a cruise, why not embrace nautical-inspired fashion? Stripes, navy and white color palettes, and anchor motifs are classic choices for a seaside adventure. A striped boatneck top paired with high-waisted shorts or a breezy skirt creates a timeless and chic daytime look.
Style Tip: Add a pair of white sneakers or espadrilles, and finish the look with oversized sunglasses and a chic crossbody bag. You’ll be perfectly dressed for a day of exploring ports like Cannes, Santorini, or Amalfi.
The day I spent in Kotor, Montenegro, was a bit chilly, so I was happy to slip into this long-sleeved striped dress from Tanya Taylor (a new to me brand), a denim jacket, and leather espadrilles from Tory Burch (old, similar here, here, and here) and a black leather tote from Coach. I have to share I’m already a big fan of Tanya Taylor as this dress might be a bit spendy but it will be one I reach for time and time again. And that’s key to me as this dress offers sustainability, quality and timeless appeal. The knit is substantial and doesnt show lumps and bumps but it’s not heavy. Definitely a win/win!
This was day four of the cruise and we dodged the rain clouds all day long. The highlight of the day was touring an olive farm that has been in the family for four centuries. Impressive! It’s currently run by three brothers and their mother! Love that! We were greeted at the entrance of the farm with fresh beignets and honey produced on the farm, along with homemade brandy. After a tutorial on extra virgin olive that needs to be picked and produced the same day, we were treated to lunch with trays of cold cuts, fresh cheese, veggies and red and white wine. It was delightful. This was one of my favorite days of the tour!
mid-length dresses and skirts
October calls for a balance between summer and autumn styles. Mid-length dresses and skirts are perfect for this time of year, offering both coverage and breathability.
Choose dresses made from slightly heavier fabrics than you would for the height of summer, such as jersey or lightweight knits. Midi dresses are especially versatile as they provide more coverage for cooler mornings while remaining comfortable for walking around sunny cities.
Style Tip: Pair your dress with ankle boots for a stylish, autumnal look. A belt can also add structure to your outfit, creating a polished, put-together vibe that’s perfect for both onboard and onshore activities.
1.
cody striped dress
2.
sweater midi skirt
3.
Gwyneth Slip skirt
4.
knit mockneck dress
5.
striped Callie dress
6.
the lea dress
7.
black Leighton midi dress
8.
almond knit midi dress
9.
black and white wavy knit
10.
lightweight Oxford dress
comfortable and stylish footwear
Given the cooler temperatures and the likelihood of walking on uneven streets in historic Mediterranean cities, you'll want shoes that are both comfortable and stylish. Since October weather can bring some rain, opt for closed-toe shoes.
Comfortable sneakers, ankle boots, or loafers are ideal for daytime outings. If you're still craving that summery feel, choose loafers in lighter colors or sneakers in a chic, neutral tone that will match a variety of outfits.
Style Tip: Look for waterproof options or bring a pair of shoes you won’t mind wearing in light rain. Avoid heavy sandals or open-toed shoes, as the weather can be unpredictable.
1.
gucci sneakers
2.
wedge loafers
3.
gazelle sneakers
4.
tulip slip-on sneaker
5.
court sneaker
6.
golden goose sneaker
7.
Sorell kinetic sneaker
8.
calf hair lug sole loafer
9.
gola sneaker
10.
penny loafer
the perfect day bag
A functional yet stylish day bag is a cruise essential. You’ll need something big enough to carry your sunscreen, water bottle, camera, and any souvenirs you pick up along the way, but small enough to feel effortless.
Style Tip: A small, chic backpack or a crossbody bag is ideal for keeping your hands free while you explore. Choose a neutral color that can match multiple outfits and add a touch of Mediterranean flair, like a woven straw bag or a tote with nautical stripes.
Shop the Outfit
Long Sleeve Striped Dress | Leather Espadrilles (old, similar here, here, and here) | Black Leather Tote
outerwear for cooler days
October weather in the Mediterranean can be unpredictable—one day you’ll be basking in the sun, and the next, you may find a brisk sea breeze or light rain. A lightweight jacket or coat is essential for those cooler days on the ship or in port.
A trench coat or a water-resistant jacket is perfect for October. It’s stylish enough for city exploration and practical enough for when the weather turns. A light wool coat or a chic utility jacket also works well.
Style Tip: Choose a jacket that’s easy to pack and doesn’t take up too much space. A jacket with a hood is a smart choice for unexpected rain showers.
accessories for function and flair
Accessories are your best friend on a Mediterranean cruise in October. Not only do they add a personal touch to your outfits, but they can also serve practical purposes, especially when it comes to adapting to the weather.
Bring along a wide-brimmed hat for sunny afternoons and a chic scarf for cooler moments. A crossbody bag is perfect for daytime outings, keeping your hands free while sightseeing. Sunglasses are still a must, as the Mediterranean sun remains strong, even in October.
Style Tip: A stylish pair of sunglasses and a versatile tote bag will keep your essentials (like sunscreen and water bottles) handy while you explore. Opt for a water-resistant tote to keep everything safe from sudden rain.
Shop the Outfit
Long Sleeve Striped Dress | Leather Espadrilles (old, similar here, here, and here) | Black Leather Tote
versatile, comfortable and stylish
When planning your daytime outfits for an October Mediterranean cruise, versatility is key. The weather can vary from warm and sunny to cool and breezy, so having a mix of layers, breathable fabrics, and comfortable shoes is essential. By packing outfits that can transition from sunny afternoons to cooler evenings, you’ll be ready for whatever your cruise throws your way—whether it’s a stroll through ancient ruins, exploring charming coastal towns, or relaxing on deck with a Mediterranean view.
Keep your wardrobe chic yet practical, and you’ll enjoy every moment of your Mediterranean adventure in style! I had a ball! Stay tuned to tomorrow’s post when I will share a few outfits I brought along for evening attire.
In Case You Missed It
Yesterday, Beth shared fall travel outfits & accessories. Click the title or image below to read the article.
Love all the gorgeous photos, Beth! And of course your sound advice on what to pack and wear. I would love someday to visit an olive garden!
I absolutely loved my visit to the Olive farm! Thanks for stopping by!
Thanks for stopping by, Nancy! I have to admit visiting the olive farm was special. It just amazes me the farm has been in their family for four centuries.
Looks wonderful- what is the cruise line?
Thx!
This is a Windstar Cruise.