Best Souvenirs
T-shirts
Particularly great as souvenirs for yourself & immediate family. Get something that’s meaningful to you and at least one size too large.
Instead of just getting something off a tourist rack that says the name of the island you’re on, find a t-shirt with local art or custom designs on it that you like, or the t-shirt of a local brewery or spa.
The biggest bonus is that it immediately expands your trip wardrobe.
Hoodies, Hats
Same suggestions and logic as for t-shirts, but can be even better if situationally and seasonally appropriate.
Refrigerator Magnets
Great for both yourself and as gifts.
When buying gift souvenirs, don’t just get something that says the name of the place unless the recipient has been there. Get a reproduction of local art or at least a depiction of a sight/monument with visual appeal.
Art
Great for yourself and as a gift.
May or may not travel well depending on size/medium. Saving art shopping for the tail end of your trip is smart, otherwise consider having art shipped.
Dish towels
Everyone can always benefit from an extra dish towel.
But this is still a case where it is best if the dish towel has something more inventive than a location name, such as a piece of art, a recipe, and or a map.
Wine
Only if you plan on checking bags or plan on having it shipped.
It’s nice to get wine when you visit and taste at a vineyard, and any given bottle of wine is generally going to be cheapest at its source. But it can be hard to manage it all. Be sensible about your luggage abilities.
Wine shipping can be quite expensive. If you end up with a surprise wine surplus, consider buying a duffle bag and putting most of your clothes in the duffle to make room for the wine in your hard-case.
Chocolate & Candy
Wait until the last day(s) of your trip, and then buy as many tins of the local candy or chocolate that you have room for in your price range. There will always be more people that you want to give these to than you will have candy to give out.