Dreaming of a fairy tale moment without wiping out your savings? Say hello to Tallinn, where medieval charm meets modern mischief and your wallet doesn’t immediately file a complaint. Spend 5 nights from $480 with flights included and live out your storybook fantasies (castle vibes, cobblestones, moody lighting… you get it).
Tallinn’s medieval Old Town is straight out of a fantasy novel, but don’t be fooled. Think Nordic cool with a little Soviet edge, shockingly good (and affordable) Nordic-Estonian food, and prices that feel downright flirtatious compared to Western Europe.
You’ll crash at Citybox Tallinn City Center (4.3/5 on TripAdvisor), a sleek, Scandinavian-designed stay that knows how to keep things simple and stylish. It’s just a short stroll from the Old Town, Roterman Quarter, and Viru Shopping Center. So, you’re never far from snacks, shopping, or shenanigans. Rooms are modern and minimalist with comfy beds, fast Wi-Fi, a desk for pretending you’ll work. Some rooms even have window seating perfect for dramatic gazing at your medieval surroundings. Did we mention that they are pet friendly too?
Pirate Tip: While we found the best rates in February, for a few dollars more you can enjoy also enjoy Tallinn in March and April.
