Gibraltar at $536 RT from the East Coast

Is it Spain? Is it the U.K.? 

Technically both. 

For over 300 years, this 3-mile long, rocky outcrop at the southernmost tip of Europe has been the ultimate tug-of-war rope for Spain and Britain — ever since the Treaty of Utrecht tossed it to the Brits in 1713. 

So what does that mean for your trip? 

Well, expect classic red phone booths standing proudly against ancient Moorish castles. Start your day with a full English breakfast, and let the aroma of tapas tempt your dinner plans. And don't forget, you'll be paying in sterling and plugging in with three-prong plugs! 

Gibraltar's economy, once wholly dominated by the military, now marches to the beat of tourism, with visitors flocking to see its WWII tunnels and onwards to the top of the Rock, for panoramic views stretching to Africa. Spoiler alert: Leave your valuables at the hotel, you might find yourself outwitted by these unexpected pickpockets! 

Tourism doesn't stop there, though, it's also well-known for its quickie weddings — think of it as the Vegas of Europe. Sean Connery got married here, John and Yoko also tied the knot here, and as luck would have it, I did too!

Learn from my mistake please: if you're going to say a hasty "I do" you should probably know the person longer than the time it takes to ride the cable car to the top of the Rock :-) 

P.S. Gibraltar also serves as an excellent jumping-off point for exploring Spain's harder to reach Mediterranean spots, like the Costa de la Luz or the Costa del Sol. Just be sure to budget some time for the border hop!