Europe and Caribbean deals, overseas car rentals, more

Need help tracking down a great travel deal? Then put our expert investigator on the case. The Deal Detective will sleuth out the best bargains that fit your needs.

Dear Deal Detective:

Do you have any information on the best way to rent a car for travel in the U.K. this summer, probably for a week to 10 days in August?

—C.D.

Dear C.D.,

The basic strategy for getting a cheap rental car overseas isn’t much different than what I always suggest for nabbing a good rental here in the U.S., but there are some U.K.-specific sources you may want to check.

This is how I’d approach it. First, find a baseline rate at Expedia, Orbitz, Travelocity, and Auto Europe. Then, see if you can beat those deals through a U.K.-based discounter such as easyCar.com or arguscarhire.com, bearing in mind that those two sites bundle CDW (Collision Damage Waiver), but with a deductible.

If you’re 100 percent sure of going and you know your exact dates, consider priceline.com‘s “Name Your Own Price” feature. You may find a significantly cheaper rate, but the price is nonrefundable.

Also bear in mind that though it may cost more to get an automatic transmission than a standard transmission car, driving on the left side of the road can be difficult enough without having to learn a new way to shift gears. From my own personal experience, I’d suggest paying more for the automatic.

Dear Deal Detective:

I’m looking for a Caribbean cruise deal in August or September. What would you recommend?

—M.P.

Dear M.P.,

There are a boatload (forgive the pun) of Caribbean cruises in August and September, so I can only give you some general guidelines without knowing more information. You’ll also need to decide whether you want to cruise for less than a week, exactly a week, or more than a week, and whether you’d rather visit the western, eastern, or southern Caribbean islands.

In general, you’ll find better deals in September. August sailings are still considered peak (the most expensive) time, even though it’s hurricane season. Most cruise ships can sail around hurricanes, but if you’re concerned then book a southern Caribbean cruise, where your trip is less likely to be affected by storms.

Since you’re looking for a deal, I’ll assume you’re more interested in mainstream or premium lines than luxury cruises. When I checked, Carnival‘s September deals started at $239 per person for a four-night cruise and $479 for a seven-night cruise. Its ships can take on a party atmosphere, and the food is good but not outstanding. Royal Caribbean is a great line for active travelers. I did a quick search on its website and found four-night cruises from $249 and seven-night cruises from $649 for August and September. All prices I mentioned are for inside cabins, which are fine if you don’t plan to spend much time in your cabin. Otherwise, I recommend slightly pricier outside cabins as a compromise, and balcony cabins if you want to splurge.

Step up to a premium line, and you can find seven-night September cruises on Princess in the $549 to $599 range. My searches on Holland America and Celebrity came up with nothing noteworthy. Be aware, of course, that cruise prices change more often than the weather, so the prices noted here are ballpark figures and may or may not have changed by the time you read this.

For more deal options, you can also contact a travel agent, look at online cruise sellers, or submit a request at CruiseCompete.com to have travel agents send you their best offers.

Speaking of cruise deals, our next question comes from a reader heading to Europe for a cruise…

Dear Deal Detective:

I’m traveling with my husband, my eight-year-old son, and one-year-old (yes, one!) daughter for my first cruise at the end of August. The trip is a 15-day Europe cruise, but I am at a loss as to whether to go with the cruise line’s shore excursions, book with other sources, or try to do it on our own (God, the pain). Please advise and also kindly provide some good sources for shore excursion tours at discounted rates. In a word … HELP!

—P.K.

Dear P.K.,

I recommend a mix of all three: cruise-sponsored shore excursions, independent local operators, and do-it-yourself trips. The key to a Europe cruise, especially a two-week one, is not to overdo it. Mix up long days of intensive sightseeing with half-day excursions, or even skip a less interesting port to hang out on the ship. Your children, especially, may tire out quickly.

The first thing to do is read through the ship’s shore excursion booklet (or read up on the tour options online). This will give you a sense of what activities are available in each port. It’s best to do full-day tours through the cruise because the ship will wait if you’re late coming back. Perhaps choose a few of these to purchase. Also, remember that most cruise lines won’t let you cancel a pre-booked excursion onboard without a penalty fee, so you may want to wait and make your tour purchases at the last minute.

I can’t recommend any specific independent companies because I don’t know where in Europe you’ll be, but I do know that many cities offer hop-on-hop-off tour buses, which take visitors to all the key spots, often with narration along the way. These are a good way to explore at your own pace without worrying about navigating foreign streets and transportation systems.

If you get a guidebook and talk to the port lecturer on your cruise, you can get a sense of which ports are small and easily accessible from the ships. These are the places where you may want to explore on your own and spend the day wandering through the city streets, stopping along the way to shop and eat and take in a museum or cultural attraction. In places like Tuscany, you may wish to rent a car and drive yourself. Many ports have car rental agencies on-site. If you plan on driving, you’d do well to purchase an English-language road map before you leave home.

Bon voyage!

Dear Deal Detective:

I live in Minneapolis and my friend lives in central Illinois. We want to meet up for a four- or five-day vacation in September to somewhere warm without costing us a ton of money. We’d be happy with a nice pool and some shopping. Any ideas?

—T.D.

Dear T.D.,

It sounds like what you really want is some good old-fashioned stress relief. To do it on a budget, your best bet for fun in the sun is probably Florida in late September after the kids go back to school and there’s less demand for flights and hotel rooms.

Since you and your friend are coming from different locations, I suggest giving Travelocity’s Meet Me In tool a whirl. It was designed to accommodate travelers just like you and your friend, who want to meet somewhere but are coming from different cities. You simply select your departure cities, your destination, and your dates (usually within two weeks), and are presented with hotel, flight, and car rental options for a single price.

For example, I found a five-night, airfare-and-hotel package to Orlando that would allow you to depart from Minneapolis for $332 while your friend departs from Chicago for $325 (these prices include your flight, hotel, and all taxes and fees). You’d stay at a three-star Orlando hotel in a room with a queen-size bed and a sleeper sofa. Did I mention the hotel also has a pool?

And now it’s time to close the book on this month’s cases. Need help finding a deal for your next trip? Email me your requests. Please be aware that due to the volume of requests I receive, I cannot always personally respond to every email. The more compelling your question—and the more specific you are with your departure city and desired travel dates—the better the chance you’ll be selected for an upcoming case.

All prices, dates, and booking details listed here were valid at the time of publication. Some information may have changed since that time.