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Caribbean Getaway for Under $300 Per Person

The Deal Detective is’s resident bargain hunter, Kate Hamman. She’s always on the lookout for new travel deals and invites you, dear reader, to submit your own questions.

Tina writes, “I am in desperate need of your help. My tenth anniversary will be on July 1st and more importantly my husband’s 40th birthday is July 2nd. The last vacation that we had was in 2007 (we take our vacation from June 26-July 7th). This year my husband advised me that we just could not afford to take a vacation … This weekend he told me if I could find a vacation for the two of us for under $1,000 that we will be able to go. I would prefer something that is all-inclusive. Once again he is thinking of the family first. Looking back at our previous vacation photos I see a different man, one without stress. I would appreciate your help in making his heart smile.”

Sad to say it, but I am seeing more and more people in your exact shoes; people who are in desperate need of a vacation, but just don’t know how to afford it. And it sounds like you two not only deserve a little time away, but also have quite a bit to celebrate. Good thing I’m a strong believer in the saying, “Where there is a will, there is a way.”

I’m not going to fib to you. Your travel dates do make it a bit more difficult. Summer is a prime period for vacation-goers, meaning prices tend to rise. You can save quite a bit by traveling during the off season. However, since your dates are pretty set, we’ll just have to do the best we can with what we’re given. With this in mind, we’ll focus more on Caribbean destinations instead of places in Europe because deals are more likely prevalent. Since finding exactly what you’re looking for at a price you can afford may create a bit of a conundrum, let’s compare some deals to see what might be the best fit. is offering a Puerto Rico package deal starting at $399 per person (without taxes and fees) for travel between May 1 and June 30. The deal includes round-trip airfare from Miami (other departure cities are available for a higher cost), four nights’ accommodations at the El Conquistador Resort & Golden Door Spa, The Waldorf Astoria Collection, buffet breakfast, a $25 match bet casino coupon, a spa discount, Trip Mate weather insurance, and a $100 coupon if it rains. The price includes $100 off with the promotional code, 100PR. You must book by April 4. This trip would cost you about $798 for the two of you, but doesn’t include extras like food and entertainment and falls a bit short in the travel dates.

Pleasant Holidays has a package deal to the Dominican Republic starting at $539 per person (without taxes and fees). The offer includes round-trip airfare from Miami (other departure cities are available for a higher cost), three nights’ accommodations at the Catalonia Royal Bavaro Resort, meals, drinks, and activities. Travel is valid May 1 through 24, but other dates are available for a little extra cash. Though this trip would cost about $1,078 for two people, it includes a stay at an all-inclusive property, which can help save on food and entertainment. is also offering a package to Nassau, Bahamas, starting at $299 per person (without taxes and fees) after $300 instant savings with the promo code, BAH300SPR. The deal includes round-trip airfare from Fort Lauderdale (other departure cities are available for a higher cost), four nights’ accommodations at the Wyndham Nassau Resort & Crystal Palace Casino, free room upgrade, and a coupon booklet with up to $250 in savings at the resort. Travel is valid between April 11 and August 31. The total cost for this trip comes to about $598 for two people. The price and dates are spot on for your needs, but this isn’t an all-inclusive resort, so you will have to factor in extra costs for meals and entertainment.

These three packages are just examples of what’s available if you take a little time to investigate. Plus, it helps to know what’s important to you, and what you’re willing to part with, i.e. travel dates, all-inclusive, or pricing. It’s also important to keep in mind the additional cost of taxes and fees when pricing vacations.

I wish you and your husband a happy anniversary, as well as a happy birthday to him, and I hope you are able to find a vacation that puts a smile back on his face and yours.

As for my other readers: How have you cut corners when planning a vacation? What are you willing to sacrifice in the name of a getaway? Also, have you found a deal that could make Tina’s heart sing? Please leave a comment below.

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