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What’s the Best Summer Vacation You’ve Ever Been On?

by Bobby HoytLeave a Comment

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Alright – I'm going to admit up front that this is probably the most selfish post I've ever written for M$M. Usually I try to put out something that's really insightful or interesting enough to start off your day on a positive note.

But, every once in a while I want to try to take advantage of the fact that I have 100,000+ people that I can go to for wisdom or their experience on certain topics.

I've always been so surprised how many people are willing to take time out of their days to write lengthy emails to me about various subjects, and I promise that I try my best to read and respond to all of them (even though I fail sometimes).

So here is my one selfish request: My wife and I are going on a vacation this summer and need help deciding where haha

I know a lot of you are big time travel junkies and “travel hackers”, so I figured the best people to ask were well…you.

Related: Should people travel if they have debt?

We're behind on the travel thing…

Like a lot of millennials, we've waited a while to really get our lives “started”. Most of our early twenties were spent being super cheap and saving up money for things like our wedding or paying off debt.

Travel was just another one of those things that fell by the wayside, but now that my income has risen a bit and I have more flexibility with my schedule – we're trying to do some catching up.

So far, we've done three big vacations:

1. The Bahamas

This was actually for our honeymoon, and we stayed at one of the big all-inclusive chains. It definitely wasn't cheap, but I guess we just wanted to splurge a bit because we had never really done anything before.

It was honestly incredible, and somewhere that I'd 100% go back to again. Our resort was on the Great Exuma (Ex-Zoom-uh) island in the Bahamas chain (which I constantly pronounced “eczema” on accident…aka the skin condition haha).

The water was straight-up incredible, and even though the island was pretty scarce as far as things to do, we still did enough in the week we were there to have a great time.

Also, I jumped in the pool with my cell phone in my pocket and lost every picture/video that we took on the trip. The phone is still sitting in a bag of rice two years later.

My wife was pissed, but these are just the type of things that I do.

2. Whitehouse, Jamaica

Last summer, we decided to do a vacation at the same big all-inclusive chain. This vacation totally blew for a couple of reasons.

The biggest one was that my wife's father passed away on our third day there. It was a horrible situation, and I doubt we'll ever go back to Jamaica because of how traumatic that was. Who knows, but I doubt we will have “good vibes” about Jamaica in the near future.

Read also: The Real Reason I Live Debt-Free

It was really hard to get back to the U.S., but we did manage and were able to take care of everything we needed to.

The other reason the vacation wasn't that cool is that we were tired of the all-inclusive thing. Sitting around on a resort and eating/drinking unlimited amounts is definitely nothing to complain about (fully aware that this entire post is a first-world problem), but it just felt like a repeat of our honeymoon in a place where the water wasn't quite as nice.

We did do some zip-lining in the jungle, which was by far the highlight of the trip. I had a GoPro strapped to my helmet and got some incredible footage, which I completely lost about two weeks later when I stupidly tried to ride a surfboard backwards behind our boat and dropped the GoPro to the bottom of the 18 feet deep creek we ski at.

Again, my wife was pissed, but these are the type of things that I do.

3. Anna Maria Island, Florida

This was the cheapest of our vacations, and easily my favorite so far. If you haven't heard of Anna Maria island, you need to go. The water is incredible, it's cheaper to visit than a caribbean island, and there's just a ton to do.

We stayed at normal beach hotels and a bed and breakfast while we were there, and it was cool to switch things up.

After staying there for about 5 days, we wanted to seriously move to Florida. But…the houses cost $1,000,000 plus and there are more tourists on the island than locals.

Related: The 50/50 Split: Renting versus Buying

After talking to a bunch of the local people we met there, we decided that it might be a better idea to purchase an investment property there some day instead of trying to move there.

I didn't destroy any electronics on or after this trip (so far).*Fingers crossed*

4. Whatever place we pick from your suggestions

This summer – we want to do something in the caribbean again. We aren't cold weather people, and we prefer something tropical.

I'd love to hear your suggestions in the comments (or email, whatever works). I will just ask that you provide some specifics on the hotel/resort you stayed at and any money-saving or fun stuff to do tips you might have.

If you have something non-caribbean, I'm open to being convinced to go there haha.

Thanks in advance!

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Posted in: Travel Hacking

About Millennial Money Man

Bobby Hoyt is a former band director who paid off $40,000 of student loan debt in 18 months on his teaching salary and then left his job to run Millennial Money Man full-time. He helps other Millennials earn more through side hustles, save more through budgeting tools and apps, and pay off debt. He is a personal finance expert who has been seen on Forbes, Reuters, MarketWatch, CNBC, International Business Times, Business Insider, US News, Yahoo Finance, and many other personal finance and entrepreneurship media outlets.

View all of Bobby’s Posts

Comments

  1. What’s the reason for having that phone in a bag of rice two years later!? ???

    Best vacation we have ever been on was to Naples, FL. We also went to Sanibel Island (saw tons of dolphins) and spent a day at the beautiful Lovers Key State Park. Now I want to go back. Ha.

    It was awesome to cash flow such a memorable vacation.

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    • Heidi

      Yes, to Sanibel! Growing up my dad was in sales and was ALWAYS traveling for business. The upside was we always had frequent flier miles to use on vacation. We went to Captiva (basically next door to Sanibel) with friends from Atlanta (we were from CA) and it was AMAZING. My mom grew up in Hawaii and kept saying, “It’s just like home!” the entire time we were there.

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  2. Well earlier this week we were in the Cancun area. All inclusives are plentiful. Beautiful water. Good night life. And if you get bored there are also ruins and underground rivers to explore.

    Alternately earlier this year we went to Martinique. I wrote a post on it a while back. No all inclusive s here so it might not appeal. Beautiful beaches though and great cultural sites. Only French is spoken though.

    I’ve also done Costa Rica. It’s beautiful, but the all inclusives are kind of like warm, it’s more of a hiking and exploring place.

    Final option in hat region I’ve personal experienced, we did Atlantis once from a charity option. Expensive but the onsite watermark on top of the beach adds to the entertainment.

    I can recommend any of the above but it depends on what your looking for. If you provide some thoughts I can give you more on any of the four,

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    • I actually encountered a lot of English-speaking individuals in Martinique… though having a basic understanding for French certainly helps! It truly is a remarkable place, and I loved that there were no resorts. I was actually asked by some locals, “How did you know we were here? Most Americans have never heard of us.” Haha!

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  3. Punta Cana!

    We went on our honeymoon there and plan on going back. The weather was amazing the entire time we were there. We went snorkeling, sail boating, parasailing, paddle boarding, and more. (I can’t for the life of me remember the place we stayed at….maybe it was all a dream)

    The pool was shaped like a lazy river so floating around all day was a blast. Serves were the nicest people in the world! Knew exactly what drink you wanted first thing in the morning and made suggestions throughout the day.

    We used CheapCaribbean.com for our last two big vacations (Honeymoon & Friendcation). They make the process stupid simple and even plan for shuttling to and from the resort to the airport. Highly recommend giving them a call to get suggestions as well.

    Planning a trip can be so fun. Can’t wait to see what other readers suggest.

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  4. Melissa

    I would recommend the Atlantis and Cancun like the Folks above. If you try Cancun there is a little island offshore you have to visit Isla Mujeres. Feels like your out of the city and has a laid back island vibe. I have always wanted to stay there but have only done a day trip each visit. Also would recommend the Marriott in Aruba. Have stayed there for a week also and would go back. Beautiful desert island and beautiful resort that isn’t all inclusive. Forces you to get out and try some local places.

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  5. One of my all time favorite places is Cinque Terre, Italy. We just took a day trip there but I wish we could have just stayed there. It’s a really time part of Italy but incredibly beautiful. Summertime will definitely be super crowded but worth it! The food and gelato are incredible =). If you do decide on Italy — know that they’re not credit card friendly so bring cash! I haven’t been very active on my blog for a year but I did write down everything about Italy if you want to check it out =).

    If you don’t want to go that far then try Puerto Rico! There’s so much to do there and should be pretty affordable =). We did a snorkeling excursion in PR and went kayaking at night to see bioluminescence.
    https://www.tripadvisor.com/Attraction_Review-g612474-d1634272-Reviews-Bioluminescent_Bay-Fajardo_Puerto_Rico.html

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    • They both sound great! I think Puerto Rico is probably more up our alley this year, but I’m sure we’ll get the European itch soon. Thanks for sharing the link!

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      • Linda

        I’m going to have to echo the Europe trips. We went to Rome/Venice in March and it was amazing! Flights are super cheap right now as well. I highly recommend Rick Steve’s books and tours. Next on our list is Spain 🙂

    • Debbi

      I totally agree with everyone suggesting Italy. Try Siena, Positano, anywhere on the Amalfi coast.

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  6. Josh

    So many options! Really depends on your budget and time of year but we have been to a number of islands and one of our favorites is St. Thomas. Part of the USVI this island is beautiful. Though not in the caribbean Bermuda is tons of fun! Cayman islands are really nice but super expensive. Have you thought about Cuba, may not have all the plush tourist options but everyone who has been there that I know absolutely loved it. One really cool place that also isn’t technically caribbean is Los Cabos, Mexico, west coast and beautiful. Good luck and have fun!

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    • St. Thomas sounds really cool – honestly hadn’t thought about Cuba yet but I know a lot of people that want to go there soon. I figured I’d let them try it out first haha. Mexico just doesn’t seem like it would be as good as the caribbean, but every picture I see from there looks incredible so it’s probably pretty legit.

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  7. Take a cruise and go to multiple Carribean destinations. My favorite is the US and British Virgin Islands.

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  8. Oooooh. Mine is going to seem a little weird, but the best place I’ve ever traveled to was South Korea. It’s expensive to get there, but hot damn, it’s such a neat place! And it’s very different from other touristy destinations like Europe or even the Caribbean. I hope I can take Mr. Picky Pincher there some day, because it’s so much freakin’ fun. 🙂

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    • Woah that would be cool! Totally not the same, but I went to Japan a few years back and it was really cool to see how much different the culture was from ours. I’m sure it’s very different in South Korea too.

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  9. Markus

    We really enjoy cruises – “forced” relaxation, don’t have to worry about the food or where you will stay (or you can eat off ship when you are in port), and a relatively inexpensive way to see a few different places. Our favorite trips are the Southern and Eastern Caribbean islands leaving out of Puerto Rico – can’t recommend enough!

    When you do get the European itch, I recommend Greece. It was my wife and I’s favorite place we have been to. The historical sites, the Mediterranean, the laid back people, and the relatively inexpensive food, etc. are all reasons we would go back in a heartbeat. The biggest downside is the cost to get there. One of the next big trips we want to do is a Greek Isles cruise.

    Hope that’s helpful – enjoy your trip!

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    • Thanks Markus! We’ve actually never done a cruise before – almost EVERYONE around us has haha

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  10. JD

    Sleeping Bear Dunes (Glen Arbor, MI)

    It is such a wonderful place (in the summer!).
    Glen Lake has a pure sand bottom with water that looks like the Caribbean. We post pictures on social media and everyone thinks we are in Jamaica. There are miles of hiking trails, bike paths, conservancy lands, beautiful beaches…. its a wonderful place. Lodging is very expensive during summer months, however.

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  11. Katlyn

    The best vacation I’ve ever been on was definitely to Hawaii for our honeymoon. We went to Oahu and Maui and both were fantastic in their own different ways. Oahu was super busy (we stayed in a Marriott on Waikiki Beach), but we had to see Pearl Harbor. Diamond Head was also a fun hike with great views at the top. The Polynesian Cultural Center was a must see as well. Maui was our favorite island of the two though, we again stayed at a Marriott because my husband had enough points for us to book the entire trip on points. So we saved a lot of money by not having to pay for hotels and therefore were able to focus on spending our money on fun stuff to do and eat. I highly recommend building up points at one hotel chain because it can really save you a lot of money. Maui has the Haleakala crater which is awesome – the sunrise or sunset tour is a must. We did jungle zip lining which we also thought was fun. Snorkeling, horseback riding, a helicopter tour, and eating at Merrimans and Mama’s Fish House were also highlights. I know it’s not the location you were looking for, but it was a great time and the water is beautiful there!

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  12. We moved to Jacksonville Beach, Fl almost 3 weeks ago and love it here! It’s not a touristy place and is so laid back! We plan on renting for at least a year (I own an investment property in GA so they’re paying our rent!) and we’re hoping the housing market will go back down before we have kids in the next couple of years and then we can buy a place at the beach!

    Anyways, this isn’t the Caribbean, but hands down Hawaii. We’ve been to the Caribbean several times (we fly for free) and there is no comparison. We’ve been to Hawaii 3 times, got engaged and married there and it blows the caribbean out of the water. There’s mountains and cliffs right next to the amazing water. There’s a ton to do, especially if you like the outdoors. We compare everything to Hawaii and it falls short lol. Sure, it’s a long flight, but totally worth it!

    After saying all this, the only place in the Caribbean that I care to go to would be St. Lucia.

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    • Ah man we want to move to Florida so bad haha. Very jealous. A bunch of people have said Hawaii so far so I’ll definitely price it out. We have a bunch of points so we can probably get a decent deal going out there. Haven’t been to St. Lucia yet but would love to go.

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  13. The best vacation(s) I’ve taken so far were to the Bahamas. They were for spring break, but a small group of 4 or 6 would have just as much fun. I rented a big cruising catamaran with a dozen college sailors and friends. We sailed from Fort Lauderdale, FL to Bimini, Bahamas. The beauty of taking your own boat is you can island hop all you want. We stopped at North Bimini for customs and to pick up the dirt cheap, but delicious local rum, then figured out where the cruise ships were stopping and when. After that we hit the beach and at night we went to the small but fun local bars. When we got bored, we left the marina and anchored off the beach then took the dingy to shore and crashed the cruise ship parties. The next night we crashed their big pool party at the mega yacht marina. Then crossed the channel down to the small growing resort and infinity pool with karaoke at night. The last day we found a half-sunken freighter and jumped off, snorkeled around the reef growing on it, then spent the evening on a small, no-name island.

    All in all, it cost each person about $1000 for everything, minus bar money, but most of the bars allowed you to bring a cooler if you bought at least one drink from them. If you aren’t a sailor, you can hire a captain with the boat rental for a reasonable amount. If you can get some friends to come along, the prices are pretty reasonable and you get to be your own tour guide. And on the catamarans, there’s so much room that one year we had 17 people on the boat with everyone having plenty of room to get around and sleep. I’m hoping to go again, or maybe this time to a different Carribean Island.

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    • Dude all of that sounds incredible. Unfortunately…my wife gets really seasick on sailboats. We were going to do a catamaran trip in the Virgin Islands and did a little test run on a friend’s sailboat. Went terribly. One day I’ll do that kind of trip without her though haha

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      • Troy

        Good call on the trial run. Half of our boat was sick as can be on the return trip. Thankfully the trip to the islands was smooth and the ones who couldn’t handle the waves took some meds and slept thru the crossing.

  14. Meg A

    It really depends on your interests/travel goals (relaxation, adventure, culture, all of the above).

    If you want a little of all of the above in an affordable price range – check out Playa Conchal, Costa Rica or Tamarrindo, Costa Rica (North Western Coast). We stayed in Playa Conchal and visited Tamarrindo. The people are some of the most friendly I have ever experienced and the food is phenomenal. You can do everything from relax on the beautiful beaches, to hike and explore the mountains/volcanoes/rain forests. The culture is rich, and possibilities are endless. Costa Rican coffee is the BOMB!! I hear the East Coast is also amazing. They have a wet and dry season, so make sure to schedule during their dry season.

    If you’re adventure finders, the Rocky Mountains, in CO are always beautiful and romantic in the Summer. Hike, bike, raft, camp, etc…

    Now, if you have the $$$$ to spend and want to cross the pond, Italy is my fave. Florence is culture heavy and incredibly romantic. Travel South to Rome and/or Naples, then hop a ferry and visit the island of Capri from Sorrento. It is one of the most beautiful places I have ever been. Its very expensive to stay on the island (we took just a day trip) but if you let me I could spend a lifetime there.

    I could really go on and on. Travel is definitely my financial vice..(insert guilty face)

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    • Really the main goal is just to relax. She works at a school district so her year is coming to a close, and I’m terrible about working too much so I just need a place to turn my brain off.

      Thanks so much for all the tips – I’ll check into these!

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  15. AARON FLICK

    St. Lucia was amazing we stayed at Sandals Grande. The thing I love about Sandals St Lucia was the three different resorts on the island all with different styles. They provide a shuttle that runs all day which provide you access to the different restaurants and you can experience different parts of the island. The local people off the resorts were super friendly, so you’re not stuck only on resort. We volunteered at a local school reading to kids which was an amazing experience. We also loved the dune buggies around the island, rainforest zip lining, to one of my favorite experiences partying in till 6am at the Friday night block party in town. They now have over water bungalows if you want a more over the water feel.

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  16. My pick is Bermuda, all though not technically in the Caribbean, possibly the best island of them all. They’re actually hosting the America’s Cup (starting today I believe), over the next month. I’ve been there around 7 or 8 times (admission: I do have family there). It’s very unique, some of the best beaches in the world. It would be more expensive than some of the other locations, but an experience second to none. : )

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    • We’ll put that on the list – going to go over everyone’s suggestions today! Got way more than I thought I would haha

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  17. Seth

    In the Caribbean check out the US Virgin Islands. They are celebrating their 100th year anniversary of Denmark selling the islands to the United States this year. To celebrate they are giving a $300 credit to travelers for activities at one of the three USVI: St Thomas, St John, and St Croix. Must spend 3 nights there and only good for 2017. I’ve never been but this might be a good year to go.

    But I will say the best vacation I’ve ever been on was earlier this year my wife and I went to Thailand. Took a week and a half and explored the city life of Bangkok, rainforests & elephant farms in Chiang Mai, and then island paradise of Ko Phi Phi and Koh Lanta. HIGHLY recommend this once in a lifetime trip. It ended up being very affordable trip to my surprise. The food was delicious, the people were extremely friendly, and the views were amazing!

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    • That’s interesting on the $300 credit – USVI has been one of our first choices so far so this is definitely good to know

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  18. Anon

    Maui is amazing. Do the Road to Hana trip for amazing scenery and go all the way around the island. Also, Haleakala mountain for sunrise is a must. You can see a sunrise from above the clouds. It’s amazing.

    You can stay in the big resorts on the west side, or go to Kihei and stay at a rental condo for a good price as well. Beautiful beaches in many places and lots of hikes and tourist things to do

    Second choice is Puerto Vallarta. Unlike Cabo, a desert, PV is a jungle climate and is green and luscious. Lots of tourist things to do and good service, since the whole economy depends on tourism.

    Third choice is a cruise, say for a week or 10 days. Great food, visit multiple places and you can really unplug since your cell phones usually won’t work and internet access is really expensive. I’ve heard really good things about the Alaskan cruises. I’ve done Mexico cruises myself and enjoyed it. Seasickness is a concern, but given the size of the ship, it is less of a concern and it’s manageable with meds.

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    • Puerto Vallarta sounds like a really cool option! My wife has done a cruise before and didn’t get sick, so we’ll check into that too.

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  19. Coming from the Midwest, we’re not huge fans of the heat/humidity. We tend to target the mountain states and northern lakes to beat the summer heat. My favorite summer trip was Yellowstone National Park. We rented a camper and spent about a week on a road trip to Devil’s Tower, Wyoming and in Yellowstone itself. You’ll never look at nature the same way again!

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    • My wife is getting more open to hiking and camping, so this could definitely be something we do in the coming years

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  20. Ali

    I play semi pro basketball which takes me all over the world. When I played in Australia I learned about couchsurfing and did it in Cairns, AUS or the Great Barrier Reef. It was the best trip I have ever done. While you are doing it as a couple I highly suggest going there. The reef is amazing, the hikes and hidden waterfalls, and the animals you can see is brilliant. Australia is typically expensive but plenty of ways to do everything having a great time and not spend over your budget. The couchsurfer let me use his Nikon underwater camera and hooked me up with an awesome local deal for scuba. I did a day adventure that went on a river boat ride to see the alligators, hike in the rainforest, and to see the views. I met up with a group of couch surfers to go on a hike and find hidden waterfalls. It is warm up north Australia as well and Hawaii is layover option when flying 🙂

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    • I’ve always wanted to go to Australia – that and New Zealand are definitely on the bucket list!

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  21. Arenal region of Costa Rica. One of the most beautiful countries in the world. Spent all of our time outside hiking, ziplining, etc. It’s safe and the locals are so nice

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    • We have some friends that go to Costa Rica quite a bit – seems like a really cool place to visit for sure

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  22. Hey there, M$M! I’ve been reading for a while but this i my first time commenting. One trip I have taken in the Caribbean recently that I really enjoyed was to the island of Martinique. There are a number of beaches to visit (more beaches than people, it seemed)! You can check out the botanical gardens, see where rum is made (and try all of the cocktails). My favorite part was that we happened to eat at a restaurant that was actually the balcony of the chef’s house. His girlfriend was the server/hostess. It was a prix fixe menu and everything was wonderful! The only other table in the “restaurant” hosted a French family with two little girls who loved having us practice our rudimentary French with them. It’s not a resort island (there’s a story about why Martinique won’t let cruise ships stop there anymore) so very few Americans go there.

    For a non-Caribbean travel experience, I cannot recommend Iceland highly enough. I just went there last month for my honeymoon and there was so much to see! We hiked on a glacier and swam in a geothermal pool and got spewed on by a geyser and saw giant waterfalls up close and visited a punk rock museum and marveled at the Northern Lights. The food is really good and the landscape is just breathtaking! There was no way we could see everything in the week we were there.

    In both places, many people speak English and both places drive on the right side of the road, so they are good “transition” countries to visit. We were treated with kindness and warmth in both locations. I’d go back to either of them (and I typically prefer to visit new places each time… but these were incredible!).

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    • Hey Kelsi!

      1 – thanks for commenting 🙂 I know it’s a bit of a jump for people that haven’t done it before so I appreciate it!

      I’m going to sit down with my wife today and go through all of these options – Martinique is definitely on the list. I’d LOVE to go to Iceland as well. Looks incredible!!!

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  23. Another awesome place is Santori Greece. It is a beautiful place, people speak english, and the sunset is wonderful.

    Of the places you listed, I vote for the Bahamas :).

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  24. Consider something beyond the Caribbean!

    Europe is the last continent I visited…and it ended up being my absolute favorite. Summertime is stunning and warm and you have lots of options for everything from beach to city to mountains to clifftop towns.

    I travel full-time and Europe is still my favorite so many years later.

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  25. Maui! Been to a few Caribbean islands but none compared. Maui has so much to do and the people are fantastic. The water is also freakishly clear. Like see the to the bottom of the ocean floor when in a hundred feet of water clear. But, not cheap.

    Thanks for the Anne Maria island suggestions. We have been trying to figure something out for ourselves this year.

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  26. A couple days behind but I would be upset if I didn’t mention Turks & Caicos specifically Provodenciales. Most relaxing place I have been to and you can do all sorts of activities if you want. Third largest reef to explore and islands full of exploration to be seen. We sat on the most amazing beach I have only seen in magazines and watched a wind surfer. That was the only other person around!

    Easy to get to and find all sorts of amazing things to do. Highly recommended!

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  27. We got married in St. Lucia– if you guys like diving and snorkeling, you can do it for cheap right from the water from a great black sand beach called Anse Chastanet. And you can gawk at the ridiculous hotel right up the mountain http://www.jademountain.com/ (never stayed there btw).

    We always use AirBnB when we travel. You get a great authentic experience (especially if you book a private room with a host), it’s super cheap, and you can often negotiate other (possibly free) services like a pick-up drop-off from the airport or road travel. The people are super friendly there (tourism is a money maker obvi). We went on a hike to gorgeous water falls, visited geothermal pools with “healing” mud beneath a volcano, and ate awesomely fresh food near the main Piton in Soufriere.

    Our favorite place to visit in the Caribbean region that is OUT of the hurricane belt is Aruba. It’s a Dutch island. Everyone speaks English, the roads are well-maintained, and the beaches are stunning. Plus, flights can be pretty cheap since Southwest bought out AirTran a few years ago. Eagle beach has beautiful sand, and the rest of the island has great hiking with really cool tide pools that are crystal clear and perfect for snorkeling. Hope you guys have fun!!

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  28. tomkat stage

    Aruba is a fantastic island to visit. We have been traveling there every year for the past 15 years.

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