The Ultimate Guide to the Caribbean

Some of you who followed our blog last year might know that we took a two-months break and started our long planned tour through the Caribbean. While at first instance, we wanted to stay on each and every island, soon we figured out that it is impossible - not just in terms of time but due to monetary reasons. The flights between the islands are horrendously expensive due to the fact that there is no competition and you cannot just take the boat. We didn't mind a lot since our plan was to see as much as possible and therefore teamed up with InterCaribbean Airways - from our point of view the most reliable of all Caribbean airlines (excluding JetBlue servicing the big islands). So after having talked about the connections, the most important is to decide which islands you want to see. Then you should check what the connections are and how you can combine it with a stay. For example we passed by St Marteen and even tough we did not plan to stay overnight, turned out that it was worth staying there for a night. If you have any further questions, ask us, we are happy to help. So let's start on our itinerary:

Cayman Islands

Our first stop were the Cayman Islands. I have to mention that we flew in with Austrian Airlines to Miami (unfortunately they are not flying to Havana during summer, they do fly but only in winter) and from there directly to Grand Cayman with Cayman Airways. Even tough we had booked the later flight, we managed to be re-booked on the spot to the earlier flight leaving Miami for Grand Cayman. During our one-night layover we stayed at the Caribbean Club, which is a luxury serviced condo with two- and three bedroom apartments directly on the famous Seven Miles Beach. My parents loved the Cayman islands as it is very similar to Florida, huge supermarkets, highways, huge streets and superb water quality! Conclusion: Extremely expensive but partly worth it. 


You name it, this was supposed to be the highlight of our trip. And in fact we haven't been disappointed. We didn't risk flying in directly from the US as a non-US citizen so we stopped by the Cayman islands which was even cheaper than the direct flight. In total we spent 5 nights in Cuba, which of course is just way too few. To better see the island I recommend 10 days to 3 weeks. Our first stop was Havana with 2 nights (we stayed at the Kempinski), drove to Vinales for a day (cigar plantations), then stayed a night in Trinidad (at the Grand Hotel) before we headed to Varadero (we stayed at Ocean Vista Azul) for a night. In any case plan at least 3 nights in Varadero to enjoy the pure waters, however be aware of the massive amounts of tourists and their uncomfortable habits (lots of drunk and partying guests, too). Me, being a more the laid back individual tourist, would avoid Varadero for the authentic Cuban feeling.  Staying at the Gran Hotel Manzana in Havana gives you access to the most unique views of town and swimming in a modern infinity-pool over a city that seems to be still in 19th century is just fabulous and worth every peso.


After our stay at the Hotel Nacional for a very short layover we arrived at the airport 3 hours earlier as suggested by the concierge, however turned out that one hour would have been enough! We were actually ready for the main highlight of the trip: Jamaica, home of coolness and Reggae lifestyle. We rented a car and toured the north coast of the island. Even tough we had a car accident  and spend our first evening at the police station plus calling around the world the following day, Jamaica was the best part of the trip for all of us - me, Lukas and even my parents. My first feeling about this place was that I am going to hate it, interestingly when I woke up the first thing I was thinking of was to never leave again. We had the chance to stay at the most unique places including Kanopi House (wow to location, service and ambiance), Round Hill Resort (residence of Ralph Lauren) and Half Moon Resort (a Caribbean classic with old school glam). 


While a must do, this place would be one of the first ones I would cut off the next bucket-list. Not only are the hotels ridiculously expensive, so is the food and drinks plus activities. Even tough we spend the majority of the time on the main attraction: Eleuthera and Harbour Island, we haven't been blown away by the beauty but by the sky-high prices. A dinner at a medium priced restaurant? Well, prepare to pay USD 170+ for the two of you. Hotels are totally bad for what they charged. Considering we paid nearly as much as for a room at the Ritz Carlton in Hongkong, our hotel in Harbour Island was nothing better than a nice youth hostel. Renting a self service apartment is a good option from our point of view but bring as much food as you can beforehand. 

Turks- & Caicos Islands

Our next stop was one of the most stunning archipelagos in the world. While not much to do besides snorkeling, water sports and relaxing under the sun, we enjoyed the two calm days at the Gansevoort property. A cool, young and dynamic resort for families and couples alike. Who should go here? Mostly families who want to do a beach vacation. Followed by our baggage being left at the Bahamas, we didn't mind much as we only needed bath shorts and a shirt (always pack this in the hand luggage as you will have the case to arrive without suitcases more than once). The next destination was Dominican Republic, where we flow directly to Santiago.

Dominican Republic

Never would I have thought about this being such a beautiful country. We landed in Santiago, took over our quite new rental car to drive to Las Terrenas on the Samana peninsula (very hidden and not much tourists) where we stayed at the Sublime Samana, a member of the Small Luxury Hotels. After two nights in this area where we went to Cascada El Limon, we headed straight through the island to the capital - Santo Domingo. To all my surprise Casas Del XVI turned out to be one of the best kept hotel secrets in the world - beautiful interior design and butler service at its best. Another two nights in Santo Domingo, where we tried to find an Apple store without success, we made us on our way to Punta Cana. Lukas' iPhone wasn't able to turn on again so we were getting really stressed to find assistance, which was impossible in the Caribbean - welcome to the end of the world. Our base in Punta Cana was the beautiful Eden Roc at Cap Cana. Would I go back? Yes immediately as Dominican Republic offers something for any kind of traveler. 

Puerto Rico

The most convenient and perfect flight (a JetBlue flight from Punta Cana to San Juan) later, we got our rental car by Sixt (plus an upgrade to a limousine as well). Unfortunately, at this point I have to declare that the only mistake was that I planned two nights only for Puerto Rico since it felt like back to civilization (it's US territory and all US brands can be found here) and the nature being totally stunning, like in an Avatar movie. We spend one night in Rincon (at Horned Dorset Primavera), whereas we arrived in style with the first night at the Ritz Carlton Reserve Dorado Beach. Both hotels were flawless, however as common in the US breakfast is extra as the service charges are. Keep that in mind and then Puerto Rico seems like the even more developed Dominican Republic. 


Short flight from Puerto Rico to Anguilla where we stayed at the Zemi Beach Hotel. Lovely island, a bit expensive but famous for the best food of the Caribbean. Not much to do besides snorkeling and sunbathing. Would spend there a maximum of 3 nights without car.

Saint Barths

Yes, this was another highlight of our trip with arriving to European territory after weeks again. Super chic airport, even more luxurious hotels and resorts plus trendy vibes in Gustavia and don't even think of going to the Beach Club without a fashionable attire. Unpack your Orlebar Brown's combined with a Ralph Lauren linen and you can't get wrong. Even tough Saint Barths is told to be expensive, we didn't find the food to be more expensive than anywhere else, in contrary it seemed pretty fair - also the food was fabulous and service at the hotels just like at Cote d'Azur or Switzerland. Definitely go there if you think you are ready for a Caribbean version of Saint Tropez. Stay at Le Toiny or Le Guanahani.

St Kitts & Nevis

Even tough Park Hyatt opened their first Caribbean resort here, we weren't impressed of either of the two islands. While Nevis is very old-fashioned and has nothing to do (we weren't even sunbathing as the beach was not as nice as on other islands plus the pool not inviting), there comes the fact that you can drive around the island in an hour or so. 

St Kitts' Southern peninsula reminded us of Amalfi Coast just with no flowers and no infrastructure, so it works if it is a fair deal in terms of price, however we would not take the long flight just because of these two islands. 

British Virgin Islands

Another stunning place that seemed to be more than perfect. Let me say that this place is only accessible to the top one percent, considering that you have to stay at one of the few privately owned islands in order to fully enjoy the beauty of these islands. We stayed at Guana Island which was the best resort we have ever stayed at - forget Aman, Guana Island is what it takes to really turn off and dream away. Result: Go there with your entire family or as a couple, you will be blown away. 


Before the trip, I thought that this island can be a real highlight. We dreamed of rum caves and stunning, long beaches. Turned out that our hotel Cobbler's Cove was nice enough and had access to the beach but everything felt cramped and the service wasn't the best we have seen. Many honeymooners prefer to go to Barbados, however it would be too calm for my kind of taste. * maybe I should note that we spend two nights in Barbados and on both days it rained so that could have influenced our opinion


After Barbados we boarded a flight to Trinidad and Tobago in order to connect to Grenada. Tough a beautiful island with lots to see and do (also called the spice island), it is one of the destinations you are fine having seen once. The beach was nice but we couldn't access it as it was pouring for all three days. Luckily we stayed at Spice Island Beach Resort, the island's number one so we were treated well at one of the world's best all inclusive resorts. Generally a nice island but not worth the long flight alone. 

St Lucia

Another total gem was this picturesque place, which we arrived after having survived the shock that our airline didn't show up in Grenada and so booked us on a flight to Barbados to change there for a flight to St Lucia. It took us a full day to fly the normally one hour flight initially booked. If you ever look for that one honeymoon spot, go for St Lucia. It was the first open-air hotel room we have ever stayed in and indeed the views were breathtaking to every hour of the day. Would you be afraid if your hotel room has no lock but is open to the nature? I would have been, but if you see the location you immediately loose all fears. Also the beach was stunning as was the food and the service. Ladera Hotel is the place to stay. Worth the long transatlantic flight? Yes!

Antigua and Barbuda

The last full stop was the island Antigua which we accessed by plane via Barbados again. Actually we were happy to leave LIAT (the local airline of the southern Antilles) behind us after the last flight with them. Just right in time for a celebration on our last island we checked-in at Hermitage Bay - one of my favorite hotels in the world. I don't know if it was because we were so hungry, but Lukas was joking about the guy in the pool looking similar to Ryan Reynolds. In the end Blake Lively popped up around the corner and we were sure, the Hollywood couple loves this resort as much as we do. Mrs V and the entire crew were putting the cream onto the cake - Hermitage Bay was the ideal place to end this trip!

Islands we skipped

Martinique, Dominica, St Vincent and the Grenadines, Tobago, Guadeloupe, Montserrat, Aruba, Curacao, Bonaire. We planned to go to St Vincent and Mystique as well as Martinique, however due to our preference to head to New York City after 7 weeks of slow life aka the island life, we were happy to change bath shorts for Steaks, noisy streets and amazing clubs.