Traveling to the Caribbean doesn’t have to be like that though. There are plenty of other options to have an indie travel experience on most all Caribbean islands, and it all starts with accommodations.

You don’t have to stay in a resort. You don’t even have to stay in a hotel. A great way to take charge of your trip and itinerary is to rent a house, condo, or apartment during your trip to the Caribbean.

Benefits of renting

Rental properties are popping up all over the world, and this option is quickly becoming popular for travelers who really like to dig into the local culture and get something more out of their trip than simple relaxation (not there’s anything wrong with that). In an area like the Caribbean, where resorts are the norm, it’s refreshing to get out of the gates and be able to interact with the local people.

The Caribbean is a beautiful area of the world, and many independent travelers don’t think of it as a destination because of their preconceived notions. There are some amazing rental properties available that could completely change your perception of islands like St. Thomas, Jamaica, and the Dominican Republic.

Price is often touted as a benefit of heading to an all inclusive resort, but with a rental, it’s possible to get by for even less money than staying in a resort. If you or someone traveling with you likes to cook, money can be saved by shopping for food and making your own meals. Markets are often the best place to truly understand and learn about the culture you are visiting, and taking a trip to the local markets each day can be an experience in itself (and it’s free!).

If you’re the type of traveler who has stayed in resorts in the past but still enjoy getting out and exploring the country you’re visiting, you can save quite a bit on transportation costs by staying in the city instead of on the outskirts of town, where many resorts tend to be located.

Rentals also give travelers the added benefit of options. Even if the mega-resort has 5 or 6 restaurants, staying in a city can provide you with many more dining and entertainment possibilities. If you end up not liking the food at a resort, you’re kind of stuck.  If you are renting and have a bad meal at a local restaurant, you simply choose another place next time out.

Where to go

Puerto Rico

Puerto Rico is one island in the Caribbean that is not littered with giant, all inclusive resorts. There are plenty of massive hotel chains, but there are also plenty of rental opportunities. Traveling to Puerto Rico is unique compared to many other Caribbean islands in that it’s quite easy and safe to rent a car and explore the entire island. Renting a house, condo, or apartment along the way is a great way to see what may soon be the United State’s 51st state.

What to do:  If you like the outdoors, then Puerto Rico has you covered.  Scuba diving, snorkeling, hiking, ziplining, biking, fishing, surfing, and golfing are just the tip of the iceberg.  Not to mention that Puerto Rico has the only rainforest located in the United States.  If you’re a beach person, then head to the islands of Vieques and/or Culebra for some crystal clear waters and white sand beaches.  If you like cities, then San Juan is the place for you.  This colonial city is perfect for photographers, and Old San Juan is easily walkable, with some top notch restaurants littered about the city.

Price: Travelers looking for rentals in San Juan, Puerto Rico can find them for as low as $50USD per night, as high as $450USD, and everywhere in between. Head to the island paradise of Vieques, and it’s possible to rent a place for as little as $55USD per night, or if you are one of the lucky ones who just won the Powerball last week, you can spend $3000USD per night for a 6-acre estate.

Jamaica

Jamaica is an extremely popular spot for travelers to the Caribbean, but many have a false assumption of safety within the country.  Many fear staying outside of resort walls. While it’s always important to exercise caution no matter where you are (even at home), Jamaica is largely safe for those travelers looking to get a different glimpse of the island than most people get, provided you use some common sense. If you’re looking to get away from it all and find the seclusion that’s simply not possible at a resort, then renting is the way to go in Jamaica. There are plenty of cottages and houses nestled in the foothills and near smaller towns that tourists may not typically visit.

What to do:  So many people come to the Caribbean for the beaches and ocean.  If you’re an avid diver (or want to become one), then check out some of the nearby reefs at Runaway Bay and Ocho Rios.  If you’re a coffee lover, then head to the Blue Mountains to try some of the best java in the world. If rum is more your thing, then tour the Appleton Rum Estate, where you can experience the production process of their rum and learn about the unique distillation process in their 200-year-old pot stills.  One of the benefits of traveling to Jamaica is how much different it is than the rest of the islands in the region.  The blend of Caribbean and African cultures makes Jamaica stand out, and often some of the best experiences come from conversing with the locals or stumbling into a nearby bar for some music.

Price: Find an apartment or condo in Jamaica for as low as $45USD/night. If you have a higher budget and want to pamper yourself, then stay in many of the amazing homes available, some for as high as $11,000/night. Of course there are many options in between, with a good number of places being available for under $100USD per night.

Virgin Islands

Both the British and US Virgin Islands provide unique experiences for travelers to the Caribbean. St. Thomas is a major cruise ship port, so keep that in mind if you are planning an indie trip here. Cruise ships don’t arrive every day, so if you are looking to avoid the massive crowds they bring, you may want to plan your trip around them.

A quieter alternative is nearby St. John, especially if you rent. Two-thirds of the island is a National Park, and the world class beaches make this a prime spot for beach bums. There are some amazing rental properties for all budgets here, and if you want to get away from it all, consider getting a place high up on the mountainside.

Tortola, a British Virgin Island, is about 60 miles from Puerto Rico and about 20 from St. Thomas. Like St. John, Tortola is a great place to come for those who like the beach. There are also other outdoor activities to be had, like hiking in The Sage Mountain Park, which has the tallest mountain in the Virgin Islands.

What to do:  If you’re heading to the US Virgin Islands, each has its own highlights.  St. John is the place to go if you’re an outdoorsman.  With two-thirds of the island as a national park, this is the least developed of the US Virgin Islands, and it’s the easiest place to strap on some boots and head out exploring.  If fishing is on your trip itinerary, think about chartering a boat and head out for some deep sea fishing, a great way to spend a day.  St. Thomas is a shopping mecca, so if you plan on bringing back some souvenirs and gifts, then this is place to go (just try to visit on a non-cruise ship day).

The British Virgin Islands boast more than 40 different islands to whet your appetite.  Tortola is the most popular, and you can head up into the mountains or chill at the beach (or both).  Snorkeling and scuba diving are extremely popular here with the crystal clear waters and abundance of underwater activity.

Price: Rentals in the Virgin Islands can be a little pricier than other Caribbean islands, but budget travelers can still make it happen here. St. Thomas has a few places around $50-$70USD/night, but expect to pay closer to $100USD. St. John and Tortola are both a little higher, with rentals as low as $95-$100USD, with the norm being closer to $150USD/night. Of course the sky’s the limit if you have the funds to do it, with rentals in all three places in the thousands of dollars per night.

This post is sponsored by Flipkey.  Flipkey is a great resource for finding rentals around the world. With over 10,000 properties in the Caribbean, FlipKey has great local options for indie travelers. FlipKey puts you in touch with vacation rental owners who can provide excellent local information and tips – not to mention good deals on lodging. They also provide travel tips and news on the FlipKey Blog.  

Photo credits:  Flipkey, Chaoleonard, Adam Seper, Ben Whitney, 

While the majority of travelers visit the Caribbean during the high season – December to March – which also coincides with the cold season in the Northern Hemisphere, the islands are cheaper to visit and offer excellent things to do during the rest of the year, too. Sure, you might end up in a storm or two, but that’s not always the case and there are always other things to do.

The present itinerary highlights the most visited islands in the Caribbean but it’s definitely not a sand-sea-sun itinerary.

Day 1-2 The Bahamas

Fly into Nassau. Enjoy the Old Town and visit Fort Fincastle. On the second day, head to Eleuthera, which can be reached by boat. Eleuthera is famous for its pink beaches.

>>read more about 5 days in the Bahamas

Day 3-4 Puerto Rico

You can fly via Fort Lauderdale into Puerto Rico from The Bahamas and it won’t exactly be a cheap option. But when you want to cover at least 4 islands during a 10-day vacation, flying becomes a priority.

Spend the first day getting to know Old San Juan , with its forts and city walls. On the second day, visit Ponce, easy to reach by road. Renting a car is probably the best option in this case. Visit the cathedral and enjoy a tour of a coffee plantation.

>>read more about 5 days in Puerto Rico

Day 5-7 Jamaica

Fly into Kingston or Montego Bay.

Make sure to take a scenic tour of Kingston. All you need is a map and your camera.

You can also plan to be more active when visiting this lovely island, but make sure to rent a car in order to get between places easily. You can take a canopy tour or you can climb a waterfall.

You must try the Caribbean cuisine and the famous Jamaican dishes.

>>read more about the Things to do in Jamaica

Day 8-10 US Virgin Islands

St. Thomas is ideal for those who want to shop and visit the popular attractions. St. John offers a nice scape from the crowds and is incredible for snorkeling. St. Croix is for the history buffs . Virgin Gorda is for the high –end travelers.

St. Croix is the least visited of the USVI and the most remove of them. So, if you are looking to escape the mass tourism, this island is your target. You can even choose a farm stay. You can visit Estate Whim Plantation Museum, which is the oldest sugar plantation museum in USVI. Fort Christiansvaern now highlights the local history but it used to protect the town from pirates.

On St. Thomas, visit Blackbeard’s Castle, which is actually a watchtower built by the Danes. Bluebeard’s Castle, on the other hand, is a fortress, also built by the Danes.

>>read about Choosing the right Virgin Island for you

Just in case you want to visit the islands in other order, here is some information:

>>Getting from Puerto Rico to St. Thomas

Photo credits: The Bahamas , Puerto Rico , Jamaica , Fort Christiansvaern

The best time to visit San Juan is from mid-April to June when the crowds are gone and the rainfall is not at its peak. It’s also the time when the prices are low and you can find good bargains.

It’s a very good idea to rent a car for some of the day trips. It saves time and allows you to explore the area at a difference pace than if you were to relay on buses.

>>read about the Things to do in Puerto Rico and book a flight to Puerto Rico

Day 1 San Juan

San Juan is the capital of Puerto Rico and where you’ll be landing. Although Old San Juan is charming , find a place to stay closer to the beach rather than the historical area. Depending on when you plan to visit San Juan, you’ll pay from US$52 per night for a double room in a hostel located close to the beach.

Take advantage of the first day to get to know the city and the area you are staying in.

>>book a room in a cheap resort in Puerto Rico

Day 2 Old San Juan

The old city is dominated by two forts and city walls dating back to the 15th century. Allow for an entire day to spend time on the narrow streets , getting wonderfully lost. Stop in the plazas to do some people watching. Take a lunch breach and delight your taste buds with Caribbean food . And yes, the best way to explore San Juan is on foot.

El Morro Fort is located at the entrance of San Juan Bay and offers stunning views of the area. San Cristobal is the largest Spanish fort in the USA and also offers amazing views of the area. Also in the historic area you can find San Jose Church, San Juan Cathedral, and San Juan Gate.

Take a stroll on the Paseo de la Princesa ,a promenade along the city walls. During the weekends, the promenade is filled with artisans and musicians.

>>read about Old San Juan : what to expect

Day 3 El Yunque Rain Forest

Take the Highway 187 – offers a superb scenic drive- to El Yunque , the only rainforest in the USA.

There are interesting trails in the forest for any fitness level. Make sure to get a map from the visitor’s center. The main trails include El Yunque Trail , Big Tree Trail and Bano de Oro Trail.

Day 4 Vieques

The islands are easily reachable by ferry from Fajardo. Once on the island, opt for the Publicos.

If the moon phase is right when you visit Vieques, consider a tour of the bay home to bioluminescent dinoflagellates, which glow when agitated. The only way to experience this is as part of an organized tour.

Otherwise, just plan for a relaxing day walking on the beach and soaking up the Caribbean feeling. Pack a picnic basket and relax in nature.

>>read more about Getting from San Juan to Vieques

Alternative Day 4 Ponce

If you don’t want to see the bioluminescent organisms (or just end up in Puerto Rico at a wrong time for that tour), plan a day trip to Ponce, the second largest city in Puerto Rico. It’s easy to reach by road and the drive is spectacular.

In Ponce, don’t miss Ponce Cathedral, Parque de Bombas – the old firehouse-, and a renovated coffee plantation. Do some people watching in Plaza Las Delicias.

Day 5 Culebra

Ferries to Culebra also depart from Fajardo and you can easily plan a day trip.

Culebra is home to some of the most beautiful beaches in the Caribbean and Flamenco Beach is the most popular. Plan to spend some time on the beach , snorkel and just soak up the atmosphere.

>>read about the Best Beaches in Puerto Rico

Photo credits: San Juan
, Old San Juan , El Yunque , Vieques , Ponce , Culebra

Itinerary assumptions

• You will be flying into and out of Nassau
• Try to find a hotel or guesthouse located further from the tourist areas
• Most tourists come to Bahamas when it’s cold in the Northern Hemisphere. You can save some money by choosing the off-season but chances are you’ll be rained on.

>>book a flight to Bahamas

Day 1-2 Nassau

Nassau is the capital of The Bahamas and the city where you’ll be flying into. It’s the hub in the area, therefore gets a lot of flights and chances are you’ll score a good deal if you book in advance and fly during the shoulder season.

Take advantage of the first day to take a walk in the Old Town. It is an interesting mixture of brightly colored Caribbean houses and abandoned buildings. By the time the sun sets, make your way to Fort Fincastle, located on a small hill south of the town. To go on a tour you have to get to the fort before 3 p.m.

Start the second day at Potters’ Cay, located under the Paradise Island bridge. Try the fresh conch salad and then head to Straw Market to test your haggling skills when buying souvenirs.

>>read more about What to Eat in the Caribbean

Day 3-5 Eleuthera

There are ferries connecting Nassau to Eleuthera (M/V Sealink is one of the companies to look for).

It is the fourth most populated island in The Bahamas , offering pink beaches and massive coral reefs. Harbour Island, located close to Eleuthera (10 min by boat), has been designated by Travel & Leisure magazine “The Best Island in the Caribbean” in 2005. It is also famous for the pink beaches. You can spend an entire day on Harbour Island , walking on the beaches and just soaking up the atmosphere. Pack a picnic basket, too.

>>read about the Best Bahamas Beaches

Aside from soaking up the sun on the beaches, you can also swim, snorkel, surf, dive, fish, sail and try some water sports.

The next day, spend some time checking out the island’s attractions. There are some interesting caves on the island, some of them home to colonies of bats. Make sure to have a flashlight with you and wear appropriate clothing for hiking.

Alternative day 5: Freeport

Alternatively, you can travel back to Nassau on Day 5 and catch a flight to Freeport . Port Lucaya is the tourist hub of the island and you can spend some time on one of the beautiful white-sand beaches in the town.

Photo credits: Nassau , Harbor Island

Weather

The temperature starts to go up but the chance of precipitation is still low. No need for a jacket at night now, but make sure to pack light clothing for the day.

Sample temperatures

Freeport avg high 25C/77F ; avg low 18C/66F
Nassau avg high 26C/79F ; avg low 18C/66F

>>read more about Weather

Accommodation & Flights

March is when the Spring Break falls so the prices stay high and the crows of students head to The Bahamas. Expect the hotels and the resorts to be (almost) fully booked and make sure to do the reservations in advance . The same is valid for flights , so plan ahead if you want to fly here during March.

Read more about:
>>Best Bahamas Hotels
>>Most Romantic Resorts in The Bahamas
>>Best Tennis Resorts in The Bahamas

Things to do

The youngsters pretty much fill the beaches now , looking for parties, tanning and fun. You can escape to less-crowded beaches , if you don’t fancy the hustle and bustle.

Or you can put on your walking shoes and explore the historical sites in Nassau. The three main forts – Fort Charlotte, Fort Fincastle and Fort Montagu – offer excellent insight into the history. Plus, the views of the areas are amazing.

Put on your walking shoes and head to one of the trails in the national park. Explore the underwater caves or just soak up the sun on the beaches.

If you travel with the kids, take them to swim with dolphins. Or plan to visit some museums.

Photo credit

Weather

Remember the weather in January? Well, it’s the same in February. It feels like early summer, with mild temperatures and almost no rainfall. It can be cold at night, though, so pack a jacket if you like to stay up late.

Sample temperatures

Freeport avg high 23C/74F ; avg low 17C/64F
Nassau avg high 25C/77F ; avg low 18C/65F

>>read more about Weather

Accommodation & Flights

February falls during the high season , so expect to find high rates at the hotels and the resorts . The same is valid for flights : prices are high and the demand is just as high.

Book the flight ahead of time and take advantage of the deals available. Or use those saved miles to lower the price. Otherwise, a hotel & flight package can save some money, too.

Read more about:
>>Best Bahamas Hotels
>>Most Romantic Resorts in The Bahamas
>>Best Tennis Resorts in The Bahamas

Things to do

What do you dream of when you head to the Caribbean? Of course, the long days at the beach . And Bahamas has plenty of beaches for its visitors. Soak up the sun, swim, snorkel or try other water sports.

If you want to do some shopping, try the Port Lucaya Marketplace. There are souvenirs to choose from, excellent food , such as conch , and don’t forget the tropical fruits, either.

Nassau offers a lot of historical sites to visit. You might want to visit at least one of the three main forts : Fort Charlotte, Fort Fincastle and Fort Montagu. They offer excellent history lessons and you get to see lovely views of the surrounding areas.

You can also explore the beaches , caves and trails in the Lucayan National Park. If you like to be active, put on your walking shoes and walk on the trails. Otherwise, you can just enjoy a lovely tan on the beaches.

Photo credit

Weather

The weather in January feels like early summer, with mild temperatures and little chance for precipitations. Temperatures might drop during the night, so pack a light jacket if you plan to stay up late. Otherwise, light clothing made from natural fabrics is excellent choices. A good pair of walking shoes and sandals are quite enough.

Sample temperatures

Freeport avg high 23C/74F ; avg low 17C/64F
Nassau avg high 25C/77F ; avg low 17C/64F

>>read more about Weather

Accommodation & Flights

The hotels start to charge the highest prices starting with mid-December, and the trend continues during January, of course. Same goes for the resorts , so your best bet is to check for accommodation in advance. You might also want to check for flight and hotel packages, as they can save some money.

If you go the independent way, book your flight ahead of time and take advantage of the deals available. Using the saved miles can lower the price, too.

Read more about:
>>Best Bahamas Hotels
>>Most Romantic Resorts in The Bahamas
>>Best Tennis Resorts in The Bahamas

Things to do

Head to the beach is one of the main reasons people visit The Bahamas. If the water is a bit too cold for swimming, you can always sit back, relax and catch a tan. Or rent a wetsuit and go diving.

The Grand Bahama Island is one of the most popular places where tourists love to spend their time. If you don’t mind the crowds, do the same. And don’t forget to check out the Port Lucaya Marketplace.

Nassau , on the other hand, offers a lot of historical sites to visit. Don’t miss visiting Christ Church Cathedral, Fort Charlotte, Fort Fincastle and Fort Montagu. They offer excellent insight into the history of the area and excellent views of their surroundings.

If you like to be more active, put on your walking shoes and explore Lucayan National Park, located in Freeport. Spend time on the beach or explore the trails. You might want to check out the underwater caves, too.

The traditional food in Bahamas is conch, served in two main ways: deep-fried or raw with a hint of lemon. And of course, the classic Caribbean dish – rice and beans/peas – can be found all over the island.

Photo credit

Weather

The wet season has ended in November so now the rainfall is very low and the sun is shining. Temperatures are going down , averaging a comfortable 24C/76F during the day. Pack light clothing and your bathing suit, of course. If you plan to go hiking or walking, bring a good pair of walking shoes. Otherwise, sandals are pretty much enough.

Sample temperatures

Freeport avg high 24C/76F ; avg low 18C/65F
Nassau avg high 25C/78F ; avg low 18C/66F

>>read more about Weather

Accommodation & Flights

The hotels charge the highest prices starting with mid-December, so if you want to visit Bahamas now, plan for a trip during the first two weeks of the month. Same goes for the resorts . And make sure to book in advance, regardless of when you plan to visit (during the high season).

Mae sure to also book your flight ahead of time. It’s possible to still find some bargains, especially if you look for deals or flight & hotel packages.

Read more about:
>>Best Bahamas Hotels
>>Most Romantic Resorts in The Bahamas
>>Best Tennis Resorts in The Bahamas

Things to do

The beaches – such as Cabbage Beach or Cable Beach – are one of the most important reasons why people come to the Caribbean islands. If you find the water a bit too cold for swimming, then you can enjoy the sun and get a lovely tan. Or you can get a wetsuit and go snorkeling.

Head to the Grand Bahama Island and check out the Port Lucaya Marketplace. You can o some Christmas shopping while you are it or just look for souvenirs. Don’t forget about the tasty Caribbean foods you can pick up at the market.

Nassau offers a lot of historical sites to visit. Put on your walking shoes and check it out. Don’t miss the Christ Church Cathedral. It’s free to visit and the architecture is superb Stop by Fort Charlotte to learn its history and see lovely views of Paradise island. Another lovely sight is Fort Fincastle. And Fort Montagu is the third main fort in Nassau.

Put on your hiking shoes and explore Lucayan National Park, located in Freeport. You can visit underwater caves, soak up the sun on the beaches or explore some trails.

If you like carnivals, then Junkanoo , held on Boxing Day (December 26) should be on your not-to-miss list. The costumes are interesting and you can take one back home as souvenir.

Photo credit

Weather

November marks the end of the off-season for The Bahamas. The rainfall drops – but you can easily expect some showers right smack in the middle of the day – and the temperatures start to go down, too. Pack light clothes, made from natural materials. Make sure to pack a pair of good walking shoes, water resistant.

Sample temperatures

Freeport avg high 26C/80F ; avg low 20C/69F
Nassau avg high 27C/82F ; avg low 21C/71F

>>read more about Weather

Accommodation & Flights

November is one of the best times to visit The Bahamas. The wet season is ending and the crowds aren’t here yet. Plus, now it’s the time when there are quite a lot of deals available.

It’s a good idea to book your flight ahead of time – although 4 to 8 weeks are quite enough. When it comes to the accommodation, there are plenty of choices, depending on your travel budget: hotels , resorts , private rentals, and so on. Search ahead of time and you’ll most likely be able to find good deals and discounts.

Read more about:
>>Best Bahamas Hotels
>>Most Romantic Resorts in The Bahamas
>>Best Tennis Resorts in The Bahamas

Things to do

The beaches are the most important part of planning a vacation in the Caribbean. Who doesn’t want to escape the cold only to head to a sandy beach to get some lovely tan? Or maybe go snorkeling or trying other water sports. Check out Cabbage Beach and Cable Beach.

If you travel with the kids, head to Grand Bahama Island, where the little ones can interact with dolphins.

And while you are here, check out the Port Lucaya Marketplace. If you look for souvenirs or just want to pick up some fresh fruits, this is a lovely place to check out.

Take a walking tour of Nassau and stop to visit Christ Church Cathedral. The architecture is stunning and you can easily spend an hour or two checking it out. It’s free to visit but pay attention to the worship hours. Also, stop by Fort Charlotte – one of the three ports still standing on the island – to explore its history and see lovely views of Paradise island.

You can also explore the Lucayan National Park, located in Freeport. From trails, to underwater limestone caves and lovely beaches, this park offers hours of things to do and places to check out.

Photo credit

Weather

December marks the start of the high season for those heading to Jamaica. It is one of the coolest and driest months of the year. It is perfect weather for sunbathing and rain might occur in the evening or early night.

Bring light clothes, preferably made from natural materials. You can get away in your swim suit top and shorts on the beach but if you want to check out the restaurants, bring something to cover you up (a tank top is a good idea and a sarong is always a good choice). Bring a pair of good water-tight walking shoes.

Sample temperatures

Kingston avg high 30C/87F ; avg low 23C/75F
Montego Bay avg high 28C/83F ; avg low 22C/73F
Negril avg 25C/77F

>>read more about the Weather

Flights and Accommodation

The start of the high season means that the fares also start to go up. Make sure to book your flight to Jamaica ahead of time and if you manage to find a hotel & flight package, it’s even better.

Generally speaking, it’s best to start the search for both flights and accommodation the earliest possible and take advantage of the early booking discounts.

>>read more about the Best Resorts in Jamaica and the Cheapest Resorts in Jamaica

Things to do

Aside from the good food , fine beaches , reggae music and rum, Jamaica has plenty of other things to offer. If you travel with the kids, don’t miss a swim with the dolphins…or the sharks.

Adventure seekers can try canopy tours, river kayaking, 4×4 off road safaris, river tubing, a beach horse ride or a buggy adventure. There are plenty of tour companies which handle such adventures. You just need to shop around.

Put on your walking shoes and explore the cities – Kingstown, Ocho Rios or Montego Bay – at your own pace. You need a map and you can also download walking tours for your iPod or other device. Or you can create your own tour.

If you like hiking, you can walk between the villages, go to remote areas or hike for three days in the Blue Mountains National Park.

>>read more about the Things to do in Jamaica

Photo credit