Summer on the Caribbean Islands

Considered one of the most beautiful beach destinations in the world, the Caribbean Islands showcase the best of white sandy beaches, diverse geography, and a unique mixture of cultures. With over 2,700 individual islands and 28 island nations, we have narrowed down our top picks with a variety of travelers in mind.

1. Guadeloupe

Guadeloupe - GuestToGuest home exchange
Deshaies Beach, Guadeloupe

A wonderful mixture of Afro-influences with French elements, this archipelago of 9 islands is the perfect destination for adventure seekers who wish to explore the vast terrain.

When to go? 

The most attractive months for travel to the island are December to May, therefore avoiding these months will save you money and from the crowds. However, for summer travel, June is an ideal time as it is the low season before summer holiday-goers arrive in July and August.

Summer temperatures in Guadeloupe:  From June to August, the temperatures remain in the high 80°F. However, the wetter months begin in July where rain falls an average of fourteen days a month.

What to do in Guadeloupe? kayakswimmingpoolbikesnorkellingsurfhikevoile

  • Active excursions: If views are what you seek at the end of an adventure, start an early morning climb up La Grande Soufrière, an active volcano that will give you a close up view of its steam.
  • If you’re an experienced diver, plan your day around Plage de Malendure, which is said to be a mecca for divers and snorkelers who wish to explore the Réserve Cousteau.
  • Relaxing activities: If you aren’t a diver, ditch your partner by the water and enjoy the sights of Pigeon Island where you can relax on the dark sand beaches, explore the step hills and indulge yourself in town.
  • Cultural activites: For a relaxing day, but still with adventure in mind, find your way to Deshaies, a charming village with fishermen and cute restaurants. The nearby beach of Grande Anse, where the main street is pedestrian-only, makes for a nice stroll.

Finding accommodation for less:

Guadeloupe - GuestToGuest home exchange

For a complet view of the Caribbean sea, stay in Cédhi’s chalet where you can find calm in the forests to fulfill your sense of adventure.

Our homes in Guadeloupe

2. Dominican Republic

Santo Domingo - GuestToGuest home exchange
Santo Domingo, Dominican Republic

Occupying the eastern half of Hispaniola, this large island is rife with culture, even by Caribbean standards! Perfect for families to let their children run free along the beach, couples seeking adventure, and lovers of culture, this island has something for everyone.

When to go? Popular travel seasons to the island include July-August and December- February. If you wish to avoid summer crowds, June is the perfect travel time.

Summer temperatures in the Dominican Republic:  Temperatures remain the same throughout the year, 85-90°F, though August and September can often have heavy rains.

What to do in the Dominican Republic? voilesurftropical-forestsnorkellingswimmingpoolculture

  • Cultual activities: To get a glimpse into the country’s long history, plan a day trip to Santo Domingo, where you can begin your day in the Zona Colonial and enjoy the 15th and 16th century architecture.
  • If you’re looking for a bite to eat, head over to Malecon, the waterfront boulevard home to many festivals, bars, and restaurants.
  • Active excursions: For culture and adventure by the water, consider Puerto Plata, which has a historical old town. The beaches of Sosua and Caberete are said to have powerful breezes and large waves ideal for the best wind and kite-surfing.
  • Relaxing activities: If you’re traveling with the family, you’re in luck as the low season occurs in the summer through early fall. Bring your family to Punta Cana for white sandy beaches, less crowds, and endless fun in the sun!

Finding accommodation for less:


If you are looking to experience the authenticity of the Zona Colonial, consider a stay in Eric’s Moroccan inspired home in Santo Domingo. His large Moroccan-style terrace is perfect for starry nights and moments with the family.

Our homes in the Dominican Republic

3. Martinique

Martinique - GuestToGuest home exchange
Mont Pelée, Martinique

For francophiles and francophones, the island of Martinique offers the finest of French products and cuisine to be enjoyed on an enchanting Caribbean island.

When to go? To avoid peak tourist crowds during the dry season (November to May), favor the summer months. July and August are village festival season and the “courses de yoles”. If you would like to find more privacy on the island and enjoy the unique ambiance among locals, try September or October.

Summer temperatures in Martinique: between 75°F and 90°F, lots of sun and occassional showers.

What to do in Martinique? snorkellingtropical-forestswimmingpoolkayakhikelocal-culture

  • Active excursions: Originally a volcanic island, the northern geographic diversity presents the ideal getaway for outdoorsy types. If the outdoors resonates with you, spend your morning hiking up Mont Pelée, which towers over the island.
  • If you make it down by afternoon, canoeing and kayaking can be enjoyed at the base of the volcano near its many waterfalls and forests.
  • Relaxing activities: If you prefer peace and quiet while you sunbathe, center your day around Diamond Beach, located in the town of Le Diamant, on the southwestern part of the island.
  • Cultural activities: Once you are well rested and ready for your next adventure, The Anse Cafard Slave Memorial is nearby and is reccommened as part of your itinerary. The memorial is consistently ranked as one of the top island attractions.

Finding accommodation for less:


If you are traveling with young children or for a friends trip, Yveline’s home offers a calm view of the sea and a glimpse of the nearby Carnavelle Island. Fully equipped with a private pool and forests at the base of the home, a stay with Yveline will complete your summer vacation.

Our homes in Martinique

4. Anguilla

Anguilla - GuestToGuest home exchange
Crocus Hill, Anguilla

Perfect for lovers of pristine beaches, the island of Anguilla has over 30 to choose from! As one of the smaller islands, it is possible to explore all 16 miles of the island in one weekend.

What to do in Anguilla?

  • Active excursions: If you’re a fan of snorkeling or scuba diving, the island contains its own coral reef full of tropical fish and marine wildlife. Or if underwater adventuring isn’t your thing, spend an afternoon at Shoal Bay and embark on a glass bottomed boat that will take you over the reef.
  • For adventures on land, hiking and horseback riding can be good ways to explore the island. Crocus Hill is the highest point on the rather flat island, and from here you can take in spectacular views of the island and sea at sunset.
  • As the island is made of limestone, a visit to The Big Springs cave, located on Island Harbour is an absolute must! Here you may view local fishermen and sailors at work as well as explore the islands museums and galleries.

Finding accommodation for less:


If you are looking to indulge in total luxury this holiday, Frederick’s custom villa will complete the vacation of your dreams. Designed by the owner, careful attention to detail was given to the property that displays spectacular views of neighboring St. Bart’s. Either Anguilla or St. Bart’s can be easily reached by boat.

5. St. Martin-St. Maarten

St. Martin - GuestToGuest home exchange
Orient Beach, St. Martin.

For the mature travelers looking to let loose on vacation, this half French-half Dutch island provides the perfect European atmosphere in a Caribbean setting.

What to do in St. Martin? voilelocal-culturesnorkellingsurfhike

  • Beach activities: Famous for its nude beaches, Orient Bay, located on the eastern coast, ranks as the top beach with the most activities on the French side of the island. Here you will find activities such as parasailing and kitesurfing.
  • Active excursions: If you are searching for more swimming, consider Friar’s Bay located on the northwestern side of the island, with smaller waves ideal for snorkeling.
  • Relaxing activities: Just ten minutes away is Happy Bay, a tiny stretch of beach that is that is worth a stroll. Away from the water and later in the day, bonfires, reggae music, and delicious food can be enjoyed at Kali’s Beach Bar, an local favorite.

Finding accommodation for less:


Eden’s home is located just 5 mins away from Orient Bay, allowing you to enjoy a pleasant stroll through the area. Whether traveling as a couple or with children, her private residence is equipped with a pool and close to many great restaurants. Perfect for your relaxing summer holiday!

Our homes in St. Martin-St. Maarten


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