35 days in Caribbean Itinerary

35 days in Caribbean Itinerary

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Route & dates

35 days in Caribbean Itinerary

Start: Riga, Latvia
Fly:  21​h
1
Simpson Bay, St. Maarten-St. Martin
— 4 nights
Fly:  3​h 45​min
2
St. George's, Grenada
— 2 nights
Fly + shuttle:  2​h
3
Port of Spain, Trinidad and Tobago
— 2 nights
Drive:  2​h
4
Crown Point, Trinidad and Tobago
— 2 nights
+2
Drive + Fly + Drive:  7​h 45​min
5
Saint James Parish, Barbados
— 3 nights
+2
Drive + Fly + Drive:  5​h 30​min
6
Saint Philip Parish, Antigua and Barbuda
— 1 night
Drive + Fly:  8​h 30​min
7
Punta Cana, Dominican Republic
— 2 nights
shuttle:  2​h 15​min
8
Bayahibe, Dominican Republic
— 2 nights
bus:  1​h 45​min
9
Santo Domingo, Dominican Republic
— 2 nights
Fly:  4​h 15​min
10
San Juan, Puerto Rico
— 2 nights
Fly:  30​min
11
Culebra, Puerto Rico
— 2 nights
Fly + Drive:  2​h 15​min
12
Isla de Vieques, Puerto Rico
— 3 nights
+2
Fly + Drive + ferry:  3​h
13
Virgin Islands National Park, U.S. Virgin Islands
— 2 nights
+2
ferry + Fly + shuttle:  10​h 30​min
14
Puerto Plata, Dominican Republic
— 3 nights
Fly:  17​h 45​min
End: Riga, Latvia

4
nights
Simpson Bay, St. Maarten-St. Martin

Simpson Bay offers luxury resort living and good access to the main areas of the island.
On the 3rd (Tue), spend a thrilling day on the water with a speed boat tour. There's much more to do: tour the pleasant surroundings at Maho Beach, sample the fine beverages at Topper's Rhum Distillery Tours, kick back and relax at Orient Bay Beach, and appreciate the history behind Brown Pelicans.

To find reviews, maps, and other tourist information, read Simpson Bay trip planner .

Riga, Latvia to Simpson Bay is an approximately 21-hour flight. The time zone difference moving from Eastern European Time to Atlantic Standard Time is minus 6 hours. Traveling from Riga in September, expect Simpson Bay to be much hotter, temps between 36°C and 31°C. Cap off your sightseeing on the 6th (Fri) early enough to travel to St. George's.

Things to do in Simpson Bay

Outdoors Parks Beaches

Side Trips

Philipsburg, Maho, Sint Maarten, Cupecoy Bay Beach, Topper's Rhum Distillery Tours
Find places to stay Sep 1 — 6:
Highlights from your plan
Speed Boats Tours
Maho Beach ©
Maho Beach
Orient Bay Beach ©
Orient Bay Beach

2
nights
St. George's, Grenada

St. George's ©
The capital of the Island of Spice, St.
On the 6th (Fri), pause for some photo ops at Underwater Sculptures, take in the exciting artwork at Art and Soul Gallery, and then kick back and relax at Grand Anse Beach. Get ready for a full day of sightseeing on the next day: steep yourself in history at Fort George, then see some colorful creatures with a scuba or snorkeling tour, and then explore and take pictures at Carenage.

Start your trip to St. George's by creating a personalized itinerary on Inspirock.

You can fly from Simpson Bay to St. George's in 4 hours. In September, daytime highs in St. George's are 36°C, while nighttime lows are 30°C. Finish your sightseeing early on the 8th (Sun) so you can travel to Port of Spain.

Things to do in St. George's

Outdoors Parks Beaches

Side Trip

South Coast
Find places to stay Sep 6 — 8:
Highlights from your plan
Grand Anse Beach ©
Grand Anse Beach
Carenage ©
Carenage
Underwater Sculptures ©
Underwater Sculptures

2
nights
Port of Spain, Trinidad and Tobago

Port of Spain ©
Port of Spain, the country's capital, sits between the sea and a scenic green mountain range, and acts as a gateway for eclectic adventures on land and sea.
Start off your visit on the 8th (Sun): kick back and relax at Maracas Beach and then identify plant and animal life at Asa Wright Nature Centre. On the 9th (Mon), you'll have a packed day of sightseeing: admire the natural beauty at Royal Botanic Gardens, then tour the pleasant surroundings at Emperor Valley Zoo, and then walk around Queen's Park Savannah.

To find more things to do, where to stay, traveler tips, and tourist information, you can read our Port of Spain trip builder app .

You can do a combination of flight and shuttle from St. George's to Port of Spain in 2 hours. In September, daytime highs in Port of Spain are 39°C, while nighttime lows are 28°C. Wrap up your sightseeing on the 10th (Tue) to allow time to travel to Crown Point.

Things to do in Port of Spain

Parks Wildlife Outdoors

Side Trip

Asa Wright Nature Centre
Find places to stay Sep 8 — 10:
Highlights from your plan
Asa Wright Nature Centre ©
Asa Wright Nature Centre
Maracas Beach
Maracas Beach
Queen's Park Savannah ©
Queen's Park Savannah

2
nights
Crown Point, Trinidad and Tobago

Crown Point ©
Your day-by-day itinerary now includes Argyle Waterfall as well as Fort King George. Kick off your visit on the 10th (Tue): admire the sheer force of Argyle Waterfall, then kick back and relax at Store Bay, then explore the gorgeous colors at Buccoo Reef, and finally kick back and relax at Pigeon Point Beach. Get ready for a full day of sightseeing on the next day: discover the deep blue sea with a scuba or snorkeling tour and then kick back and relax at Nylon Pool.

To find out how to plan a trip to Crown Point, use our trip itinerary maker.

Traveling by combination of shuttle and flight from Port of Spain to Crown Point takes 2 hours. Alternatively, you can ride a ferry. In September in Crown Point, expect temperatures between 36°C during the day and 30°C at night. Wrap up your sightseeing by early afternoon on the 12th (Thu) to allow enough time to travel to Saint James Parish.

Things to do in Crown Point

Parks Outdoors Beaches

Side Trips

Tobago, Scarborough
Find places to stay Sep 10 — 12:
Highlights from your plan
Pigeon Point Beach ©
Pigeon Point Beach
Fort King George ©
Fort King George
Store Bay ©
Store Bay

3
nights
Saint James Parish, Barbados

Saint James Parish ©
Saint James Parish, with its white sand coastline and modern coastal developments, has gained a reputation as a favorite haunt of the rich and famous.
Start off your visit on the 13th (Fri): admire the landmark architecture of St. Nicholas Abbey, enjoy the sand and surf at Carlisle Bay, then take in nature's colorful creations at Hunte's Gardens, and finally explore the fascinating underground world of Harrison's Cave. On the 14th (Sat), you'll have a packed day of sightseeing: Head underground at Animal Flower Cave, admire the natural beauty at Andromeda Botanic Gardens, then see the interesting displays at Sunbury Plantation House, then enjoy the sand and surf at Bottom Bay, and finally pause for some serene contemplation at Our Lady of Sorrows Roman Catholic Church.

To see photos, more things to do, where to stay, and tourist information, read Saint James Parish online trip builder .

The Route module can help you plan travel from Crown Point to Saint James Parish. September in Saint James Parish sees daily highs of 36°C and lows of 30°C at night. Wrap up your sightseeing by early afternoon on the 15th (Sun) to allow time for travel to Saint Philip Parish.

Things to do in Saint James Parish

Parks Outdoors Beaches

Side Trips

Bridgetown, Saint Joseph Parish, Saint Peter Parish, Saint Philip Parish, Harrison's Cave.
Find places to stay Sep 12 — 15:
Highlights from your plan
Hunte's Gardens ©
Hunte's Gardens
Harrison's Cave. ©
Harrison's Cave.
Bottom Bay ©
Bottom Bay

1
night
Saint Philip Parish, Antigua and Barbuda

Saint Philip Parish ©
Encompassing the southeastern end of the island of Antigua, Saint Phillip Parish epitomizes the best of what this Caribbean destination has to offer tourists from around the world.
You've now added Nelson's Dockyard to your itinerary. Start off your visit on the 16th (Mon): explore the striking landscape of Nelson's Dockyard, then view the masterpieces at Things Local Gallery, and then steep yourself in history at Shirley Heights.

For more things to do, other places to visit, ratings, and tourist information, use the Saint Philip Parish sightseeing planner.

Explore your travel options from Saint James Parish to Saint Philip Parish with the Route module. In September, plan for daily highs up to 36°C, and evening lows to 29°C. Wrap up your sightseeing on the 16th (Mon) early enough to travel to Punta Cana.

Things to do in Saint Philip Parish

Nature Parks Historic Sites

Side Trip

English Harbour
Find places to stay Sep 15 — 16:
Highlights from your plan
Nelson's Dockyard ©
Nelson's Dockyard
Shirley Heights ©
Shirley Heights

2
nights
Punta Cana, Dominican Republic

Punta Cana ©
In an area boasting beaches that face both the Atlantic Ocean and the Caribbean Sea, vacations in Punta Cana have been popular with tourists since the early 1970s.
Your day-by-day itinerary now includes Bavaro Beach. On the 17th (Tue), enjoy the sand and surf at Bavaro Beach and then take an exotic tour of a safari tour. On the next day, kick back and relax at Macao Beach, look for gifts at HARRISON'S Fine Caribbean Jewelers, and then take a memorable tour with Tours.

For where to stay, traveler tips, other places to visit, and tourist information, use the Punta Cana tour itinerary app .

Explore your travel options from Saint Philip Parish to Punta Cana with the Route module. In September, daily temperatures in Punta Cana can reach 36°C, while at night they dip to 28°C. Finish your sightseeing early on the 18th (Wed) to allow enough time to take a shuttle to Bayahibe.

Things to do in Punta Cana

Outdoors Wildlife Tours
Find places to stay Sep 16 — 18:
Highlights from your plan
Macao Beach ©
Macao Beach
Swim with Dolphins
Safaris

2
nights
Bayahibe, Dominican Republic

Located on the shore of the Caribbean Sea, the town of Bayahibe has grown from a fishing village into a bona fide tourist destination, with visitors mainly drawn to the many dive sites just off the coast.
Kick off your visit on the 19th (Thu): make a trip to Altos de Chavon, then stop by Museo y Fabrica de Puras, and then discover the deep blue sea with a scuba or snorkeling tour. Get ready for a full day of sightseeing on the 20th (Fri): take a pleasant ride with a tour on horseback, then get engrossed in the history at Altos de Chavon Regional Museum of Archaeology, and then get some thrills on the water with a speed boat tour.

To find where to stay, reviews, and other tourist information, refer to the Bayahibe travel planner .

Traveling by shuttle from Punta Cana to Bayahibe takes 2.5 hours. September in Bayahibe sees daily highs of 37°C and lows of 28°C at night. Finish up your sightseeing early on the 20th (Fri) so you can catch the shuttle to Santo Domingo.

Things to do in Bayahibe

Outdoors Tours Wildlife

Side Trip

La Romana
Find places to stay Sep 18 — 20:
Highlights from your plan
Scuba & Snorkeling
Altos de Chavon ©
Altos de Chavon
Speed Boats Tours

2
nights
Santo Domingo, Dominican Republic

Santo Domingo
Santo Domingo, the capital of the Dominican Republic, remains the oldest continuously inhabited settlement in the New World.
Kick off your visit on the 21st (Sat): contemplate in the serene atmosphere at Catedral Primada de America and then don't miss a visit to Zona Colonial. Get ready for a full day of sightseeing on the next day: examine the collection at Columbus Lighthouse (Faro A Colon), explore the historical opulence of Alcazar de Colon, and then take in the architecture and atmosphere at Basilica Cathedral of Santa Maria la Menor.

Plan my Santo Domingo trip by asking Inpirock to come up with tips and suggestions.

Getting from Bayahibe to Santo Domingo by bus takes about 3 hours. Finish your sightseeing early on the 22nd (Sun) so you can travel to San Juan.

Things to do in Santo Domingo

Historic Sites Museums
Find places to stay Sep 20 — 22:
Highlights from your plan
Catedral Primada de America
Catedral Primada de America
Zona Colonial ©
Zona Colonial
Alcazar de Colon ©
Alcazar de Colon

2
nights
San Juan, Puerto Rico

San Juan ©
Founded by the Spanish in 1521, San Juan is the oldest city under U.S.
Your day-by-day itinerary now includes El Yunque Rain Forest. On the 23rd (Mon), identify plant and animal life at El Yunque Rain Forest, get engrossed in the history at Catedral Metropolitana Basilica de San Juan Bautista, then take a memorable tour with Tours, and finally skim along the rocks with a canyoning and rapelling tour. On the 24th (Tue), you'll have a packed day of sightseeing: get to know the fascinating history of San Juan National Historic Site, appreciate the extensive heritage of Old San Juan, and then brush up on your knowledge of spirits at Casa BACARDI Puerto Rico.

For photos, traveler tips, and tourist information, go to the San Juan trip builder .

You can fly from Santo Domingo to San Juan in 4.5 hours. Alternatively, you can do a combination of shuttle and flight; or ride a ferry. In September in San Juan, expect temperatures between 38°C during the day and 30°C at night. Cap off your sightseeing on the 24th (Tue) early enough to catch the flight to Culebra.

Things to do in San Juan

Wildlife Nature Parks

Side Trips

Casa Bacardi, El Yunque Rain Forest
Find places to stay Sep 22 — 24:
Highlights from your plan
Old San Juan ©
Old San Juan
El Yunque Rain Forest ©
El Yunque Rain Forest
Sitio Histórico de San Juan ©
Sitio Histórico de San Juan

2
nights
Culebra, Puerto Rico

Culebra ©
With much of Culebra a nature refuge, the tropical island has been protected from overdevelopment, chain hotels, and the cruise set.
Start off your visit on the 25th (Wed): get lost in a book at Culebra Public Library and then kick back and relax at Flamenco Beach. On the 26th (Thu), you'll have a packed day of sightseeing: step off the mainland to explore Culebrita Island, enjoy the sand and surf at Zoni Beach, and then see the interesting displays at Museo Historico de Culebra.

For ratings, maps, traveler tips, and other tourist information, refer to the Culebra vacation builder site .

Culebra is just a short distance from San Juan. September in Culebra sees daily highs of 37°C and lows of 30°C at night. Wrap up your sightseeing on the 26th (Thu) to allow time to travel to Isla de Vieques.

Things to do in Culebra

Parks Outdoors Beaches
Find places to stay Sep 24 — 26:
Highlights from your plan
Flamenco Beach ©
Flamenco Beach
Culebrita Island ©
Culebrita Island
Zoni Beach ©
Zoni Beach

3
nights
Isla de Vieques, Puerto Rico

Isla de Vieques ©
For sixty years until 2003, most of the Isla de Vieques was closed off to the public, with the US Navy using the island's beaches and surrounding waters for drills and testing of new military machinery, such as bombs.
Start off your visit on the 27th (Fri): take a leisurely stroll along Malecon and then kick back and relax at Sun Bay. Get ready for a full day of sightseeing on the next day: stroll through La Chiva, find your balance on the water with some of the best stand-up paddleboarding in the area, and then take a leisurely stroll along Mosquito Pier.

To find ratings, reviews, more things to do, and other tourist information, use the Isla de Vieques sightseeing planning website .

You can do a combination of flight and car from Culebra to Isla de Vieques in 2.5 hours. Alternatively, you can ride a ferry. Expect a daytime high around 36°C in September, and nighttime lows around 29°C. On the 29th (Sun), wrap the sightseeing up by early afternoon so you can travel to Virgin Islands National Park.

Things to do in Isla de Vieques

Outdoors Parks Beaches
Find places to stay Sep 26 — 29:
Highlights from your plan
Sun Bay Beach ©
Sun Bay Beach
Caracas Beach ©
Caracas Beach
La Chiva ©
La Chiva

2
nights
Virgin Islands National Park, U.S. Virgin Islands

Virgin Islands National Park ©
The hills, valleys, and tropical rainforest of Virgin Islands National Park tell only half the story, with just as much (if not more) to be found under the sea.
Your day-by-day itinerary now includes Waterlemon Cay, Salt Pond Bay and Cinnamon Bay Beach. Start off your visit on the 29th (Sun): kick back and relax at Cinnamon Bay Beach, explore the activities along Salt Pond Bay, then head off the coast to Waterlemon Cay, and finally see the interesting displays at Cinnamon Bay Archeology Museum & Lab.

To see ratings, photos, where to stay, and more tourist information, refer to the Virgin Islands National Park online travel route planner .

Traveling by combination of flight and ferry from Isla de Vieques to Virgin Islands National Park takes 3 hours. In September, plan for daily highs up to 37°C, and evening lows to 30°C. You'll have a few hours on the 1st (Tue) to wrap things up before traveling home.

Things to do in Virgin Islands National Park

Parks Outdoors Beaches
Find places to stay Sep 29 — Oct 1:
Highlights from your plan
Trunk Bay ©
Trunk Bay
Annaberg Sugar Plantation ©
Annaberg Sugar Plantation
Hawksnest Beach ©
Hawksnest Beach

3
nights
Puerto Plata, Dominican Republic

Puerto Plata ©
Although out of fashion in the past decades, major revitalization efforts have made a trip to Puerto Plata a growingly popular option for the adventurous travelers.
27 Charcos has been added to your itinerary. Start off your visit on the 2nd (Wed): stop by Estrella Avenida, take in the awesome beauty at Pico Isabel de Torres, and then take in the dramatic scenery at 27 Charcos. Get ready for a full day of sightseeing on the 3rd (Thu): cool off at Ocean World Adventure Park.

To find ratings, maps, other places to visit, and other tourist information, go to the Puerto Plata road trip site .

The Route module can help you plan travel from Virgin Islands National Park to Puerto Plata. Expect slightly colder evenings in Puerto Plata when traveling from Virgin Islands National Park in October, with lows around 26°C. On the 4th (Fri), wrap the sightseeing up by early afternoon so you can travel back home.

Things to do in Puerto Plata

Parks Nature Theme Parks
Find places to stay Oct 1 — 4:
Highlights from your plan
27 Charcos ©
27 Charcos
Pico Isabel de Torres ©
Pico Isabel de Torres

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