A Travel Price Comparison for Families, Couples, and Backpackers Grand Cayman vs. Kennebunkport for Vacations, Tours, and Honeymoons

Should you visit Grand Cayman or Kennebunkport?

Which is cheaper to visit? Which is more expensive for vacation?

Which city should you visit? Read on to compare the activities as well as the prices of travel for Grand Cayman and Kennebunkport. We'll break down costs for accommodation, food, transportation and more to help you learn more about these two destinations. Then, you can figure out if either of these two places are accessible based on your travel budget, schedule, and interests. So, let's dig into it.

Where Should I go: Grand Cayman or Kennebunkport?

Grand Cayman

When people think of the Cayman Islands, they typically think of offshore bank accounts and sunny, cruise ship ports. Grand Cayman has more to offer travelers than a playground for the wealthy or a short stopover for cruise passengers. This tropical island is the largest of the three Cayman Islands, it is a shopper's heaven, a center for global finance and an ideal vacation spot.

Kennebunkport

Kennebunkport is a beautiful coastal town in southern Maine that attracts a number of tourists who enjoy it's quaint atmosphere, upscale shopping, and great restaurants. While the town's history is grounded in the shipbuilding and fishing industries, it long ago became a summer holiday destination for wealthy New Englanders. The town is now one of the wealthiest areas in the state of Maine. It's also notable as the location of Walker's Point, which is a vacation estate for the Bush Family.

For some great organized tour ideas, see The Best 3-Week Tours in United States of America, and The Best Bicycle Tours in United States of America.


Which place is cheaper, Kennebunkport or Grand Cayman?

These are the overall average travel costs for the two destinations. These travel costs come from the actual spending of real travelers.

The average daily cost (per person) in Grand Cayman is $242, while the average daily cost in Kennebunkport is $269. These costs include accommodation (assuming double occupancy, so the traveler is sharing the room), food, transportation, and entertainment. While every person is different, these costs are an average of past travelers in each destination. What follows is a categorical breakdown of travel costs for Grand Cayman and Kennebunkport in more detail.



Accommodation
  • Accommodation Hotel or hostel for one person
    Grand Cayman $149
    Kennebunkport $124
  • Accommodation Typical double-occupancy room
    Grand Cayman $298
    Kennebunkport $248
Compare Hotels in Grand Cayman and Kennebunkport

Looking for a hotel in Grand Cayman or Kennebunkport? Prices vary by location, date, season, and the level of luxury. See below for options and compare which is best for your budget and travel style.

Hotels in Grand Cayman


Hotels in Kennebunkport


Kayak helps you find the best prices for hotels, flights, and rental cars for destinations around the world. Compare prices for multiple destinations when planning your next trip.


Our Analysis
We've analyzed the average and typical hotel prices based on guest reviews, star ratings, and hotel amenities here: Grand Cayman Hotel Prices and Kennebunkport Hotel Prices.

Local Transportation
  • Local Transportation Taxis, local buses, subway, etc.
    Grand Cayman $31
    Kennebunkport $49

Hired Cars and Shuttles in Grand Cayman

Also for Grand Cayman, here are a few examples of actual transportation services:

  • Private Transfer from Airport to morritts: $180
  • Privat Transfer from Owen Roberts Airport GCM to George Town Port: $103

Is it cheaper to fly into Grand Cayman or Kennebunkport?

Prices for flights to both Kennebunkport and Grand Cayman change regularly based on dates and travel demand. We suggest you find the best prices for your next trip on Kayak, because you can compare the cost of flights across multiple airlines for your prefered dates.





Food
  • Food Meals for one day
    Grand Cayman $67
    Kennebunkport $115

Entertainment
  • Entertainment Entrance tickets, shows, etc.
    Grand Cayman $41
    Kennebunkport $21

Tours and Activities in Grand Cayman

For Grand Cayman, here are a few prices for actual activities, tours, and tickets provided by various companies:

  • StingrayCity ,Coral Garden & Starfish Tour. : $69
  • 2 Stop Reef Snorkel and Glass Bottom Boat Adventure: $35
  • 3 Stop Boat Tour Stingray City Coral Gardens and Starfish Point: $65
  • Acquarius Stingray City and Snorkel Tours: $79
  • Cayman 2 in 1 Combo Tour Stingray City Reef Snorkel Adventure: $77
  • Cayman 3 in 1 Combo Adventure Stingray City Reef Snorkeling: $104
  • Cayman Adventure Stingrays Starfish plus Crystal Caves : $89
  • Cayman Bioluminescent Bay Night Tour: $144
  • Cayman Combo Tour: Starfish Point, Stingray City & Coral Gardens: $119
  • Cayman Crystal Caves Tour in Grand Cayman: $143
  • Cayman's Classic Food Tasting & Cultural Experience: $179
  • CaymanVisitor Hide & Seek GeoTour Self-Drive Tour: $13

Tours and Activities in Kennebunkport

Also, here are some specific examples of entertainment, tickets, and activities for Kennebunkport.

  • 90 Minutes Ghost Walking Tour in Kennebunkport: $35
  • From Boston: Kennebunkport Day Trip & Optional Trolley Tour: $125
  • Kennebunkport, Maine: Lunchtime Culinary Walking Tour: $150
  • 2-Hour Historical Walking Tour: $50
  • A Tasty Lunchtime Walking Tour: $160
  • Haunted Ghost Walking Tour: $35

Alcohol
  • Alcohol Drinks for one day
    Grand Cayman $13
    Kennebunkport $31
Typical Alcohol Prices in Grand Cayman

Below are a few samples from actual travelers for alcohol and nightlife costs in Grand Cayman:


  • Beer
    $4.95

Sample the Local Flavors in Grand Cayman

Here are a few nightlife and alcohol tours and activities from local tour providers in Grand Cayman:

  • Cayman Spirits Co. Distillery Tour Pass Ticket Only: $24
  • Cayman Art and Wine Tour: $150


When comparing the travel costs between Grand Cayman and Kennebunkport, we can see that Kennebunkport is more expensive. However, the two cities are actually relatively comparable in price, as the difference is somewhat minimal. Generally, this means that you could travel with generally the same travel style and level of luxury in each place. Even though Grand Cayman is in Caribbean Islands and Kennebunkport is in North America, both of these destinations have relatively similar prices of travel. Generally, the levels of luxury and expenses are the same for these cities even though they are geographically far apart.

If you're trying to decide if either of these two destinations are within your price range, also see Is Grand Cayman Expensive? and Is Kennebunkport Expensive?.


Which is Bigger, Grand Cayman or Kennebunkport?

Grand Cayman has a larger population, and is about 20 times larger than the population of Kennebunkport. When comparing the sizes of Grand Cayman and Kennebunkport, keep in mind that a larger population does not always imply the destination has more attractions or better activities. So, always research the type of place that you want to visit along with the activities and attractions that interest you.


When is the best time to visit Grand Cayman or Kennebunkport?

Kennebunkport has a temperate climate with four distinct seasons, but Grand Cayman experiences a warm climate with fairly sunny weather most of the year.

Should I visit Grand Cayman or Kennebunkport in the Summer?

The summer attracts plenty of travelers to both Grand Cayman and Kennebunkport. Warm weather and sunshine bring visitors to Grand Cayman year-round. Furthermore, many travelers come to Kennebunkport for the hiking, the small town charm, and the family-friendly experiences.

In the summer, Grand Cayman is a little warmer than Kennebunkport. Typically, the summer temperatures in Grand Cayman in July average around 28°C (83°F), and Kennebunkport averages at about 69°F (20°C).

Grand Cayman gets a good bit of rain this time of year. In July, Grand Cayman usually receives more rain than Kennebunkport. Grand Cayman gets 179 mm (7 in) of rain, while Kennebunkport receives 2.6 inches (66 mm) of rain each month for the summer.


  • Summer Average Temperatures July
    Grand Cayman 28°C (83°F) 
    Kennebunkport 69°F (20°C)

Should I visit Grand Cayman or Kennebunkport in the Autumn?

The autumn brings many poeple to Grand Cayman as well as Kennebunkport. Grand Cayman attracts visitors year-round for its warm weather and sunny climate. Additionally, many visitors come to Kennebunkport in the autumn for the hiking trails, the shopping scene, the small town atmosphere, and the natural beauty of the area.

In October, Grand Cayman is generally much warmer than Kennebunkport. Daily temperatures in Grand Cayman average around 27°C (81°F), and Kennebunkport fluctuates around 49°F (9°C).

Grand Cayman receives a lot of rain in the autumn. Grand Cayman usually gets more rain in October than Kennebunkport. Grand Cayman gets 238 mm (9.4 in) of rain, while Kennebunkport receives 3.3 inches (84 mm) of rain this time of the year.


  • Autumn Average Temperatures October
    Grand Cayman 27°C (81°F) 
    Kennebunkport 49°F (9°C)

Should I visit Grand Cayman or Kennebunkport in the Winter?

Both Kennebunkport and Grand Cayman are popular destinations to visit in the winter with plenty of activities. The warm climate attracts visitors to Grand Cayman throughout the year. Also, most visitors come to Kennebunkport for the museums, the shopping scene, and the cuisine during these months.

Kennebunkport can be very cold during winter. Grand Cayman is much warmer than Kennebunkport in the winter. The daily temperature in Grand Cayman averages around 24°C (76°F) in January, and Kennebunkport fluctuates around 21°F (-6°C).

In January, Grand Cayman usually receives less rain than Kennebunkport. Grand Cayman gets 58 mm (2.3 in) of rain, while Kennebunkport receives 3.4 inches (86 mm) of rain each month for the winter.


  • Winter Average Temperatures January
    Grand Cayman 24°C (76°F) 
    Kennebunkport 21°F (-6°C)

Should I visit Grand Cayman or Kennebunkport in the Spring?

Both Kennebunkport and Grand Cayman during the spring are popular places to visit. Plenty of visitors come to Grand Cayman because of the warm climate and sunshine that lasts throughout the year. Also, the spring months attract visitors to Kennebunkport because of the small town charm and the natural beauty.

In the spring, Grand Cayman is much warmer than Kennebunkport. Typically, the spring temperatures in Grand Cayman in April average around 26°C (79°F), and Kennebunkport averages at about 43°F (6°C).

Grand Cayman usually gets less rain in April than Kennebunkport. Grand Cayman gets 48 mm (1.9 in) of rain, while Kennebunkport receives 3.3 inches (85 mm) of rain this time of the year.


  • Spring Average Temperatures April
    Grand Cayman 26°C (79°F) 
    Kennebunkport 43°F (6°C)

Typical Weather for Kennebunkport and Grand Cayman

Grand Cayman Kennebunkport
Temp (°C) Rain (mm) Temp (°C) Rain (mm)
Jan 24°C (76°F) 58 mm (2.3 in) 21°F (-6°C) 3.4 inches (86 mm)
Feb 24°C (76°F) 51 mm (2 in) 24°F (-5°C) 3.5 inches (89 mm)
Mar 25°C (77°F) 31 mm (1.2 in) 33°F (1°C) 3.6 inches (91 mm)
Apr 26°C (79°F) 48 mm (1.9 in) 43°F (6°C) 3.3 inches (85 mm)
May 27°C (81°F) 131 mm (5.1 in) 53°F (12°C) 3.3 inches (85 mm)
Jun 28°C (82°F) 183 mm (7.2 in) 63°F (17°C) 3.1 inches (79 mm)
Jul 28°C (83°F) 179 mm (7 in) 69°F (20°C) 2.6 inches (66 mm)
Aug 28°C (82°F) 172 mm (6.8 in) 67°F (20°C) 2.6 inches (66 mm)
Sep 28°C (82°F) 212 mm (8.3 in) 59°F (15°C) 3.1 inches (78 mm)
Oct 27°C (81°F) 238 mm (9.4 in) 49°F (9°C) 3.3 inches (84 mm)
Nov 26°C (79°F) 141 mm (5.6 in) 39°F (4°C) 4.8 inches (123 mm)
Dec 25°C (78°F) 57 mm (2.3 in) 27°F (-3°C) 4.1 inches (103 mm)