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

Should you visit Grand Cayman or Boston?

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 Boston. 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 Boston?

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.

Boston

Boston is one of the oldest and most historic cities in New England. It is also the capital of the state of Massachusetts and the largest city in the region. The city proper covers 48 square miles and has a population of more than 600,000. The Greater Boston area has 4.5 million people and is the tenth largest metropolitan area in the country.

For some great organized tour ideas, see The Best Photography Tours in United States of America, and The Best Camping Tours in United States of America.


Which place is cheaper, Boston 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 Boston is $291. 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 Boston in more detail.



Accommodation
  • Accommodation Hotel or hostel for one person
    Grand Cayman $149
    Boston $166
  • Accommodation Typical double-occupancy room
    Grand Cayman $298
    Boston $332
Compare Hotels in Grand Cayman and Boston

Looking for a hotel in Grand Cayman or Boston? 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 Boston


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 Boston Hotel Prices.

Local Transportation
  • Local Transportation Taxis, local buses, subway, etc.
    Grand Cayman $31
    Boston $37

Hired Cars and Shuttles in Grand Cayman

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

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

Typical Local Transportation Prices in Boston

Some typical examples of transportation costs in Boston are as follows:


  • Taxi
    $35
  • Subway Daily Pass
    $9.00

Hired Cars and Shuttles in Boston

Some specific examples of transportation prices in Boston:

  • Round trip Airport Transfer: Boston Logan to Downton Boston : $300
  • Private arrival OR departure transfer in Boston (hotel OR airport pick-up): $196
  • Private Transfer in Boston (BOS) Airport/Home/Hotel/Work : $190
  • Private Transfer from Newport Port to Boston Logan Airport (BOS) : $192
  • Private Transfer from Newport Cruise Port to Boston city hotels: $192
  • Private Transfer from Flynn Cruise Port to Boston Airport (BOS): $81
  • Private Transfer from Boston Logan Airport (BOS) to Newport Port: $192
  • Private Transfer from Boston City to Boston (BOS) Airport: $113
  • Private Transfer from Boston City Hotels to Newport Cruise Port: $192
  • Private Transfer from Boston Airport to Providence RI: $294
  • Private Transfer from Boston Airport (BOS) to Flynn Cruise Port: $82
  • Private Transfer from Boston (BOS) Airport to Boston City: $112

Is it cheaper to fly into Grand Cayman or Boston?

Prices for flights to both Boston 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
    Boston $86

Food Tours and Cooking Classes in Boston

Also, here are some specific examples of food and dining related activities in Boston.

  • Self Guided "The North End Pizza, Cannoli and Picnic" Solo Walking Tour : $5.50
  • Morning Walks with Salem Food Tours: $34
  • Boston Freedom Trail History and Food Tour: $39
  • Freedom Trail History and Food Tour: $39
  • Pizza Beer and Paul Revere Tour: $65
  • Boston Pizza Lovers Food & History Walking Food Tour: $69
  • North End Pizza Walking Tour with 3 Slices & Cannoli: $69
  • 2-Hour Pasta Making Cooking Class With Local Chef in Boston: $75
  • North End Food Experience with Pizza, Meats & Cheese: $75
  • Pizza, Beer, and Paul Revere Tour: $75
  • City Cruises Harbor Buffet Lunch or Dinner Cruise: $89
  • Boston’s Politically Incorrect North End Food tour: $98

Entertainment
  • Entertainment Entrance tickets, shows, etc.
    Grand Cayman $41
    Boston $33

Tours and Activities in Grand Cayman

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

  • CaymanVisitor Hide & Seek GeoTour Self-Drive Tour: $13
  • Diamonds and Cocktails a Shopping Experience in Grand Cayman: $25
  • 2 Stop Reef Snorkel and Glass Bottom Boat Adventure: $35
  • Grand Cayman Hop On Hop Off Island Adventure: $40
  • Stingray City and Snorkeling Tour Starfish Point Adventure: $53
  • Stingray City, Snorkeling, & StarFish Adventure: $55
  • Stingray City and Starfish Experience with Coral Reef Snorkeling: $55
  • Stingray City Catamaran Sunset Tour: $59
  • West Bay Sightseeing Tour Plus Seven Mile Beach Visit: $65
  • 3 Stop Boat Tour Stingray City Coral Gardens and Starfish Point: $65
  • Stingray City Sandbar Experience: $65
  • StingrayCity ,Coral Garden & Starfish Tour. : $69

Typical Entertainment Prices in Boston

Some typical examples of activities, tours, and entrance ticket prices in Boston are as follows:


  • Two Tickets to Celtics Game
    $101
  • Duck Tour
    $32

Tours and Activities in Boston

Some specific costs of activities, tours, and entrance tickets for Boston are as follows:

  • Boston Massachusetts Private Photography Tour: $130
  • Freedom Trail Walking Tour: $26
  • Salem Witch Tour: $80
  • "Ghosts of Boston" Walking Ghost Tour: $30
  • "Witch Trials" Walking Tour in Salem: $30
  • 1 Hour Boston Segway Tour: $69
  • 1 If By Land Walking Tours: $45
  • 1 or 2 Day Hop-On Hop-Off Trolley Tour of Boston With *20+ Stops: $48
  • 1692 Salem Day Tour: $35
  • 1692 Salem Night Walking Tour: $35
  • 2 Hour Boston Historical and Heritage Walking Tour: $5.00
  • 2-Day Niagara Falls USA Tour from Boston: $49

For more ideas for your next trip, check out Free Things to Do in Boston, Must-See Monuments and Memorials In Boston, and The Best Things To Do in Boston with Kids.


Alcohol
  • Alcohol Drinks for one day
    Grand Cayman $13
    Boston $27
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

Sample the Local Flavors in Boston

Some specific costs for nightlife related activities in Boston:

  • Boston Bar Crawl Back Bay Beat Bar Craw: $15
  • Boos and Brews Haunted Pub Crawl: $29
  • Boston Haunted Pub Crawl: $35
  • Haunted Pub Crawl of Historic Pubs and Taverns: $35
  • 2 Hour Historic Pub Crawl in Boston: $35
  • Salem Booze and Brews Haunted Pub Crawl by US Ghost Adventures: $36
  • Boston Ghosts Boos and Brews Haunted Pub Crawl : $36
  • History Pub Crawl Tour Along the Freedom Trail: $56
  • Boston Freedom Trail History Pub Crawl Small-Group Tour: $60
  • Freedom Trail History Tour and Brewery Taste: $71
  • Sushi Making Class at a Local Brewery in Boston: $75
  • Sushi Making Class at a Local Distillery in Boston: $75


When we compare the travel costs of actual travelers between Grand Cayman and Boston, we can see that Boston is more expensive. And not only is Grand Cayman much less expensive, but it is actually a significantly cheaper destination. Since Grand Cayman is in Caribbean Islands and Boston is in North America, this is one of the main reasons why the costs are so different, as different regions of the world tend to have overall different travel costs. So, traveling to Grand Cayman would let you spend less money overall. Or, you could decide to spend more money in Grand Cayman and be able to afford a more luxurious travel style by staying in nicer hotels, eating at more expensive restaurants, taking tours, and experiencing more activities. The same level of travel in Boston would naturally cost you much more money, so you would probably want to keep your budget a little tighter in Boston than you might in Grand Cayman.

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 Boston Expensive?.


Which is Bigger, Grand Cayman or Boston?

Boston has a larger population, and is about 20 times larger than the population of Grand Cayman. When comparing the sizes of Grand Cayman and Boston, 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 Boston?

Boston 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 Boston in the Summer?

The summer brings many poeple to Grand Cayman as well as Boston. Grand Cayman attracts visitors year-round for its warm weather and sunny climate. Additionally, the beaches, the city activities, the music scene, and the family-friendly experiences are the main draw to Boston this time of year.

In the summer, Grand Cayman is a little warmer than Boston. Typically, the summer temperatures in Grand Cayman in July average around 28°C (83°F), and Boston averages at about 73°F (23°C).

Grand Cayman receives a lot of rain in the summer. Grand Cayman usually gets more rain in July than Boston. Grand Cayman gets 179 mm (7 in) of rain, while Boston receives 2.9 inches (74 mm) of rain this time of the year.


  • Summer Average Temperatures July
    Grand Cayman 28°C (83°F) 
    Boston 73°F (23°C)

Should I visit Grand Cayman or Boston in the Autumn?

Both Boston and Grand Cayman are popular destinations to visit in the autumn with plenty of activities. The warm climate attracts visitors to Grand Cayman throughout the year. Also, many travelers come to Boston for the city's sights and attractions, the shopping scene, the music scene, and the natural beauty of the area.

In October, Grand Cayman is generally much warmer than Boston. Daily temperatures in Grand Cayman average around 27°C (81°F), and Boston fluctuates around 54°F (12°C).

It's quite rainy in Grand Cayman. In October, Grand Cayman usually receives more rain than Boston. Grand Cayman gets 238 mm (9.4 in) of rain, while Boston receives 3.3 inches (84 mm) of rain each month for the autumn.


  • Autumn Average Temperatures October
    Grand Cayman 27°C (81°F) 
    Boston 54°F (12°C)

Should I visit Grand Cayman or Boston in the Winter?

Both Boston and Grand Cayman during the winter 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, many visitors come to Boston in the winter for the museums, the Christmas ambience, the shopping scene, the theater shows, and the cuisine.

Boston can get quite cold in the winter. Grand Cayman is much warmer than Boston in the winter. The daily temperature in Grand Cayman averages around 24°C (76°F) in January, and Boston fluctuates around 29°F (-2°C).

Grand Cayman usually gets less rain in January than Boston. Grand Cayman gets 58 mm (2.3 in) of rain, while Boston receives 3.4 inches (87 mm) of rain this time of the year.


  • Winter Average Temperatures January
    Grand Cayman 24°C (76°F) 
    Boston 29°F (-2°C)

Should I visit Grand Cayman or Boston in the Spring?

The spring attracts plenty of travelers to both Grand Cayman and Boston. Warm weather and sunshine bring visitors to Grand Cayman year-round. Also, most visitors come to Boston for the beaches, the activities around the city, and the natural beauty during these months.

In the spring, Grand Cayman is much warmer than Boston. Typically, the spring temperatures in Grand Cayman in April average around 26°C (79°F), and Boston averages at about 48°F (9°C).

In April, Grand Cayman usually receives less rain than Boston. Grand Cayman gets 48 mm (1.9 in) of rain, while Boston receives 3.5 inches (89 mm) of rain each month for the spring.


  • Spring Average Temperatures April
    Grand Cayman 26°C (79°F) 
    Boston 48°F (9°C)

Typical Weather for Boston and Grand Cayman

Grand Cayman Boston
Temp (°C) Rain (mm) Temp (°C) Rain (mm)
Jan 24°C (76°F) 58 mm (2.3 in) 29°F (-2°C) 3.4 inches (87 mm)
Feb 24°C (76°F) 51 mm (2 in) 30°F (-1°C) 3.7 inches (94 mm)
Mar 25°C (77°F) 31 mm (1.2 in) 38°F (4°C) 3.7 inches (95 mm)
Apr 26°C (79°F) 48 mm (1.9 in) 48°F (9°C) 3.5 inches (89 mm)
May 27°C (81°F) 131 mm (5.1 in) 58°F (15°C) 3.2 inches (82 mm)
Jun 28°C (82°F) 183 mm (7.2 in) 68°F (20°C) 3.1 inches (79 mm)
Jul 28°C (83°F) 179 mm (7 in) 73°F (23°C) 2.9 inches (74 mm)
Aug 28°C (82°F) 172 mm (6.8 in) 72°F (22°C) 3.2 inches (82 mm)
Sep 28°C (82°F) 212 mm (8.3 in) 64°F (18°C) 3.1 inches (79 mm)
Oct 27°C (81°F) 238 mm (9.4 in) 54°F (12°C) 3.3 inches (84 mm)
Nov 26°C (79°F) 141 mm (5.6 in) 45°F (7°C) 4.3 inches (108 mm)
Dec 25°C (78°F) 57 mm (2.3 in) 33°F (1°C) 3.9 inches (99 mm)