diff --git a/packages/@aws-cdk/aws-apigateway/lib/base-path-mapping.ts b/packages/@aws-cdk/aws-apigateway/lib/base-path-mapping.ts
index 066ec229b832f..0df48fcb89e3b 100644
--- a/packages/@aws-cdk/aws-apigateway/lib/base-path-mapping.ts
+++ b/packages/@aws-cdk/aws-apigateway/lib/base-path-mapping.ts
@@ -56,8 +56,14 @@ export class BasePathMapping extends Resource {
     super(scope, id);
 
     if (props.basePath && !Token.isUnresolved(props.basePath)) {
-      if (!props.basePath.match(/^[a-zA-Z0-9$_.+!*'()-]+$/)) {
-        throw new Error(`A base path may only contain letters, numbers, and one of "$-_.+!*'()", received: ${props.basePath}`);
+      if (props.basePath.startsWith('/') || props.basePath.endsWith('/')) {
+        throw new Error(`A base path cannot start or end with /", received: ${props.basePath}`);
+      }
+      if (props.basePath.match(/\/{2,}/)) {
+        throw new Error(`A base path cannot have more than one consecutive /", received: ${props.basePath}`);
+      }
+      if (!props.basePath.match(/^[a-zA-Z0-9$_.+!*'()-/]+$/)) {
+        throw new Error(`A base path may only contain letters, numbers, and one of "$-_.+!*'()/", received: ${props.basePath}`);
       }
     }
 
diff --git a/packages/@aws-cdk/aws-apigateway/test/base-path-mapping.test.ts b/packages/@aws-cdk/aws-apigateway/test/base-path-mapping.test.ts
index c3da93e83ba26..69e7e98d9146f 100644
--- a/packages/@aws-cdk/aws-apigateway/test/base-path-mapping.test.ts
+++ b/packages/@aws-cdk/aws-apigateway/test/base-path-mapping.test.ts
@@ -8,7 +8,7 @@ describe('BasePathMapping', () => {
     // GIVEN
     const stack = new cdk.Stack();
     const api = new apigw.RestApi(stack, 'MyApi');
-    api.root.addMethod('GET'); // api must have atleast one method.
+    api.root.addMethod('GET'); // api must have at least one method.
     const domain = new apigw.DomainName(stack, 'MyDomain', {
       domainName: 'example.com',
       certificate: acm.Certificate.fromCertificateArn(stack, 'cert', 'arn:aws:acm:us-east-1:1111111:certificate/11-3336f1-44483d-adc7-9cd375c5169d'),
@@ -33,7 +33,7 @@ describe('BasePathMapping', () => {
     // GIVEN
     const stack = new cdk.Stack();
     const api = new apigw.RestApi(stack, 'MyApi');
-    api.root.addMethod('GET'); // api must have atleast one method.
+    api.root.addMethod('GET'); // api must have at least one method.
     const domain = new apigw.DomainName(stack, 'MyDomain', {
       domainName: 'example.com',
       certificate: acm.Certificate.fromCertificateArn(stack, 'cert', 'arn:aws:acm:us-east-1:1111111:certificate/11-3336f1-44483d-adc7-9cd375c5169d'),
@@ -53,11 +53,11 @@ describe('BasePathMapping', () => {
     });
   });
 
-  test('throw error for invalid basePath property', () => {
+  test('specify multi-level basePath property', () => {
     // GIVEN
     const stack = new cdk.Stack();
     const api = new apigw.RestApi(stack, 'MyApi');
-    api.root.addMethod('GET'); // api must have atleast one method.
+    api.root.addMethod('GET'); // api must have at least one method.
     const domain = new apigw.DomainName(stack, 'MyDomain', {
       domainName: 'example.com',
       certificate: acm.Certificate.fromCertificateArn(stack, 'cert', 'arn:aws:acm:us-east-1:1111111:certificate/11-3336f1-44483d-adc7-9cd375c5169d'),
@@ -65,7 +65,31 @@ describe('BasePathMapping', () => {
     });
 
     // WHEN
-    const invalidBasePath = '/invalid-/base-path';
+    new apigw.BasePathMapping(stack, 'MyBasePath', {
+      restApi: api,
+      domainName: domain,
+      basePath: 'api/v1/example',
+    });
+
+    // THEN
+    Template.fromStack(stack).hasResourceProperties('AWS::ApiGateway::BasePathMapping', {
+      BasePath: 'api/v1/example',
+    });
+  });
+
+  test('throws when basePath contains an invalid character', () => {
+    // GIVEN
+    const stack = new cdk.Stack();
+    const api = new apigw.RestApi(stack, 'MyApi');
+    api.root.addMethod('GET'); // api must have at least one method.
+    const domain = new apigw.DomainName(stack, 'MyDomain', {
+      domainName: 'example.com',
+      certificate: acm.Certificate.fromCertificateArn(stack, 'cert', 'arn:aws:acm:us-east-1:1111111:certificate/11-3336f1-44483d-adc7-9cd375c5169d'),
+      endpointType: apigw.EndpointType.REGIONAL,
+    });
+
+    // WHEN
+    const invalidBasePath = 'invalid-/base-path?';
 
     // THEN
     expect(() => {
@@ -77,11 +101,83 @@ describe('BasePathMapping', () => {
     }).toThrowError(/base path may only contain/);
   });
 
+  test('throw error for basePath starting with /', () => {
+    // GIVEN
+    const stack = new cdk.Stack();
+    const api = new apigw.RestApi(stack, 'MyApi');
+    api.root.addMethod('GET'); // api must have at least one method.
+    const domain = new apigw.DomainName(stack, 'MyDomain', {
+      domainName: 'example.com',
+      certificate: acm.Certificate.fromCertificateArn(stack, 'cert', 'arn:aws:acm:us-east-1:1111111:certificate/11-3336f1-44483d-adc7-9cd375c5169d'),
+      endpointType: apigw.EndpointType.REGIONAL,
+    });
+
+    // WHEN
+    const invalidBasePath = '/invalid-base-path';
+
+    // THEN
+    expect(() => {
+      new apigw.BasePathMapping(stack, 'MyBasePath', {
+        restApi: api,
+        domainName: domain,
+        basePath: invalidBasePath,
+      });
+    }).toThrowError(/A base path cannot start or end with/);
+  });
+
+  test('throw error for basePath ending with /', () => {
+    // GIVEN
+    const stack = new cdk.Stack();
+    const api = new apigw.RestApi(stack, 'MyApi');
+    api.root.addMethod('GET'); // api must have at least one method.
+    const domain = new apigw.DomainName(stack, 'MyDomain', {
+      domainName: 'example.com',
+      certificate: acm.Certificate.fromCertificateArn(stack, 'cert', 'arn:aws:acm:us-east-1:1111111:certificate/11-3336f1-44483d-adc7-9cd375c5169d'),
+      endpointType: apigw.EndpointType.REGIONAL,
+    });
+
+    // WHEN
+    const invalidBasePath = 'invalid-base-path/';
+
+    // THEN
+    expect(() => {
+      new apigw.BasePathMapping(stack, 'MyBasePath', {
+        restApi: api,
+        domainName: domain,
+        basePath: invalidBasePath,
+      });
+    }).toThrowError(/A base path cannot start or end with/);
+  });
+
+  test('throw error for basePath containing more than one consecutive /', () => {
+    // GIVEN
+    const stack = new cdk.Stack();
+    const api = new apigw.RestApi(stack, 'MyApi');
+    api.root.addMethod('GET'); // api must have at least one method.
+    const domain = new apigw.DomainName(stack, 'MyDomain', {
+      domainName: 'example.com',
+      certificate: acm.Certificate.fromCertificateArn(stack, 'cert', 'arn:aws:acm:us-east-1:1111111:certificate/11-3336f1-44483d-adc7-9cd375c5169d'),
+      endpointType: apigw.EndpointType.REGIONAL,
+    });
+
+    // WHEN
+    const invalidBasePath = 'in//valid-base-path';
+
+    // THEN
+    expect(() => {
+      new apigw.BasePathMapping(stack, 'MyBasePath', {
+        restApi: api,
+        domainName: domain,
+        basePath: invalidBasePath,
+      });
+    }).toThrowError(/A base path cannot have more than one consecutive \//);
+  });
+
   test('specify stage property', () => {
     // GIVEN
     const stack = new cdk.Stack();
     const api = new apigw.RestApi(stack, 'MyApi');
-    api.root.addMethod('GET'); // api must have atleast one method.
+    api.root.addMethod('GET'); // api must have at least one method.
     const domain = new apigw.DomainName(stack, 'MyDomain', {
       domainName: 'example.com',
       certificate: acm.Certificate.fromCertificateArn(stack, 'cert', 'arn:aws:acm:us-east-1:1111111:certificate/11-3336f1-44483d-adc7-9cd375c5169d'),
@@ -111,7 +207,7 @@ describe('BasePathMapping', () => {
     // GIVEN
     const stack = new cdk.Stack();
     const api = new apigw.RestApi(stack, 'MyApi');
-    api.root.addMethod('GET'); // api must have atleast one method.
+    api.root.addMethod('GET'); // api must have at least one method.
     const domain = new apigw.DomainName(stack, 'MyDomain', {
       domainName: 'example.com',
       certificate: acm.Certificate.fromCertificateArn(stack, 'cert', 'arn:aws:acm:us-east-1:1111111:certificate/11-3336f1-44483d-adc7-9cd375c5169d'),
diff --git a/packages/@aws-cdk/aws-apigateway/test/integ.base-path-mapping.js.snapshot/manifest.json b/packages/@aws-cdk/aws-apigateway/test/integ.base-path-mapping.js.snapshot/manifest.json
index a57c7ce4a9fcd..0049bafae7b8e 100644
--- a/packages/@aws-cdk/aws-apigateway/test/integ.base-path-mapping.js.snapshot/manifest.json
+++ b/packages/@aws-cdk/aws-apigateway/test/integ.base-path-mapping.js.snapshot/manifest.json
@@ -81,6 +81,12 @@
             "data": "MappingTwo551C79ED"
           }
         ],
+        "/test-stack/MappingThree/Resource": [
+          {
+            "type": "aws:cdk:logicalId",
+            "data": "MappingThree36BBA1B6"
+          }
+        ],
         "/test-stack/BootstrapVersion": [
           {
             "type": "aws:cdk:logicalId",
diff --git a/packages/@aws-cdk/aws-apigateway/test/integ.base-path-mapping.js.snapshot/test-stack.template.json b/packages/@aws-cdk/aws-apigateway/test/integ.base-path-mapping.js.snapshot/test-stack.template.json
index 52d687e8b3f2d..022e83846fdab 100644
--- a/packages/@aws-cdk/aws-apigateway/test/integ.base-path-mapping.js.snapshot/test-stack.template.json
+++ b/packages/@aws-cdk/aws-apigateway/test/integ.base-path-mapping.js.snapshot/test-stack.template.json
@@ -70,6 +70,16 @@
      "Ref": "ApiF70053CD"
     }
    }
+  },
+  "MappingThree36BBA1B6": {
+   "Type": "AWS::ApiGateway::BasePathMapping",
+   "Properties": {
+    "DomainName": "domainName",
+    "BasePath": "api/v1/multi-level-path",
+    "RestApiId": {
+     "Ref": "ApiF70053CD"
+    }
+   }
   }
  },
  "Outputs": {
diff --git a/packages/@aws-cdk/aws-apigateway/test/integ.base-path-mapping.js.snapshot/tree.json b/packages/@aws-cdk/aws-apigateway/test/integ.base-path-mapping.js.snapshot/tree.json
index 2a9baa7dc204d..814e1397b0795 100644
--- a/packages/@aws-cdk/aws-apigateway/test/integ.base-path-mapping.js.snapshot/tree.json
+++ b/packages/@aws-cdk/aws-apigateway/test/integ.base-path-mapping.js.snapshot/tree.json
@@ -217,6 +217,34 @@
               "fqn": "@aws-cdk/aws-apigateway.BasePathMapping",
               "version": "0.0.0"
             }
+          },
+          "MappingThree": {
+            "id": "MappingThree",
+            "path": "test-stack/MappingThree",
+            "children": {
+              "Resource": {
+                "id": "Resource",
+                "path": "test-stack/MappingThree/Resource",
+                "attributes": {
+                  "aws:cdk:cloudformation:type": "AWS::ApiGateway::BasePathMapping",
+                  "aws:cdk:cloudformation:props": {
+                    "domainName": "domainName",
+                    "basePath": "path",
+                    "restApiId": {
+                      "Ref": "ApiF70053CD"
+                    }
+                  }
+                },
+                "constructInfo": {
+                  "fqn": "@aws-cdk/aws-apigateway.CfnBasePathMapping",
+                  "version": "0.0.0"
+                }
+              }
+            },
+            "constructInfo": {
+              "fqn": "@aws-cdk/aws-apigateway.BasePathMapping",
+              "version": "0.0.0"
+            }
           }
         },
         "constructInfo": {
diff --git a/packages/@aws-cdk/aws-apigateway/test/integ.base-path-mapping.ts b/packages/@aws-cdk/aws-apigateway/test/integ.base-path-mapping.ts
index 9d3a31a3a205e..f25b572545f49 100644
--- a/packages/@aws-cdk/aws-apigateway/test/integ.base-path-mapping.ts
+++ b/packages/@aws-cdk/aws-apigateway/test/integ.base-path-mapping.ts
@@ -27,6 +27,13 @@ export class TestStack extends cdk.Stack {
       basePath: 'path',
       attachToStage: false,
     });
+
+    new apigateway.BasePathMapping(this, 'MappingThree', {
+      domainName,
+      restApi,
+      basePath: 'api/v1/multi-level-path',
+      attachToStage: false,
+    });
   }
 }